The 4 Best Bainbridge Island Trips from Seattle

1.Guided Seattle Sailing Adventure from Bainbridge Island

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

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…”

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

★★★★★★★★★★5.0 · 26 reviews

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 💯”

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3.Full-Day Small-Group Bainbridge Island Wine and History Tour

★★★★★★★★★★5.0 · 14 reviews · from $299Best value

Join guide Daniel in a Mercedes van for a nine-hour Bainbridge Island outing limited to seven people. Ride the ferry, walk through Bloedel Reserve, visit the Japanese American Exclusion Memorial, enjoy lunch, and taste local wine or beer.

“Daniel was an AWESOME, Tour Guide, knowledgeable, accommodating, organized, and thoughtful. Our tour on Bainbridge included a variety of activities and sites - we learned a lot and had a lot of fun times.”

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4.All – Inclusive Bainbridge Island Winery & Dinner Tour

★★★★★★★★★★5.0 · 13 reviews · 3 hours 30 minutes (approx.) · from $350

Meet your guide at the Bainbridge Island Museum of Art, then visit three or four island wineries in a heated, air-conditioned vehicle. You may meet winemakers, taste new wines from the barrel, enjoy dinner, and take home a souvenir glass. Guide Paul has earned praise for his warm hosting.

“Great excuse to go to Bainbridge! The Rolling Bay winery was superb! We will be going back for sure!”

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