Hidden Gems

This Whimsical Portland Hotel Is Like a School of Magic You Can Sleep In

School may be out forever, but you can still check in here.

Flickr/Mark McClure
Flickr/Mark McClure
Flickr/Mark McClure

Driving along 33rd Avenue in the Portland neighborhood of Concordia, you’d be forgiven for mistaking the lengthy Italian Renaissance-style building for a school. The warm, tan exterior walls and long wings extending outward from the arching colonnaded entrance give off a familiar, scholastic air. But instead of students and teachers wandering the long halls, now it’s guests in pajamas.

Part of McMenamins-a collection of Pacific Northwest hotels, brewpubs, movie theaters, music venues, and restaurants known for their whimsical artwork and decor-the Kennedy School is a former elementary school turned funky, fantastical hotel. Founded by two Portland natives, the McMenamins brand rehabilitates old, historic properties like schools or farms into eccentric, art-filled hotels.

The Kennedy School is one of the best places to experience this signature McMenamins ambiance, feeling like a school out of a fantasy novel. Think Hogwarts meets Portland’s weird and quirky vibes. With colorful, hanging lanterns and light fixtures that dangle in the air, warm wood tones, low-lit hallways, imaginative artwork that seems to spring off walls, and aura of secrets and mystery, it does seem like a place where the line between reality and fantasy blurs together.

McMenamins Kennedy School
McMenamins Kennedy School
McMenamins Kennedy School

Transformed classrooms-turned-guestrooms still have their original blackboards. Class photos adorn the hallways for decoration, with workbook sheets repurposed as wallpaper. Vibrant artwork inspired by stories from the buildings’ past adorn walls, doors, headboards, and other surfaces. The rooms in the newer English Wing each have a literary theme like One Hundred Years of Solitude by Gabriel Garcia Marquez.

Where the teacher’s lounge once was, you can soak in a heated outdoor pool tiled in colorful ceramics and surrounded by plants. And for once, going to the principal’s office is a good thing, because that’s where the reception is located.

McMenamins Kennedy School
McMenamins Kennedy School
McMenamins Kennedy School

McMenamins also produces craft beer, wine, and even spirits, so each location has plenty of bars. Roaming the halls, you’ll find four bars tucked into different corners of the school, including one housed in the old boiler room and another called the Detention Bar. Inside a former girls bathroom is the onsite Concordia Brewery (don’t worry-it’s been thoroughly cleaned and redone).

A nifty restaurant that spills out into a lush courtyard dining area has replaced the former cafeteria. Instead of sports, the gymnasium hosts live music, dances,and other events. And as if all that wasn’t enough, the auditorium is now stuffed with comfy couches to lounge in for film screenings.

Flickr/Quinn Dombrowski
Flickr/Quinn Dombrowski
Flickr/Quinn Dombrowski

Along with its historic bones, it’s the artwork and decor that gives Kennedy School the aesthetic of an actual school of magic. McMenamins’ quirky artwork is the work of nearly 50 artists, and has been dubbed ‘historical surrealism’ since each work is based on or inspired by the building’s history with fun twists.

“It’s a blank canvas,” says company historian Tim Hills, whose exhaustive deep dives into the history of each property uncovers stories to inspire the artists and pay homage to the building’s former lives. “It’s kind of an adventure, you can never guess what happened in these places.”

Flickr/Mark McClure
Flickr/Mark McClure
Flickr/Mark McClure

Hills collected blueprints, old documents, photos, and testimony from former students, teachers, and neighbors, turning the information over to the artists. From paintings to mosaics to wood panels, the artwork ranges from depictions of classroom lessons to interpretations of events where the artists take a little creative liberty.

“Every artist is a little different,” Hills says. “Some try to tell the story exactly how it was, others play with it.”

For more background information about the different pieces, you can take a self-guided tour of the school’s artwork.

McMenamins Kennedy School
McMenamins Kennedy School
McMenamins Kennedy School

Preserving the history of the Kennedy School through its art and architecture, guests can soak up all the information during their stay without fear of homework or quizzes. First built in 1915 and named after landowner John Daniel Kennedy, the Kennedy School was also used as a community center for events like town hall meetings and collection drives. Faced with dwindling enrollment in the mid 1970s, the school was officially closed in 1975 and set to be demolished due to its poor state. Led by former students and heads of the PTA, neighborhood residents, and the Portland Development Commission, the community rallied to save the building.

