United StatesChesapeake Bay

Incredible sailboat hire in Chesapeake Bay, United States

Average of 239 reviews in this area.
1 - 18 of 31 listings
31 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. FG
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    What an amazing experience! We loved Captain Alberto and Grace. They let us take the wheel for a little bit, allowed us to play our own music, and talked to us about sailing and the Chesapeake Bay. Overall it was an incredible experience. They were so hospitable and wonderful. Highly recommend!

  2. BD
    Charter this 42ft Hunter Passage Sailboat in Edgewater, Maryland and sail on the beautiful Chesapeake Bay

    We had a wonderful 5 hr trip with captain Bill. Great scenery and a very nice boat. Bill and his crew are very knowledgeable and easy going. All you need to do is bring your good mood, and relax. We can't wait to do it again!

  3. TS
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    We can't wait to come back and experience new marine adventures with Captain Joe and his Sol Searcher again. According to my 13 y.o. kid, it was one of the best birthdays she has ever had. The sailboat is so beautiful, spacious, and comfortable. Captain Joe was very hospitable, friendly, and considerate. He told us a lot about sailing and made my daughter's dream come true - we saw a rare and hardly accessible caisson structure Baltimore Harbor Lighthouse. It was amazing! Upon return we had some delicious brownies baked by Joe's wife. Always appreciate a personal touch. We felt very welcome and had a great time! Highly recommend this captain and his gorgeous sailboat!

  4. KC
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Captain Joe is an excellent sailor and has great communication. When I booked the private charter I reached out to let Joe know that I would be proposing on his vessel, we had a few date changes that joe worked through with me flawlessly. The pictures on the listing do not do this boat and captain justice! 10/10 would recommend!

  5. SF
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    We had an amazing sail with Captain Joe! The boat was beautiful and spacious, and Captain Joe was very attentive to all of our needs. Can’t wait for another sail in the future!! Would definitely recommend this experience with Captain Joe!

  6. SH
    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    This trip was above and beyond ! The boat is spacious, beautiful, and comfortable. Everything was seamless and we spent a wonderful time sailing, swimming, and relaxing on the various parts of the boat.