The 2 Best Ways to See Chicago

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See the City From the River

The Chicago River is actually a system of rivers and canals that run through the heart of the city. The river is both natural and a feat of human engineered innovation. by reversing the flow and implanting a series of locks, the river could handle the growing sewage issues as well as meet the needs of the growing city life. The bridges across the river are a beautiful way to walk above the river amongst the cityscape and most have stairs leading down to riverfront walkways with cafes, bars and resting points to enjoy the riverfront.

One of the most exceptional ways to truly see the magnificence of the city is from an archictectural boat tour that cruises down the river. The tours run from May-November nearly all day long, but the best tours are the evening cruise when you can experience the transition from day to night, from sunlight to city lights. It is truly an unforgettable experience that everyone should have. Tourists and locals alike enjoy these tours!


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See The City From Above

When you are amidst the sea of skyscrapers it is often difficult to get a feel for the whole city. Taking your view from the top changes your perspective and gives you a grand scope of Chicago from above. You have two options for viewing city this way. First, the observation deck from the John Hancock building on Michigan Avenue, which puts you closer to the lakefront, or the Willis Tower “skydeck” which puts you smack dab in the middle of the Chicago loop. Both do a great job in getting you up really high for fabulous views. Do your research and plan your itinerary according to which part of the city you will be in and what works for your family best. I have done both and find them equally satisfying.


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Chicago is awesome no matter how you do it, but these two unique ways of seeing the city are sure to make your experience memorable and that’s what traveling is all about-creating memories.

 

Chicago 15 Year Old Adventure

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Celebrating our Kids with their Very Own Adventures

We love to celebrate the various milestones of our kids. They each look forward to choosing their own adventure with mom and dad at 10, 15, and 20. Sometimes we throw in others, too, if the opportunity presents itself. Family adventures are always going to happen, but we like to celebrate the uniqueness of each kid and enjoy the time relating to them individually. Rowan chose Chicago for his 15 year old adventure!


The jump from age 10 to age 15 is enormous. So much happens during those years and it gives us as parents a good launchpad to connecting with our teens. A successful adventure with a teen surprisingly looks pretty similar to one as a 10 year old.  I can’t emphasize enough how far it goes to reaching a child’s heart by being interested in what he/she is interested in. For our family, these adventures are about going and doing what that child wants to do.


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I know we all live on a budget, but I implore you to splurge in a way that makes your kid feel special. After all, these are memories you are creating, not just something that will be thrown away after a few months. We bought good seats to watch Ro’s favorite MLB team in the most iconic ballpark ever and a fun ride on the Red Line to the game with all the other Cubs fans! Rowan is a foodie with an extremely mature palate so we ate our way through the city at restaurants he requested. Of course one of his favorites was the hot dog at Wrigley-gotta get that Chicago dog! We had a swing and a miss with a restaurant we TRIED for 2 hours to get in to and ended up with a late night stop at Portillo’s for an Italian beef sandwich. We walked along the lakefront to get a glimpse of all the sailboats, saw Millennium Park, finally we made a stop at the Art Insitute.


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One of the best ways to see Chicago is from the riverfront and from ON the river. If you spend any time walking downtown in the loop you will cross over one of the many bridges. The city has done so much to clean up the riverfront walkways, so when the weather is pleasant you will find a lot of people down there enjoying the restaurants, bars, and boat life. The other splurge we indulged in was the sunset evening cruise on the architectural boat tour. Don’t miss this!!! Learning about the different buildings in the city from the different eras is super interesting and you get to do it all while cruising down the river. Spend the extra few bucks to do it as the sun begins to go down so you can see the changes from light to dark. it is an unforgettable experience.


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The other best way to really see the city is from the top. There are two locations you can do this from: The Hancock building on Michigan Ave and Willis Tower on State St. Either way, you will get fantastic views of the lake and the city from up above and you can’t help but feel so small up there.


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There are a host of other activities to do as adults or with children. We focused on what Rowan wanted to do for the weekend. Here is a list of other ideas for your time in the Windy City.

Shopping on Michigan Ave for the popular retail stores or look in the Wicker Park area for more boutique shopping.

♠ Every museum is awesome: The Field Museum to see Sue the dinosaur, The Museum of Science & Industry, The Art Insitute of Chicago, the Adler Planetarium, the Chicago Children’s Museum, the  Chicago Sports Museum, the Richard H. Driehaus Musuem, Frank Lloyd Wright’s Robie House and more.

♠ Chicago Bears Soldier Field, The United Center, Wrigley Field sports venues

♠ Chicago pizza options include Lou Malnati’s, Pizzeria Uno, Pizzeria Due, Giordano’s, and Gino’s East to name a few. That deep dish pizza is special! Every Chicagoan has their favorite spot-mine is definitely Lou Malnati’s!

Navy Pier is great for kids with all kinds of arcades, outside games, beer gardens for parents while kids play, and the big Ferris wheel.

8 Tips to Planning a Multi-Family Adventure

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Multi-family adventures can be an incredible way to experience a new place or perhaps enhance a re-visit destination. However, there are also some major differences in the way you plan and do this type of vacation. After all, compounding the number of people involved is sure to add a layer of logistics. I have come up with a few tips on how to plan a multi-family adventure so that everyone walks away with lasting memories and continued relationships in tact.

