Awwww memories. I was married on Orcas and flew in on Kenmore air with my grooms party a couple days early for bachelor mayhem. We made a water landing at Rosario and had a rental car waiting in the parking lot with just a sticky note with my name on it and the keys inside. It was so easy and so fun and really not that expensive. I've always wanted to do one of the Kenmore Air trips where they just drop you at a secluded beach and come back in a few days.
Kenmore Air is awesome, but beware bad weather in those dinky planes. We flew into Victoria once, from Vancouver, and the wind was blowing us purely sideways -- our motion was exactly 90 degrees to the direction we were pointing. They shut the airport (or whatever you call it when it's water) immediately after our flight. I left my breakfast in a bag, the only time I've ever come close to barfing on a plane. I'm still sorry for the other passengers. I've never experienced anything anywhere near as rough, and I hope I never will.
Seems a little spendy compared with the ferries. You can get airfare to most places in the western US for the same price as going to the San Juans via Kenmore Air. That being said I'd totally love to do it someday.
Doe Bay is the place to stay. They have a fire pit, plus private cabins, massage, multiple hot tubs, a sauna, and a pretty kickass restaurant onsite.

Also, they will send a shuttle to pick you up.
Kenmore also flies the Port Angeles out of Boeing Field.

It's kind of awesome - you go right over the Bangor Sub Base.
A caravan with pontoons is pretty sweet, but I like them better with jump doors...
The film festival sounds great, but Orcas: meh. We stayed at Doe Bay, which was wildly overpriced for an uninsulated, tiny cabin crammed up against two other cabins. The food was similarly expensive and poor quality. If you're going to get on a spendy, utterly fabulous seaplane, go to Salt Spring Island or Stehekin.
Oh, I've long dreamed about flying Kenmore Air. I've just never been able to convince myself (and my fellow carpoolers) to splurge for the flight to Orcas. The per person prices are lightly splurgy, but for a carload of people it always seems extremely extravagant.
Orcas is great for biking, if you have the legs. And Doe Bay Resort is overrated.
I've stayed at Doe Bay many times over the years and I love it. But if you're expecting a typical resort experience, it's not for you.
Glad to hear you had a great time on Orcas. Kudos to Jared and his many merrymaking volunteers. Looking for to OIFF having a long run. Heartwood on Orcas was happy to host The Stranger winners. And, you are totally right about all the great eateries on our 52 square mile patch in the Salish Sea. Come back soon...TEDxOrcasIsland is 11/8/14.
Airplanes, Resorts, Film Festivals, Ferries, all wonderful, variable, etc. but Orcas is about the island itself if you ask me. (I know, you didn't). Orcas Island is a journey, no matter how you get there, or where you stay. Worth the price of admission and of taking excellent care of it.

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