The Best Sailboat Rentals Near Northwest Territories

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.

Hunter 29' Sailing Charter! Discover Alaska

Encore was an amazing sailboat in a beautiful area. Kate was very easy to communicate with and very helpful throughout the whole process. The boat is well equipped with everything you will need for a few days out in the bay. We spent both our nights in thumb cove, where we found the anchoring conditions to be the best in the area. Truly beautiful boat and surroundings made for a pristine trip.

Hunter 29' Sailing Charter! Discover Alaska

We had the most incredible time aboard!! Checking in and out the boat was a breeze and dealing with Nate and Kate was very smooth. The day we were supposed to go out wasn't ideal and Nate offered to change to the following day which was beautiful. We will definitely be back and recommend this company in the future! Thanks again, Dan & Kirsten

Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC

If I could give 10/5 stars, I would. We had an engagement shoot and David and Alison exceeded all our expectations. They were fun, friendly, and professional. They made us feel at ease during the sail. Super knowledgeable. They toured us around and knew exactly where to take photos. We had an exceptional time and are already thinking of our next sail with them two. We highly recommend David and Alison for all your sailing needs. Definitely the BEST Captain and Crew out there!

Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC

My friends and I had an incredible time and we absolutely loved the whole sailing boat experience. The views are breathtaking on the Sea to Sky shore. We will definitely go back for another sailing trip. Thank you David and Harli for giving us an unforgivable trip

Charter Jeanneau 50 DS Sailing Yacht in English Bay

Chris and his wife were amazing. I Did a surprise proposal. They were so professional they greeted us outside the boat with uniforms. Both of them helped my whole family get on board safely. He Gave us all the guidelines to be safe. Really cared for our safety. We were around some crazy boaters that night and they had no clue what they were doing and Chris jumped into action saved us every time, he’s well prepared for anything that might happen. He’s a very trust worthy captain his background shows for it. His sail boat is amazing it’s huge and it’s spacious and clean. It’s really nice and well maintained. I would definitely rent again. Price is amazing for what you get and him and his wife have such a great personality. They also helped us off load and take stuff back to our cars amazing people. Highly recommend renting from him. Safest captain