Sailing with The Moorings in the British Virgin Islands

My family had been kicking around a sailing trip for years. With my oldest son going off to the Army, we decided that if it was going to happen; it had to be this summer. Planning for the trip took almost a year in advance. Read the supply list here. We decided a trip with The Moorings was the best way to sail around the British Virgin Islands.

We flew from NYC to St. Thomas and then boarded a ferry to Tortola. Packing light for a sailing trip is important not just for space on board the boat, but also important for the ferry ride. The ferry charges a fee for suitcases, but not for backpacks or over-the-shoulder bags. Each person carried their own clothes in a backpack/bag and we also had 2 suitcases full of things for the boat (snorkels, floaties, etc.). We stayed the night in Tortola, where we visited the beach, went hiking, and stopped by a rum distillery.

The next day, we dragged our tired selves to the dock where our Moorings trip began. When we arrived, we checked in and were greeted by Captain Andrew. Captain Andrew, who has been a Mooring’s captain for 30 years, had organizing and checking in to a science. He suggested I double-check on equipment rentals, find out where our food order was, and the lowdown on the boat.

I’ve been asked a few times about preparing food on the boat. You can order food through Moorings or a local grocery store. This must be done weeks in advance. There is a chance, though, that whoever you order through won’t have the exact product you want, so they’ll toss in the closest thing to it. Same thing with drinks. You can order alcoholic and nonalcoholic beverages. Riteway and Bobby’s Marketplace are two options if you are ordering through a local grocery store in the BVI. The food gets delivered to your boat. Before you leave, make sure all of your order is there. Not all of our orders came at once. It came in 2 trips.

Most of our meals were at local restaurants. I preferred restaurants with a family vibe instead of a beach vibe. When you’re at a restaurant in the British Virgin Islands, remember you’re on island time. I’m used to restaurants in the United States that serve you up quickly, hoping to turn your table over for more business. In the BVI, that’s not the case. They’ll take your order when the timing is right and you won’t get the check till you ask for it. Everything about the BVI is laid back.

Jumping off a Floating Restaurant in the BVI

We made some meals onboard. There’s a grill on the back of the boat and a small oven in the saloon. Having a family as the boat rocked on the waves was a nice way to spend an evening. Cleaning up wasn’t much fun, but when is cleaning up fun?

Since we have a large family (6 of us), we needed a large catamaran. Thankfully, the Moorings 5000 was available. The Moorings 5000 is a 4-cabin catamaran with air conditioning. There was a large saloon/kitchen area with a large table. There was also a large table on the back of the boat. The front had 2 shaded seated areas and a trampoline where the kids loved to sit on bean bags. There was an upper deck that was a great place to enjoy at night that also had a large table. We never felt cramped on board and my favorite moments were relaxing on the catamaran.

After we unpacked our groceries and belongings, we went over an itinerary with Captain Andrew. When going on a sailing trip, it’s important to be flexible. Sailing trips offer more flexibility than most vacations. Often time, it can be stressful on a vacation to fit everything in. With sailing, you don’t need to worry about schedules. You just go. We told our captain we love snorkeling and since he knew the area like the back of his hand; he pointed out the best places for us to dive. With that as our primary goal, we pushed off from the dock and the wind was immediately in our hair. Well, I don’t have hair, but you get the idea.

The relaxed nature of a sailing trip is the biggest selling point for me and why I want to go back and do another one right now. Your day begins by waking up to the sound of waves and birds. After eating breakfast, you can either chill wherever you are or set sail to the next destination. You don’t have to pick an arrival time or a time you have to leave. You just go whenever you want. And, if you decide to switch it up on the fly, no big deal. It’s a perfect vacation for anyone that needs to unwind.

Our only goal for each day was to find a good snorkeling spot, and each day that goal was achieved. I took photos with my Olympus Tough and you can see them here. We also loved jumping off the boat while it was anchored or moored. We had floating mats in the water and the kids loved to relax on them.

We also vacationed with another family, and they had their own sailboat. Most nights, we moored close to one another. We either swam from boat to boat or took a dinghy. We enjoyed many diving/jumping competitions. If you are taking a smaller sailboat, think about taking a small fan with you. The smaller boats don’t have AC and it gets hot inside the cabins.

Every minute on board was a treasure. We were blessed with beautiful weather throughout our trip. Spending time onboard with the family was precious, as was spending time on board with my nose in a book. We also played games. There was a tv on board, but we never used it.

Before our trip, I wondered if it would be weird to be traveling with a total stranger. It wasn’t. Captain Andrew became the 7th member of our family during our vacation. When sailing with a captain, it is the responsibility of the clients to feed the captain. When we cooked, we offered our captain a plate. He took care of himself mostly, but we always offered. When eating out, it’s up to the people on vacation if they want to pay for the captain or not. It’s not required, but it’s a gracious gesture. We took our captain out to eat with us once. We always offered, though.

Going on a sailing trip is a bucket list vacation. I’m thankful my family got to experience one before we shipped off in all different directions. If you’re thinking about chartering a boat, check out The Moorings. They have boats throughout the world. Greece currently has my attention.

Disclaimer: I partnered with The Moorings for this story. The experience, words, and memories are my own. 


Some video of 3 of the bedrooms and the galley. #Moorings #sailing #boats #boat #catamaran #travel #traveltiktok #travelblogger #fyp #familytravel #travellife #bvi

♬ Swear By It – Chris Alan Lee


This vacation will be hard to top. #sail #sailing #moorings #travel #traveltiktok #traveling #vacation #catamaran #bvi #virginislands #boat #fyp

♬ original sound – TheJasonGreene


♬ original sound – TheJasonGreene


Life with The Moorings. #Moorings #travel #boat #traveltiktok #ocean #catamaran #life #sailing #travellife #travelblogger #dads #travelvideo #vacation #fyp #foryoupage

♬ original sound – TheJasonGreene


  1. Sounds like a great adventure with alot of flexibility, including exciting times and relaxing free times. Thanks for sharing this with us. What a great idea for families and all those wanting to have a unique experience, without buying a boat 🙂

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