Skagway Sunset Sailing Cruise

Sail Northwest Adventures Magical and Unforgettable! We sailed with Capt Brendan on Hopscotch in late May 2026 and it was the absolute best excursion of any cruise we have taken. After a short walk from our cruise ship berth to the small boat harbor, we were greeted by Captain Brendan and boarded Hopscotch. Since this was my first time on a sailboat, I was unsure what to expect but by the end of our 2.5 hour long adventure, I fell in love with sailing and Alaska. The boat itself is spacious, beautifully maintained and piloted by someone with a deep, authentic love for the water, the geography and the history of Skagway. We motored out to the end of the fjord and sailed our way back in. Along the way, Brendan shared his passion for the mechanics of sailing (answering my million questions) and the surrounding geography and wildlife. There was a seating section of the boat that was enclosed if you wanted to keep warm while still enjoying the scenery as well as bean bag chairs on the forward section which allows you to literally kick back and enjoy the breeze. I learned so much about the local wildlife and the people who live and work in the town. We even had the most magical moment of our entire vacation when a humpback whale popped up near the boat and we were able to observe it for about 20 minutes on our way back in to the harbor. Brendan was incredibly kind and patient. He put my mind at each right away with explaining everything we were gonna do and all the noises we were going to hear. He constantly checked in with us to make sure we were comfortable. I cannot imagine having had a better first sailing experience. If you had to pick just one excursion on your Alaska trip, this is the one! We had fairly magical time that we will never forget.

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