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Fly Out: Fly Away To the San Juan Islands

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Fly Away to the San Juan Islands


San Juan Flyout 2026
 

Join us on San Juan Island from Thursday, September 10th until Sunday, September 13th, 2026 for a relaxing but adventurous weekend with activities selected by YOU!  While only 185 NM from Portland, this magical, scenic archipelago of islands in the Strait of Juan de Fuca feels a world away.

 

On this fly-out, we chose the place, but you choose the pace.  The Earthbox Inn and Spa in Friday Harbor on San Juan Island will serve as our base of operations. Owned by CAA’s very own Roger May, it’s only 4 blocks from both the airport and the ferry terminal.  Relax in the jacuzzi, swim in the only indoor heated pool on the island and unwind with a massage at the on-property spa. CAA has a block of rooms available to reserve, and many are pet-friendly. CAA members will enjoy a 10% room discount.


San Juan Flyout 2026
 

Fly into Friday Harbor Airport (KFHR) VFR or IFR and enjoy the abundant secure transient parking, full-service FBO and complimentary shuttle service from your CAA Hosts, Mark & Aimee Tipperreiter. During the fly-out, you will enjoy nightly happy hours in the hotel’s garden courtyard and at least one group dinner, as well as complimentary shuttle service from your CAA hosts during your stay. We’ll organize activities throughout the weekend based on your input, which could include any of the below, and more!


San Juan Flyout 2026

On-Island Activities Could Include:

  • Whale watching, kayaking, hiking and biking
  • Brewery, winery and distillery tours and tastings
  • Nosh on freshly-shucked oysters, steamed mussels and more at Wescott Bay Seafood Farm.
  • Wander the quaint, historic fishing village of Friday Harbor, whose main streets are dotted with acclaimed galleries, cute boutiques, antique stores, unique shops, restaurants and artwork.
  • Muse at the island’s Sculpture Park & 3 museums - Whale, Historical & Art.
  • Uncover the island’s Pig War history at the American and English Camps
  • Visit the historic Roche Harbor Resort and marina. Shop for arts, crafts and souvenirs and then enjoy a sundowner and Taps at sunset at McMillen’s on the water. 

Island-Hopping Flying Day Trips Could Include:

  • Exploring Orcas Island’s Eastsound on foot, then renting a bike or a car to summit Mt Constitution in Moran State Park
  • Golfing at the Lopez Island Golf Club (a 5-minute walk from the Lopez Island airport!)

Additional Details:

This fly-out is limited to 24 people.  Your $200 deposit secures your spot and includes transportation while on the island, evening happy hours in the hotel’s garden courtyard, and one group dinner.  Lodging, travel to and from the island, fuel, tie-down and TBD activity costs are a-la-carte. Any unused, excess deposit funds will be returned to participants.








 
 

Date and Time

Thursday, September 10, 2026, 8:00 AM until Sunday, September 13, 2026, 5:00 PM

Location

Friday Harbor, San Juan Island, WA  
USA

Contact(s)

Mark Tipperreiter

Aimee Tipperreiter

Category

Fly-Outs

Registration Info

Registration is required
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