Pacific Northwest: The San Juan Islands

6 DaysStarting at $3,995


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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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 Grand B&B
  • Ending Point:

    Eastsound – 9:00 am – Orcas Island

Dates & Prices

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Family Departure

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


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 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.