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Page 12 of 41 • 966 listings
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Chesapeake Bay
United States

Rudolf
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Charles and his wife are amazing people who went above and beyond to offer us an amazing sailing experience all while teaching us about the various aspects of boating life. Book them for your next adventure, you won’t be disappointed.
EL
Emelyne
36ft Sailing Catamaran Charter for Up to 20 People in Cancún
Great experience. We were a bit late and they were able to accommodate us. We had a great time on the boat. Would do it again!
LM
Liz
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!

Elisabeth
Welcome Aboard Optimystic! Create a beautiful memory on the water.
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) ⚓️⚓️⚓️
DS
Dahlia
Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.
Thank you for a fantastic day!! The crew were super courteous, relaxed, welcoming and highly competent. The sail itself was lovely. They pointed out the best snorkeling spots and changed up the itinerary for us with no notice when we decided ON THE BOAT on swimming with the turtles and adding an extra hour! The entire experience was perfect from the ease of booking, the prompt responses to my multiple email questions, the extra adventure add-ons … to the boat itself which is is impeccably kept. The cabin is the cleanest we have ever been in, and we have sailed a lot! The drinks and food were fresh and delicious. All in all a Father’s Day to remember!!
vc
vince
Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.
Great trip, real sailing, amazing captain and crew. Best experience we've had ever on a charter sail. Fun at the beach, snorkeling from the boat, and really, really good BBQ. If you're looking for something special to do while in the Bahamas - this is it.