A Perfect San Juan Islands Weekend Itinerary
- Thomas Tangen
- 5 days ago
- 3 min read
The San Juan Islands are where forest meets sea, ferry meets bike, and small-town charm meets epic PNW views. Just a ferry ride away from Anacortes, this island chain is a quiet escape filled with wildlife, slow mornings, and sunset kayaking. Whether you're going solo, with a partner, or tagging along with friends, this San Juan Islands weekend itinerary gives you the best of the islands in just three days.
Day 1: Ferry Ride, Friday Harbor, and Sunset Strolls
Morning:Start your journey with a scenic ferry ride from Anacortes to Friday Harbor on San Juan Island. If you’re traveling in summer, book a reservation ahead of time (especially if bringing a car). The ride itself is part of the magic—keep your eyes peeled for orcas or porpoises along the way.
Midday:Arrive in Friday Harbor and grab lunch at Cask and Schooner, a cozy pub with harbor views and a solid fish and chips plate. After lunch, stroll around the marina, check out the local art galleries, or stop by Pelindaba Lavender's flagship shop for a calming sensory reset.
Afternoon:Walk or drive to Lime Kiln Point State Park, aka Whale Watch Park. Even from shore, there’s a solid chance of spotting orcas if the timing is right. The short trails here offer clifftop views, a lighthouse, and benches for slow, thoughtful moments.
Evening:Head back into town for dinner at Downriggers, which features seafood with a view. Cap the night off with a drink at Cease and Desist Bar, or take a sunset walk along Spring Street before settling in.
Day 2: Wildlife, Water, and Small-Town Exploring
Morning:Fuel up with breakfast at Rocky Bay Cafe, a local favorite. Then it’s time for one of the most iconic San Juan experiences: a kayaking tour. Book with Discovery Sea Kayaks or San Juan Outfitters and paddle along the rugged coastline, possibly spotting seals, otters, or even whales.
Midday:After a morning on the water, enjoy lunch at San Juan Island Brewing Co. Try one of their seasonal IPAs and order a wood-fired flatbread or fish sandwich. The patio is a great spot to relax and people-watch.
Afternoon:Drive to English Camp—a historic park with trails, tidepools, and picnic spots. For a more adventurous hike, take the trail up Young Hill for sweeping views of the island and Vancouver Island in the distance.
Evening:For dinner, try Coho Restaurant, known for upscale local ingredients and a curated wine list. If the weather cooperates, catch the sunset at South Beach—one of the best and most underrated coastal viewpoints in the islands.
Day 3: Slow Start, Island Hopping, or Scenic Return
Morning:Start your final day slow with coffee and pastries from Salty Fox Coffee. Sit near the water and enjoy the quiet rhythm of island mornings. If you’re up early, walk the Friday Harbor Labs trail—a peaceful, forested loop near the water.
Option A – Stay on San Juan Island:
Visit the San Juan Islands Sculpture Park near Roche Harbor
Stop by Roche Harbor Resort for lunch and walk through the historic property and marina
Option B – Day Trip to Orcas Island:
Take the inter-island ferry to Orcas
Hike Mount Constitution in Moran State Park for panoramic views
Visit the village of Eastsound for local shops and food before heading back
Afternoon Return:Catch your ferry back to Anacortes in the afternoon or early evening. Be sure to check the sailing schedule and arrive early, especially on Sundays.
The San Juan Islands offer the perfect mix of calm exploration, cozy eateries, and wild beauty. Whether you spend your weekend spotting whales, sipping coffee near the dock, or watching the sun melt into the Salish Sea, it’s hard not to feel like time slows down out here.
Want a customized San Juan Islands weekend itinerary that matches your style—more hiking, more wine, or more art? I can build one just for you.Planning a trip to Orcas, Lopez, or a special event in the islands? Drop a comment and I’ll write about it in a future field report.
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