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, thoughtful, and adaptable. Our half-day experience welcomes every skill level, allowing guests to learn together as a crew under the guidance and hospitality of Captain Paul. The lessons learned on the water build more capable sailors—and greater confidence in ourselves.
Private All-Inclusive Sailing Coaching
For one to three guests
Rate: $700
Applicable taxes are additional. Gratuity is appreciated but never expected. -
![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
Together, we’ll explore sail trim, navigation, anchoring, and what it means to work well as a crew. Sailing teaches us to pay attention, adapt to changing conditions, and make many thoughtful decisions that collectively govern how a sailing adventures is experienced and enjoyed and how the boat sails
Private All-Inclusive Sailing Coaching
For one to four guests
Rate: $225 minimum of 2 hours
Applicable taxes are additional. Gratuity is appreciated but never expected. -
![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
Together, we’ll plan passages, study tides and currents, navigate between islands, and adjust as conditions change. Each day builds seamanship, confidence, and connection—while teaching us how to lead, care for one another, and create experiences that will not soon be forgotten.
Add a Learn-to-Sail Immersion to Any Charter
Hands-on sailing instruction throughout your experience
$225 per day
Sailing lesson with Paul was such an enjoyable way way to learn. He brought his infectious energy and happiness, and we can tell teaching people how to sail is his passion. We learned to use our senses to find the wind direction and sail into the wind by tacking. He gave us jobs on the sailboat from the start, which made us all very engaged and invested in the common goal - moving the boat in the right direction. Then the jobs switched so we can learn another role. Once the boat gets up to speed, it's a great feeling. Smoothing sailing with the sound of bubbles and wind, and not a drop of diesel in use.
A couple hours later we ran into a challenge because the winds stopped. How does one sail when there is no wind? Well, Paul knew where to find wind by being a keen observer of the water. Even the challenging part was fun because it is a lesson to be flexible and adapt to the conditions.
You hear young people say, "It's a vibe," it totally is a vibe on Paul's boat. He had awesome music, a smorgasbord of snacks, drinks, space to lounge on the trimaran, and a happy dance from time to time. We are hooked. Hasta la proxima.
If you were thinking about learning to sail, Paul is the definitely the guy to learn from.
- Courtney 9/13/26
Learn to Sail
Personalized sailing instruction for up to four passengers on Whidbey Island, Washington.