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The first hurdle in planning a multi-family adventure is choosing a location. Often times this step happens organically, coming out of an excited and shared desire amongst family or friends. In our case, longtime friends asked me to help them plan a trip to Yellowstone National Park and jokingly said she just wanted to take us along so we could show them everything ourselves. Crazy thing is that we had already marked summer of 2018 to take our kids back to celebrate. Twenty years before, John and I met while working in Yellowstone National Park and wanted to introduce our kids to our magical place. Other friends overheard our conversation and wanted to join in. What started as a casual conversation quickly became the beginning of a plan. If you are starting from scratch and already have in mind who you want to travel with, I recommend starting the conversation with a few destination ideas and see how they are received.

Tip 1: Choose a destination that everyone is (mostly) equally excited about.

You cannot start off with a compromise right from the beginning so make sure all family units WANT this. Consider the variety of activities that are offered and if there is enough for everyone to be satisfied. Think about the group and the things you have in common and will enjoy doing together.

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Tip 2: Begin your planning 3 months earlier than you typically would.

Planning amongst multiple families takes extra time because many parties need to weigh in on many decisions. Now that we have all become accustomed to using video conferencing platforms, that would be a great way to get everyone together to discuss the planning. Start off with a list of MUST DO activities and make sure everyone has time to process their decisions.

Tip 3: Delegate the areas of planning based on who has specific gifts and/or interests.

Our good friend Matt is a wizard at finding the best flights and airline deals and knows the best way to use airline miles/points. I immediately put him in charge of that aspect of the planning. John and I know Yellowstone really well and so we planned our route and where we should stay on which nights. If you have a foodie in your group, that person needs to research restaurants and reservations for large groups. Work with your strengths and more will get done in a shorter amount of time with less frustration.

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Tip 4: Create a shareable document to add new information and keep everyone organized.

Sharing information and keeping everyone updated is crucial. This also allows for edits and changes that everyone can see with their own eyes. In a few instances we had to split up on accommodations-it could not be avoided, but at least we had that document to keep track of where everyone was on which night. This also helps to make sure all bases are covered and that there are no holes in the agenda. If we booked an activity we included confirmation numbers and details about who was doing that activity. Breaking things up by each day keeps it well organized.

Tip 5: Poll your people about what they want out of the adventure.

We found that taking a quick survey of our own individual families would have been a good thing to do ahead of time. We did not do this and wish we had. Getting an idea of what is desired from the vacation (lounging on a beach for a week OR hiking 15 miles a day through rough terrain) before you leave can help in the plans. Asking each family member one thing that was on their bucket list for the trip would have helped to divide up into groups better (6 go horseback riding while 5 go hiking and 4 go fishing) in advance. Instead we were left winging it on the fly and it was tough and at times we may have hurt feelings or not heard the quieter in the group. Polling ahead would ensure that no one’s number one desire gets left out. *Sidenote: sometimes this can’t be helped. We had planned an entire afternoon for the older boys to fish, but the weather was awful with very cool temps, whipping wind and spitting rain. You can’t always plan around the weather. Sadly this was a big desire for the boys, but we just couldn’t make it happen.

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Tip 6: Leave room/space for down time

Not every family travels at the same pace. Some families like to milk every moment out of their vacation because they only take one trip every two years. Other families like to travel at a slower pace and enjoy each activity and not feel rushed on to the next one. You must allow for each family to have some time just to themselves. You don’t want to make the others tired of you and vice versa. It’s important to leave some space from each other in order to preserve the relationship for the long term. It’s also important to acknowledge that not everyone’s need for downtime will happen at the same time. Be flexible with this and try to come up with a schedule that meets most of the needs.

Tip 7: Prepare your people that there will be compromises

There is no perfect travel world even on the best days, but when you are dealing with a large group and multiple families with lots of dynamics you need to know that you will make more compromises than usual. It’s best to prepare everyone for this before you even leave on your trip. Keep it positive by showing them that their number one activity is on the agenda and that while they may not love everything the group does, they will get their adventure during the trip.

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Tip 8: Be sensitive to budgets

It goes without saying that not every family is in the same financial situation, but beyond that each family values things differently. Perhaps one family prefers to eat all meals self-cooked so they can put that money toward experiences while another family looks forward to a vacation without any cooking at all. Either way, everyone can still have a good time together while being respectful of each other. Having those discussions up front is best and communicating what’s important in the budget will only help keep things light.

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These are the best tips to get you planning a memorable multi-family adventure. In the end, you want an adventure that brings joy to everyone and keeps the relationships in tact for the future. A little extra logistical push can help preserve all of that. Looking back through these photos makes me ready to plan the next time we can get together with lifelong friends and create memories.

24 Hours: Rocky Mountain National Park

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When to Go

This amazing U.S. National Park is one that can be revisited multiple times and can be enjoyed throughout the seasons. We visited in early June on a beautiful, clear and sunny day with perfect hiking temperatures in the 60-70 degree range. If you are visiting in the busy season (May-September) you will be forced to park in a lot and then take a shuttle to the popular trailheads. It was very busy the day we were there and lots of people were on the trail with us. We even had to wait in line for a shuttle, so be patient and enjoy meeting others.

Most Popular Hike

We chose the Emerald Lake hike for its length (just under 4 miles roundtrip) and popularity for fantastic scenery. It was a perfectly gorgeous day and we wanted to see the beauty of the park. It’s not a difficult hike at all and you get so much reward for your work. It was a challenge for us, though, coming straight from sea level. The start of the Bear Lake trailhead is at about 9500 ft. elevation and you’ll end up over 10,000 ft. so it’s not a big gain, but our bodies just weren’t used to being up that high! We took our time and enjoyed stopping at the two other lakes on the trail. Both Nymph Lake and Dream Lake have beautiful vistas and the sunny blue skies cast a shimmer on the surfaces.

