The Best Sailboat Rentals Near Road Town

Private Luxury Sailing Experience out of Old San Juan

The boat is exactly as pictured and is very clean. Captain Willie and crewmate David were great. They ensured we had a great time. I would definitely charter this boat again. If you’re thinking about it, just do it!

46' Oyster Sailboat in St. Thomas, Virgin Islands

Shana and Nick were the best captains! Served lunch and delicious cocktails! Snorkeling and a relaxing sail. Perfect day!

Half Day Private Charter in US Virgins Islands onboard 43' Wooden Sailing Yacht "Cimarron" with Captain Rick

Fabulous day with a knowledgeable captain on a very comfortable boat. Captain Rick customized the trip to our group’s every need and preference. He and his assistant Rachel provided an uniquely memorable Caribbean experience we can highly recommend.

Sailing Cruise Saint John

Book now! This was such a memorable experience! From the line of communication, to Shana amazing Mediterranean platter to captain in training Jaya keeping my son company, it was amazing! From pick up to drop off such a wonderful experience. We cannot wait to see them again this time hopefully in Maine!

Best Day Ever! Private, All Inclusive & Custom Sailing, Snorkeling, Adventure!

We chartered Saltwater Taffy whilst on a recent cruise to St Thomas. The 4 of us had the best time ever. Great communication from Rosie on the days before the sailing. We were met at the ship by Brad and driven to the boat where we met Rosie and Bosun the cat. We set sail straight away into turquoise waters and we were quickly under sail. We chose to snorkel with turtles so we went to Scott beach, got kitted up with snorkels and Brad took us to the beach in the motor rib. It’s really easy to get in and out of the water from the swim platform. We swam for about 10 minutes until we found the turtles. They are just so graceful. Brad got some great underwater pics. We then went back to the boat where Rosie had been preparing an amazing lunch and cocktails. We then motored back to the dock. Best day ever and we will be back to do it all over again. Thanks so much. Suzanne, Chris, Pam and Ricky xxxx

Best Day Ever! Private, All Inclusive & Custom Sailing, Snorkeling, Adventure!

What a wonderful day at sea! Four of us joined Rosie , Brad and mascot Bozun for a day of sailing and snorkeling. The customer service was top notch. The food was some of the best we had on St. Thomas and Rosie's presentation was so appetizing. While snorkeling we saw an octopus, a barracuda, an eagle ray and countless beauftiful coral, fish and sea urchins. Our hosts chronicled our day and we received pictures and videos of our experiences. We would definitely recommend Rosie and Brad.