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

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