United StatesChesapeake Bay

Incredible sailboat hire in Chesapeake Bay, United States

Average of 157 reviews in this area.
1 - 18 of 23 listings
23 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. DH
    Dan
    Let's Go Sail in Gloucester Point, Virginia

    Bill was awesome. Very communicative leading up to the sail with weather, directions, and other logistical specifics. The trip left and returned on time, Bill was very knowledgeable about the boat and the area, let my wife and I take the helm several times and the boat was in great condition. Would totally sail with Cpt Bill again.

  2. CH
    Carter
    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    James was incredibly responsive and great to rent from. The boat handles really well in light wind, and the mainsail system is great! All the sail systems are in good order. Other than a few non critical issues with the boat, everything was great. thank you!

  3. CB
    Cathy
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    We had a wonderful time sailing with Captain Alberto and his wife Grace! My husband and I and two of our friends went for an afternoon cruise as a birthday celebration. The boat was beautiful and they were friendly and gracious hosts. I was interested in learning more about sailing and Captain Alberto (an experienced sailing instructor) was a great teacher. Captain Alberto was also very responsive and helpful when we were making the arrangements for the trip. We hope to have an opportunity to do this again, and highly recommend a trip with Captain Alberto!

  4. DR
    Danielle
    41' Lagoon Cruising Catamaran in Maryland, United States

    Booked a trip with Captain Jess for a bachelorette party. We had so much fun! The captain was friendly and experienced. And his catamaran was the perfect size for us. We’d definitely set sail with Captain Jess again!

  5. JM
    Judi
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Fantastic day on the Bay. Alberto has an outstanding sailing background and great knowledge that contribute enormously to the sailing experience. Awesome way to end the season and look forward to Booking again next Summer.

  6. 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.