A coastal scene with a large mountain rising from the water, a small beach with houses along the shoreline, and a sailboat anchored in the bay under a partly cloudy sky off the island of Palmerola.
A beach scene with white sand, turquoise water, a sailboat anchored near the shore, and an island in the distance. Cloudy sky with overcast weather and green foliage partially framing the image.
A boat with two people on the water at sunset, with a large rock formation in the background and sky filled with warm colors.
A sailboat is anchored near the rocky shore of a calm, greenish-blue body of water, surrounded by a dense forest of trees under a clear blue sky.
Person jumping off a rocky cliff into a body of water with buildings and hills in the background under bright sunlight.
A scenic view of a waterfront with a small boat docked at a pier, seen through tall pine trees. Two people are sitting on a bench by the water, overlooking the scene. The sky is partly cloudy.
People on a boat watching fireworks over a coastal town at night.
Harbor view of colorful Italian seaside town with hillside buildings and mountainous backdrop.
A group of people on a paddleboard in clear blue ocean water, with one man standing and holding a drink in the air, and several others around him holding onto the paddleboard. There is a sailboat in the background under a cloudy sky.
A person sitting on a rocky cliff next to a boat and a large sailboat anchored in the water, with other people swimming nearby and mountains in the background.
Group of hikers walking along a rocky trail near a body of water at dusk, with mountains and a boat anchored in the water in the background.
A wooden dock extending into a body of water with a sailboat moored, surrounded by trees and hilly terrain, under a partly cloudy sky.
A coastal town with a harbor filled with boats, buildings lining the shoreline, and a mountain in the background under a partly cloudy sky.

Adventures inspired by curiosity, connection, and a love for life on the water.

Come for a day sail aboard Windy in the Pacific Northwest, or set out on an immersive week-long catamaran vacation abroad. Every experience offers a unique way to explore the beauty of the world around us.

International Destinations

  • Beach scene with white umbrellas, lounge chairs, and people relaxing near rocky cliffs and clear blue water, with sailboats anchored offshore.

    Italy

    Along the Amalfi Coast and into the Pontine Islands, vibrant seaside towns line the shore as generations of maritime culture, local cuisine, and island traditions shape an unforgettable journey best explored from our catamaran.

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  • A smiling couple standing on a rocky hillside overlooking a deep blue ocean with a sailboat anchored near rocky cliffs, with hills in the background on a clear sunny day.

    Greece

    Leaving Athens behind, we set course for the Saronic Gulf Islands, where modern Greek life unfolds alongside an ancient past—visible in historic harbors, ancient amphitheaters, and the warmth of the people who welcome us ashore.

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  • View from inside a cave overlooking the ocean with a small boat floating on the water, distant small islands, and a sailboat in the background.

    Thailand

    Along Thailand’s Andaman coast, limestone islands rise from emerald waters in Phang Nga Bay and the Phi Phi Islands, revealing one of Southeast Asia’s most remarkable sailing landscapes.

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Pacific Northwest Itineraries

  • A small sailboat is anchored near a shoreline with large driftwood logs on a pebble beach, surrounded by dense forest on a clear day.

    San Juans – Full Day Sail

    Explore the sandstone formations and forested islands of the San Juan Islands, where each stop offers new opportunities to experience this rich marine ecosystem, from scenic lookouts to relaxing on the nets of our trimaran.

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  • People relaxing on a sailboat on the water, with a view of the horizon and distant shoreline, during sunny weather.

    Penn Cove – Full Day Sail

    Depart the Captain Whidbey Inn for a full day of exploration on the water. Sail to remote beaches, share a picnic lunch ashore, and unwind under sail while those interested are invited to take part in sailing.

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  • A red brick building on a pier by the water with signages for gifts, food, coffee, exhibits, public deck, with people walking and a sailboat docked nearby.

    Penn Cove – Half Day Sail

    Lounge on the open nets during a half-day sail through the protected waters of Penn Cove. Marine life, coastal scenery, and hands-on sailing create a calm yet engaging experience aboard our performance trimaran.

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  • Person lying on a towel on sandy beach near two boats, with water and people swimming in the background, framed by leafy branches.

    Multi Day – Camp Sail

    Join us for three nights and four days to touring the San Juan Islands during the Perseids meteor shower, where days are spent sailing between islands and evenings are spent watching meteors streak across the night sky.

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  • A lakeside scene with a white railing pathway in the foreground, several people walking and chatting, lush green trees, and colorful buildings including a hotel named 'Hotel de Haro' on a hillside, with a clock tower and American flags. The reflection of the scene is visible on the calm water.

    Multi Day – Resort Sail

    Explore the Pacific Northwest by air, land, and sea with Captain Paul. Each multi-day journey is shaped around your group, combining active days of exploration with relaxed evenings at favorite island inns.

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  • Seaplane flying over water with a city skyline in the background during sunset.

    Multi Day-Sailing Retreat

    This retreat blends sailing, island hiking, floatplane travel, and restorative sauna and cold-water experiences, with evenings spent by the fire at Captain Whidbey Inn.

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  • Three women on a boat, smiling and holding watercolor paintings they created, with water and trees in the background.

    Plein Air Sail - Full Day

    Set sail into landscapes rich with color and natural beauty. Sketch and paint alongside fellow artists while exploring under the care and guidance of Captain Paul.

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Two people are sitting on a bench near the water, on James Island in the San Juan Islands, with trees and boats in the background on a calm day.

Featured itinerary:

Perseid meteor shower Camp Sail

Spend four days and three nights sailing through the San Juan Islands during the peak of the Perseid meteor shower. Days are spent exploring the islands under sail. Evenings bring dark, moonless skies with little light pollution, ideal conditions for watching meteors streak across the horizon.

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Client Reviews

Our sailing adventure was a "symphony of moments" and everything harmonized perfectly. Paul’s expertise with sailing created a very calm atmosphere.

— Em

“This was the best trip our family has ever had, BOOK IT! ”

— Chris Tuff

“We had such a memorable 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.”

— Katie

Explore a different way to come together as a community.

Paul draws from years of experience as a captain, photographer, and facilitator to share the practice of sailing during leadership events, retreats, and weddings. These experiences create space for connection, teamwork, and time on the water together.

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