Our experience chartering sailboats in the Caribbean over the years brings us a lot of joy and fond memories. Let’s explore a bit about each experience and place. We will conclude with a few recommendations for chartering your own sailboat in the Caribbean.

The Grenadines

We are not sailors, although my husband has tried on several occasions, so we always opt for a crewed boat. Our first sailing experience was many years ago on our honeymoon. We booked a stateroom on a very large (>100 feet), monohull yacht leaving from the harbor in Saint Vincent, Grenada. We sailed the lower Grenadine islands of Bequia, Mystique, Mayreau, and Palm Island, to name a few. It was a wonderful experience, although I was quite seasick on the first night. We already had the Caribbean islands in our blood, but this experience cemented our love for the beauty and diversity of the islands. The company we booked through is no longer in service.

St. Martin/Saint Maarten

Our next sailing adventure was years later aboard a catamaran. We were invited to join two other couples on a birthday celebration for a seven-night adventure that left out of St. Martin. The catamaran was spacious, with queen beds, dry baths, air-conditioned cabins, and a lovely captain and first mate who took care of every need. We had somewhat of an itinerary, but each morning the captain held a meeting to give us options for the day. It was relaxing, peaceful, and just a marvelous experience overall.

The company we booked through was Moorings. They offer chartered services from multiple locations throughout the world. Options include bareboat, skippered, crude, and cabin charters. This is a highly reputable company and one we certainly recommend.

British Virgin Islands

Our next sailing adventure was out of Saint Thomas on a 50-foot monohull. We were the only guests aboard besides the captain and his first mate. On this vacation we were celebrating a new stage in our lives, so we booked the boat. For 10 nights.

Our cabin was air-conditioned, and we kept cool enough. The wet bath was adequate, but not ideal. The captain was a part-time physician from Wisconsin and the first mate was his significant other. Captain Dave knew the USVI and the BVI like the back of his hand. He was an excellent sailor and cook! Since we were the only guests, we had plenty of options each day, and we sailed and explored nearly every island in the area. Water toys on the boat included a kayak and snorkel gear.

Believe it or not, we found Captain Dave through the VRBO website. Until then, I didn’t know VRBO offered these unique vacation options. The charter fee was all-inclusive, which included the captain, the first mate, and all food and drinks on the boat. When we went ashore for lunch or dinner, we paid.

One of my favorite parts of this trip was the sailing we did at night. Beautiful and magical all at the same time! Unfortunately, Captain Dave is sailing in other parts of the world and is no longer chartering his boat.

U.S. Virgin Islands

Our most recent experience in April 2023 was only for two nights, but still thrilling. We used VRBO again to locate Captain Alex. His monohull was about 40 feet with three cabins, one of which he used to sleep in. Another couple whom we had invited along, joined us on their first overnight sailing experience, and they loved it! This charter only included the captain, no first mate.

We stayed several days in advance at the Ritz Carlton Club on St. Thomas, then took the ferry from St. Thomas to Cruz Bay, St. John. It’s about a 20-minute ferry ride. Captain Alex picked us up in his dinghy and ferried us and all our luggage out to his sailboat. He provided breakfast and lunch as part of his chartering fee. On our first night on the boat, we purchased deli meat, bread, and cheese to eat for dinner while watching the sunset over the Caribbean. The second evening, we all went ashore for dinner and Captain Alex joined us.

This cruise was considered half board and the daily rate was $980 a night for the entire boat, with the skipper. We split the cost with the other couple, thus making the experience about $500 per night, per couple. There were no additional costs, except the gratuity we gave the captain, which was $100 per couple. This was an amount of our own choosing.

Our Recommendations

If you are new to sailing, we recommend an all-inclusive crewed charter, as it allows you to fully enjoy the experience without having to worry about navigation, safety, cooking, or cleanup! For two to four guests, either a monohull or catamaran will work fine. We do feel that catamarans have a little more room and are easier to walk around, but they are also likely to be a little more expensive. If there are more than four guests, a catamaran or a motor yacht is the best choice. The catamaran will be less expensive.

Overall, our experience chartering sailboats in the Caribbean has been fabulous. It is a wonderful way to fully immerse yourself in the natural beauty and unique culture of this part of the world. With so many options available, you’re sure to find the perfect sailboat, destination, and itinerary to suit your interests and preferences. It’s a good idea to research each type of boat and the various options available before making a final decision. You want to ensure that you choose the right boat for your needs and preferences.

Please read our other post for information on the different types of sailboats, the best locations, and what it costs to charter a boat in the Caribbean. If you want general information on visiting the U.S. Virgin Islands, take a look here.

If you have additional questions or need some advice, please send us an email. We are here to help.