This Immersive Alaska Pop-Up Experience Is What the World Needs Right Now

One AFAR editor spent four days on a remote Alaskan island sleeping in a canvas tent, foraging for berries, and taking daily saunas. Sound like your ideal trip? There’s still room to sign up for the Guest House 2019 this fall.

This Immersive Alaska Pop-Up Experience Is What the World Needs Right Now

Daily activities, like huckleberry picking, will change each weekend at the Guest House as summer turns to fall in Alaska.

Photo by Lyndsey Matthews

As I hopped off the water taxi onto the rocky black sand beach at Hesketh Island, Alaska, Seth O’Donovan greeted me and two other guests with a wide grin. Further up the shore, her partner Tony Weston shucked oysters and poured glasses of bubbly at a makeshift bar. The bivalves had been sourced from nearby Jakolof Bay Oyster Company and were served with a foraged bull kelp vinaigrette on a bed of evergreen branches from the island. The sparkling wine was a 2017 Conundrum Blanc de Blanc from California—but only because grapes don’t grow in Alaska.

Located in Southcentral Alaska’s Kachemak Bay, Hesketh Island is close enough to the Kenai Peninsula wildfires that I could see the smoke plumes as I flew into Homer earlier that day on a turboprop plane, but far enough away that it felt like some sort of coastal Shangri-La where volcanic cliffs covered in pine trees plunged into the ocean. I was attending the first of the seven weekends of the Guest House, a pop-up village on the island that went far beyond your standard glamping experience; here travelers connected intimately to the land and Homer community through hyperlocal fine food and workshops with Alaskan craftspeople. The four- and five-day retreats run through October 6, 2019, and there are still spots to book on a few of the later weekends this fall.


Where the forest meets the waters of Kachemak Bay at Hesketh Island.

Photo by Lyndsey Matthews

The brainchild of O’Donovan, current head of food at Colorado’s Dunton Hot Springs resort and a former server at the French Laundry in Napa Valley, the Guest House began last year as a series of pop-up dinners around Aspen. But it blossomed into something much bigger after O’Donovan met Susie Jenkins-Brito, a commercial fisherwoman from Bristol Bay, Alaska, at a retreat for food and agriculture professionals. They then connected with Madeline McLean, a natural wine expert and chef based in Berlin, and Evie Witten, the fermenter behind Evie’s Brinery in Anchorage, and together the four women built the pop-up on the remote island from the ground up.


The canvas walled tents have real beds—no sleeping bags here—and wood-fired stoves.

Photo by Lyndsey Matthews

After we slurped up nearly half a dozen oysters on the beach, O’Donovan showed us to the canvas tents we’d call home for the weekend. The Guest House Alaska can accommodate up to eight guests per weekend in four tents; mine was set in a forested area near the island’s sauna. All four tents featured plenty of creature comforts, including real beds made up with cozy linens and wood-fired stoves.


Even the dishware is made nearby, including these ceramics by Homer local Lisa Wood.

Photo by Lyndsey Matthews

Once I settled in, I made my way up the hill to the main house for dinner. As I entered the minimalist Scandi-style cabin—one of the few permanent structures on the island—I could smell the sourdough Weston had just taken out of the oven. Over a dinner of bean soup, abundant local greens, and island-foraged raspberries that stained our fingers bright red, I learned that even the tableware had a story at the Guest House. The blue ceramic bowls the soup was served in were made by Homer pottery artist Lisa Wood, the silverware was thrifted from shops in Alaska, and the etched-glass beer steins were a wedding present O’Donovan’s mom had been gifted way back when. In fact, most of the glasses I drank out of over the weekend belonged to O’Donovan’s collection of matrilineal china, which she’s gathered from her mom, grandmothers, and friends’ mothers over the years.


After sweating it out in the sauna, make the short run down to the beach for a bracing dip in the water.

