The Best Cruising Catamaran Rentals Near Winnipeg

FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

My first sailboat ride was absolutely incredible. The entire experience was so relaxing, and I felt comfortable from the moment we stepped on board. The crew was incredibly accommodating with photos and made sure we had the best spots to capture the views. The scenery was truly stunning, and everything about the trip felt calm and effortless. I couldn’t have asked for a better first sailing experience.

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

If you’re in the Bay Area, going with Jan and the Hokahey is a no brainer. Excellent communication from booking to boarding. Great conversation and knowledge of the area. Beautiful boat with room indoors for a warm setting out of the breeze, and plenty of room to spread out and sit up high and see the views or lay on the trampoline mesh up front to listen to the waves. Excellent experience, would recommend to anyone.

FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

We had such a lovely, charming ride into a misty and foggy sky! The dolphins came so close to the boat, the air was so fresh, and the sandbar was so beautiful that we got off and explored! Johnny made the experience so memorable for our family adventure!

FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

We had the absolute best time with Johnny! What an awesome sunset cruise, even for late December when it was a little chilly. It was so relaxing and so easy to work with Johnny. We had a great time chatting and spending 2 hours with him and would definitely love to come back when it’s warmer! Extra points for letting me captain the ship for the last 20 minutes :)

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.

Chicago's Largest Chartered Catamaran!

Captain Brian and Russell were A W E S O M E!!! From the beginning, Brian was great ... very responsive to inquiries and follow up questions. During the cruise, that's when our experience went from GREAT to AWESOME! Brian and Russell were great, on-time, professional and courteous. They took good care of us and just let us relax. Thank you for making our UChicago graduation celebration weekend a fun and memorable experience! HIGHLY RECOMMEND cruising the lakefront and swimming in the Play Pen!!