Location OverviewResort Sail to the San Juan Islands
Arrive by float plane or ferry for a sailing adventure that blends long summer days aboard Windy with the charm and comfort of seaside inns and small island towns.
Begin with two nights at historic Roche Harbor, with days spent exploring nearby islands, beaches, and walking trails, along with opportunities to paddleboard, swim, and enjoy our daily picnic lunches ashore. Along the way, we keep watch for seals, bald eagles, and whales as we explore this rich ecosystem where Captain Paul grew up.
We then sail north to Orcas Island, where evenings are spent enjoying the restaurants, shops, and galleries of Eastsound. By day, we explore destinations such as Sucia and Clark Island aboard Windy. Guests are welcome to take the helm and sail with Captain Paul or simply relax and take in the scenery as we travel between the islands and enjoy the unique activities each destination offers.
2026 availability:
August:
Roche Harbor → Lopez 3rd - 7th all inclusive private charter for up to 2 passengers: $4,600 + tax + tip sold out
Custom dates may be available upon request. Please reach out to inquire.
Guests can travel by ferry from Anacortes or by float plane from Seattle. We’re pleased to assist with coordinating your travel details.
“We had such a great time on the water with Paul.”
We had such a great time on the water with Paul. Paul produces a combined environment for having fun while learning how to sail. You can be as engaged as you want, hands on, and sail or simply relax. Paul puts a great spread of food and drinks out and is unendingly chearful, funny and full of energy and information about the area we sailed in. We already have our trip planned for next year and are doubling down on the experience with time on the water and travel. We are so lucky to have Paul and his fun Tri in our home area. Thank you so much Paul!
Sailing Itinerary
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Skyline Marina
San Juan Island can be reached by ferry or float plane arriving at our meeting location in Roche Horbor mid day on day one to get settled at Hotel De Haro and set out for our first evening sail.
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Roche Harbor
Leaving the Amalfi Coast behind, we sail to the island of Capri, navigating among iconic grottos, super-yachts, and dramatic limestone arches. After lunch and a swim, we cross the Gulf of Naples to Ischia, where we anchor beneath the striking Castello Aragonese, an island castle once home to exiled royalty and medieval nobility.
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Watmough Bay
Watmough Bay is one of the San Juan Islands’ hidden gems. Guests can take a short hike to a breathtaking viewpoint over the cove, or simply relax on the beach and enjoy a swim in the calm, sheltered waters.
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Bird Rocks
These small rocky islands sit at the entrance of Penn Cove and are home to seabirds and seals and sea lion. Sailing past, we often spot cormorants drying their wings and seals lounging in the sun
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James Island
We’ll stop at James Island, a quiet marine park with beaches and trails, the perfect spot to enjoy lunch and stretch your legs before we sail on.
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Sunset Sail back to Skyline Marina
We’ll end the day with a peaceful sail back toward Skyline Marina, watching the sky change colors as the sun sets over the islands.
Explore our trip map
Please familiarize yourself with the region through our custom trip map. Each pin marks a stop on our tour and offers a glimpse into the experiences we look forward to guiding you through during your time aboard.
