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Family Sailing Adventure aboard a Catamaran

Planning a family Caribbean sailing trip

We’ll admit it, in our family, we have a few landlubbers. So when we go on and on about how amazing it is to be on a boat, some of our family’s eyes glaze over with that look of “here we go again”. This past winter we finally convinced our extended family and friends to join us in a weeklong family sailing adventure aboard a Catamaran in the British Virgin Islands. We were already familiar with sailing the beautiful BVI’s so it seemed like the perfect place to introduce our family to this lifestyle.

After what seemed like months, or maybe years, we got a crew of 7 together and started planning well in advance. The hardest part was convincing those that weren’t keen on spending all that time on a boat was that a vacation on a boat is the best of both worlds, as there would be plenty of opportunity for shore excursions. I managed to paint the picture that we’d be free to go where the wind took us, and every day we’d anchor in one of the beautiful anchorages and take the dinghy to shore. With the promise of solid ground, our crew seemed happy.

Monohull, Catamaran, Power or Sail?

BVI Sailing Choosing your boat

There are many types of boats to choose from for your family sailing adventure

The second discussion point was what type of boat we would charter. I must admit that up to this point, we’ve only been on monohulls. But since a few crew members weren’t used to the movement of a sailboat, and because there were 7 of us, we opted for a 44ft catamaran. There were of course other reasons for choosing this, such as the amenities and comfort of two hulls, each with 2 cabins and separate heads. One couple in our group convinced everyone else that 4 cabins with 4 heads was the best solution for our family sailing adventure.

At first, I had thought it was a bit too much (in previous charters, I was lucky if there was more than 1 head for the entire boat), but now that the trip is over, I must say having your own personal space and bathroom/shower was amazing. Since there were 3 couples plus a friend (anyone single?), it’s easier to share a small head with your significant other than with other members of your family!

Provisioning A Catamaran for Vacation

provisioning for family sailing adventureAnyone try to decide what and where to eat when the family is visiting? You know that everyone will have their preference and no one will agree until someone just makes an executive decision and picks a place. It won’t satisfy everyone, but usually they’ll just grumble about it but go with the flow.

Well, it’s no different when trying to decide on provisions and meals for 7 days for a large group of people. The way we approached it is we created a spreadsheet with a list of grocery items and let everyone look through it, add items they really wanted, as well as enter in quantities. We started with some basic meal ideas, then worked back to the ingredients we’d need. Luckily, the charter base had many resources and links to local grocery stores that had online ordering forms.

Some people might decide to go with the provision list that the charter company or grocery store recommends for your group size and length of sailing. But we had specific ideas on what we wanted to cook so we took the decision making into our own hands.

Overall, we were lucky and mostly agreed on what to buy and how much. Although at one point we had too much butter so we all had a good laugh when our father decided to stick the WHOLE bar of butter into some vegetables that were being sautéed. Check out these “butter vegetables” as we named this side-dish. Although delicious, they were a bit buttery!

If you have a group of people that gets along and is easy going, you may want to create your own shopping list. But if you’d rather not think about it, most charter companies have provision lists you can just pick from. They’ve done this many times and know the amount of food you’ll need.

Of course, you can always go ashore and enjoy the local fare. Many of the places we anchored at had food available on shore at one of the restaurants or resorts nearby.

Catamaran Sailing: The Ultimate Team Building

While sailing from island to island in the beautiful Caribbean waters is a dream come true, it’s not without some work. We did not opt for one of those charters with a captain and crew. (There is nothing wrong with that and we have friends who did it, but being such water nerds, we want to do everything ourselves!)

We each had a role to play and a job to do at certain parts of our trip. For the most part, it was a super relaxing vacation. However, there were times when we needed to work as a crew, in synch and listening to the instructions of the captain (for this adventure, I was the captain!). This was mostly during anchoring or tying up to a mooring ball for our stay. We also worked together as a team adjusting the sails when island hopping, preparing the dinghy for shore excursions, and cooking and cleaning up.

Catamaran Sailing Underway

Enjoying a beautiful day island hopping on our chartered catamaran

It worked out really well as everyone was relaxed, listened to any instructions, and wanted to help. Catching a mooring ball became one of the favorite crew activities. They would all gather on the bows of the catamaran, and try to direct me to the perfect position for them to grab the mooring and secure the boat to it. At times, I was laughing as everyone was waving this way and that as they each had an idea of where the best place would be for them to grab the mooring.

It was a nice experience and for those landlubbers among us, they really started to appreciate the freedom and awesomeness of being able to sail from one island to the next. During the cruises from one destination to the next, everyone enjoyed themselves by taking in the views, reading a book, or simply hanging out on the trampoline between the hulls in the front. I think that was the favorite spot for several of the crew. This was definitely a great family sailing adventure.

Sailing a Catamaran

Family sailing adventure in BVI

Learning the ropes on our first day of our family sailing adventure

For me, one of the most memorable parts of the trip is the sailing we did between the BVI’s. Our trek consisted of sailing from West End to Norman Island, then to Marina Cay, the Baths, Virgin Gorda, and on to our return port at Nanny Cay. We stayed 2 nights in Virgin Gorda near the Bitter End since our crew really loved that spot.

