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    Incredible sailboat rentals in Chesapeake Bay, United States.

    Average of 281 reviews in this area.
    1 - 18 of 23 listings
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
    hour$150
    Super Owner6 guests

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
    hour$150
    Super Owner6 guests

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    J70 Daysailer rental in Hampton
    hour$100
    Super Owner4 guests

    J70 Daysailer rental in Hampton

    41' Lagoon Cruising Catamaran in Maryland, United States
    day$1,849
    12 guests

    41' Lagoon Cruising Catamaran in Maryland, United States

    Charter 44' Orana Cruising Catamaran In Deale, Maryland
    day$2,400
    10 guests

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    Yamaha Sr210 Bowrider For 7 People In Washington, DC
    hour$175
    7 guests

    Yamaha Sr210 Bowrider For 7 People In Washington, DC

    Beneteau 41ft Sailing Charter in Annapolis, Maryland
    hour$180
    8 guests

    Beneteau 41ft Sailing Charter in Annapolis, Maryland

    Let's Go Sail in Gloucester Point, Virginia
    hour$90
    6 guests

    Let's Go Sail in Gloucester Point, Virginia

    Sunset Champagne Cruise on the Chesapeake Bay
    hour$399
    6 guests

    Sunset Champagne Cruise on the Chesapeake Bay

    Overnight Cruise for up to six people in Rock Hall, Maryland
    night$1,199
    6 guests

    Overnight Cruise for up to six people in Rock Hall, Maryland

    23 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. Melissa
      Melissa
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      We had the best time with Captain Alberto! He was so nice and professional. His many years of experience is obvious and he shared so much of his knowledge with us. Our time together gave us such a huge appreciation and love of sailing! We can’t wait to go again!

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

      This 34' Hunter is comfortable, clean, fun to sail, and has excellent sleeping accommodations. We had a great sail across the Chesapeake bay in 3-4' waves and felt safe and secure the entire time. You will not be disappointed with this charter. James (the boat owner) is a class act and will always go the extra mile to make your charter experience unforgettable. If you're considering a charter on the Chesapeake, this is the boat for you! I hope to see you next year, James!

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

      Sailing with Captain Joe was like spending an afternoon sailing with your buddy Joe. Friendly, gracious, knowledgeable, and highly skilled Joe made for a relaxing and enjoyable sail. The Beneteau is a very comfortable and roomy boat and we would definitely book another sail with him!

    4. LT
      Lisa
      Beneteau 41ft Sailing Charter in Annapolis, Maryland

      Captain Gus is a very experienced sailor and isn’t fazed by much of anything. We were comfortable with him as our captain and enjoyed chatting with him as our host. He gave us all jobs within the limits of what we were comfortable with. We had a day with a crisp breeze and gusts to 25 knots.

    5. EM
      Erin
      Charters 33' Cape Dory Cruising Monohull In Kilmarnock, Virginia

      Our trip was just perfect. We were looking for a true sailing experience, and Captain Russ gave us that. My husband was at the wheel almost the entire trip, talking all things sailing Capt Russ. Meanwhile I enjoyed the sun and sounds of the water against the boat and the wind in the sails from up front. It was a peaceful and enjoyable trip, despite the wind giving out on us towards the end. We'd book with Captain Russ again in a heartbeat!

    6. Debra
      Debra
      Get away for a day or weekend! Charter 44' Catalina Sailboat!

      We had an awesome time on Captain John's sailboat. He was the perfect host - safe, engaging, experienced, informative, and fun. We could not have asked for a more perfect afternoon on such a beautiful sailboat. We will definitely be back to sail again! Highly recommend. P.S. Also lots of laughs :)