United StatesChesapeake Bay

Incredible sailboat hire in Chesapeake Bay, United States

Average of 149 reviews in this area.
1 - 18 of 21 listings
21 results

Hire or charter a sailboat for a memorable experience in Chesapeake Bay

Are you ready for a fun adventure out on the open water onboard a sailboat in Chesapeake Bay? Hire or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Chesapeake Bay is a wonderful sailboat hire destination.

Using GetMyBoat to book your next sailing experience

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit hire enquiries, and pay for your hire or charter from the convenience of your phone or computer. We offer a secure platform for customers to facilitate a seamless hire transaction. For boat owners, we connect millions of customers to their boat and provide the security and safe checks on each hire transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat customer reviews for Sailing in Chesapeake Bay.

  1. EB
    Enje
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    I cannot say enough about Captain Joe and the SolSearcher! This was my first time chartering and he made the process easy and memorable. He provided detailed instructions which appropriately communicated procedures and expectations (even highlighting the speed limit drop as I approached the marina). His warm friendly greeting set the tone for our sail. The vessel was clean and spacious. The views were spectacular. The memories made, ...unforgettable. In short, my experience on the SolSearcher ushered in a much needed peace in the middle of such a crazy time (#2020). I loved my sunset cruise and will definitely be chartering with Capt. Joe again.

  2. DB
    Daniel
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    What a wonderful afternoon! I can't speak highly enough of this experience. We had an incredible time sailing with Captain Joe. Everything, from booking, to preparing, to the actual trip was quite literally smooth sailing. Our only regret is that we didn't book the boat for longer! We will definitely be back for more on this gorgeous boat. Very highly recommended.

  3. AL
    Alyson
    Get away for a perfect weekend! Charter 44' Catalina Sailboat

    We had a great day on the water with Jack! He is an absolute expert sailor with a gorgeous sailboat. He was accommodating from beginning to end and I definitely would go on his boat again. I highly recommend Jack and I am glad I connected with him through this website. Shoutout to first mate Jeff!

  4. JH
    Jennifer
    Charter 44' Cruising Catamaran In Deale, Maryland

    Rob was so communicative and helpful throughout the entire booking process, and our experience on the boat was even better! Not only was it a beautifully appointed vessel, but our captain Adam took such wonderful care of our group. We can never outdo this day-- just plan when we can do it again!

  5. KH
    Karen
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Our group of 6 friends enjoyed a terrific sunset cruise on Captain Alberto's boat. Captain Alberto is clearly an experienced sailor. He and his lovely wife were both very welcoming and we really enjoyed their company. Overall it was a wonderful evening and we all highly recommend it!

  6. KL
    Kevin
    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Great boat in a great location. We spent two nights aboard. Pop the table down, throw the cushion on and use it for sleeping, it was quite comfortable. There's an ice chest and a fridge, so plenty of space to keep things cold. TV and microwave are also on board, but we used neither. Galley is fully equipped with a propane stove and oven, and plenty of cookware. There's also a small propane grill on board but we did not use it. We spent one night on a mooring ball in Swan Creek and another on the hook at Warton Creek. Had plenty of space and ahncored in six feet of water. The draft on the vessel is about 4.5. Jim met us at the boat and gave us a good orientation and then helped get us under way. Overall it was a great trip, the eastern shore of the Chesapeake is a true gem. Enjoy!