United StatesChesapeake Bay

Incredible sailboat hire in Chesapeake Bay, United States

Average of 160 reviews in this area.
1 - 18 of 22 listings
22 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. SR
    Steven
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    The vast amount of 5 star reviews are a testament to Captain Alberto's spectacular service and expertise. We booked a trip for my girlfriend's birthday and it was absolutely perfect. I'd rate 10 stars If I could. We will definitely be going back!

  2. JB
    Jenna
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Captain Joe was an incredible host and captain on our early Spring sail. He was kind, thorough, and hospitable with delicious treats to snack on. He knew the area and would point out interesting facts as well. He was casual, easy to talk with, and overall very easy going. We highly recommend Captain Joe for you sailing adventures. A wonderful way to spend the afternoon away from the laptop and enjoying the fresh air! Thanks, Joe!

  3. 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.

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

    Captain Alberto is the best! The boat was very nice and I learned a lot about sailing. We enjoyed the experience. Thanks.

  5. 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!

  6. 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!