Photo by Lyndsey Matthews

The rest of the weekend unfolded over a loose schedule that began with 7:45 a.m. yoga on the house’s deck followed by slow and relaxing breakfasts of coffee and oatmeal topped off with island-foraged huckleberries and honey made in Homer. I embraced the island’s limited cell phone service and filled my mornings with time in the sauna or walks on the beach, where I counted the jellyfish that had washed up on shore overnight (more than a dozen) and the different types of lichens and moss growing on driftwood (at least four).

Afternoons were reserved for long lunches—Homer locals are invited to take the water taxi over to join on Friday afternoons—and workshops hosted by Alaskan craftspeople. I joined a seaweed foraging and cooking demonstration by two women from the nearby community of Ionia; upcoming weekends include sourdough baking and sea salt harvesting classes.

That said, you won’t find a strict itinerary on the Guest House’s website—and that’s on purpose. In a world where so much information can be had online, O’Donovan wants some things to be a surprise. She believes that once you remove expectations from travel, transformational experiences happen.

“The way we do hospitality and travel right now is that it’s all about this one kind of predicted, self-fulfilled moment that we can Instagram,” O’Donovan told me one evening as we chatted outside on the deck over white negronis made with gin from Juneau’s Amalga Distillery.

“We’ve completely lost [the practice of] putting ourselves in situations where we might actually be changed,” she continued as bush planes buzzed overhead and seagulls squawked near the beach. “We can’t be changed by just getting what we want all the time. To me, that’s the value of meeting new people and being in new lands and eating different food. It’s those moments that make me rethink the world.”

“That’s why this hyperlocal approach and perspective is so important. I could set up a high-end hospitality experience anywhere, but if it’s not rooted in what that specific piece of land has to offer, then nothing’s changed in us. We’ve just had another whitewashed experience in another beautiful place.”

O’Donovan says she was inspired to expand the concept and location of the Guest House beyond Aspen and even Colorado, especially after reading Consulting the Genius of the Place: An Ecological Approach to a New Agriculture by Wes Jackson, a leader in the sustainable agriculture movement. In his book, he talks about respecifying land for crops that would naturally grow there. “I want to reclaim that same principle in hospitality,” she said.

“I don’t want someone to come to Alaska and be able to count on the same experience and things that they counted on when they were in Australia,” she said. “That’s why this hyperlocal approach and perspective is so important. I could set up a high-end hospitality experience anywhere, but if it’s not rooted in what that specific piece of land has to offer, then nothing’s changed in us. We’ve just had another whitewashed experience in another beautiful place.”


Workshops at the Guest House—like this seaweed foraging class—change each weekend.

Photo by Lyndsey Matthews

As for the future of the project, the hope is to continue to travel and find new places “that we can then open up for other people to discover in a way that’s really about the site—and not about how I look on Instagram in the site,” O’Donovan said. Potential future locations that came up over the weekend included Iceland, and she mentioned a possible return to Alaska. But for now they’re focusing on this year’s Alaska pop-up.

When we finished the last few sips of our negronis, O’Donovan headed back inside to help Weston finish cooking dinner, and I lingered a few more moments outside, soaking in this special place and the seemingly never-setting Alaskan sunset.

How to book it

The Guest House 2019: Alaska Adventure starts at $2,750 per person based on double occupancy for five-day retreats, which are still available for programs running between September 11–15, September 25–29, and October 2–6, 2019. (Four-day retreats are sold-out.) All activities, lodging, meals, and water taxi transportation to Hesketh Island from Homer included, but flights are not. Bookable now at

How to get there—and a note on the wildfires

The wildfires currently burning on the Kenai Peninsula have not affected the Guest House activities on Hesketh Island. However, you’ll want to book a flight to Homer from Anchorage instead of driving. Traffic on the Sterling Highway that links Seward to Homer has been both delayed and closed intermittently over the past week due to the fires.

>> Next: Plan Your Trip With AFAR’s Guide to Alaska

Lyndsey Matthews is the Senior Commerce Editor at AFAR who covers travel gear, packing advice, and points and loyalty.
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