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 sailboat anchored near a rocky shoreline with green shrubs, with mountains in the background during sunset.
A coastal town with a harbor filled with boats, buildings lining the shoreline, and a mountain in the background under a partly cloudy sky.
Person jumping off a rocky cliff into a body of water with buildings and hills in the background under bright sunlight.
A wooden dock extending into a body of water with a sailboat moored, surrounded by trees and hilly terrain, under a partly cloudy sky.
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 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.
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 boat with two people on the water at sunset, with a large rock formation in the background and sky filled with warm colors.
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 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.
The image shows a whale fin emerging from the water near the side of a boat, with the ocean and sky in the background.

Pacific Northwest day sails to immersive week-long journeys abroad.

“Adventures shaped by curiosity, connection, and a love for life on the water.”

Each year, we return to familiar ports and anchorages, deepening our connection to the places and communities 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 traditions that find their way back to our galley and the meals we share aboard. Guests experience these places not as tourists, but as welcomed visitors arriving and departing by water as sailors have for generations.

International Destinations

  • 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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Pacific Northwest Itineraries

  • 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 variety of sea life, best seen from the nets of our trimaran. This itinerary offers a unique perspective on our home waters and makes a perfect addition to your Whidbey Island visit.

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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.

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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

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.

Learn more

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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