The 14 Best Sailing Trips in Seattle

1.Evening Colors Sunset Sail Tour in Seattle

★★★★★★★★★★5.0 · 593 reviews · 2 hours (approx.) · from $59Our pick

Leave Bell Harbor Marina for a roughly two-hour sunset sail aboard Seattle’s historic tall ship. You can help hoist the sails, watch the skyline and mountain views from Puget Sound, and buy a drink onboard. The crew may fire a cannon salute, and the trip returns to its marina meeting point.

“Everything was perfect, weather, vibe, whole thing. The crew seemed so happy to be there and having a great time. It’s nice to see people who enjoy their jobs”

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2.Seattle Sailing Harbor Tour

★★★★★★★★★★4.5 · 473 reviews · 2 hours (approx.) · from $39Best value

Sail Elliott Bay aboard a historic tall ship on a two-hour trip from Pier 66. You’ll see Seattle’s waterfront, the Space Needle, and, on a clear day, Mount Rainier and the Olympic and Cascade ranges. The crew may invite you to help raise the sails. Captain names reported on past trips include Eric and Anthony, but staffing can vary.

“Perfect time, the crew was professional and nice, we had some drinks, with amazing views while we sail, the weather was great too!”

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3.Tall Sailboat Sunset Harbor Cruise

★★★★★★★★★★4.8 · 223 reviews · 2 hours · from $79

Board the schooner Bay Lady at Pier 66 for a two-hour sunset sail through Seattle Harbor. The captain and crew run the trip in English, and you can relax on deck, buy a drink or snack, or try raising the sails and steering. Views may include the Space Needle, Smith Tower, the Olympic Mountains, and Mount Rainier on a clear day.

“Had a great time with my kid talking to the crew about pirate facts and swordfighting. Was a perfect first time out on the water for the kid. Loved the grade A Dad jokes told by the Captain.”

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4.Seattle Sunset Sail BYOB

★★★★★★★★★★5.0 · 187 reviews · 2 hours (approx.) · from $71

Spend about two hours sailing from Seattle’s waterfront on a 70-foot yacht, with views of the Great Wheel, Space Needle, Olympic Mountains, and Mount Rainier when conditions allow. Bring your own food and beer or wine for guests 21 and older. Crew members such as Phil, Matt, Anna, and Bree have helped make the trip friendly and relaxed, though the crew can vary.

“What a great experience! Friendly crew who answered questions but didn't narrate -- which we appreciated after a long day of sightseeing and listening to tour guides! We brought our own wine, bread, cheese and deli meats, from Pike Place Market, which was plenty for dinner. Regular seating is limited, so be prepared to sit on the deck -- there's not much room to walk around. We were fine but it's not suitable for those with mobility issues. We were lucky to have calm clear weather and enjoyed a spectacular sunset. Two hours is just long enough!”

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5.Seattle Sailing Experience BYOB

★★★★★★★★★★5.0 · 172 reviews · from $60

Spend about two hours aboard a 70-foot ocean-racing yacht as the crew hoists the sails and, when conditions allow, switches off the engine. You’ll cruise Puget Sound with views of Seattle and the surrounding mountains. Bring your own snacks, beer, or wine. This is a relaxed sail, not a narrated city tour.

“This was just as described, a basic sail on Puget Sound. Limited seating. Check in early to get your boarding passes as you board by number and therefore have best seating choice”

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6.Seattle’s Best Private Sailing Adventure on the Puget Sound BYOB!

★★★★★★★★★★5.0 · 126 reviews · 3 hours (approx.)

Set sail from Shilshole Bay Marina on a private three-hour trip aboard the S/V Kingsley, with a captain such as Russ, Mark, or Dylan. Bring your own drinks, help handle the sails or relax as the boat passes Seattle’s skyline, mountain views, and possible seals or porpoises. Choose a daytime or sunset departure for your group of up to six.

“Such a fun time on the water! The sailing was exceptional and Russ was a fantastic captain. The water, the environment and the company made for an enjoyable afternoon that we will cherish.”

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7.Sunset Sailing Cruise

★★★★★★★★★★4.8 · 114 reviews · from $71

Spend two hours on Elliott Bay aboard a 70-foot ocean sailing yacht, with views of Seattle, the Olympic Mountains, and Mount Rainier when conditions allow. Bring your own food and drinks, including beer or wine. The crew includes a captain and deckhand; recent sailings have featured guides Anna and Matt.

“We had a great experience. The guides were knowledgeable and very personable. We had a scheduling problem (our fault) and they were very helpful in getting it resolved so we could do the cruise. The scenery and sunset were great!”

