The Best Sailboat Rentals Near Cleveland

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!

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

Amazing time! Ben is a very experienced and knowledgeable captain , he taught us how to steer the boat and answered all our questions. Hes very nice and made the ride great! You also get an amazing view of the city that you can’t get anywhere else I brought my boyfriend as a birthday present and it was perfect!

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

Ben was an awesome captain and a pleasure to be around during our two-hour trip. His boat is the perfect setting for a romantic date night, and I highly recommend experiencing the sunset on board, the views were absolutely amazing!

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.