The Best Sailboat Rentals in California

Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

Captain Mark is the best!! He was so accommodating, allowing for flexibility as I wasn’t sure if it would be 4 or 6 people. He made me feel at ease right away and communicated all the details we needed from the start, checked in before the trip and the day of, gave us tips for parking, shoes, weather, etc. He bought ice and had it on board so I wouldn’t have to worry about that detail. I really wanted to see dolphins and saw some in the distance as we were heading back to harbor. He promptly turned around to catch up to them and make sure I was able to have that experience, which was so thoughtful and appreciated! We all felt safe and comfortable and relaxed, which made for a perfect afternoon on the water. I’ll definitely be booking with him again, and my friends said they will as well! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ all around!

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.

Hawaiian Breeze in Marina del Rey

Captain Ross was fantastic professional, friendly, and made us feel completely safe the entire time. The boat was clean, modern, and had plenty of space to relax. The weather was perfect, and Ross doubled as an excellent tour guide, sharing great insights along the way. Couldn’t have asked for a better day on the water. My group and I are already planning to book again soon!

Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

Wonderful sailing experience. A professional captain, excellent service, and a very pleasant atmosphere on board. Everything was great — highly recommend! ⭐⭐⭐⭐⭐

Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

’Twas a gloomy day—your typical San Francisco midday gloom. Fog with teeth. Mist that clung like a secret. A chilled, still air that made the Bay look calm enough to trust… which is exactly how it gets you. Me and the missus had one objective: sail for the Golden Gate and get that clean, cinematic sweep under the red steel. Simple, right? Except nothing in that water is simple. The currents run their own agenda out there—silent, relentless, and utterly indifferent to whatever romantic plan you brought with you. Captain Jan sized up the day the way a seasoned operator reads a dossier. No drama. No bravado. Just facts. “Sure,” he said, steady as a man who’s seen worse, “but it’ll be a one-way trip in these currents.” That was the moment I knew we were in good hands. And don’t let his youthful appearance fool you—he’s not that young. Argh! The boat—ahem, catamaran—Hokahey, was clean, dialed-in, and quietly ready for business. There’s a cozy spot to keep you out of the wind when the Bay starts throwing attitude, a bathroom (critical), and most importantly… snacks. The kind of detail that tells you the person running the show has done this before and knows what matters when you’re out there with nothing but gray sky and cold water for company. The wind didn’t cooperate—no grand, billowing sails cutting through the fog like a movie poster. But here’s the thing: the engine is quiet and makes serious speed. No rattling chaos, no grinding clatter—just a smooth push through the chop like the vessel had its own mission and we were simply along for the ride. We tracked close to Alcatraz, its silhouette looming like a warning. Closed in on the Golden Gate, the great red arc appearing and disappearing through the mist like something you weren’t supposed to find. We chose not to explore Angel Island—call it discretion, call it timing, call it a tactical decision—and cruised the dock area as well, soaking in the city’s edge where steel, salt, and history all collide. No rush. No worries. No forced itinerary. Just a smooth, delightful, private cruise in the Bay—executed with calm precision and a kind of confidence you can’t fake. If you want a low-stress, high-quality sailing adventure that still feels like you earned it—Jan and the Hokahey are the way to go. Enjoy… and thanks, Jan.

Sail in Modern Luxury Beneteau Oceanis 37 Yacht

Brian was an amazing host! We had a great time celebrating a birthday and Brian couldn’t have been more accommodating and pleasant. His boat is immaculate and very well kept. He even let us drive the boat and taught us some things about sailing. We would highly recommend Brian!