Great sailboat rentals near San Diego, California.

Sailing Reviews in San Diego

1. AS

   Andrew

   San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event

   Our birthday celebration aboard the Jada was nothing short of exceptional. The yacht is stunning, the atmosphere was perfect, and the crew delivered a flawless experience - attentive, welcoming, and effortlessly on point throughout the entire day. Every moment felt seamless and elevated. It was one of those days you wish you could relive again and again. We’ll absolutely be back.

2. SM

   Suzanne

   Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat

   We had an amazing time! Ryan was super helpful during booking and Captain Matt was great! Overall great experience, the boat was comfortable and very spacious for the 12 of us to move and socialize.

3. CG

   Christine

   Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat

   Great boat, kind and knowledgeable captain….highly recommend booking with Ryan!

4. 

   Jonathon

   42ft Catalina MkII Sailing Yacht in The San Diego Bay, California

   Excellent staffing at Sterling Sails. We had a great time. Elizabeth and Cody were wonderful. The vessel waa great. Weather was perfect. Couldn't have had a better time. My only gripe was that, after booking, they send you a text message with information, and one of the bulletpoints is an instruction to tip the captain 20%. While i loved the captain, she is awesome, such an instruction violates GetMyBoat's TOS and feels audacious in this economy. (January 2026). It is written as an instruction, not a request, is not mentioned in the GetMyBoat advertisement, and it chips away at the joyfulness of the experience through imposition of pressure to tip. If the boat ownership is not paying their staff well enough, they need to fix that. But to ask consumers to spend $800, and then tell them "wait, now that you've given us $800, we are letting you know you must give us an additional $160," is insanely out-of-touch and quite frankly offensive. Pay your employees better and don't turn a "tip" into a mandatory posr-booking surcharge.

5. DT

   Dj

   San Diego Catamaran Charter | Private Sunset Sail & Harbor Cruises - 12 guests

   My wife and I had a great time, the trip exceeded our expectations, we even had a whale sighting!

6. ML

   Michelle

   Beautiful Jeanneau 58' Sailboat in San Diego

   The experience on Julie’s boat was perfect! Nunya is even more beautiful in real life, and Julie was so accommodating and really made the experience comfortable. The views we got while sailing were unmatched. We would definitely return and recommend to all our friends!