“This place meant so much to residents,” Hills says.

Out of several proposals to give the building new life, the neighborhood and the city selected the vision of
McMenamins founders Mike and Brian McMenamin. Purchased in spring 1997, the renovated ‘school-tel’ reopened later that year, ringing in the new era with the original principal’s bell.

Flickr/James Carnes
Flickr/James Carnes
Flickr/James Carnes

Like the Kennedy School, it’s the art, excellent craft beer, and all things peculiar and strange that make Portland Portland. If you get the inclination to leave school grounds, Kennedy is a great basecamp for exploring Northeast Portland, especially the galleries, vintage stores, coffee shops, restaurants, and bars of the neighboring Alberta Arts District. You can also zip out of town for hiking and waterfall chasing a la TLC in the Columbia River Gorge.

If you find yourself won over by the Kennedy School’s charms, you can check out McMenamins’ 61 other properties around Oregon and Washington. At least nine locations are on the National Register of Historic Places. Their other hotel properties include the St. Francis School in Bend, Oregon, a former Catholic School with secret rooms, and Edgefield in nearby Troutdale, a (deep breath) county poor farm-turned-hotel-slash-brewey-slash-winery-slash-distillery-slash-outdoor-entertainment-venue. Whew.

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Zoe Baillargeon is a contributor for Thrillist.

Hidden Gems

Get Refreshed on This Tranquil Florida Island

Come for the beaches, stay for the shrimp festivals and pirates.

The Ritz-Carlton, Amelia Island
The Ritz-Carlton, Amelia Island
The Ritz-Carlton, Amelia Island

Between Key West, Everglades National Park, Miami, and an adorable rodent named Mickey Mouse, Florida reigns as the quintessential summertime vacation destination. But amidst all the well-trod destinations, one comparatively quiet island on the state’s northernmost coast is an oceanic sleeper hit with all the “fun in the sun,” minus the hordes. In fact, Amelia Island is so far north-about 45 minutes north of Jacksonville-that it’s practically Georgia, with native flora that looks more Savannah than South Beach and with historic lore and nautical noshes to match.

Part of the same string of barrier islands that hug Georgia’s coast, Amelia Island is the first of that chain to cross the state line. Considering its geographic proximity, it’s no wonder that the 13-mile-long island is draped in Spanish moss and is refreshingly cooler than the rest of the sweltering state. It’s a place of Native American stories and swashbuckling history, of tortoises and gingerbread pirate ships, and of shrimp festivals and CBD-infused spa treatments. Amelia was populated for centuries by the Timucua people before Spanish explorers, pirates, and Civil War fortresses came barging in, and long before the island’s Fernandina Beach became a bastion of brick-lined sidewalks, Victorian buildings, fudge shops, and saloons.

Unlike the palm tree-lined calamity of South Beach, the swarming theme parks of central Florida, the burnt rubber of Daytona Beach, or even the surprising New Orleans-y vibes of Pensacola, the serenity of Amelia Island, woven with trout-filled waterways and lined with luxury hotels, feels like a slice of Floridian life all its own.

The Ritz-Carlton, Amelia Island
The Ritz-Carlton, Amelia Island
The Ritz-Carlton, Amelia Island

Where to stay on Amelia Island

Rising like a castle on the sandy shores, The Ritz-Carlton, Amelia Island is the queen of the island. And like any regal queen, the property celebrated its 30th anniversary in 2021 in style, with a thorough glow up. The crown jewel of Amelia Island glistens even more brightly these days, with refreshed balcony-equipped rooms, design touches and tones inspired by the surrounding natural landscape, and enough high-quality restaurants to cater a jubilee.

Steps from the beach, the property is the ultimate oceanfront oasis, equipped with Floridian essentials like an 18-hole golf course, a fully loaded spa with CBD-infused massages and their signature zero-gravity touch therapy in hand-woven hammocks, and heated pools with chic, shaded cabanas. Guests can embark on the resort naturalist program, taking a leisurely walking tour around the property to learn about the flora and fauna, including the rare chance to see both sand-digging gopher tortoises and marsh rabbits on the same dune, surely contemplating a footrace. With a big concentration on the culinary (more on that later), the hotel offers monthly “chef’s theater” cooking demonstrations, as well as “Hook, Line & Cruise” outings, where guests embark on fishing excursions, culminating with ceviche prepared by a chef back on the dock.

