The Best Sailboat Rentals Near Philadelphia

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.

Sailing NYC aboard 34' Catalina

Sailing with this boat was a truly beautiful and magical experience!! It was comfortable and looked fresh too. We had a wonderful captain and he was very experienced and smooth! Ian was very responsive and accommodated us with our specific timing at sunset. My husband and I really enjoyed our night on the water!