The Best Sailboat Rentals Near Portland

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.

42 Sailing Monohull Tours in Sausalito

Captain Rick is great! You will be at ease while you have fun with a very fine mariner! His boat Gentle Storm is well maintained! The playlist for sailing was great! He is generous, kind, funny and a pleasure to sail with any day!!

Catalina 30 sailboat in Portland, Oregon

Captain Shane warmly welcomed us into his boat. He was really accommodating throughout the course of sailing. I love the conversations and trivia he tells us about the views. The boat was superb and amazing! I love it with or without the mainsail. Overall, our experience was really great! We will definitely want to do this again with him as our Captain.

Luxury Italian Sailing Yacht on the Puget Sound — Seattle

We booked a last minute sail with Matt and it was the perfect addition to our Seattle trip! We brought our 5 month old baby and young children ages 3 and 5 and everyone had such a great time. The boat is gorgeous and Matt and JB are excellent company. We all really enjoyed learning about sailing from these two as well. Highly recommend!

Luxury Italian Sailing Yacht on the Puget Sound — Seattle

Highly recommend this bespoke experience on the Serafina with Matt. The boat is beautiful and easily accommodated 5 adults and one child for a very leisurely sail around Shilshole and Elliot Bay. When we decide to charter again we will definitely look to Matt and the Serafina.

Luxury Italian Sailing Yacht on the Puget Sound — Seattle

We had an amazing time sailing with Matt and JB. While visiting Seattle for the first time, we wanted to get on the water to experience the natural beauty of the Sound and take in the skyline on the return. At a Bainbridge Island cove, we anchored and enjoyed a well-curated cheeseboard and wine before our return to the city. The boat is beautiful and immaculate, with exceptional sailing performance. We are grateful for Matt and JB‘s kindness and hospitality.