For something a bit more intimate, Amelia Island boasts quaint inns like Elizabeth Point Lodge, a Nantucket-style cottage B&B right on the beach. Their smattering of suites and guest rooms are equipped with four-poster beds, balconies, and a charming front porch lined with rocking chairs. Closer to downtown Fernandina Beach, Williams House is a B&B that oozes romance and charm, with two-course breakfasts each morning and 10 rooms scattered across three carriage houses and Antebellum mansions.

Timoti's Seafood Shak
Timoti’s Seafood Shak
Timoti’s Seafood Shak

Binge on shrimp and blackened fish tacos

Say what you will about Florida, but the state has good seafood-some of the best in the country, in fact. Amelia Island in particular is the kind of nautical nirvana where chefs go fishing early in the morning and then serve their catch at lunch, or even fillet it on the marina dock right before your eyes.

On the casual end of the spectrum, Timoti’s Seafood Shack in downtown Fernandina Beach is the kind of place that slings Spongebob-worthy crab patty burgers, fried oyster baskets, hush puppies, and blackened mahi tacos-and hangs signage that reads “No shoes, no shirt, no shrimp!”

Nestled under a bridge at a marina, Down Under has become a dockside institution all its own. Formerly a fish camp that sold bait to fishermen before being turned into a seafaring restaurant in 1982, it’s become an iconic stopover. Anglers looking to drop anchor at the dock hunker down on the huge deck for creamy crab dip, peel-and-eat shrimp, and grouper Monterey, broiled under a layer of molten Monterey Jack cheese and caramelized onions.

Salt at The Ritz-Carlton, Amelia Island
Salt at The Ritz-Carlton, Amelia Island
Salt at The Ritz-Carlton, Amelia Island

On the higher end, seafood shines at the myriad restaurants at The Ritz-Carlton. Coast is the most locally inspired, offering an elevated take on Florida’s bounty. They source fish and seafood from local fishermen for dishes like shrimp Louie salads, garlic-buttery shrimp boules (basically a kind of shrimp chowder in a fresh bread bowl), and blackened flounder sandwiches, alongside pimento-filled arancini and fried green tomatoes slathered in gooey Burrata. Poolside Coquina takes a Latin approach, with bracingly fresh catch-of-the-day ceviche, spicy shrimp aguachile, and whole roasted fish wrapped in banana leaves and spritzed with lime.

Then there’s Salt, the ritziest of the restaurants at The Ritz, so named for its emphasis on infused sea salts. Expertly deployed by seasoned chef Okan Kizilbayir, the regal restaurant features ever-changing tasting menus inspired by both land and sea, served up in artful presentations with sauces poured table side and dainty scoops of ice cream gilded with edible gold. Whether a la carte or prix fixe, Kizilbayir’s menu changes constantly, from a squid ink paella with lobster soffrito to a schnitzel-looking blackened skate with a lustrous butternut escabeche broth. If you can snag a reservation, it’s all best enjoyed at the two-person chef’s table in a wine-filled room inside the kitchen.

For something more sugar than salt, hit up the aptly dubbed Fernandina’s Fantastic Fudge. This cute and kitschy sweet shop is still stirring fudge, pralines, caramels, and other treats the old fashioned way. They churn the goods with long wooden paddles, then fold and flip the cooled concoction with so much gumption that there are fudge stains on the ceiling.

The Palace Saloon
The Palace Saloon
The Palace Saloon

Drink with buccaneers and ghosts

Indoor-outdoor bars with live music are a popular pastime on the island, exemplified by local cornerstones like Green Turtle Tavern. The huge bar looks like a lowcountry cabin, or like a real life version of True Blood‘s Merlotte’s. But instead of vampires and bottled blood, it’s country bands and reggae musicians with a side of frozen strawberry margaritas.

Just around the corner, Palace Saloon peddles a different kind of kitsch-the type that involves boozy punch and ghost stories. Established in 1903, it’s one of the oldest continuously operating bars in Florida, even discreetly making sales through Prohibition. In its earliest heyday, this rustic watering hole was a veritable Cheers for thirsty ship captains. Nowadays, it’s a preserved-in-time relic outfitted with a dusty jukebox, mosaic-tile floors, and an ornate wood bar that looks like something out of Hill House-which makes sense, considering the saloon may or may not be haunted by the booze-loving ghost of a former bartender. The drink of choice? The deceptively boozy Pirate’s Punch, made with banana liqueur, triple sec, white rum, Amaretto, grenadine, orange juice, and pineapple juice.

