United StatesChesapeake Bay

Awesome sailboat rentals in Chesapeake Bay, United States.

Average of 7 reviews in this area.
3 listings

Rent a sailboat to explore the waters of Chesapeake Bay.

Chesapeake Bay is a great place to rent or charter a sailboat. Sailing is always a memorable experience, and it's extra special when you can share it with family and friends. Learn how to sail from a captain if it's your first time, or charter a sailboat and let a captain worry about the details. Choose from a range of sizes depending on the size of your group and desired event you want onboard the sailboat. Whether it's for a family reunion, an anniversary, or a party of sorts, sailboat charters are the perfect boat choice in Chesapeake Bay. Get onboard a sailboat in Chesapeake Bay and enjoy your time out on the water.

Using GetMyBoat to book your next sailboat.

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

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

GetMyBoat customer reviews for Sail in Chesapeake Bay.

  1. PK
    Pankaj
    Get away for a perfect weekend! Charter 44' Catalina Sailboat

    Wonderful experience with Jhon on his Velocity. We had wonderful day . We had lots of fun. Jhon is best Captain. We will be back again. Thanks Jhon and wife for hosting our family.

  2. 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!

  3. OY
    Olivia
    Get away for a perfect weekend! Charter 44' Catalina Sailboat

    My friends and I had an absolute amazing time! Captain Jack was an amazing host, super caring, very experienced and very welcoming. He took us sailing and took us to a beach bar and the whole day was fun from start to finish. I 100% recommend this Charter!

  4. AM
    Alison
    43' Sailboat Cruises in Chesapeake Bay, Annapolis MD

    Awesome crew!!! Such a nice view and smooth ride... 100% recommended

  5. LB
    Lauren
    43' Sailboat Cruises in Chesapeake Bay, Annapolis MD

    Wonderful trip and we enjoyed it all!!!