The 12 Best Sailing Trips in Seattle

1.Seattle Sailing Harbor Tour

★★★★★★★★★★4.5 · 473 reviews · 2 hours (approx.) · from $39Our pick

Sail Seattle’s waterfront on a historic tall ship from Pier 66. 2 hours of skyline views, possible Mount Rainier, and onboard restrooms.

“The ride was awesome great views wonderful and friendly and knowledgeable crew and even enjoyed the Seattle rain along the way got to check something off of a bucket list item was a great experience overall”

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2.Tall Sailboat Sunset Harbor Cruise

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

Sail Seattle Harbor at sunset on the Bay Lady from Pier 66. Help hoist sails, steer by wind, and enjoy skyline lights with a bar onboard.

“We got lucky and the weather was fantastic. We enjoyed a beautiful sunset on the boat. The crew were really knowledgeable and extremely welcoming.”

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3.Seattle Sailing Experience BYOB

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

A 2-hour BYOB sail on a 70-foot yacht from Seattle’s Alaskan Way, with skyline views, trained crew, and wind-powered cruising.

“Beautiful, well maintained boat; friendly and professional crew. This is an excellent value, just make sure to dress for the weather!”

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

★★★★★★★★★★5.0 · 126 reviews · 3 hours (approx.) · from $549

Private 3-hour Puget Sound sailing from Shilshole on S/V Kingsley. Day or sunset, BYOB, skyline views, wildlife, small group up to 6.

“Our family of 3 had a wonderful experience. Winds were low that day, so not much "sailing," but Russ still made it a great afternoon! He was full of information and fun conversation. We hung out in the Sound, ventured near the Locks, and watched some seals swimming near the rocks. Sunny and temps in the 80s, so no jacket/sweatshirt needed for us. Beautiful surroundings, very peaceful. Highly recommend Russ and his tour.”

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5.Sunset Sailing Cruise

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

A 2-hour Seattle sunset sail on a 70 ft ocean yacht over Elliott Bay, with skyline views, Mount Rainier, BYO drinks, and friendly crew.

“Loved the sunset cruise! Our guide was so nice! She spoke and explained everything so well! The weather and the sunset were beautiful!”

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6.Sailing Cruise

★★★★★★★★★★4.9 · 90 reviews · from $49

1.5-hour sailing on Elliott Bay from Pier 56 for great skyline and Mount Rainier views. Bring your own food on a 70ft sailboat.

“Great way to spend a few hours! It was a beautifully sunny day, not super windy. Our guides were helpful and informative. Definitely would do it again!”

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7.Guided Seattle Sailing Adventure from Bainbridge Island

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

Private 2-hour sailing from Bainbridge Island across Puget Sound, with Seattle skyline, Mt. Rainier views, and quiet sail time.

“A wonderful sail on Elliot Bay with Captain Scott. He gave us loads of background information about the area, wildlife, general history and social life. A very enjoyable afternoon.”

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8.Elliott Bay Sailing Cruise

★★★★★★★★★★4.7 · 40 reviews · from $60

2-hour Elliott Bay sail from Pier 56, bring-your-own booze, skyline and mountain views, friendly crew, high-performance yachts, $60.

“Crew friendly and proficient with their sailing abilities. Thought we would go further into the Puget sound but we stayed in the bay. Just went straight out and turned around to come back. Was also hoping for more info on the areas we were looking at, but crew was more interested in talking to another local about restaurants etc.. who was on the boat too.”

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

★★★★★★★★★★5.0 · 26 reviews · from $475

Private 2-hour luxury sail from Bainbridge to Seattle skyline on a 44 ft classic ketch with Captain Ben and calm Puget Sound views.

“First visit to Bainbridge. We had such a nice time sailing and weather was perfect. Getting to enjoy the water was a treat and our captain was super.”

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10.Mid-Day & Sunset Sailing on Seattle’s Majestic Puget Sound

★★★★★★★★★★5.0 · 23 reviews · 2 hours 30 minutes (approx.) · from $120

Mid-day or sunset sail on Puget Sound from Shilshole Bay. Small group of 6, fleece onboard, wildlife, Rainier and Olympic views.

“Our day was hazy and cool but I'm not sure if it could have been any better. The Olympic Mtns were steeped in clouds and mist which gave them a magical aurora. When the sun set behind them the color radiated though the clouds lighting up the sky making the light on the water sparkle.”

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11.Sail Bainbridge Island & Seattle Waters – Classic Sailboat

★★★★★★★★★★5.0 · 3 reviews · 2 hours · from $445

Private 2-hour sailing from Bainbridge Island to see the Seattle skyline, islands, wildlife, and maybe whales on a classic ketch.

“I loved this sail so much the first time that we brought our kids along for the second experience, and they absolutely loved it too! As a returning customer, I can honestly say it’s totally worth the cost, and don’t think twice—do this, you won’t regret it! We saw a rare elephant seal, which was incredible to witness, and Captain Ben also saw orcas with clients the day before—something I didn’t even know we might see! Going to have to go a third time. Be sure to grab a coffee from the adorable, Instagram-famous Pegasus Coffee at the marina before heading out—it's the perfect start—and they also offer amazing sunset…”

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12.Puget Sound Sailing Adventure

★★★★★★★★★★5.0 · 1 reviews · 3 hours · from $549

Private 3-hour Puget Sound sailing for up to six from Seattle. Calm views, wildlife chances, hands-on sailing if conditions allow.

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