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 12 of 39 • 930 listings
898
Miami
Florida
703
Cancún
Quintana Roo
502
Isla Mujeres
Quintana Roo
368
Tampa
Florida
354
Los Angeles
California
349
Lake Michigan
United States
326
Puerto Vallarta
Jalisco
317
Miami Beach
Florida
310
Cabo San Lucas
Baja California Sur
296
Marina
Cabo San Lucas
295
Nuevo Vallarta
Nayarit
285
Chicago
Illinois
240
Tampa Bay
Florida
240
Saint Petersburg
Florida
237
Marina Vallarta
Puerto Vallarta
226
Clearwater
Florida
223
Cartagena
Bolivar
209
Chesapeake Bay
United States
BF
Barb
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Highly recommend sailing with Captain Charles on the Optimystic! Was like hanging out with an old friend. Beautiful boat and fun time!
ET
Ellan
Captained Luxury Lagoon 560 Catamaran In The Bahamas
Our large group of 21 with a mix of adults and kids had a great time! This was on our list for the Bahamas and it was the most epic part of our trip. We would highly recommend this company, if we are ever back, we already know who to call!
EB
Elias
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Charles is fantastic, he and his wife went above and beyond to make everything go flawlessly, and the boat is gorgeous

Angela
Captained Luxury Lagoon 560 Catamaran In The Bahamas
10/10 recommend. Crew was wonderful and food was excellent. Our group had an amazing time!
MT
Michelle
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
We had the absolute best time with Gerald. From the moment we stepped on the boat, we were treated like family. His kindness, generosity, and genuine spirit made the entire experience feel so special. What stood out most was not only how much fun we had, but how it truly felt like we made a new friend. Gerald’s knowledge of the area is expert level, and he shared so many great insights that made the day even more enjoyable. This was such a memorable experience for our group, and we cannot recommend him enough. We will absolutely be back.
AK
ALEXANDER
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Excellent experience from first contact until and beyond offboarding. Very family friendly. Definitely 5* experience. Will book again next time. The trip from the pier to the Atlantic is a great experience by itself. Sailing on the ocean is a dream come true. Enjoy!