The Best Boat Rentals Near Wellfleet

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.

Come Sail & Party on Maybellene our well cared for 34' Beneteau Yacht

A beautiful evening that far exceeded our expectations. Dave was a fantastic captain and host giving us a relaxing and memorable experience on our sunset cruise. Bottle of wine, lovely snacks and the boat was pristine. Don’t think twice about adding this to your itinerary for a spectacular evening.

Sunset Charter for 6 persons - Private 42 trawler- Hyannis Ma. Starts at 6pm

A real pro! Captain John's experience is expansive and impressive. His attention to detail, love for the water and passion are evident. He went above and beyond to ensure all of our requests were met. What an awesome experience. We made a new friend and amazing memories! Book with John, you will be glad you did.

27' Blackfin Center Console in Osterville & Barnstable, Cape Cod

Mike is the consummate professional and an absolute stud. He builds rock walls with his bare hands and his equipment is top notch. Picks you up, drops you off, on time and had the best recommendations on what to do based on our preferences. This experience was absolutely amazing and was one of the best days of our lives. We will absolutely be using Mike again on our next and future high seas adventures.

8 Person Center Console Rental in Osterville Massachusetts

Bill was the best captain. He was attentive and wanted to make sure everyone was happy and doing what they wanted. We had a mixed age group but they all enjoyed it. Seeing MV from the water and relaxing on the beach in Chappy was a highlight! We definitely recommend Bill!

8 Person Center Console Rental in Osterville Massachusetts

We had such a fun time with Captain Bill! This was the perfect outing for our group of 7. Captain Bill had great music and a very clean boat. Awesome time overall. We would recommend Captain Bill to anyone looking to have a fantastic day on the water.