The Best Sailboat Rentals Near Manteo

50ft Catamaran Charter with Water Toys - Annapolis, MD

We intentionally booked a late afternoon cruise around the Chesapeake so we would return around sunset to get great views and photos. Kristal was super responsive in preparing us and Captain Wayne and his 'first mate' Mish were super helpful with capturing the perfect photos. We would definitely book again!

38-ft Hunter 376 Sailing Adventure in Annapolis

Captain Alberto and Grace are wonderful hosts and guides. They have a wealth of sailing and life experience to share during your trip. They were very flexible with us during a proposal event.

Melges 24 - One Design 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.

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.

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 ⭐️⭐️⭐️⭐️⭐️