I was nervous to book my first bareboat charter. On top of that I wanted a company that partnered with ASA certified instructors so that I could learn how to sail but also use my 7-day charter as a vacation. Waypoints checked all the boxes and then some. The communication through Alex (my Waypoints planner) before my trip helped me to set my nerves at ease. I even got a phone call a few days prior to my trip to let me know that the day my plane landed there was a festival that had many of the roads shut down leaving the transfer from the airport to the marina a little tricky. Waypoints didn’t have to do that but it’s the customer service you’ll get when booking through them. I also experienced “an issue” when the boat I booked was taken out of the fleet by the owner. Instead of putting me on a similar boat, they upgraded me to a larger boat which had better amenities at no cost to me!! Again, customer service at its finest. If you ever find yourself booking a trip in the USVI and are in need of a captain, I would highly recommend Captain Tony! He balanced teaching me sailing with making sure I had enough time to spend with my wife and four kids. He was knowledgeable of the USVI and even went out of his way to help us provision the day before. Thanks Waypoints, we will be back sooner rather than later!
JS Km
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May 19, 2026
We had an excellent experience with Waypoints St Thomas on our most recent trip, an April 2026 week of bareboating on Fiyolo. This was our second time with Waypoints (May 2025 on Island Curtisea) and both times were great. Our 2026 trip was eight friends (four couples), most of them first time bareboating, and everyone had a great time. Fiyolo having the power dinghy lift, power winch, AC, and watermaker spoiled us nicely! The Waypoints base staff are very helpful and friendly. The check in and check out were smooth and easy. We did our bulk provisioning via delivery to the base from Cost U Less, and filled in the gaps at Moe’s market. During our booking search, Waypoints did a good job explaining the BVI latest restrictions, and we chose based on this to book to stay in the USVI. We were very happy with our choice to stay in USVI. We will definitely look first to Waypoints for future charters both in USVI and other bases. My only negative experience was that I paid a credit card processing fee due to misunderstanding the booking payment page, look carefully and you should find an option to pay by debit card which avoids the fee.
JJ Wittkamper
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December 18, 2025
Thank you to the USVI crew! We just finished our 4th year in a row chartering with them. Communications were good, boat worked as advertised, and getting off and back on the dock was smooth. We really appreciate your personalized service. Makes us feel like we are coming home when we arrive on the dock, and sad to leave, when it’s time to go home.
Ken R
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May 17, 2026
Friendly knowledgeable staff, convenient location to charter from. Good selection of boats to charter - catamaran and mono hulls. Docks ate safe; bathrooms are clean and well stocked with clean towels. This is our second year chartering with this STT team, and third year with Waypoints company.
Grant Daley
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May 26, 2026
Our experience with Waypoints was outstanding! Not only was communication clear and consistent prior to, the team was professional with the customer always number one!
Our boat was amazing, with every convenience provided, clean and suited for activities. Special consideration goes to our captain, Tony Castagno, who was patient, kind, attentive, informative and loads of fun. I am certain our trip would not have been a 5 star plus experience without the most amazing captain ever.
We will certainly travel with Waypoints again. Not a single concern comes to mind, a once in a lifetime experience.
Thank you Waypoints, Alex, Larry, Chelsea and to you, our new friend, Captain Tony!
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3562 Honduras, St Thomas, VI 00802
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I was nervous to book my first bareboat charter. On top of that I wanted a company that partnered with ASA certified instructors so that I could learn how to sail but also use my 7-day charter as a vacation. Waypoints checked all the boxes and then some. The communication through Alex (my Waypoints planner) before my trip helped me to set my nerves at ease. I even got a phone call a few days prior to my trip to let me know that the day my plane landed there was a festival that had many of the roads shut down leaving the transfer from the airport to the marina a little tricky. Waypoints didn’t have to do that but it’s the customer service you’ll get when booking through them. I also experienced “an issue” when the boat I booked was taken out of the fleet by the owner. Instead of putting me on a similar boat, they upgraded me to a larger boat which had better amenities at no cost to me!! Again, customer service at its finest. If you ever find yourself booking a trip in the USVI and are in need of a captain, I would highly recommend Captain Tony! He balanced teaching me sailing with making sure I had enough time to spend with my wife and four kids. He was knowledgeable of the USVI and even went out of his way to help us provision the day before. Thanks Waypoints, we will be back sooner rather than later!
We had an excellent experience with Waypoints St Thomas on our most recent trip, an April 2026 week of bareboating on Fiyolo. This was our second time with Waypoints (May 2025 on Island Curtisea) and both times were great. Our 2026 trip was eight friends (four couples), most of them first time bareboating, and everyone had a great time. Fiyolo having the power dinghy lift, power winch, AC, and watermaker spoiled us nicely! The Waypoints base staff are very helpful and friendly. The check in and check out were smooth and easy. We did our bulk provisioning via delivery to the base from Cost U Less, and filled in the gaps at Moe’s market. During our booking search, Waypoints did a good job explaining the BVI latest restrictions, and we chose based on this to book to stay in the USVI. We were very happy with our choice to stay in USVI. We will definitely look first to Waypoints for future charters both in USVI and other bases. My only negative experience was that I paid a credit card processing fee due to misunderstanding the booking payment page, look carefully and you should find an option to pay by debit card which avoids the fee.
Thank you to the USVI crew! We just finished our 4th year in a row chartering with them. Communications were good, boat worked as advertised, and getting off and back on the dock was smooth. We really appreciate your personalized service. Makes us feel like we are coming home when we arrive on the dock, and sad to leave, when it’s time to go home.
Friendly knowledgeable staff, convenient location to charter from. Good selection of boats to charter - catamaran and mono hulls. Docks ate safe; bathrooms are clean and well stocked with clean towels. This is our second year chartering with this STT team, and third year with Waypoints company.
Our experience with Waypoints was outstanding! Not only was communication clear and consistent prior to, the team was professional with the customer always number one! Our boat was amazing, with every convenience provided, clean and suited for activities. Special consideration goes to our captain, Tony Castagno, who was patient, kind, attentive, informative and loads of fun. I am certain our trip would not have been a 5 star plus experience without the most amazing captain ever. We will certainly travel with Waypoints again. Not a single concern comes to mind, a once in a lifetime experience. Thank you Waypoints, Alex, Larry, Chelsea and to you, our new friend, Captain Tony!