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Page 163 of 412 • 9,870 listings
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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!
SS
Serlin
Mastercraft XT-24 Premier Watersports Experience at Clearwater Beach
Frank and the captain were absolute pleasures to work with. They made the whole experience very smooth and me and my friends had a wonderful time with all of the activity choices as well!

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) ⚓️⚓️⚓️

Shyam
Lagoon Catamaran 40ft in Cozumel, Quintana Roo
The entire crew did a great job! They made special accommodations to pick me up at a different doc near my hotel. They provided 6 hours of service and took me to various locations that they thought would be interesting for snorkeling, beaches and lounging and using water amenities. They provided good food snack items (soda, beer, liquor, ceviche, water, etc). They provided optional options for us to even go fishing! I will be using this team when I go back to Cancun.
DK
Dmitri
Charter 36ft Sloop In Westbrook, Connecticut
We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!
kc
karla
Family fun Bayliner boat NJ/NYC
My party and I had an amazing time with Eli!We were organizing a surprise party on the boat and Eli was accommodating to our time, patient and helped us set everything up! Great captain. He took us to the Statue of Liberty and the all around the skyline, provided beautiful views of the city. 10/10. I would recommend a friend to book with him!