The Best Sailboat Rentals in Chesapeake

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

I highly recommend a sail with Captain Bill. The entire experience was exciting and relaxing at the same time. Whether an experienced sailor or a novice with boats, just being on the open water will refresh and invigorate. 5 ⭐️⭐️⭐️⭐️⭐️

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.

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!

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

Let's Go Sail in Gloucester Point, Virginia

Captain Bill was a fantastic host for our inaugural sailing adventure in the York River out of Gloucester Point, VA. We booked him for a Saturday afternoon in June for a 2:30 to 5:30 cruise and it was everything we could have asked for and more. He explained the region's waters and relation to the Chesapeake Bay as well as the naval and nautical history of the area in addition to teaching us about his boat and how to sail it properly. We wanted to be immersed in the experience and he let us be very hands on, giving direction for assisting with deploying the sails, commanding the helm, reading the wind and performing the tacking maneuvers while being at the helm. We also had a chance to relax on the forward section of the deck as Bill took over, he passed our libations to us and helped us enjoy the experience of sailing while soft music played that even invited an interaction with one of the regions local dolphin who accompanied and entertained us for well over a half an hour on our return up the river. What an awesome way to spend an afternoon.

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.