San Juan & Orcas Islands

San Juan Islands Cultural Walking Adventure

6 DaysStarting at $4,795


Get ready to be inspected by a wild Orca making a “spy hop” 20 feet off the port bow.  To discover huge grape- and pumpkin-colored sea stars clinging to the shaded side of a boulder at low tide. To go sea-kayaking, meet artisanal producers of wine, lavender, gin and ceramics, hike scenic mountain trails surrounded by blue water and green islands. It’s all ready and waiting for you, right now, in the San Juan Islands. They’re jewels—just remote enough—sprinkled across fine blue waters, accessible only by ferry, but not far from Seattle. Surrounded by snow-capped peaks, the islands are in the heart of the Pacific Northwest’s “banana belt”. They’re gorgeous, too, from their mountainous heart to their photogenic shorelines. With Classic Journeys, you get to do it all with no hassles and non-stop fun. The San Juan Islands are a classic off-the-grid destination, a well-kept secret of Northwesterners for decades.  Now it’s your turn. Come experience them in Classic Journeys style. 

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Classic Journeys provides unbeatable access to experiences around the globe.”
Travel + Leisure


San Juan island’s Friday Harbor is your start point, where you’ll set off on a spectacularly scenic walk looking out to Mt. Rainier and the Cascade mountains. Your first day draws to a close with a delectable farm-to-table dinner, and unforgettable San Juan sunset. The next morning, a picturesque walk follows our favorite route for eagle and falcon-spotting, finishing at a fascinating sculpture garden. That afternoon, you’ll feel like we’ve teleported you to the French countryside. In fact, you’re in Westcott Bay, where you can taste award-winning local cider brandy, crafted by our friends Rich and Suzy. Sea kayaking off the wild west coast starts day 3, where Orca whales often make an appearance. (If you don’t fancy paddling, no problem, we’ll arrange a boat ride instead.) After a morning on the water, the afternoon’s activity is exploring a lavender farm. You’ll have to pinch yourself to remember you’re not in Provence.

Now for some island-hopping, over to idyllic Orcas Island. You’ll hike Moran State Park, home to the highest point in the San Juans and no end of show-stopping scenery. An afternoon stroll takes you through the isle’s only winery, for a vineyard picnic and personalized wine tasting. Just when you thought you couldn’t see more wildlife, along comes day 5, when a private boat takes you to secret spots for encounters with grey whales, humpbacks, porpoises, seals, sea lions, otters, bald eagles and much more. After a relaxing morning on your final day, you’ll say adios to this archipelago. Either take the ferry, or for one last treat book a seaplane back to Seattle. Maybe you’ll extend your trip with more days exploring the Pacific Northwest…Or, head home to share memories of a spectacular stay in the San Juans.

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  • Starting Point:

    Friday Harbor – 2:00 pm – Lobby of Friday Harbor House
  • Ending Point:

    Eastsound – 9:00 am – Lobby of Outlook Inn Orcas Island

Dates & Prices

The earlier you book, the more choice you’ll have and the lower your price. And you can always change your mind — you won’t be charged to transfer to a different trip before your final payment is due. Talk with one of our travel experts at 800-200-3887.

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Family Departure

Select our “Family Departure” to travel with other families.

Why Choose Classic Journeys

Travel + Leisure has awarded Classic Journeys the #1 World’s Best Tour Operator multiple times and says, "Classic Journeys provides unbeatable access to experiences around the globe." Here’s what that access means for you.

  • Experience the world on foot and at eye level. Each day, join your guide on the most cinematic footpaths in the region.
  • Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, share their lifelong connections as well as engaging anecdotes about the history and culture of the region.
  • Small groups that provide you unrivaled access. An average of fewer than 10 guests per departure means we can offer you special access to sites like Stonehenge so you experience the stone circle when it’s closed to the general public, a guided visit to Zion Narrows that other companies cannot arrange because of larger group sizes, and vineyard walks with a count and countess in Tuscany.
  • Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in the region you’re exploring, including rainforest lodges, 16th century villas, and award-winning properties that show up on World’s Best and Gold lists.
  • Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of the places you visit with us. From gourmet picnics to coveted local restaurants, our meals offer you opportunities to explore native food traditions and fine dining.
  • Handcrafted itineraries with all activities included. With our long-term friendships, we know our walking tour regions more personally than anyone else. So you get thoughtfully curated itineraries that combine explorations of the villages, organic farms, archeological sites and the people who know them best.
  • Sustainable travel that supports the places you’re visiting. We put our local currency into the pockets of the people who live where we travel. It’s your guarantee that you’ll have authentic, up-close experiences on your trip. Best of all, our person-to-person approach helps sustain their ways of life.
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Friday Harbor House

With its views of Friday Harbor and the ferry landing, this hotel offers rooms with Zen-like atmosphere, a picture window, fireplace and an oversized, jetted tub-for-two. Don’t miss the continental breakfast with homemade granola and local specialties.

Outlook Inn

The Oulook Inn boasts gorgeous views of Fishing Bay, and surrounded by charming shops, restaurants, and galleries that can be reached on foot. A farmers’ market is open in the summer and fresh, local cuisine can be found year-round.

What’s Included

  • 5 breakfasts, 2 lunches and 2 dinners
  • Full-time experienced guide(s) who are with you throughout the trip and handle behind-the-scenes logistics
  • Admissions to scheduled events as noted in the detailed daily itinerary
  • Gratuities for hotels, meals, and baggage
  • All land transportation during the trip

Above & Beyond Benefits

Invisible Check-In

  • When your group arrives, we whisk you and your bags to your room immediately. No waiting – no tipping.

Privileged Access Events

  • One-of-a-kind access to remarkable people, places and activities arranged just for you.

Perfect Pairings Dinners

  • A special dinner prepared by one of our favorite chefs with a procession of wines tailored to each course.

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