The Best Sailboat Rentals Near Hamilton

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

Nina is a fantastic person, fantastic captain and a fantastic company. 2 of us and a doggie went on a short adventure with her and it couldn’t have been a better experience. We had so much fun, laughter and comfort with her on her boat that i can barely put this in words. We will definitely do this over and over again. Highly recommend!

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) ⚓️⚓️⚓️

Cruising Monohull Rental in Kingston

Great sail. Our captain Rob was very knowledgeable and easy to talk to. He let us help with some of the sailing and then we sat at the front of the boat and enjoy the view. It was a perfect day weather wise. Had a great time overall.

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.

41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

John recently took my family out on Lake Michigan and he made the trip a great experience - communicative, nicely kept boat and very competent as a captain! I appreciated how he answered my youngest questions and was so thoughtful with them. Would recommend.