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Wildlife Story

Despite the crowds, we did get some wildlife sightings. In fact, on the way back we came across a spot where a mama elk had bedded down her new calf about 50 yards from the trail. We were well aware of the situation and used caution as we approached. John and I have both been on dozens of trails both populated and backcountry with years of experience. The kids not so much at this point, so this day was a great learning experience. John was out ahead and I was at the end with the three kids in between us. John began to walk the trail into an open area where the mama elk was eating and keeping an eye out. John got about 1/2 through the open space when the mama CHARGED him. The kids and I, with stopped hearts, retreated in a panicked silence. John ran. He ran. What??? He knows better than to turn his back on a wild animal, but his instincts took over. She was just showing him who was boss and stopped short, but Lord I almost lost my lunch. The kids and I opted to climb up and embankment off trail and found the trail and John after circumventing the scene. It was so surprising that she charged John of all people with so many on the trail that day.

We all experienced firsthand our place in the wild, which is to say that WE are the visitors. That mama elk had every right to be there and to protect her baby. We were the ones interrupting and invading her space. The rest of the hike went off without a hitch and I would say the entirety of the hike took about 3.5 hours. You could certainly do this more quickly, but we took our time and enjoyed the views and being together and taking photos. 

Trail Ridge Road

When we got back to the car we took the drive up to the Alpine Visitor Center via the Trail Ridge Road. Wow! The views were incredible, the wind was fierce and John drove like his family’s life was in his hands. It was a really neat way to see the park, but know that the road is narrow and has steep drop offs. If you aren’t a fan of heights, this may be too exciting for you! You will climb all the way to 11,760 ft above sea level and it is magnificent! Be certain to check road conditions and to see if the road is open all the way through or at least to the Alpine Visitor Center-the road is NOT open year-round.

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Quarantine Photo Scavenger Hunt

Where I’m at right now as a Mom, April 2020

If you are anything like me you’ve been wildly vacillating between cruise ship director mom and figure out your own boredom mom. I can even be both those moms in the same day! Navigating these strange times with kids at home has been both exhausting and revealing. We have one tween and two teens all at different levels of schooling and socializing so keeping them occupied, entertained, and on track is not easy. Typically I don’t put this kind of pressure on myself-after all, raising children has little to do with making sure they are entertained at all times. But, we find ourselves living in a time of a global pandemic which is way outside the bounds of normal. Thus I find myself vacillating.

What to do When Your Kids Can’t GO on Spring Break

Last week the kids had spring break, which meant no e-learning, no assignments, and still nowhere to go. John was supposed to be with our oldest looking at colleges and making a whole trip out of it. Our daughter was supposed to be at the beach with friends. Disappointments were swirling and yet we were to be home looking at the same walls and binging on more Netflix. I took some liberties and I planned a little activity for the kids.

Some of you may not agree with how I handled this, but I’m okay with putting myself out there. I thought long and hard about how to handle the situation and came up with the best solution to give my kids a great experience with little to no contact with others. After pre-arranging some things with neighbors and family I wrote up clues for a photo scavenger hunt around our city. I had a list of about 20 things/people they needed to document with a photo. Our oldest can drive and so I sent the three of them off for the day.

There was one clue they couldn’t figure out and I realized that it was a reference that was too old for them. HA! All in all, they had a great day riding around together figuring out all the clues and taking their silly photos. For certain one of the greatest silver linings of this quarantine time is all of the sibling bonding. My kids have always gotten along really well and I credit that to the emphasis we have put on our family trips. Those who travel together REALLY get to know each other well. When you share hotel rooms and life altering experiences you bond and that bonding carries over to the everyday life stuff. And here we are. We are in the everyday life stuff. All. The. Time. Every. Day. All. Day. Long. We are here for it and we’re embracing it as much as we can.

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Until we can gather together again we will keep coming up with our social distancing plans for the kids every so often. Take a look at a few of our ideas for the photo scavenger hunt and feel free to adapt it to your kids and your circumstances. You could easily turn this into a neighborhood hunt if needed.

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  • A boat
  • A city bus
  • An entire family in front of their home
  • All 3 kids on a golf course
  • A business that is closed
  • A fire Hydrant
  • An uplifting yard sign
  • A flowering tree/bush
  • Ordering in a drive thru
  • A set of identical twins (their grandma lives with hers!)
  • Grandparents in their yard
  • A barn
  • A body of water
  • A restaurant that they can’t wait to eat at when it opens
  • A float in a pool
  • A baseball field
  • Their school sign
  • A dog that is not ours
  • A motorcycle
  • A flag

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All clues were written for them to figure out what photo was needed, so these are just examples of what objects they had to photograph. You can easily come up with what works for your family and could even do this all on a walk. I think I’ll come up with another one when some of our restrictions are loosened up. These were all able to be done from the car or within the appropriate distance needed.

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Costa Rica Surf Camp Adventure

Vista Guapa Surf Camp

In early March before the Coronavirus took over, Shep and I took a mother son adventure trip to Costa Rica. Shep’s top priority while we were there was learning to surf, but this would be our first time learning so I did a lot of research about a good/safe place for beginners. I came across Vista Guapa Surf Camp in Jaco, which is on the Pacific side of the country.

