The Best Sailboat Rentals Near Gilbert

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.

Incredible 36' Cruiser For Rent

I want to start off thanking God for people like Captain Chris. I had the absolute pleasure of celebrating my 33rd birthday with Captain Chris, and I truly cannot recommend him enough. From start to finish, he exceeded every expectation. His boat was spotless, and his sailing was incredibly smooth—it honestly felt effortless and relaxing the entire time. What stood out the most was his professionalism and kindness. He was extremely accommodating, answered every call leading up to the trip, and made sure we had clear directions and everything we needed. He welcomed everything we brought onboard without any hesitation and never once made us feel uncomfortable or restricted—he simply allowed us to enjoy our time fully. Captain Chris has such a calm and respectful presence that at times we even forgot he was there, yet everything ran perfectly. That balance is rare, and he handled it beautifully. This experience meant more to us than just a birthday celebration. Our family had just experienced a loss, and this day gave us a moment to breathe, laugh, and reconnect. It truly felt like a healing escape, and Captain Chris played a huge role in creating that space for us. It felt like we were in a movie, and he was the one helping bring it all together behind the scenes. I’m beyond grateful for the experience and for his energy, professionalism, and generosity. If you’re thinking about booking—do it. You will not be disappointed. He is absolutely stellar. Thank you again, Captain Chris, for making my birthday unforgettable. 💛

42 Foot Bertram Trojan Motor Yacht in Los Angeles

Ryan was amazing! His personally complimented our experience. He was available to assist us, but was also able to make us feel like we were there alone for our intimate proposal ! So glad to have him as apart of our engagement!

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.

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.

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!