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8.Sailing Cruise

★★★★★★★★★★4.9 · 90 reviews · from $49

Leave Pier 56 for a 1.5-hour sail on Elliott Bay aboard a 70-foot ocean racing sailboat. A US Coast Guard-licensed captain and deckhand handle the boat and share local information as you look back at downtown Seattle, Bainbridge Island, West Seattle, and the Olympic and Cascade ranges. Bring your own food and drinks; an ice-filled cooler, blankets, and jackets are provided.

“Smooth sailing, nice route, calm waters. Discrete staff. Pleasant experience. Wished for more wind/speed”

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9.Guided Seattle Sailing Adventure from Bainbridge Island

★★★★★★★★★★5.0 · 82 reviews · 2 hours (approx.)

Join Captain Scott of Sail Rumbera for a private two-hour sail from Bainbridge Island. Walk from the ferry landing and Winslow to the departure area, pass through Eagle Harbor, then raise the sails and take in Seattle, Mount Rainier, the Olympic Mountains, and Puget Sound. Expect local history, a chance to help sail, and possible wildlife sightings.

“Our family enjoyed the peaceful sail around the sound. Being from out of town and non sailors, Scott provided us with engaging information on sailing and the areas history. Would highly recommend for anyone looking to see the area in a relaxing atmosphere out on the water.”

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10.Elliott Bay Sailing Cruise

★★★★★★★★★★4.7 · 40 reviews · from $60

Meet the Sailing Seattle crew at Pier 56 for a two-hour sail aboard one of two U.S. Coast certified yachts, originally built for ocean racing and refitted for comfort. Bring your own food and drinks, dress warmly, and enjoy views of downtown Seattle, Elliott Bay, and, if conditions allow, Mount Rainier and the Olympic Mountains.

“Rex was great and was a very nice relaxing time. Thanks”

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11.Sail Bainbridge Island & Seattle Waters – Luxury Classic Sailboat

★★★★★★★★★★5.0 · 26 reviews

Join Captain Ben for a two-hour private sail on a 44-foot ketch, departing Bainbridge Island for a route along the island shore or toward Seattle’s skyline. Your group of up to six can take the wheel, learn sailing basics, or relax while you watch for mountain views and wildlife. The meeting point is on Bainbridge, a 30-minute ferry ride from Seattle.

“Somehow we managed to find a rare day in the Puget Sound — no wind at all! But Captain Ben still gave us a great tour that even our college-age kids enjoyed. The sailboat was beautiful and Capt. Ben has a wealth of knowledge about the area. We’ll be back to try sailing!”

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12.Half Day Sail Orcas Island

★★★★★★★★★★5.0 · 15 reviews · 3 hours (approx.)

Spend about three hours sailing around Obstruction Pass with an experienced captain who teaches sailing terms and gives you hands-on time at the helm. The private lesson costs $680 for up to six people, with morning or afternoon departures. The captain is named Nate or Nat in accounts of the experience, so confirm who will lead your outing when booking.

“Do it! Nat is the absolute best! So knowledgeable and makes sure everyone is comfy. You will need to dress warmly any time you're out to Seattle but other than that, you don't really need anything.”

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13.Sailing Charter

★★★★★★★★★★5.0 · 5 reviews · 1 to 3 hours (approx.) · from $195

Set sail from John Wayne Marina aboard the Ingrid Princess, an ocean-going, full-keel ketch, for a small-group trip on the Strait of Juan de Fuca. Captain Tracy offers English-language sailing instruction, drinks, and a chance to take the helm or help handle the sails. No sailing experience is needed; the charter lasts about one to three hours.

“What a beautiful and peaceful outing. Just what we wanted. This was our first time sailing and it was great!”

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14.Sail Bainbridge Island & Seattle Waters – Classic Sailboat

★★★★★★★★★★5.0 · 3 reviews · 2 hours

Sail for two hours from Bainbridge Island aboard a 44-foot classic ketch with Captain Ben, a USCG licensed captain with more than 5,000 miles of ocean passage experience. Take the wheel or relax on deck while you look for sea birds and marine life, with Seattle, Bainbridge Island, and distant Mount Rainier in view.

“Our family had an unforgettable sailing trip with Sail Bainbridge. It’s about a 30-minute ferry ride from downtown Seattle to the beautiful Bainbridge Island, where we also checked out some charming shops and great cafes during our day. The Sail Bainbridge boat is absolutely gorgeous, super sturdy and comfy, making us feel safe and relaxed the whole time. Captain Ben was so friendly, knowledgeable, and passionate about sharing the area’s natural beauty. Sail Bainbridge has been doing this for 10 years, and after looking at other options around Seattle, we knew they had the most beautiful boat and offered private sails just for our family instead of group trips with…”

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