Back at the encompassing Ritz-Carlton, The Lobby Bar, despite its modest name, wows with meticulous mixology. Their roster includes old fashioneds smoked in an elaborate glass box that looks like an A+ science project, alongside jaw-dropping sushi platters large enough to satiate a great white.

The Ritz-Carlton, Amelia Island
The Ritz-Carlton, Amelia Island
The Ritz-Carlton, Amelia Island

Lounge on beaches full of history

In addition to aforementioned ocean-to-table fishing excursions, Amelia Island is teeming with outdoor recreation for the naval historian, the paddle boarder, and everyone in between. Naturally, beach-going is a primary pastime here, with 13 miles of sandy shoreline and more than 40 public access points with free parking. (Pro tip: If you have a Florida license plate, you’re allowed to drive your vehicle right onto the beach in select areas, for optimal sunrise vibes.)

The island’s beaches are divvied into three main sections: the Main Beach, Central Amelia Island, and American Beach. The former is nicknamed the “family zone” for its beachfront restaurants, mini golf, volleyball courts, playgrounds, and picnic shelters. Whereas Central Amelia Island has more recreational options, like paddle board rentals, kayaking, and walking and biking trails through marshy Egans Creek Greenway. Then there’s American Beach, a parcel of shoreline set aside in 1935 by the Pension Bureau of the Afro-American Life Insurance Company to combat the state’s segregation laws. Over the years, it served as an oceanic getaway for famed sunbathers like Ray Charles and James Brown, and today it’s a stop on Florida’s Black Heritage Trail.

On the very northern tip of Amelia Island, Fort Clinch State Park is a mashup of nature and ironclad Civil War lore. Nestled along the St. Mary’s River that separates Florida from Georgia, and lined with rows of olden cannons, sits a brick fortress that was initially constructed in 1847 to defend the US against foreign invaders, a la the War of 1812. Following the start of the Civil War, the fort began under Confederate control until Union troops took over in 1862. Today, visitors can explore the fort’s various labyrinthine rooms or branch out and hike along oak-lined trails throughout the 1,400-acre park.

Amelia Island
Amelia Island
Amelia Island

Party like a pirate

As evidenced by the kitschy taverns, fudge-flinging candy shops, and the omnipresence of wooden pirate statues scattered throughout Fernandina Beach, Amelia Island isn’t shy about getting eccentric. Indeed, it’s prime territory for some of the quirkiest fetes in Florida, like the wildly popular Isle of Eight Flags Shrimp Festival. A celebration of one of the island’s most popular provisions (as seen on every restaurant menu in the vicinity), the festival is like Lollapalooza for shellfish. Celebrations are comprised of parades, art shows, artisan vendors, elaborately decorated shrimp boats, pirate-themed costume contests, and the Miss Shrimp Festival Pageant. Held annually in late-April and/or early-May, it’s not uncommon to see giant shrimp floats roving through downtown Fernandina Beach and dogs trotting by in shrimp costumes, past a sea of food vendors slinging all manner of shrimpy specialties.

Speaking of pirates, their swashbuckling lore inspires another seasonal pastime here on the island. The deep waters at Port Fernandina were once an easy retreat for pirate ships, and therefore used to be a haven for the likes of Blackbeard and Luis Aury. The island is now a haven for another kind of pirate ship-one made of gingerbread. The S.S. Amelia is an annual holiday tradition at The Ritz-Carlton, where a giant gingerbread pirate ship drops anchor in the lobby for the season, complete with cookie cannons, a candy-filled treasure chest, masts and sails, and of course, a pirate captain who is technically edible.

Other happenings include the annual Right Whale Festival, held every November as an altruistic celebration of the whale that comes to northeast Florida to give birth. The family-friendly event is designed to raise awareness for the endangered species, offering edutainment elements alongside food trucks, live music, and ocean-themed activities for kids.

Then, come new year, you won’t be surprised to learn that instead of a ball drop, Amelia Island hosts a shrimp drop in downtown Fernandina Beach. A giant bedazzled shrimp is lowered at the stroke of midnight, beckoning a whole new year of fishing, ceviche-eating, and gingerbread piracy.

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Matt Kirouac is a travel writer with a passion for national parks, Disney, and food. He’s the co-founder and co-host of Hello Ranger, a national parks community blog, podcast, and app. Follow him on IG @matt_kirouac.

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