Trip OverviewFull Day Sail on Penn Cove
Join us for a summer day exploring Penn Cove. Sail through the mussel farms and along the shoreline to the historic Coupeville Wharf with a view of the waterfront from the perspective of the water.
After a brief stop, we continue on to our lunch location. Relax on the beach or explore the shoreline by paddleboard as lunch is prepared and served beachside overlooking the Cascade Mountains. Throughout the day, you’re welcome to take the helm and learn the basics of sailing, or simply settle in and enjoy the scenery and wildlife as Windy sails. Each daytrip can be tailored to your group’s interests.
2026 Availability
7 Hour Sailing Times:
11:00 am - 6 pm
Private all-inclusive charter with lunch 1–4 passengers: $1,150 + tax + tip
Booked dates are removed from this page.
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3rd, 4th, 5th, 6th, 9th, 10th, 11th, 12th, 13th, 17th, 18th, 19th, 20th, 24th, 25th, 26th, 27th
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26th, 27th
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10th, 11th, 12th, 13th, 17th, 18th, 19th, 20th
Sailing itinerary
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Meet at 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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Tour 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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Dock at the Coupeville Pier
After about an hour and a half of exploring by sail, we’ll stop at the Coupeville Pier to stretch our legs, use the restroom, and learn about this charming town before setting sail to our lunch anchorage.
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Explore Penn Cove
After our stop at the Pier, we will set sail down the bay on a tour of Penn Cove in search of a beach location to enjoy lunch, beach walks, and the opportunity to paddle board.
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Paddle board tour before lunch
One of the unique things about sailing on Windy is our hands-on approach to the experience. Don’t miss the chance to get out on our paddleboards before lunch on the beach.
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Lunch on the beach
As we roll out the Italian tablecloth and prepare lunch, guests enjoy time on the beach before gathering together for a meal inspired by local ingredients and the flavors of the region.
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Return to Captain Whidbey
After a day of adventuring, we’ll enjoy the afternoon winds as we sail Windy back up the bay and return to the dock in the evening light.
We had such a memorable and fabulous time on board with Captain Paul. His knowledge of the surrounding environment and his ability to make us feel at home on the water were truly incredible. Sharing travel stories, laughing, and experiencing something new was an absolute pleasure. Thanks so much, Paul! Can’t wait for the next adventure.
- Katie
General Information
How do we reserve our trip?
Contact us by email with your preferred listed date, and reserve your trip with a 50% nonrefundable deposit by credit card.
What is included in the all-inclusive trip price?
Two rounds of alcoholic and non-alcoholic beverages, lunch, snacks, and photographic coverage of your trip by Captain Paul.
What’s not included in the trip price?
All onshore expenses, gratuity, and transportation to and from the boat.
Can we request a custom itinerary?
Yes, within the time and area of our charter. If you’d like to create a journey elsewhere, please let us know.
What are the guest requirements?
Guests must be comfortable on boats with prior expirience, able to swim, willing to wear a provided life jacket, and meet a per-person weight limit of 250 lbs, with a maximum total of 850 lbs for up to four guests.
Can you accommodate dietary restrictions & preferences?
With advance notice, we’re happy to accommodate when possible. Just include any details in your email.
What is your age limitation?
Our age limitation is based on the size of our child life jackets, which typically fit children around 4–5 years old depending on weight. Please specify in your email, as we love having families aboard.
