Explore our Sailing Experiences


Morning & Evening Sails on Penn Cove

Whether you’re curious about sailing, excited to spot local wildlife, or simply looking to relax on the water, our 2-hour sails are a perfect way to experience the magic of Penn Cove this summer.

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Half-Day Sail on Penn Cove

Set sail from Captain Whidbey for a 3.5-hour tour through Penn Cove — by water and land — with time to sail, learn about local wildlife and history, and explore the charm of the historic Coupeville waterfront.

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Full Day sail on Penn Cove

Experience the freedom of day sailing as we explore the best of Penn Cove — all from the comfort of our sailboat.

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Day Sail to the San Juan Islands

Set sail for a day in the San Juan Islands—a unique journey through a stunning archipelago, with multiple island stops and open-water sailing on a warm summer day.

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Multi Day Sail to the San Juan Islands

Explore the Salish Sea on a multi-day sailing experience through the San Juan Islands—featuring overnight island camping or the option to stay at the iconic Rosario Resort. 

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