Great sailboat hire near Chesapeake, Virginia

Average of 13 reviews in this area.
4 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. 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, Virginia is a wonderful sailboat hire destination.

Using GetMyBoat to hire your next sailboat

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.

  1. JS
    Janessa
    Annapolis/Chesapeake Sail Escape with Classic Captain--and Classic Boat!)

    Captain Paul and Lucas were superb! We had a wonderful sail and they even let us learn and help with each step of the sailing process. They were so friendly and had us laughing the whole trip. We plan to come back again for an overnight trip. Highly recommend!!

  2. KB
    Kierra
    Annapolis/Chesapeake Sail Escape with Classic Captain--and Classic Boat!)

    Captain Paul was amazing. His teammate Cynde was awesome and together, they made the perfect team for a family Mother's Day excursion. Whenever I am in the Annapolis area, I will DEFINITELY be re-booking with Captain Paul, an excellent Captain and Annapolis native (and expert!) With Captain Paul, expect a beautiful vessel, intriguing Annapolis history lesson, and laughs from start to finish. Booking with Captain Paul is really your best bet. DO IT!

  3. AZ
    Ariel
    Annapolis/Chesapeake Sail Escape with Classic Captain--and Classic Boat!)

    Amazing day at sea for our anniversary! Captain and crew were amazing, fun, engaging and accommodating! We will definitely be booking another trip!

  4. 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.

  5. 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!

  6. 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