The Best Sailboat Rentals Near Cape May

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

We had an absolutely perfect experience with our captain! From start to finish, everything was seamless—professional, friendly, and so attentive. The boat was in excellent condition, and the captain made us feel safe and comfortable the entire trip. His knowledge of the area and smooth handling of the boat made the day unforgettable. We couldn’t have asked for a better experience. Highly recommend!

The Only 40ft Hinckley Sailboat in Manhattan

I highly recommend chartering Captain Andy's sail boat! Everything in the listing was exactly as described and his boat was perfect for a day on the water. He answered all of our (admittedly dumb) questions about NYC and was super friendly and took plenty of photos of us when asked. I have no complaints and would definitely charter Captain Andy's boat again!

38-ft Hunter 376 Sailing Adventure in Annapolis

This was our crew’s second trip with Capt Alberto and was a second great experience. Capt Alberto shares his passion for sailing and teaching sailing! Capt and Grace are incredibly kind and make a great day spent out on the bay!

Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️

38-ft Hunter 376 Sailing Adventure in Annapolis

Thank you so much Captain Alberto & Grace. We had a fabulous time and enjoyed learning about sailing. Thanks for trusting us to help steer and tack the boat. We had so much fun. You are a great teacher. We wish we could have stayed out longer.

The Only 40ft Hinckley Sailboat in Manhattan

My group and I had an incredible experience with Captain Andy. He was warm, accommodating, and an excellent captain throughout the entire trip. He truly made the day unforgettable for all of us, and we can’t wait to set sail with him again. The sailboat, Nanette Marie, was stunning so comfortable and perfect for capturing beautiful photos.