Location OverviewExplore Penn Cove
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 waters offer views of Mount Baker, the Olympics, and the Cascade Mountain 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.
Included:
Safety equipment, sailing guidance, paddle boards, light appetizers and refreshments. Lunch is included on our full-day experiences.
Capacity:
Private charters are designed for groups of up to four guests. Families and adult groups are welcome.
Departure Location:
Penn Cove sails depart from and return to the Captain Whidbey dock.
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Wake at the Inn. Enjoy coffee and breakfast a quiet walk through the grounds and a short stroll to the dock for your morning or afternoon sail. Book your stay below.
Penn Cove Sailing Expireinces
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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
Set out for a full day of sailing on Penn Cove, with time to explore quiet beaches, paddle board along scenic shorelines, and enjoy a picnic ashore.
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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
Available as a shared small-group sail or private charter.
Step aboard and sail Penn Cove, where steady winds and scenic views make a great addition to a summer day on Whidbey Island.
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Crab & Sail
Spend the day sailing and crabbing. Pull pots from the trimaran, before gathering ashore for a fresh crab lunch.
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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.
What makes sailing on Windy unique?
High-performance sailing designed for comfort, connection, and adventure.
Comfort on Deck
Expansive trampoline seating, deck cushions, and a heated cabin create inviting spaces to relax throughout the day.
Thoughtful Safety & Amenities
Modern Mustang inflatable life jackets, onboard refrigeration, a private marine toilet, and a Bluetooth sound system create a comfortable, fun onboard atmosphere.
Engaging Performance Sailing
Windy’s lightweight trimaran design delivers a stable, hands-on sailing experience for small groups of up to four guests.
“Windy is both thrilling and comfortable — one of the most enjoyable boats I’ve ever sailed. Her width and amenities make the experience easy and comfortable for everyone. With Captain Paul at the helm, you’re in expert hands.”
— Joe R.
