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Incredible sailboat rentals in Virginia, United States.

Average of 43 reviews in this area.
1 - 18 of 60 listings

Rent or charter a sailboat for a memorable experience in Virginia.

Are you ready for a fun adventure out on the open water onboard a sailboat in 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. Virginia 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 Virginia.

  1. md
    megan
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt Alberto and his wife, Grace, were amazing! We were running a bit late waiting on the rest of our guests and they accommodated us time wise by adding time to our excursion at the end. Alberto allowed my boyfriend to sail the whole time and he was thrilled. We will definitely be back!

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

    A great thank you to the captain and his wife! This has been one of the most memorable birthdays for my daughter. Thank you so much for accommodating us at the last minute and for making this occasion that much more special. You both were such a amazing spirits and great company! Our friends and family adore you both. Once again, thank you so so much for making this a memorable time in our lives! We will definitely be back and we will definitely recommend you to our friends and family!

  3. DL
    David
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Captain Alberto is a very experienced sailor. Went with friends on a half day and we had a great time. I also learned a lot that I will be able to use when I sail alone with friends. If you are thinking of hiring him for a day, you should.

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

    Capt Alberto is the best- very knowledgeable & relaxed- we all had a great time. Hoping to do this again next year!

  5. LV
    Larry
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt. Alberto is an extremely knowledgeable sailor who can make sailing fun for both the experienced and inexperienced sailor. He has a great deal of technical knowledge and can explain it very well. Our sail was delightful even though the weather was not 'ideal'. We're sure others will enjoy their time sailing as we did.

  6. 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!