Post Surf Sunset Dinner

What to Expect

The camp is comprised of 3 bungalow duplexes nestled into the side of a mountain with sweeping views of the Pacific coastline, a yoga platform/house, a pool area with workout platform, and a main house at the base of the mountain with lobby and areas where breakfast is served. Each bungalow is lined with windows and has high wood paneled ceilings. The interior has a breezy understated beach feel kept clean and tidy. The hammock and chair on the front porch give some extra chill space and the perfect opportunity to watch the sunset.

Bungalow views

Each morning a delicious breakfast of eggs, beans & rice, fresh fruit juices, sausage, fresh fruit, and oatmeal is served on the outdoor porches of the main house. Yoga on the outdoor roofed platform is typically offered once per day depending on the tide schedule. Everything revolves around the tides here-the best surf times are the priority. High tide times are posted in the main house and the schedules are hashed out the evening before during dinner or on the ride home. For the most part all meals, surf lessons, and yoga sessions are enjoyed as a group. Don’t be afraid to take an excursion outside the group, but part of the charm of this particular accommodation is to do things as a camp. Shep and I loved it! Kandace and crew were exceptionally attentive and sensitive to the needs of the group. We liked not having to come up with plans on our own, but really liked that we had a vote within the group. We felt at ease, safe, and cared for in every situation.

Another surf day

Learning to Surf

Shep had his sights set on learning how to surf so we took lessons 3 days in a row. The lessons began as the tides came in and lasted about 2 hours as the waves grew and then died down again. Jaco Beach is an awesome place for beginners to learn. The water is warm, the waves are consistent and not overwhelming, and the beach isn’t huge so it’s not overcrowded. We each had an instructor to ourselves and we started out on the beach with body positioning and some basic surf vocabulary. Before too long we were in the water and being shown how to control our boards safely and given some wisdom and watching and battling the waves as we paddled out. The first day was about safety and having success getting up on the board. Both Shep and I were able to get up on the first day and it was hugely encouraging. On the second day my body was fighting it, but Shep was rocking it. To be honest I am a little afraid of the water, but Shep is not. His fearlessness overcame the obstacles while I let me fear keep me tense. My instructor had to keep reminding me not to hold my breath and breathe steadily which really helped. On the third day Shep was exhausted and didn’t progress much, but he was still so happy and having fun. I was able to drop in to some waves and really get the full experience on the third day and it was exhilarating. My body paid for it for the next week, but it was totally worth it!

Shep surf
Mama surf

Who Wants to Go on a Surf Camp Adventure?!?!

We cannot recommend Vista Guapa Surf Camp enough! We had the time of our lives learning to surf and enjoying this beautiful part of Costa Rica. If your family loves adventure and learning new skills, this is the way to do it. I cannot stress enough how perfect this trip is for tweens and teens and something the whole family can enjoy together. Lots of family time, but also each person is learning at their own level and speed in the surf lessons. The camp also has options for bike rentals to take down to the beach, sunset SUP sessions and fun options for activities at night. We did a s’mores and pool night that was perfect for our last night there. The only question at this point is when we get to take the rest of our family back!

Mother – Son Adventure in Costa Rica

Costa Rica sunset view
Sunset view over the Pacific Ocean

Back in November 2019 our youngest, Shep (11), was having a really tough time finding anything to put on his Christmas list. Pretty unusual, right? He finally said he just wanted to go on a road trip. Loved that idea! John and I talked it over and he was all for it. I had so many options and ideas, but kept running into a timing issue with his school schedule. The only time I could really pull him out of school was at the very beginning of March, which didn’t lend itself to a really strong road trip. Heading out West for a week in March was going to be difficult, so we decided to make it a bigger adventure. I had enough miles to get Shep and me to somewhere great and so I decided on Costa Rica. Man was he surprised on Christmas morning!!! He and I planned our mother son adventure itinerary together and came up with our activities. Follow along below and take notes for your next adventure.

As a mother son adventure duo we were looking for a hotel in La Fortuna that gave us easy access to our outdoor adventure activities AND had a pool and a restaurant on site. We did not have a rental car during this trip and needed to keep things simple. If you decide to rent a car in Costa Rica, know ahead of time that insurance is required and is expensive. After being on the roads we now understand why-and we were there during dry season. I honestly cannot imagine doing the driving during rainy season!

Volcano Lodge, Thermal Experience & Hotel: La Fortuna, Costa Rica

Volcano Lodge was exactly the right fit for us as mom and son. The accommodations were basic, but extremely clean; breakfast was included on site; and not only was there a pool, but they also had natural thermal pools.

The staff was excellent from the moment we checked in at the outdoor lobby. They offered great help in organizing our outdoor activities and made us feel cared for while we were guests. The grounds and thermal pools here are really gorgeous and you will enjoy the flora and fauna as you relax and view the Arenal Volcano from many locations inside the hotel grounds. Our room had its own thermal jacuzzi with volcano view and we had fun with it.

Thermal jacuzzi
Personal Thermal Pool Jacuzzi with a volcano view

Know that this particular hotel is near the town of La Fortuna, but is not within walking distance of the main town where restaurants, storefronts and adventure companies can be accessed. However, it was a quiet location tucked away from the busyness. All of our activities picked us up directly from our hotel, so we were in no way inconvenienced. Shep and I enjoyed Canyoneering (rappelling down waterfalls), kayaking on Lake Arenal, and hiking around the volcano. There are SO MANY activities to choose from including horseback riding, treks of various distances, stand up paddle boarding on the lake, zip lining, ATV tours and more. La Fortuna is the adventure capital of Costa Rica and you will find tourists of all kinds here from budget backpackers to high end luxury travelers.

