Awesome sailboat rentals in the Caribbean.

Sailing Reviews in Caribbean

1. GS

   Genevieve

   Private San Juan Bay Cruise 37' Sailboat

   I booked with Captain Luis for my sister’s 30th birthday trip, and we all had the best experience! There were 4 of us in San Juan for a long weekend and this was the highlight of our trip. We felt safe, welcome, and taken care of the whole ride - the captain brought refreshments including Sangria that his wife had made which we all loved. He sailed us around and anchored at a beautiful spot to jump in and swim which was so fun. I highly recommend!

2. gm

   gabriella

   Lagoon 450 Sailing Catamaran Charter in Saint Martin Community

   This was a great experience. Captain Sup and Tom were amazing. Provided a little breakfast, mixed us drinks the entire ride, provided waters and sodas, stopped us at 3 different places and allowed us to get out and float, paddle board, swim, and snorkel. They made the experience amazing! Bluetooth and wifi on the boat and they picked us up and dropped us off right on time. We were 13 girls on a bachelorette and there was plenty of room for us all to lay out, sit, tan, and have fun. 10/10 recommend

3. LB

   Leanna

   Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

   I truly cannot say enough great things about Anthony and Mile. From the moment we stepped on board, everything exceeded our expectations. The boat was absolutely stunning—beautifully maintained and equipped with all the fun extras that made the day unforgettable. The food was not only delicious but thoughtfully prepared and presented. Most importantly, the entire experience was filled with fun, laughter, and amazing memories. Every detail was perfect, and it was worth every single penny. Thank you both for an incredible day on the water—we’ll definitely be back!

4. AK

   Aja

   Lagoon 450 Sailing Catamaran Charter in Saint Martin Community

   We had an amazing sail to Anguilla! The views were breathtaking, the catamaran was clean and comfortable, and the crew was so friendly and attentive. Communication was smooth and everything was as listed. Don't hesitate to book with Captain Sup! Everyone said it was their favorite day of the trip!!

5. MC

   Mev

   Luxury Catamaran Lagoon 52' Capacity up to 40

   Thank you! Captain, crew and chef were all phenomenal! Attentive, helpful and polite - all around great experience! Highly recommend this boat and crew. We had a group of 10 adults and 10 teens. Everyone raved about our day with the Sea Warriors. Just book them for a fun, luxury experience that is customizable for your group. 5 stars all the way.

6. VM

   Vera

   46 feet luxury yacht in Montego Bay with round trip transportation!

   My friends and I had an amazing experience and would definitely recommend. Everyone was extremely accommodating and kind. The yacht was absolutely beautiful and exceeded our expectations. We had the time of our lives.