Location OverviewResort Sail to the San Juan Islands
Departing from Skyline Marina, we begin our journey by crossing Rosario Strait for James Island. Along the way, always be on the lookout for local wildlife like harbor seals, porpoises, bald eagles, and, if we’re lucky, orcas.
We’ll anchor for lunch and explore the islands before heading out for our next paradise, Watmough Bay, where you can explore the shoreline, hike to the lookout, swim, or try paddleboarding near the kelp beds, all while soaking up the summer sun.
On the return sail, you’re welcome to join Captain Paul at the helm and learn the basics of sailing or sit back and enjoy the peace of the wind in the sails as we make our way back to Anacortes. Onboard snacks & refreshments are included.
2026 availability:
August:
Roche Harbor → Lopez 3rd - 6th all inclusive private charter for up to 4 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
We’ll meet at Skyline Marina in Anacortes, where parking and restrooms are available. From here, we’ll step aboard and set out toward the San Juan Islands.
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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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Boulder Island
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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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.
