Great sailboat rentals near Chesapeake, Virginia.

Average of 13 reviews in this area.
3 listings

Step onboard a sailboat for an unforgettable experience in Chesapeake, Virginia.

Get ready for a fun adventure when you hit the open water onboard a sailboat in Chesapeake, Virginia. 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, Virginia is a wonderful sailboat rental destination.

Using GetMyBoat to rent 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.

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GetMyBoat customer reviews for Sailing in Chesapeake.

  1. RN
    Raymond
    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    Capt. Bill was amazing. He took great care of our family and everyone got a chance to work on the boat. Capt. Bill is very knowledgeable about the history of the area and sailing. Thanks

  2. JB
    Jim
    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    A great first time sailing experience for all involved. All three of us got to contribute to the operating of his sailboat. He gave us a great introduction to the art of sailing.

  3. CH
    Cyndi
    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    My family of 5 had a wonderful day sailing with Bill to celebrate my husband's 40th birthday. Bill was very knowledgeable and excellent at explaining things to my children, even letting them each take the helm. We felt very at ease and safe our entire trip. I am already recommending him to friends.

  4. LN
    Linda
    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    Mom, Dad, & three GROWN children went out on a wonderful outing with Captain Bill. He was a gracious host & his beautiful sailboat was spectacular! Enjoyed the experience immensely & seriously considering sailing lessons next spring. His boat was not only in immaculate condition but very comfortable for all five adults (plus the amiable captain). We were thrilled to see dolphins and hear about the area's history. We sailed 14.9 memorable miles. I gave a 5 star rating because the ratings don't go to 10. Honestly, how does one rate a great memory that lasts a lifetime? We weren't sure if the weather was going to be a wash out for a few days out, but Captain Bill kept in contact via email with weather updates and was extremely accommodating to what would work best for us. The weather wasn't what one would call picture perfect but I thought it was awesome having so much of the water to ourselves. We only saw one other sailboat. This was an exhilarating experience with a knowledgeable captain and I can't recommend him enough!

  5. JM
    Josh
    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    I had my four children with me ages 5 to 12 the captain was very kind and understanding to them teaching them new things my son it was comfortable taking the helm and the captain enjoy teaching him the other kids not so much but that was okay however not to be prejudiced because they are my children but they are exceptionally good kids my youngest commented that she was upset she would not be seeing Captain bill the next day and on how much she liked him. we will be back to sail in August we learned about the wind the ocean and how to read it wheeler and practical knowledge and history of the area The boat was beautiful the captain was awesome it was a great day my kids will remember forever I am not one to give A+ review without truly meaning it

  6. AM
    Austin
    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia