United StatesChesapeake Bay

Incredible sailboat rentals in Chesapeake Bay, United States.

Average of 63 reviews in this area.
1 - 18 of 24 listings
24 results

Rent 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? Rent 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 rental 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 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 Sailing in Chesapeake Bay.

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

    We had the most amazing sail even though we didn’t have the most ideal weather. Capitan Joe motored is out to “find the wind” and we were able to enjoy both tranquility and the blissful breeze of a non-thunder cloud. The brownies and fresh raspberries were a nice indulgence as we glided peacefully back to the marina. We can’t wait to go out again!

  2. SC
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Captain Alberto and his wife were an absolute delight! He is incredibly knowledgeable in sailing and he made us feel welcome and at home on his sailboat. My entire family had such an amazing time, and I would recommend to anyone! If you have an opportunity and want a wonderful, safe, and fun experience, choose this charter!

  3. JS
    Juan Pablo
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt. Alberto is the MAN!! His boat was incredibly comfortable, he was such a gracious host, was very conscious of our vibe and was very amenable!! I plan on sailing again with Capt. Alberto very soon. Thank you!!!

  4. NS
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Rented for 7 hours with 3 kids and my wife. The boat was clean. It seems Captain had just washed it before our arrival. Captain Alberto is very knowledgeable and really enjoyed the conversation. He took us to a great restaurant on a creek. Overall, I would rent this boat again.

  5. DB
    Charter the Beneteau Oceanis 440 Sailing Yacht in Tracys Landing

    We booked this trip last minute and no expectations or plans of what we wanted to do and Richard was able to provide us with options and ensured we had a great trip. Boat was very comfortable with plenty of room for more people. Really enjoyed the relaxed atmosphere and flexibility to change plans depending on which way the winds were blowing.

  6. sm
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    A lovely captain and comfortable vessel to explore the Chesapeake. Highly recommend Alberto for anyone looking for a relaxing day trip and sailing lesson! A hands on adventure and perfect escape with family or friends.