The Best Boat Rentals in Chesapeake Bay

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!

50' Come enjoy the DC view on the Potomac river aboard Sancha. $300HR to $400HR

What a great experience for my team!!! Everyone loved this different way to visit DC- service was impeccable. The boat was perfect for our group of twelve. Lisa and Marque were amazing. Couldn't have asked for more !!! They had cocktail ice and coolers ready and a beautiful charcuterie tray we added on. Thank you !

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.)

$400HR Weekday | $750 HR Weekend| 6-20PPL

AJ was wonderful to work with - very professional, great communication! Shawn, our captain, was very welcoming an made sure we got amazing photos of the monuments and skyline at night. So much fun!

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!