Each day, we sailed for just a few hours, which is something we promised our land locked family that we wouldn’t be doing long stretches (I’ll write about some of our other sailing trips which focused more on the sailing… stay tuned). We were very lucky with the weather the whole time. The winds were fair and sun was out. There was a previous time I was sailing that area and we had to outrun an incoming storm. No need to do that this family sailing trip as we couldn’t have asked for better weather. At times the wind was so light we trimmed our sails close so that we’d get at least some speed, but it felt like we were sitting still.

I was glad the crew wanted to learn and help. Even though we had an automatic winch, we had volunteers who wanted to manually hoist the sails. All the better!

As I mentioned, the crew really did help when mooring, and also when we pulled up to the dock at Marina Cay to refill our water supply.

Family Sailing Adventure: Fun Activities off and on the boat

A trip to the blue Caribbean waters wouldn’t be complete without fun activities on and off the boat. When planning a trip with your family, you need to make sure you prepare for some fun activities. These include things to do while on the boat, not just off the boat.

For our family sailing trip, we brought along several things from home:

  • A floating football to toss around
  • Several board games
  • Books and Kindle’s
  • Playing cards

We weren’t sailing with small kids, so that was enough to entertain the adults. We also rented some equipment from the local suppliers:

  • 2-person kayaks
  • Snorkeling gear
  • Pool noodles

With all of the above, we had enough variety to keep us entertained for the whole trip. Every night after dinner we would play some board games. Along with some dessert and drinks, we all had lots of laughs and a great time. The evenings flew by.

During the day after we’d arrive at our stopover, we would jump in the water, toss the football around, snorkel and even explore the area by kayak.

Water Fun:

Like I said, we had kayaks, snorkeling gear, a dinghy and pool noodles, so we had plenty of equipment for jumping in the water.

The kayaks were great because they were 2-person and it made it more fun to go in pairs. On one such excursion, we got hit with a crazy storm and had to paddle back to our boat with near zero visibility. Glad it was a quick storm that just passed through and by the time we got back to the boat, it was pretty much over.

I must say that I wasn’t sure about getting pool noodles for a sailing trip, but now I think they are a great idea. For the not-so-strong swimmers, and even those that are, pool noodles are great for just floating and relaxing in the water. You jump off the boat, and float around with ease. They were quite popular and we all enjoyed being able to just float near the boat during the day.

Of course, no trip to the BVI would be complete without doing some snorkeling. There are many places to snorkel and even if you go ashore, you can wade out into the water and jump in and explore underwater life. Either bring your own or rent the gear, it is very much worth it!

Shore Excursions:

Family Sailing Adventure Shore Excursion Hiking Views

Stunning views from our hike on Virgin Gorda. You can see Saba Rock below

We also did a lot of shore excursions and exploring. Each island we moored at, we would all get in the dinghy and head to shore in the afternoon to do some exploring. Whether it was just to hang out on the beach on Norman Island, outside of Pirates Bight, or go to the Baths, we would always get to land.

On this family sailing adventure, we had some great shore excursions. The most challenging of shore excursions was The Baths. For those that have been there, you know that you can’t take your dinghy right up to shore. There is a dinghy tie-up and you must swim the rest of the way in. This time, they added an additional buoyant line all the way to shore so at least you could pull yourself in along it. For our land loving family, this was quite an adventure. First, we took the dinghy from our boat to the dinghy tie-up area. Then everyone jumped in and we all went single file to shore. After exploring the Baths, which was quite a long walk, we hung out on one of the beaches before swimming back to our dinghy.

Another great shore excursion on our family sailing trip was hiking the trail behind the Bitter End Yacht club. Amazing views from up there and an amazing family hike. It was much longer than we all expected, and every corner we took, we thought to ourselves “this doesn’t look like the end of the trail”. But the views were spectacular and it was well worth it.

Benefits of a family sailing adventure

BVI Sailing Adventure Sunset

Enjoying one of the many sunsets while anchored for the night

As you can read, we had an amazing time with our family doing the things that we all enjoy. Balancing out everyone’s wishes really makes for a trip everyone will be satisfied with. For us seafarer’s, we had our good share of sailing and of course living on a boat for a week, so we were happy. For our land loving side of the family, we did daily shore excursions which included hiking, relaxing on beaches, and exploring each island, so that made them happy as well.

While we did things as a group, there are plenty of activities to do where everyone can do their own thing. At times, not everyone wanted to kayak, so only a pair went out. Other times, a pair took the dinghy and decided to go ashore to do more exploring after everyone just wanted to hang out on the boat. As long as no one is forced to do what they don’t want, everyone can enjoy a family sailing trip like this!

To this day, we still talk about the trip and reminisce about some of the events that occurred. The best part is that we are all planning to do another trip just like this. The hard part is getting everyone’s schedules to align! For now, we’ll just start planning and dreaming again.

Note: Our family sailing trip took place several months before hurricanes Irma and Maria. We were all saddened by the destruction we saw, but we’re already planning to re-visit as all of us fell in love with the BVI’s. BVI Strong!