The Best Sailboat Rentals Near Gloucester Point

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

Sailing with Captain James was a dream!! You will not regret this experience! Not only is he hospitable, he is full of life and passion which only made our trip better. We enjoyed every part of our trip the only sad part was that we didn’t book longer. 100/10 would book with Captain James again!!

38' Hunter 376 Cruising Monohull in Annapolis, Maryland

Our family of four, who are experienced sailors, appreciated the opportunity to sail with Alberto and his lovely wife, who shared lots of great stories and reflections of sailing on the Bay. The boat was perfect for a day of sailing, and exactly how described on the website. It was clean and comfortable and we felt completely welcomed, and were able to participate in sailing activities as we desired, while also relaxing and enjoying some downtime. Great time sailing!

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.)

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

I highly recommend a sail with Captain Bill. The entire experience was exciting and relaxing at the same time. Whether an experienced sailor or a novice with boats, just being on the open water will refresh and invigorate. 5 ⭐️⭐️⭐️⭐️⭐️

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

Lovely experience, James was really patient and understanding. Boat was clean and had everything we needed. 10/10 experience will definitely book again.