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    Paint the Town

    4.0 (2 reviews)
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    1 month ago

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    Celia M.

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    Sailing Seattle - Cheers to BYOB

    Sailing Seattle

    (125 reviews)

    Waterfront

    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.

    Very friendly crew. Captain Phil willingly shared information about himself and the sailboat…read more We got to see a few dolphins along the way. My only regret was not taking drinks with us. I totally missed reading this when we booked this cruise.

    Paint the Town - paintandsip - Updated May 2026

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