SEATTLE · SAILING
Good sailing trips fill up weeks ahead and the great ones go first. Below: the 9 to book early, what each includes and how they differ.
Set sail from Pier 66 Bell Harbor Marina aboard Seattle’s historic tall ship for about two hours. You’ll see the waterfront, Space Needle, Elliott Bay, Olympic and Cascade ranges, and possibly Mount Rainier. The crew may invite you to help raise the sails, with drinks, snacks, blankets, and restrooms available onboard.
“It was really something different. Wish we could have music or some kind of singing.. it was just a little boring.”
Board the schooner Bay Lady at Pier 66 for a two-hour sunset sail across Seattle Harbor. You can relax on deck, buy beer, wine, cider, or snacks, and possibly help raise the sails or steer. Expect city views, Olympic Mountain sunsets, and Mount Rainier on clear days.
“The whole experience was excellent. The crew were knowledgeable, friendly and helpful. The sailing was smooth with a sighting of porpoises and amazing views of the skyline. Would absolutely recommend this.”
Board a 70-foot ocean-racing yacht at 1201 Alaskan Way for a two-hour sail on Puget Sound. The crew, including Captain Phil and first mate Anna, handles the sails while you bring your own snacks, beer, or wine and watch Seattle, mountains, and possibly orcas from the water.
“This was a great way to get out of the busy city. Was super peaceful to be on the water and it was nice to interact with the crew. Very sweet men running the business. Thank you for a great time!”
Spend three hours aboard the S/V Kingsley with Captain Russ, Mark, or Dylan, sailing from Shilshole Bay between Seattle and Bainbridge Island. Help handle the sails or relax with your own drinks while watching for seals, porpoises, eagles, and clear-day views of Mount Rainier.
“I wanted to surprise my husband who had been an avid sailor with a special trip with our grandson and his fiancée for his 84th birthday and Mark made sure that everything went smoothly and that we had a great sail in Elliott Bay.”
Spend two hours aboard a 70-foot sailing yacht with a captain and deckhand, watching Seattle, the Olympic Mountains, and Mount Rainier from Elliott Bay. Bring your own food, beer, wine, or soft drinks. Crew members such as Anna and Matt may share the sailing duties and local stories.
“The skipper & first hand were both excellent, the water was calm & weather superb. Highly recommend 👍”
Spend 1.5 hours sailing from Seattle’s Pier 56 on a 70-foot ocean racing sailboat. Your English-speaking captain and deckhand guide you across Elliott Bay while you enjoy skyline, Mount Rainier, Bainbridge Island, and mountain views. Bring your own picnic and drinks, with blankets, jackets, and an iced cooler provided.
“Smooth sailing, nice route, calm waters. Discrete staff. Pleasant experience. Wished for more wind/speed”
Meet Captain Scott near Bainbridge Island’s Waterfront Park, walk aboard from the ferry and Winslow area, then cruise Eagle Harbor and Puget Sound under sail. Your private group may see seals, eagles, Seattle landmarks, Mount Rainier, and the Olympic Mountains while learning local history.
“We had a great experience on our private sail around the Seattle harbor. From the moment we stepped aboard, the atmosphere was calm, welcoming, and relaxing—exactly what we were hoping for. The boat itself was very comfortable with plenty of seating, perfect for sitting back and enjoying the views. Our captain, Scott, truly made the tour special. He was warm, conversational, and had a treasure trove of interesting stories about the area, sailing, and local history. It felt more like sailing with a knowledgeable friend than just a tour guide. One thing that really stood out was how attentive and accommodating he was—especially when helping one of our travelers who…”
Meet Sailing Seattle at Pier 56 for a two-hour cruise on a high-performance yacht. Bring your own beer, wine, food, and warm layers, then enjoy open-deck views of Seattle, Elliott Bay, the Olympic Mountains, and possibly Mount Rainier.
“It was a nice day to say, with sun out and mild winds we could have had a great sailing experience in the puget sound waters but the sail boat for whatever reason never went far from the shore line and”
Join Captain Ben aboard a private 44-foot sailing ketch for two hours on Puget Sound. Depart Bainbridge Island, take the wheel or relax, and look for Seattle views, Olympic Mountains, island coves, wildlife, and distant volcanoes.
“This trip was fantastic! Ben was wonderful and we left the trip wishing we had had more time. Definitely recommend 💯”
Pick a waterfront, a market aisle or a mountain road.