Arenal Lake kayak adventure
We did a kayak adventure on Arenal Lake

El Establo Mountain Hotel, Santa Elena in the Monteverde Region

El Establo Hotel
El Establo Hotel-Rooms with Balcony views

We chose this hotel based on reviews from several friends we follow on Instagram and we really wish we had stayed longer. The hotel is absolutely fabulous with restaurants on site, a host of trails to walk, unbelievable views and lovely rooms. This is THE spot with the best location and luxury accommodations at an affordable price. We spent only one night here as we were specifically seeking out a cloud forest zip lining adventure because what would a mother son adventure be without zip lining?!?! We had an awesome day at Selvatura Park where we zip lined and walked the hanging bridges trail. There is a lot more to do there, but we had to keep moving. In all honestly, if there had been an opportunity for us to stay longer, we would have. Most tourists choose either La Fortuna or Monteverde as a base for adventures and it probably would have been best for us to do only one with a week’s vacation. There is so much to see and do in this area of the country, but taking Shep out of school for longer than a week was not going to work this time. But, we do not regret experiencing a totally different ecosystem. Although La Fortuna and Monteverde appear close to one another on the map, there is not a good and direct way to link the two. We opted to piece a trip together that included a shared van ride along with a long ferry across Arenal Lake. This worked well for us because we didn’t have much luggage. You could also pay for a private transfer. If you have a rental car, plan about a whole day of difficult driving. When we bring the rest of the family back to Costa Rica we will spend more time exploring Monteverde for sure.

Shep zip lining
Shep getting ready to take off on the zip line at Selvatura Park
Hanging Bridges
Shep walking the Hanging Bridges at Selvatura Park

Vista Guapa Surf Camp: Jaco, Costa Rica

Vista Guapa surf camp

Shep’s top priority in Costa Rica was learning to surf, but this would be both our first time learning so I did a lot of research about a good/safe place beginners. It wouldn’t be a proper mother son adventure without some big aspirations! Not too deep into my research, I came across Vista Guapa Surf Camp in Jaco, which is on the Pacific side of the Costa Rica.

The camp is comprised of 3 bungalow duplexes nestled into the side of a mountain with sweeping views of the Pacific coastline, a yoga platform/house, a pool area with workout platform, and a main house at the base of the mountain with lobby and areas where breakfast is served. Each bungalow is lined with windows and has high wood paneled ceilings. The interior has a breezy understated beach feel kept clean and tidy. The hammock and chair on the front porch give some extra chill space and the perfect opportunity to watch the sunset.

Vista Guapa bungalow view
Incredible views from the bungalow at Vista Guapa

Each morning a delicious breakfast of eggs, beans & rice, fresh fruit juices, sausage, fresh fruit, and oatmeal is served on the outdoor porches of the main house. Yoga on the outdoor roofed platform is typically offered once per day depending on the tide schedule. Everything revolves around the tides here-the best surf times are the priority. High tide times are posted in the main house and the schedules are hashed out the evening before during dinner or on the ride home. For the most part all meals, surf lessons, and yoga sessions are enjoyed as a group. Don’t be afraid to take an excursion outside the group, but part of the charm of this particular accommodation is to do things as a camp. Shep and I loved it! Kandace and crew were exceptionally attentive and sensitive to the needs of the group. We liked not having to come up with plans on our own, but really liked that we had a vote within the group. We felt at ease, safe, and cared for in every situation.

Sunset SUP
SUP sunset adventure!

Shep had his sights set on learning how to surf so we took lessons 3 days in a row. The lessons began as the tides came in and lasted about 2 hours as the waves grew and then died down again. Jaco Beach is an awesome place for beginners to learn. The water is warm, the waves are consistent and not overwhelming, and the beach isn’t huge so it’s not overcrowded. We each had an instructor to ourselves and we started out on the beach with body positioning and some basic surf vocabulary. Before too long we were in the water and being shown how to control our boards safely and given surf wisdom while watching and battling the waves as we paddled out. The first day was about safety and having success getting up on the board. Both Shep and I were able to get up on the first day and it was hugely encouraging. On the second day my body was fighting it, but Shep was rocking it. To be honest I am a little afraid of the water, but Shep is not. His fearlessness overcame the obstacles while I let me fear keep me tense. My instructor had to keep reminding me not to hold my breath and breathe steadily which really helped. On the third day Shep was exhausted and didn’t progress much, but he was still so happy and having fun. I was able to drop in to some waves and really get the full experience on the third day and it was exhilarating. My body paid for it for the next week, but it was totally worth it!

Shep surf lesson
Shep taking a surf lesson from Christian
Mama surf lesson
Mama dropping in on a wave during a surf lesson

This is the first Mother Son adventure trip I have ever done, and also the first one-on-one trip with a child. It was never specifically a part of our plans as parents to ever try this, but the opportunity came along and we went for it. I can’t say enough wonderful things about it. I birthed 3 children within 5 years, so my time with any of them one-on-one has been extremely limited. Shep’s love language is quality time and boy did he get it. 7 full days of quality time on a mother son dream adventure in a fabulous location. Do it. If you’ve been floating this idea out there, do it. No we don’t have it all planned how we will make it happen for the other two, but I know their wheels are turning and that makes me excited. Shep and I were able to focus on the things he was interested in without having to compromise with the rest of the family. We do that on our family vacations and it’s worthwhile for us all to know how to operate within the family unit, but this was special.

