The Best Sailboat Rentals Near Portsmouth

Sunset Sail Buzzards Bay in a Classic Sloop!

I recently had the pleasure of sailing with Captain Freddie on his boat for a surprise two-hour cruise with my girlfriend, and it was an unforgettable experience. From the moment we stepped aboard, we were treated to breathtaking views of Buzzard's Bay and a sense of tranquility that only the open water can offer. The scenic beauty of the surroundings was truly stunning, and we found ourselves captivated by the serene atmosphere that only a sailboat can provide. Freddie was an absolute delight and contributed significantly to the enjoyment of our trip. His friendly and attentive personality put us at ease, and his passion for sailing was evident throughout the journey. He told us all about his restoration of his boat and made sure we were comfortable and well taken care of. We knew nothing about sailing, and he explained all about how the sails work, answered my endless questions, and his expertise and seamanship were evident. We felt completely safe under his guidance. The overall experience was nothing short of magical. From the sunshine and fresh air to laughing and relaxing on the deck while Freddie told us all about the area and his tales of trips to Martha's Vineyard and beyond. I scored some serious romance points with my lady by booking this trip. I would 100% sail with Captain Freddie again without hesitation.

43' Sailboat, Bristol RI & Beyond

We had a wonderful time with Catian Francis :) He is a lot of fun and makes you feel at home on his yacht. Things wemt very smooth and we can highly recommend having a exceptional sailing experience with him. Heiner

Sailing Adventure Aboard 44' Hunter Sailboat

I cannot rave more about how AMAZING our experience was with Geoff! 1000 stars! It was absolutely beautiful and he made sure we had the best view of the sunset. We booked with him for an engagement photoshoot and he was super professional, fun, and incredibly helpful throughout helping us get the perfect shots. I’d recommend booking with Geoff for any occasion. I will definitely book again! Thanks Geoff!

Sailing Adventure Aboard 44' Hunter Sailboat

Geoff was awesome! His sailboat was very clean and he was very accommodating. My wife and I went out to watch the sunset in Portsmouth and the itinerary was perfect. Geoff was really pleasant and we’ll definitely book with him again.

43' Sailboat, Bristol RI & Beyond

Our trip with Captain Francis was beyond our expectations. Two of my young adult kids were interested in learning to sail and Captain Francis spent the day with them teaching them all the basics with hands on training. Myself and my oldest daughter spent the day on the bow relaxing and enjoying the views and the sun. The boat was well equipped with all that we needed and Captain Francis was accommodating with any request. We will definitely be back and Table4Two will always be our first choice for sailing the Bristol/Newport waterways. Thanks for a Wonderful day on the water.

Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

Our sail with David was great! Even though we had light winds, we still covered a lot of ground. David is very capable and knowledgeable, and he also knows a lot about the area and the maritime region. The boat is in very good condition and very roomy. We ended up with 4 guests and were very comfortable. We expect to sail again with David in the future.