The Best Sailboat Rentals Near Toledo

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

We had a wonderful time on Captain Bill's boat! We booked a 2-hour charter and it was the perfect quick escape for our family of 6. The crew was friendly and welcoming. The boat had plenty of space to relax. It was a smooth, stress-free experience ideal for families or friends needing a taste of the water.

Charter 44' Orana Cruising Catamaran In Deale, Maryland

Our group of seven spent a fabulous half day with Captain Rob and Mate Dianna. Couldn't have been happier with the whole experience. Communication was quick and easy. On board, they were super friendly and engaging. The vessel itself was spotless and super comfortable as we hung out on the front "trampoline" area, sailing around the Bay. Thanks for such a fun adventure. We are already talking about a future engagement!

38-ft Hunter 376 Sailing Adventure in Annapolis

We had a lovely experience out on the bay. Captain Alberto let my husband steer the boat & put the kiddos to work as well. We were able to play & relax as well while out on the water. Very family credibly experience and lovely to get to know the captain & his wife! Overall 5 stars for a sailing experience on the bay!

Welcome Aboard Optimystic! Create a beautiful memory on the water.

Charles was an outstanding guide. Before the outing (which was a birthday gift for my fiancé) he even offered to pick up a cake so that it could be a surprise. He and his wife made us feel at home right away as if we were out just sailing with friends. It was a gorgeous late afternoon / sunset sail with the option of swimming and cooking on the boat. We didn't rush back. Riding on the bow was so relaxing. He took time explaining sailing tips to my fiancé and let him drive the boat for awhile. Communication was clear. We'd love to book again with Charles and Renee!

38-ft Hunter 376 Sailing Adventure in Annapolis

We had such a great time! The boat was perfect and Alberto and his wife were great hosts. It’s a good sized boat, kid-friendly (they had kids life jackets), and the cabin was spacious with plenty of room to eat.

Charter 42' Lagoon Catamaran in Annapolis, MD

We had an amazing day on the bay with Captain Adam! He was super communicative leading up to the trip, providing amazing instruction to make it as easy as possible to get aboard. While on board the vessel was very clean and comfortable and he and his team were knowledgeable about the area. Highly recommend! They’re lovely!