The Best Sailboat Rentals Near Fairport Harbor

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)

38' Hunter 376 Cruising Monohull in Annapolis, Maryland

Captain Alberto and Grace were amazing, and helped with a very romantic sunset sail. The were ver gracious, accommodating, and knowledgeable. If we get the chance we will definitely come back and hire them again!

Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

If you’re looking for a unique and fun way to celebrate a special occasion, or just want to take advantage of the beautiful weather and get out on the water, this is it! I booked a Sunday afternoon trip with friends to celebrate my 36th birthday and it absolutely exceeded my expectations. Captain James was communicative and professional leading up to the trip; he’s a skilled captain and a joy to be around. His catamaran is clean and safe, and equipped with everything you could need, including a sound system and bumpin’ playlist! I will absolutely be booking with him again.

Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

James is a wonderful captain! Our crew had the most amazing time!! The views were so picturesque! It was a chilly, fall morning but absolutely perfect!

Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

Our experience with James was nothing short of incredible! We booked a short rental for our engagement pictures session, and James’ boat was beautiful, immaculate, and incredibly picturesque. James was quick and incredibly safe as well as a very skilled captain who accommodated multiple pick ups/drop offs for our shoot and did everything in his power to get the pictures we wanted. We would recommend him for photography or a nice sailing day - we will definitely be back!

35ft C&C 35 Sailboat in Toronto

We (dad+mom+7yo son) had an amazing 2-hour trip with Peter in Sep 2024! Enjoyed very much every minute of it. Learned a lot about sailing and had a chance to try it out under the captain's guidance. And we really really enjoyed the conversation with Peter. I definitely recommend Peter and his boat "Restless" !