Find The Best Boat Rentals in Chesapeake, Virginia.

Chesapeake Reviews

1. AW

   ALEXDecember, 2022

   22' Cape Craft 2200 DC Powerboat in Virginia Beach!

   Great experience with Max from beginning to end. Took 2 people and 1 dog to False Cape. Super communicative and happy to work with our schedule and requests. He was on time, the boat was nice and he was all around just a nice guy to talk with. No issues and would recommend a boat trip with Max to anyone!

2. CH

   CyndiMay, 2020

   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.

3. LN

   LindaSeptember, 2017

   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!

4. JM

   JoshApril, 2017

   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

5. DH

   DanOctober, 2020

   Let's Go Sail in Gloucester Point, Virginia

   Bill was awesome. Very communicative leading up to the sail with weather, directions, and other logistical specifics. The trip left and returned on time, Bill was very knowledgeable about the boat and the area, let my wife and I take the helm several times and the boat was in great condition. Would totally sail with Cpt Bill again.

6. SR

   ShannonJuly, 2018

   Melges 32 - The Ultimate Racing Experience

   The boat was in perfect condition, ready for anything we could ask for. Doug sails and races on a weekly basis, often in this particular boat, so his feel for the boat, the wind, and the waters we sailed in are well honed. The boat is forgiving, and Doug was unflappable. An encouraging beginner experience, and very fast under experienced guidance. I did not hope for as good an experience, and cannot offer a higher endorsement. Top marks.