Sunset Dinner
Sunset dinner up high in the rainforest

As a side note, Shep and I had crazy timing with this mother son adventure. When we returned back home the beginning of the COVID19 craze began. Our flight arrived back to South Carolina on March 8, 2020. Shep went back to school for 5 days, but by the end of the 3rd day in school it became apparent that everything was changing and changing very quickly. We were given notice on Saturday that no one in SC would be going back to school for a minimum of 3 weeks. I always hold these trips in a pretty loose grip, but I sure am glad we had a great adventure together in Costa Rica. We can’t wait to go back someday!

Adventure on the Big Island

Big Island black sand beach adventure
Big Island lush valley

After spending 2 weeks in Maui we took a short hopper flight over to Hilo for some adventure on the Big Island. We had one week to explore this huge place and we had plans to see as much of it as we could. Rowan turned 16 the day we flew to the Big Island and we had fun celebrating this mile marker with him. What an incredible way to turn 16!

Turning 16 on the Big Island

Hilo and Beyond Adventure on the Big Island

We started our time in Hilo by visiting Akaka Falls and Rainbow Falls. Both are easily accessible with fairly short walks and a rain forest ambience. These are not the type of waterfalls we had experienced in Maui, to be sure. These were for observing only. The kids were disappointed because they wanted to experience them, but the rules and regulations felt really different on the Big Island. Maui was more tactical and tangible, but we found that the Big Island was more hands off and enjoyed by observation. So, we simply changed our expectations.

We discovered that we could snorkel at Carlsmith Beach Park (Four Mile) very near Hilo. Take your water shoes as they volcanic rock is very rough on your feet. The area was incredibly crowded and the current was strong for being so shallow and sheltered. The boys didn’t have much success in seeing much that was exciting, but Holland and I unexpectedly got to swim with sea turtles VERY up close. I really think if you’re patient and peaceful, the beauty comes to you. I would also recommend getting there earlier in the day than we did so the crowds don’t get too overwhelming.

We took several hours to visit the Hawaii Tropical Botanical Garden, which is located about 15 miles north of Hilo on the coast. The garden is run as a non-profit nature preserve that a family cleared and planned privately. With entry fees at $20 for adults and $5 for kids aged 6-16 we felt it was well worth the money. The trails are hilly, but there are golf carts available for those who are unable to make their own way. You will be provided with a map and you will want to follow it so you don’t miss anything. Bring your own insect repellent and have your camera at the ready. We ooohed and ahhhhed our way through the trails.

Big Island Botanical Gardens
Ginger flower at Botanical Gardens

Adventure in Volcanoes National Park Area

Volcanoes National Park was our next stop. We stayed at an Airbnb near the park entrance. It was the perfect spot and we loved being near the park. We enjoyed several hikes, saw the petroglyphs, and really enjoyed the chain of craters road. The views were sweeping and gorgeous. Do not feel bad about stopping 10 or more times along the road just to get out in the coastal breeze and to gape at the coastline. The water was so blue-just amazing!

Volcanoes National Park on the Big Island
Adventure on the Big Island
Deep blues of the Big Island

Adventure to Kona and North of the Big Island

The rest of our time on the Big Island we made our way along the coast on Route 11. We stopped along the way to see Punalu’u Beach with its black sand and sun bathing sea turtles. After that we stopped at Kealakekua Bay State Historical Park where you get a glimpse of the Captain Cook Monument across the bay. We opted not to take the long hike and had missed our opportunity for kayaking out there, so getting a glimpse was the best we could do.

Turtle on black sand beach

Our next Airbnb was up on the Northwest side of the island near Kamuela, north of Kona. We loved this place-away from the busyness of Kona and we had a view from on high with incredible sunsets from the backyard (including from the outdoor shower). Hapuna Beach (entry fee and gets crowded, so get there early!) is a great spot for swimming, snorkeling, reading on the beach and relaxing. We hadn’t had much down time over the past 3 weeks so we took advantage of it. Adventures and trying to see as much as we can are so important to us, but it felt good to slow down for one day.

Amazing sunset on the Big Island

One of the best things about driving all over the Big Island was listening to Gypsy Guide, an amazing ap that you can download to your phone that will follow your car with GPS. Gypsy Guide will give some suggestions about areas to stop and lookouts to enjoy, but they also have a running commentary giving the history of the locations you are seeing and driving through. We are big fans of Gypsy Guide and it’s nice to learn some things along the way. We made our way up to Hawi, a town on the Northern side of the island where we stopped for ice cream and a little shopping before making our way as far as we could go with our rental car. Our last night on the Big Island we went back to Hapuna Beach and decided to swim until the sun set over the ocean horizon. The sun making its way, melting into the horizon was a metaphor for our summer. We were so happy to be together for 3 weeks, but it was all coming to and end and the kids would start school in less than a week. It was magical and wonderful and the perfect way for us to end our incredible 3 week Hawaiian adventure!

Last Night of The Big Island Adventure

Family Sailing Adventure in BVI

sailing catamaran in BVI
Our catamaran for 9 nights!

Dream Trip

It’s no surprise that our family likes to adventure and try new things. Our oldest, Rowan, has really taken to building his sailing skills. He first learned basic skills through Boy Scouts summer camp and we have looked for a variety of ways to give him further opportunities. A big focus of our family adventures is celebrating our kids and facilitating their dreams and interests. On top of this, John has begged to do a family sailing trip because he has always viewed it as a “dream trip”. Have I mentioned on this blog yet that I get horribly seasick just looking at a boat in the water? I’ve consistently pushed this trip off out of fear of ruining the entire experience for everyone else and not enjoying any of it for myself. My weak point is that my husband and son REALLY wanted to make this dream trip happen. I got over my fears and sought help by getting a prescription patch to use for the duration of the trip.

