Trip OverviewHalf Day Sail on Penn Cove
Come explore Penn Cove by sail. Whether you’re an experienced sailor or brand new to the water, Penn Cove offers a protected sailing environment with consistent afternoon winds throughout the summer.
Departing from the Captain Whidbey Inn, with a midway stop at the Coupeville Pier, this experience offers a unique perspective of the region and adds a true sense of adventure to your day. Guests leave with a deeper understanding of the geology, history, and local charm of these waters, shared by Captain Paul as he guides you through his home waters.
Each listed date offers two departures: 10 am and 2:30 pm. Booked dates are removed from this page.
2026 availability
Private all inclusive charter 1–4 passengers: $575 + tax + tip
3.5-Hour Sailing Times
10:00 am- 1:30 pm, 2:30 pm - 6 pm
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3rd 10am | 2:30pm · 4th 10am | 2:30pm · 5th 10am | 2:30pm · 6th 10am | 2:30pm · 9th 10am | 2:30pm · 10th 10am | 2:30pm · 11th 10am | 2:30pm · 12th 10am | 2:30pm · 13th 10am | 2:30pm · 17th 10am | 2:30pm · 18th 10am | 2:30pm · 19th 10am | 2:30pm · 20th 10am | 2:30pm
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26th 10am | 2:30pm · 27th 2:30pm
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10th 10am | 2:30pm · 11th 10am | 2:30pm · 12th 10am | 2:30pm · 13th 10am | 2:30pm · 17th 10am | 2:30pm · 18th 10am | 2:30pm · 19th 10am | 2:30pm · 20th 10am | 2:30pm
Sailing Itinerary
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The Captain Whidbey
Meet at the Captain Whidbey Inn 15 minutes before departure to use the restroom, grab a coffee, and join us at the dock for a brief safety orientation before setting sail.
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The Mussel Farms
Our first course takes us toward the mussel farms, sailing past seals and herons while learning about the history of shellfish farming in the nutrient-rich waters of Penn Cove.
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The Coupeville Pier
After about an hour and a half of sailing, we’ll arrive at the Coupeville Pier and step ashore to stretch our legs along the historic waterfront. Returning to Windy, we’ll set sail once more toward Blowers Bluff.
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Upwind sail
On our upwind sail, join Captain Paul at the helm for the opportunity to sail Windy, while others relax and enjoy the ride. Along the way, an appetizer featuring locally sourced treats will be served.
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Return to The Captain Whidbey
With a new appreciation for the cove and a deeper connection as a group, we’ll bring Windy back to the dock together as a crew. Time on the water has a way of bringing people closer together.
“I was lucky enough to spend the day with Paul on the Windy, and what an experience it was!”
We enjoyed the amazing views that Penn Cove has to offer, wove our way through the shellfish farms, learned of local marine life, and enjoyed the incredible company and perspective that Paul adds.
The Windy herself is a nimble beauty that effortlessly glides through the water like a knife through butter. We ended the day with some snacks and drinks, smiling the whole way home.
-Brooks
General Information
How do we reserve our trip?
Email us with your preferred date to reserve your trip. A 50% non-refundable deposit by credit card confirms your booking, with the remaining 50% collected at the dock prior to departure.
What is included in the all-inclusive trip price?
Our complimentary beverage offerings, one appetizer, snacks, and photographic coverage of your trip by Captain Paul.
What’s not included in the trip price?
All onshore expenses, gratuity, and travel to and from the boat.
What are the guest requirements?
Guests should be comfortable boarding and moving around a sailboat, confident in their ability to swim, and willing to wear a provided life jacket. For safety reasons, each person must not exceed a weight limit of 250 lbs.
