Great sailboat rentals near San Diego, California.

Sailing Reviews in San Diego

1. AS

   Andrew

   Sail San Diego on 68ft classic Sailing Yacht

   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. 

   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.

4. 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!

5. SL

   Sofiia

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

   It was an amazing Birthday celebration for my mom. We have spent 3 hours on the Tigress from 5:30-8:30, and it was magical. Beautiful views all around. Ryan, the owner, was super helpful and nice. He navigated our booking process and answered all of questions swiftly. Our captain Matt was also incredible. He gave us space but also communicated and joked when appropriate, and by the end felt like one of our own! The boat itself is well equipped, clean and very comfortable. The 8 of us were able to lounge and move around freely. There is a bathroom with running water and a fridge on board, which is convenient and a huge plus. Overall it was a great experience and I definitely recommend to choose them!

6. AF

   Ashley

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

   We loved our private sail with captain Matt! The boat was so comfortable and perfectly stocked with drinks and blankets. Matt made sure we saw the sea lions and all the points of interest along the coast. He answered all our questions and couldn't have been nicer. Booking the trip was so easy too! I messed up and booked our initial trip for the wrong date. I panicked and Ryan responded to my inquiry within minutes and saved the day. He was so accommodating and helpful. From the booking to the whole sailing experience I have not one complaint. These guys are truly the best.