Location OverviewA Day Sailing in the San Juan Islands
The San Juan Islands sit between Whidbey Island, Vancouver Island, and the Canadian mainland, at the meeting point of the Salish Sea and the Strait of Juan de Fuca. This archipelago of forested islands, narrow channels, and protected anchorages has long been traveled by water, first by Coast Salish peoples and later by fishermen, traders, and curious sailors like us!
Join us as we explore the islands’ beaches, trails, and wildlife during the summer months. Our itineraries offer an easy escape into the islands for a day or a long weekend, all within close proximity to Seattle, Washington.
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For those looking to explore the Pacific Northwest in depth, a stay at Captain Whidbey paired with sailing to the San Juan Islands offers a rich and memorable experience of this remarkable place.
Included:
Safety equipment, sailing guidance, paddle boards, light appetizers, lunch, and complimentary refreshments.
Capacity:
Private charters are designed for groups of up to four guests. Families and adult groups are welcome.
Departure Location:
San Juan sails depart from Skyline Marina in Anacortes.
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![A red wooden building on a pier over water, with people walking and a sailboat docked nearby at the Coupeville pier.]()
Full Day Sail
Join us on an adventurous day sailing through the San Juan Islands, with multiple island stops, a lunch prepared for you on the beach and open-water sailing aboard our performance trimaran.
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![A sailboat named 'WINDY' anchored near the rocky shore with a swimmer approaching from the water during daylight, with a forested island and cloudy sky in the background in Penn Cove.]()
Multi Day - Camp Sail
Explore the Islands on a multi-day sailing experience, featuring overnight island camping, meals prepared with locally sourced ingredients, followed by nights of stargazing during the Perseid meteor shower.
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![Two women sitting on a boat deck, relaxing by the water with a distant shoreline and trees, enjoying a sunny day In Penn Cove.]()
Multi Day - Resort Sail
Spend your mornings exploring quaint sea side towns and your days sailing to different islands. When evening comes after a day of adventure, return ashore for dinner and a restful night at a our favorite local inns.
Our Trimaran
Guests – 4
Interior heat - Main Cabin Dimensions – 24' by 18'
Sail plan – Mainsail, Jib, Screecher, and asymmetrical Spinnaker
Windy offers a comfortable, unique day-sailing experience, with an 18-foot beam and expansive nets between her hulls that create a surprising amount of open, enjoyable space on the water. Her modern sail plan and performance-driven design ensure every outing is engaging and exhilarating for both first-time boaters and seasoned sailors.
Windy combines lightweight performance with comfort, making her ideal for sailing the waters of Penn Cove and the San Juan Islands. A private onboard toilet and cozy cabin heater provide comfort throughout the day, while on-deck blankets keep you warm. Automatic life jackets from Mustang Survival provide state-of-the-art safety for every guest.
