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    Paint the Town

    4.0 (2 reviews)
    Closed 9:00 am - 5:00 pm

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    Sailing Seattle

    Sailing Seattle

    4.6
    (126 reviews)

    An absolute must this summer if you live in or near Seattle! I had such a great time. The crew was…read moreinformative and kind, and the views were out of this world. I'm so sad that I just discovered this sweet family owned business only recently! From here on out, I'm bringing visiting guests, family, and friends on this tour. Surprisingly affordable at $40 for locals, I definitely recommend. Spoiler- you're allowed to bring drinks on board!

    This is a great way to experience a Seattle sunset. My friends and I decided to do a sunset sail…read moreand was impressed with the overall experience. This sailing was 2 hours long and the stays within Elliott Bay. Sailing Seattle has a fleet of 3 yachts. We were on a their largest vessel, S/V Obsession. This ocean racing yacht was designed by Sparkman & Stephens and was built for training US America's Cup teams. This yacht can accommodate up to 48 passengers and has a total length of 70ft. We boarded from Pier 56 and settled in for the 2 hour narrated journey. Boarding was seamless. The yacht has some non-slip surfaces and grab handles to help with balance and traction. Seats are first come first serve. After a brief safety demonstration on life vests, we set off on our sunset sail. This experience was further enhanced by their BYOB rule. We were allowed to bring our own snacks, wine, and beer. Our sailing path weaved in and out of ferry lanes and we completed some sharp turns, really showcasing the agility of the yacht. We pulled in after sunset providing everyone a beautiful nighttime view of downtown Seattle and waterfront. Service was fantastic. The crew was friendly and efficient. My biggest recommendation when doing the sunset cruise is to layer up (sweater/jacket) or even bring a nice blanket.

    Paint the Town - paintandsip - Updated June 2026

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