Getting Started

Start your planning with where you will enter the BVI. There are two options to get to Roadtown, Tortola where you will set sail from. You can fly to St. Thomas and take the ferry over to Tortola or you can fly to St. Juan, Puerto Rico and take a hopper flight over to Tortola. As far as I can tell there is no way to get to the island directly unless you fly private jet. John’s cousin found the best flight to St. Thomas and then pre-arranged ferry tickets. Our family took advantage of a two night stay in San Juan because we wanted to see it. Our tickets were via American Airlines to San Juan and then we we booked separately on an island carrier to Tortola. We flew in on a Saturday, rented a car and spent the first night at Sebastian’s. There are not many places to stay on the island because so much of the island was destroyed by Irma and Maria hurricanes. Book ahead! Sunday morning we went to church because we LOVE visiting different churches wherever we adventure and spent the rest of the day grocery shopping and getting ready to board the boat. Sunday night we got on the boat and unpacked our suitcases and got familiar with the boat systems and double checked our provisions. We spent the night on the boat at dock. First thing Monday morning we had our non-optional inspection and orientation with the chartering company which took about 45 minutes. Within 10 minutes of the orientation we were anchor’s away. You could fly in on Sunday, but give yourself plenty of time to set yourself up so you can get an early orientation and set sail sooner.

Staying the night at Sebastian's on Tortola, British Virgin Islands
Holland ready for the island life on Tortola, British Virgin Islands
Sunset at Sebastian's on Tortola
Playing games and sunset swimming at Sebastian’s on Tortola

How We Sailed as a family

Our experience was a bareboat charter, which means we did NOT have a crew and did all of the sailing, mooring, cooking, etc. on our own. We were able to do this because of the experience of the people on our vessel. Both John and Rowan have good skills, but we also had John’s cousin with us who has made many sailing trips in the BVI and has skippered several times. If you are not comfortable with sailing on your own, know that you can hire a crew through the charter service to do it for you. We used Sunsail charters out of Roadtown, Tortola and found the process to be both organized and seamless. After checking in with the charter service we made a grocery run for staples and water that we loaded on to the catamaran and got ourselves settled in our berths.

family sailing adventure in BVI
Getting the sails untangled and set

Our vessel had 4 cabin berths that housed 2 people each that contained a bed, under floor storage and a bathroom with a shower, toilet, and sink. There was an extra single cabin reached by a hatch only where our 15 year old slept (bed and tiny storage only). We also had the option to convert the dining room to a bedroom for two more sleeping spots if we had needed it. Let me be clear-staying on a sailboat is much like camping on a boat. The kicker is that you get to go to sleep under the stars and wake up to some of the most beautiful water in the world.

Mooring for the night

There are a variety of ways to set up your itinerary through the islands. My best advice to you is to research which islands offer restaurants and have a good number of mooring spots. Some coves fill up earlier in the afternoon and you will be left finding another spot to sleep for the night that may not have a place to eat. We did several nights in popular spots and ate on the island and other more remote spots where we cooked aboard the catamaran. Don’t worry, your catamaran will come with a dinghy to get your party to the island docks! Always have cash on hand to pay for your mooring location. It kind of works like renting a campsite for the night, but you can’t reserve ahead of time. Flexibility and fluidness is key when you’re in the islands and will help you have a more relaxed and enjoyable vacation. After all, it is the island way of life.

family sailing adventure Anegada Island
Dinner on Jost Van Dyke at Hendo’s Hideaway

The truth is that you can do as little or as much sailing as you want. Our family wanted some good sailing and so we took advantage of the winds when them came our way. We had a loose itinerary and made sure we kept up our on board provisions so we could take off on a longer haul sail if we wanted to. Other days we chose the lazy life. I can promise you that you will want to do both to really get the full experience. Here is a map (not to scale) for your reference in how the islands are arranged.

A lazy day on and around Sandy Spit
sunrise family sailing adventure BVI
Good morning BVI

Some of the must see stops, in our opinion, and in no particular order:

  1. The Baths on Virgin Gorda – In this magical place you can take your dinghy partially to shore and then swim in the rest of the way. You MUST have a dry bag and water shoes to make this trip. Hike through the boulders and tide pools all the way up to the restaurant for amazing views and chill time, then make your way to Devil’s Bay for the clearest, more beautiful water you have ever seen.
  2. The Indians near Norman Island for incredible snorkeling. There is a reef in this spot where you can swim among incredibly bright and magical sea life. Keep in mind how far you swim away from your dinghy so you can manage your fatigue. The waters here are not super calm so you will get tired as you swim around.
  3. Anegada is a long sail, but totally worth the trip. There is a restaurant there and you can call ahead from your boat to place your order to make sure they have enough food to accomodate your party. The ambience here gives you a much more remote and isolated feeling. Just pristine waters and glorious sand.
  4. Spanish Town is a beautiful bay and a great spot to moore for the night, but it can get busy. The restaurant there has some of the best food and drinks!
  5. Jost Van Dyke is a very popular location and will have a fun atmosphere with a lot of people and bars and restaurants. A lot of people use this as a meet up spot. You will find the popular Soggy Dollar Bar and Hendo’s Hideout here.
  6. Sandy Cay & Sandy Spit are very chill-not much to do here but hang out on the sand and relax, but is a favorite among the regulars. I suspect most people stop here after they’ve had a few wild nights on Jost Van Dyke-ha!
  7. Beef Island/Buck Island area which is a part of Tortola offers a lot of shopping and more of a “town” feel. The Full Moon party will be at this site, which our family did not participate in but almost everyone else does. Things can get a bit wild and busy and that was not the type of trip we were looking for.
family sailing trip Devil's Bay at The Baths
Devil’s Bay at The Baths on Virgin Gorda
The Baths Virgin Gorda family sailing adventure
The Baths on Virgin Gorda-look at that water!
Snorkeling in BVI family sailing adventure
Snorkeling at The Indians we saw a lot of Brain Coral
I see you little fishy
Snorkeling at The Indians

