Sail with Us
Experience OverviewLearn to sail with us
Penn Cove Sailing Club is a boutique sailing school offering personalized sailing instruction for up to four passengers on the Salish Sea
Our mission is to connect locals and visitors with the beauty of Penn Cove through immersive sailing experiences that inspire learning, exploration, and meaningful connection in our community.
Whether you’re an experienced sailor or new to the water, Captain Paul offers a welcoming learning environment aboard Windy, his performance trimaran.
What’s included:
Personal safety equipment, sailing instruction, snacks, and refreshments.
Capacity:
Our charters are booked privately and accommodate up to four guests on board. Families and adult groups are welcome.
Home Port
Sailing lessons are privately booked and depart from either the Captain Whidbey dock or the Coupeville Wharf. For San Juan Island retreats, departures are from Skyline Marina.
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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
Sailing teaches us to be calm, calculated, and adaptable, encouraging good decision-making and proactivity in facing challenges.
We believe that lessons learned on the water make us more self-sufficient sailors and empower us as individuals.
Our half day caters to all skill levels, allowing students to learn together as a crew under the guidance of Captain Paul.
Private all inclusive coaching 1-3 passengers: $675 + tax + tip
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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.]()
Hourly training on your vessel
Sailing teaches us to plan a sail on the water, navigate to our destination, and embrace the freedom that sailing provides.
Sailing takes a lifetime to master—begin that journey with a day on Penn Cove with Captain Paul. Immerse yourself in an introduction to docking, anchoring, sail trimming, and itinerary planning, gaining hands-on experience to set you and your group on course to becoming sailors.
Private Coaching (1–4 Guests)
$225 per hour · 2-hour minimum + tax
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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.]()
Learn to sail retreat
A multi-day sailing retreat deepens the experience beyond a single destination. Together, we plan passages between islands, study tides and currents, anchor, and adapt to changing weather conditions. With each day on the water, you refine sail trim, practice navigation, and build confidence through real-time decision-making.
Over several days, the rhythm of sailing begins to settle in — developing seamanship, teamwork, and the awareness required to move safely and confidently between destinations.
Add a Learn-to-Sail Immersion to Any Charter +$225 per day
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Learn to Sail
Personalized sailing instruction for up to four passengers on Whidbey Island, Washington.