The Escaper staff recently took a 5-day sailing excursion around the British Virgin Islands, and I have to tell you, it put every beach vacation I’ve ever taken to shame. One year ago, we learned that it was possible to rent a 36-foot catamaran and sail the beautiful Caribbean. Nevermind that we didn’t have a whole lot of experience with sailing – there were several boating companies that would provide us with the necessary training given that we had some experience. 5 days with the ocean as our playground and the freedom to explore any island we desired – yes, please. Friends and family thought it sounded both risky and too good to be true – but we assured them it wasn’t. Detailed below is our amazing experience and what we recommend if you’re feeling a little adventurous too.

The Planning

Planning for this trip was not for the faint of heart and credit for most of the scheduling goes to Phil, who is the master of vacation details. Once we had decided on a boating company, we worked closely with Tortola Marine Management (TMM) to be sure that we thought through the essentials. In addition to the obvious need for a passport, a plane ticket, and plenty of spending money, we also determined that a ferry ticket was necessary to travel from St. Thomas to the island of Tortola. Provisions (read: groceries) would also need to be ordered prior to arrival. Our little group had a lot of fun discussing our pack list for this voyage. This is the type of trip where packing light is to your advantage. We’ve detailed our pack lists for males and for females on the blog. You’ll probably spend most of your time in your swimsuit but take our advice and pack a poncho just in case you encounter some rain (Though the weather is in the 70s and 80s most of the year, it does rain from time to time).

The Journey There

We flew into the island of St. Thomas in the U.S. Virgin Islands. It’s a beautiful place and there are several amazing resorts to take advantage of. We decided to spend the night at The Frenchman’s Reef and Morning Star Marriott Beach Resort and we were not disappointed. With beautiful pools and cocktails waiting for us, it was a nice way to ease into our trip and break up the travel.

The Frenchman’s Reef and Morning Star Marriott Beach Resort



The next morning, after we were refreshed, we grabbed a cab to catch the early ferry to the Island of Tortola. Note that this is a cash only culture and plenty of spending money is needed to get around. The ferry ride took about an hour and when we hopped off the boat from the U.S. Virgin Islands into the British Virgin Islands, we then needed to go through the very casual customs process. Once that was over, it was into another cab and off to the management office for TMM to pick up our boat.

The Boat


While our group chose to sail without a captain (Phil and James underwent a 2 hour training in order to sail the boat on their own), other vacationers might choose to take a captain with them on their trip. The 36-foot catamaran fits four comfortably and comes with two bedrooms and two bathrooms. For those with smartphone addictions, don’t worry, wi-fi is available on the boat. The quarters are tight but you’ll spend most of your time on the deck of the boat, in the water, or exploring the islands. Curious about the living quarters? Here’s a video of what our boat looked like inside and out (and don’t forget to check out more videos on our YouTube channel):

The Experience

How many people can say they sailed a 36-foot boat in the Caribbean? The experience of learning to sail was enough to say this vacation was a trip of a lifetime. Not only was it fun to experience life on a boat, but also it was incredibly peaceful and beautiful. You could lie on the deck in the sunshine, watch the mountains go by, or jump off the back of the boat into the crystal clear blue ocean. You could participate in snorkeling, hiking, swimming, cliff diving, shopping, and more. There were bars and restaurants waiting at every island, some less inhabited than others. But don’t just take our word for it, here’s a photo recap to share with you from our own experience:





Wondering about the weather and the wind? The orientation of the BVIs, creates a relatively wind and wave free zone. This means that sailing is typically drama free.