You will need to be pretty strategic with your packing on a trip like this. Plan to only bring soft sided suitcases because you won’t be able to store large hard cases because there simply isn’t space. Here is a list of other items you will want to have with you on the sailboat.

  • Snorkle mask and tube-the boat will provide fins
  • Water sandals or shoes
  • Quick dry full size towels-try these
  • Dry bag/dry baggie for clothing & shoes, but also for phone and cameras
  • Reef safe sunscreen
  • Clothespins to hang towels, swimsuits, etc. to dry on boat
  • GoPro or other underwater camera
  • Polarized sunglasses
  • Sweatshirt for when the sun goes down
  • Biodegradable body wipes because you won’t be able to shower every day
  • Powerbank to charge all of your electronics
sunset swim at Sebastians on Tortola BVI
Sunset swim at Sebastian’s on Tortola

Family Adventure in Maui Hawaii-The Aloha State

Aloha vibes at Big Beach
Ahhh paradise on the island of Maui

If you are looking for the ultimate destination for family adventure you must visit Maui! Well it’s true the aloha spirit is alive and well in Maui. Hawaii is a beautiful land filled with beautiful people, and the perfect place for a family adventure vacation. One spring we received a call from John’s best friend inviting us to spend some time with him and his family in Maui. Our friends were temporarily living in Maui and had space for all 5 of us in their Ohana. We had a moment to make a quick decision…Wait, who am I kidding? There was no decision to make, we were headed to Maui at the end of July!!!

Maui setting with palm trees

After several weeks of our family being fragmented, we reunited on the island of Maui where we stayed in the smaller, less touristy town of Paia. We were able to walk to coffee shops and restaurants with unbelievable poke, acai bowls and ice cream as well as boutique shopping. There was a selection of local beaches like Trevaris and Sugar Cove where we could swim until dinnertime, and watch families teach their little ones how to surf. We often had the beach to ourselves, so don’t be afraid to seek out a smaller beach for a more chill vibe. The resorts don’t always have the best beaches.

Maui view from the Road to Hana
Sugar Cove Beach in Paia

Find the Family Adventure in Maui!

waterfall adventure as a family on the road to Hana

Paia is the jumping off point for the road to Hana. This is the perfect day for any family wanting to really adventure. First: download the gypsy guide app on your phone, which will give you tips for where to stop along with interesting facts as you drive. Second: pack your water bottles, snacks, swimsuits, quick drying towels, and your camera. Third: set your alarm so you can get on the road fairly early. You will have a full day of activity with a lot of driving in between. Two small tips as you make the trek: Auntie Sandy’s banana bread stand only takes cash but it totally worth the stop, and Red Sand Beach is awesome and CLOTHING OPTIONAL. We failed to remember this fact and really gave our kids something to remember-HA!

Black Sand Beach in Maui
Red Sand Beach in Maui

Do the vacation things, but adventure like a local family!

Hands down our favorite “excursion” was to drive up to the top of Haleakala for a sunset picnic. You do not need to hire an outfitter to do this unless you want to do high level star-gazing. We simply loaded up our chairs, warm clothes, picnic food and wine, paid the entrance fee (or use your National Parks Annual Parks pass), and got ourselves a nice spot above the clouds to take it all in. The evening we were up there, a local couple was getting married. Can you imagine getting married in such a beautiful setting?!?!

Haleakala sunset picnic in Maui

Maui Beaches & Activities

I know people think Maui is just for honeymoons or relaxing, but I’m here to tell you we made the most of our time on the island. We did SO MUCH adventuring. Depending on the time and energy you have, consider any of the following activities: a drive in the Upcountry, Lahaina with the grand banyan tree, a short hike to the blowhole, cliff jumping at Black Rock Beach, snorkeling at Molokini Crater & Turtletown. Fight the urge to park your bottom in a chair at the same beach every day. Eat at Maui pie and Coconuts; get a refreshing drink at Aloha Lemonade. And surely not to miss are the gorgeous beaches of Wailea-Big Beach and Polo Beach. Be advised that the ocean currents around the island are strong and not every beach is a swimming beach.

Sugar Cove Beach in Maui

One last note on the epic beaches in Maui. ALL beaches on the island are public. You do not need to be staying at a specific resort or hotel to enjoy their beach front. It may take some creative parking, but the resorts all have walking paths to get to the beach without having to trounce through their hotel. For example if you want to cliff jump off Black Rock, it’s located at the Sheraton. Park in the parking garage for day guests and use the paved paths to walk down to the beach. We also did this at Polo Beach and spent an entire day in our own little spot away from the crowds and right next to Oprah’s house! That’s right-even her beachfront is public. If you have small children, staying at a resort might make the most sense, but if your kids are teenagers like ours consider renting a place and adventuring out on your own.