The Best Sailboat Rentals Near Pine Island Center

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

We can’t thank Captains Dave & Joe enough. From the communication with Bailey, to the overall experience.. everything went smooth and easy. I booked for my friend’s Bachelorette Party and they made our time worth while. I definitely recommend for any occasion. Both Captains Dave and Joes made sure we were equipped with everything and comfortable during our sailing. My favorite part was swimming and lounging on the floatable pools.. oh, and seeing dolphins! Overall 10/10 experience!

Sail Miami! Beautiful Beneteau 43 Cruising Monohull

I recently rented a 43 ft sailboat for a romantic sunset proposal, and the entire experience was nothing short of magical. From the moment we arrived, Captains Christopher and Alain went above and beyond to make the evening truly unforgettable. They were extremely polite, professional, and genuinely invested in helping create a special moment for us. The sailboat itself was spotless—clean, well-maintained, and perfectly set up for a romantic evening on the water. As we sailed into the golden hour, Christopher and Alain played a beautiful mix of romantic songs and tasteful Bossa Nova music that set the perfect mood. The location of the marina was also incredibly convenient, which made getting there and back stress-free. Everything came together seamlessly, and I couldn’t have asked for a better setting for such an important occasion. Highly recommend this experience to anyone looking to create a memorable and intimate evening at sea!

''Escape Exclusivo, Aventura ilimitada en nuestro Yate''

Truly had the best time with the crew and on the boat. Booking went so smoothly and the crew gave us the best time celebrating our bride. Will book with them again in the future!

''Escape Exclusivo, Aventura ilimitada en nuestro Yate''

This was the best experience ever. The boat is even better in person. The crew is so amazing and really made sure we were taken care of. I would highly recommend booking this and will definitely use them next time I’m in town. They communicate very quickly and the experience was seamless. It was such a special moment for the bachelorette party we were on. I can’t say enough good things honestly. It was fantastic!!

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

Listing was awesome! Captain Dan and his crew were amazing and worked with my bachelorette party so well! Could not recommend them more.

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

Bailey's luxury catamaran was gorgeous and the sunset cruise we took for my husband's 40th birthday with family was a very special experience. Captain Dave and Emma were so nice and accommodating for our group of 12. They provided us with ice and beverages as well as utensils and napkins for the catered platters we brought. We were also able to connect to the sound system to play our music for the entire trip. We had perfect weather and got to see dolphins frolicking prior to heading out into the Gulf for a gorgeous sail and stunning sunset!