Location OverviewPenn Cove on Whidbey Island Washington
Penn Cove is a long, protected inlet on the west side of Whidbey Island, opening into Saratoga Passage and the Salish Sea. On clear days, these surrounding waters offer views of Mount Baker, the Olympic Mountains, and the Cascade Range.
Fed by the tides of the Salish Sea, the cove’s nutrient-rich waters support shellfish farming and a thriving marine ecosystem. Blue herons, harbor seals, and occasionally transient orca whales are among the wildlife often encountered on our sails. These are also the home waters of Captain Paul, who has spent years exploring and sharing this remarkable place.
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Our sailing charters begin and end at the Captain Whidbey dock, making the inn a great place to stay while sailing with us on Whidbey Island.
What’s included:
Personal safety equipment, sailing instruction, inflatable paddleboards, and onboard snacks and refreshments.
Capacity:
Our charters are privately booked for groups of up to 4 guests. Families and adult groups are welcome.
Home port:
Our Penn Cove charters depart and return to the Captain Whidbey dock.
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![A red wooden building on a pier over water, with people walking and a sailboat docked nearby at the Coupeville pier.]()
Half day sail
Spend the afternoon sailing Penn Cove from the unique perspective of our trimaran.
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![A sailboat named 'WINDY' anchored near the rocky shore with a swimmer approaching from the water during daylight, with a forested island and cloudy sky in the background in Penn Cove.]()
Full day sail
Step away from the busyness of life on land and join us for a summer’s day exploring Penn Cove by sail.
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Crab & Sail
Combine the hands‑on experience of crabbing with the leisure of sailing. Pull pots from our trimaran, and enjoy lunch featuring the catch of the day in a secluded cove.
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![Two women sitting on a boat deck, relaxing by the water with a distant shoreline and trees, enjoying a sunny day In Penn Cove.]()
Custom sailing experience
Interested in planning a custom sailing experience? Please reach out, and we would love to collaborate with you.
Our Trimaran
Guests – 4
Interior heat - Main Cabin Dimensions – 24' by 18'
Sail plan – Mainsail, Jib, Screecher, and asymmetrical Spinnaker
Windy offers a comfortable, unique day-sailing experience, with an 18-foot beam and expansive nets between her hulls that create a surprising amount of open, enjoyable space on the water. Her modern sail plan and performance-driven design ensure every outing is engaging and exhilarating for both first-time boaters and seasoned sailors.
Windy combines lightweight performance with comfort, making her ideal for sailing the waters of Penn Cove and the San Juan Islands. A private onboard toilet and cozy cabin heater provide comfort throughout the day, while on-deck blankets keep you warm. Automatic life jackets from Mustang Survival provide state-of-the-art safety for every guest.
