By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
Page 15 of 38 • 890 listings
920
Miami
Florida
625
Cancún
Quintana Roo
471
Isla Mujeres
Quintana Roo
424
Tampa
Florida
393
Miami Beach
Florida
376
Los Angeles
California
370
Lake Michigan
United States
293
Cabo San Lucas
Baja California Sur
290
Puerto Vallarta
Jalisco
280
Chicago
Illinois
267
Fort Lauderdale
Florida
266
Nuevo Vallarta
Nayarit
266
Saint Petersburg
Florida
259
Marina
Cabo San Lucas
259
Hollywood
Florida
247
Dania Beach
Florida
239
Clearwater
Florida
236
Cartagena
Bolivar
Elisabeth
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) ⚓️⚓️⚓️
DL
Dylan
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Had the best time. Great boat and experience. Communication,knowledge, and time was phenomenal. A+
NA
Nicole
Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco
Everyone I worked with while planning a sailing excursion for my team was amazing. I called lots of times to get answers to questions regarding the itinerary and the team was very helpful and responsive. The team went above and beyond in all aspects and the trip was fantastic. I would highly recommend this company!
WF
Wayne
Kelly was professional and courteous for the booking and all questions that came afterward and very accommodating when we wanted to preview the boat, working with the caterer, etc. Captain Cesar and the entire crew were wonderful and very helpful during the entire trip. It was a great experience! Thank you!
Ana
Catalina 30 sailboat in Portland, Oregon
Captain Shane warmly welcomed us into his boat. He was really accommodating throughout the course of sailing. I love the conversations and trivia he tells us about the views. The boat was superb and amazing! I love it with or without the mainsail. Overall, our experience was really great! We will definitely want to do this again with him as our Captain.
HS
Harman
Charter Jeanneau 50 DS Sailing Yacht in English Bay
Chris and his wife were amazing. I Did a surprise proposal. They were so professional they greeted us outside the boat with uniforms. Both of them helped my whole family get on board safely. He Gave us all the guidelines to be safe. Really cared for our safety. We were around some crazy boaters that night and they had no clue what they were doing and Chris jumped into action saved us every time, he’s well prepared for anything that might happen. He’s a very trust worthy captain his background shows for it. His sail boat is amazing it’s huge and it’s spacious and clean. It’s really nice and well maintained. I would definitely rent again. Price is amazing for what you get and him and his wife have such a great personality. They also helped us off load and take stuff back to our cars amazing people. Highly recommend renting from him. Safest captain