Family Sailing Adventure in BVI

sailing catamaran in BVI — Our catamaran for 9 nights!

Dream Trip: Family Sailing Adventure

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 with a Sailing Adventure

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, US Virgin Islands and take the ferry over to Tortola or you can fly to St. Juan, Puerto Rico and take a hopper flight over to Tortola. Flights directly to Tortola are available, but expensive. 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.

Tips on Sailboat Chartering

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 hurricanes. Book ahead! Sunday morning we went to church because we LOVE visiting different churches wherever we adventure. The rest of the day we grocery shopped and got ready to board the boat.

Sunday night we 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 you need plenty of time to set yourself up so you can get an early orientation and set sail sooner.

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 experience in the BVI and has skippered several times. If you are not comfortable with sailing on your own 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 and got ourselves settled in our berths.

family sailing adventure in BVI — Getting the sails untangled and set

What to Expect on the Sailboat

Our vessel had 4 cabin berths that housed 2 people each. The berth 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 where our 15 year old slept (bed and tiny storage only). Some catamarans have the option to convert the dining room to a bedroom for two more sleeping spots if needed. 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.

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 early in the afternoon. You don’t want to 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.

Sometimes we chose 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 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.

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

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. You will have amazing views and chill time. Then make your way to Devil’s Bay for the clearest, more beautiful water you have ever seen.
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.
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.
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!
Jost Van Dyke is a very popular location and will have a fun atmosphere with 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.
Sandy Cay & Sandy Spit are very chill-not much to do here but hang out on the sand and relax. It’s a favorite among the regulars. I suspect most people stop here after they’ve had a few wild nights on Jost Van Dyke-ha!
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. Things can get a bit wild and busy and that was not the type of trip we were looking for.

epic family sailing trip Devil's Bay at The Baths

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

You will need to be pretty strategic with your packing on a trip like this. Plan to bring soft sided suitcases becausethey are easier to store due to a lack of space. Here is a list of other items you will want to have with you on the sailboat.