The Best Sailboat Rentals Near District of Columbia

38-ft Hunter 376 Sailing Adventure in Annapolis

Capt. Alberto and his wife were awesome hosts! They were totally flexible about our schedule and it was great to hear about his prior sailing experiences. It was great to be with such an experienced host! We will definitely book with them in the future!!

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

With Ian, our special 250th July 4th celebration became even more unforgettable. From the marina, we enjoyed spectacular views of the fireworks. What made the evening truly exceptional was Ian's personalized dock tour—something only possible because of his close relationship with the marina. It gave us experiences we never expected, including seeing the historic tall ships, watching the special boats on the river, and getting a close look at the Macy's fireworks barges as they prepared for the show. Ian went out of his way to make sure our family had a remarkable experience. Seeing my granddaughter dancing on the deck of his romantic sailboat to the music Ian thoughtfully selected, with the fireworks lighting up the sky in front of her, is a memory we will cherish forever. Thank you, Ian, for making our Independence Day celebration so magical. We will definitely be back on your sailboat for another special occasion soon!

38-ft Hunter 376 Sailing Adventure in Annapolis

Capt Alberto and his wife were SO AMAZING!! They taught us how to sail and we sailed across the Chesapeake. Their boat is beautiful and their company is great. I highly recommend everyone book if they are looking to sail in the Annapolis area for a few hours, learn about sailing, and have a relaxing time.

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

Ian is an incredible host that is super passionate about his work. Every detail is thought out from the onset. He is very inviting and chilled yet extremely professional. Ian guided us through everything we would like to know about and gave many of his experienced recommendations. We had an incredible time out at sea, and are looking forward to booking our next voyage!

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

Icarus is a great boat and very well equipped. The sails and everything else on the vessel are in great shape and the fact it only draws 4' 6" is perfect for the Chesapeake. I spent a week on Icarus and everything worked well. The value of chartering Icarus is undeniable. I plan to charter Icarus again. Icarus has a lot of sail area, so if the winds are strong douse the headsail early.

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

We had a wonderful time on Captain Bill's boat! We booked a 2-hour charter and it was the perfect quick escape for our family of 6. The crew was friendly and welcoming. The boat had plenty of space to relax. It was a smooth, stress-free experience ideal for families or friends needing a taste of the water.