Adventures shaped by experience, curiosity, and a love for the outdoors.
Every year, we return to familiar ports and anchorages, deepening our connection to the place and the communities who live there. With every arrival, the experience grows richer.
We don’t just observe the culture; we live it. Restaurant owners welcome us to their tables like family, and market vendors guide us toward the ingredients that carry the region’s traditions back to our galley and the meals we share aboard. We experience these places not as tourists, but as welcomed guests.
Our days are full yet never hurried, and when the journey comes to a close, you’ll often find yourself in a quiet moment of reflection with those you chose to share this adventure with.
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![Beach scene with white umbrellas, lounge chairs, and people relaxing near rocky cliffs and clear blue water, with sailboats anchored offshore.]()
Italy
The Amalfi Coast and the Pontine Islands, set along Italy’s western shore in the Tyrrhenian Sea, offer dramatic coastline and a vibrant maritime culture shaped by centuries of life on the water.
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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
Across the islands of the Saronic Gulf, Greece’s ancient past remains present in historic harbors, island villages, living traditions, and the warmth of the Greek people.
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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, creating one of Southeast Asia’s most remarkable sailing landscapes.
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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
Come sail Penn Cove and discover the rich sea life surrounding the mussel farms as we pass Madrona-lined shores on our way to the historic Coupeville waterfront and wharf.
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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 Daysail
Spend a full day exploring Penn Cove. Sail beyond the waterfront, enjoy lunch on the beach, paddle board along the shore, and experience the freedom of sailing aboard Windy with Captain Paul for the day.
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![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 Juan Daysail
The San Juan Islands form a vast archipelago of forested islands, quiet coves, and wildlife-rich waters. Explore this unique Pacific Northwest ecosystem from the comfort of our trimaran, with countless places waiting to be discovered.
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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.]()
Camp Sail
Join us for three nights and four days to explore 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.]()
Resort Sail
Experience the Pacific Northwest by air, land, and sea with Captain Paul. This multi-day itinerary is tailored to your group, offering an immersive way to explore the region while returning each evening to the comfort of our favorite island inns.
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![Seaplane flying over water with a city skyline in the background during sunset.]()
PNW Retreats
This retreat blends sailing, island hiking, floatplane travel, and restorative sauna and cold-water experiences, with evenings spent in the comfort of Captain Whidbey Inn. Join us as we slow down and connect more deeply with the region and with each other.
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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
Set sail into environments rich with color and natural scenery, connect sketch and paint with the company of your fellow artists under the care and guidance of Captain Paul.
Featured itinerary:
Perseid meteor shower Camp Sail
Join us for three nights and four days exploring the San Juan Islands during the Perseid meteor shower. Spend your days sailing between islands and your evenings watching meteors streak across the night sky.
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.
