The question I asked every travel writer when submitting to the Uproxx Fall Experience Guide was the same, “Why now?” “Why is this entry relevant at this very moment?” It’s a question they turned right back on me when I suggested Portland — the town where I was raised — to sit atop the pack as our #1 destination. And when people asked me that question, whether it was my fellow contributors, my Deputy Editor, or my friends back home, they asked it with an eyebrow arched and some serious emphasis on both the “why” and the “now.”

The implication, especially from my friends in P-Town, was that I was letting nostalgia cloud my judgment. Because Portland has, undoubtedly, fallen on difficult times (Rolling Stone just called it a “far-right proving ground” last week). Certainly, there’s more visible tension than during in the Rip City / “littlest big city” years back in the 1990s; the hipster food boom / “most liveable city” era of the 2000s; or the Portlandia / “Keep Portland Weird” wave of the 2010s. Visiting Portland for two months over the summer, I saw unhoused encampments stretching entire city blocks, stolen bike chop shops that spilled out into busy streets, and beloved buildings covered in tags or boarded up. I also heard story upon story of the violence that has erupted with troubling frequency throughout the city. Clashes that have marred the historically attended, predominantly peaceful BLM protests, marches, and gatherings (and resurfaced as recently as last month).

At times, my conversations about my home city got pretty heavy. So seriously, why now? Of all the years, why pick Portland in 2021?

To answer that question is to challenge the very idea of why we travel. Is it always about having a glossy vacation, unmarred by real-world concerns? I hope not. I like daiquiris on the beach more than most and I can laze in a spa with the best of them, but if that’s as deep as your trips ever get, travel starts to seem frivolous. It’s a slippery slope from “I only go on vacation to relax” to languishing with the lotus-eaters.

Going to Portland right now isn’t going to be purely relaxing. Even if you stay in the city’s newest hotels, eat at its most acclaimed restaurants, and visit its most buttoned-up bars, you will see reminders of social unrest and interact with the unhoused population. Don’t look away (better yet, get involved — donate time, resources, or money to the Blanchet House or the Portland Rescue Mission). Confronting big issues is an essential part of travel. So is helping beloved destinations recover by infusing local economies with cash. Uproxx has always believed that, since we first started covering travel. 

A trip to PDX this fall is a chance to be part of the evolution of a travel destination that has appeared on the “must visit” lists of so many outlets over the years and could use a good jolt of tourist dollars right now. It’s an opportunity to bear witness to the city in all its complexity, rather than just going because you heard about the good donuts and craft beer. It also opens the door to exploring a city in transition on many levels — a fact which is plain to see when you look through the prism of Portland’s most notable obsession: food. 

While the first Portland food revolution (roughly 2001-2010) was about the creativity and skill of chefs who were mostly white, mostly male, and mostly all tattooed with the same pig butchering chart, its current wave is much more inclusive. Eem was a 2020 hot list pick for restaurants and its white curry with burnt ends epitomizes the synergy that’s possible when the “star chef” model is abandoned. Chefs Akkapong Earl Ninsom of Lang Baan, Hat Yai, and Paadee and Matt Vicedomini of Matt’s BBQ and Matt’s BBQ Tacos joined together to create a restaurant that highlighted both of their talents. The results are astounding and Ninsom’s newest venture, Lazy Susan, has been the standout hit of the pandemic.

Moreover, after the Portland food scene became emblematic of the city’s larger issues with diversity and inclusion, BIPOC voices have begun to make inroads in the food and beverage sectors. George Johnson, founder of Assembly Brewing, PDX’s first Black-owned brewery, has drawn rave reviews both for his beer and his Detroit-style pizza. In wine, Bertony Faustin became the first Black winemaker in Oregon back in 2008, opened a tasting room downtown at the height of the political tension in 2020, and has since mentored Tiquette Bramlett, the first Black woman to run a winery in US history (Vidon Vineyard, in nearby Newberg).

“Portland was at a ‘lowest point’ during 2020,” Faustin told me recently. “That spring and summer put a magnifying glass on the city’s issues, but I feel like we’re on the uptick now in a major way. Regardless, you can’t wait ’til everything is creamy to take part. That’s why I opened The Crick, my tasting room when I did. Because of my career as the first Black winemaker in Portland, I felt like it was my role to come downtown and show people that it’s a good place to start a business, even in the tough times. There are opportunities now that might not have been available for news businesses, especially for minority business owners.”

(If you’re looking for more Black-owned food in Portland, I regret to say that my beloved Stoopid Burger closed during the city’s extended shutdown, but Nacheaux — a Mexican-Cajun fusion concept with an inventive menu that inspires fierce customer loyalty — is new and getting tons of love. A comprehensive directory of Black-owned Portland-based food options can be found here.)

More than any city I’ve visited this year, the crucial social justice conversations of the past half-decade seem to be leading to a tangible shift in PDX. Over the summer, I saw bands and comedians recognizing the traditional Indigenous owners of the land they were performing on — a formality of almost all events in Australia but one that’s relatively new in the US. It’s a good change and one I’d never witnessed, pre-pandemic. That cultural respect isn’t just lip-service, either, The Native American Community Advisory Council is helping the city decolonize public spaces, including the removal of the once-iconic duck pond at Westmoreland Park, returning the waterway to a wetland featuring traditional foods.

Meanwhile, I spoke with waitstaff and Uber drivers and Portland Tourism officials and locals young and old about the unhoused community in the city and — to a person — the conversations were filled with compassion and nuance. The city I currently live in, Laguna Beach (CA), also has a very visible unhoused community and I rarely hear so much empathy from locals. That’s not to say that all people agreed on the matter, this is a conversation that has been central to the city’s identity since I was a child and it’s not an easy fix. But it’s worth noting that people across the city seem to have genuine regard for the humanity of the unhoused.

Writing in a “travel list” format about the positive and negative aspects of the 104 days of continuous protests (and the many subsequent protests) in Portland after the murder of George Floyd is virtually impossible. With that said, the groups that have come out of those protests will certainly help to guide the city’s new era. Portland’s paper of note, The Oregonian, published a comprehensive review of the one year anniversary of the protests and didn’t attempt to draw any easy conclusions about the success or failures. Instead, they made the point that public protests are part of how the local culture evolves and, in that, a piece of the city’s identity. 

So rather than visiting hoping not to see protests of any sort, it’s worthwhile to wonder what any protests you might see have to say about the city (and what they might teach you about your own biases and beliefs). Speaking personally, the protests I saw in the city were all very mellow #BLM car parades. (It goes without saying that you should avoid planned Proud Boys rallies or any other alt-right or anarchist events.)

Though travelers may harbor concerns about Portland after a rough year in the news, hotel properties aren’t banking on their hesitation lasting long. 2018 and 2019 were big years for hotel openings in the city and that pace looks to resume early next year. There are five properties set to open in 2022 and early ’23, including the first Tokyo Inn on the West Coast, the first Proper in the PNW, and hotels from Hyatt and Ritz-Carlton. Two hotels actually managed to open in 2021, too. Moxy Portland is sleek, boasts multiple gathering spaces, offers bike rentals, and features rooms that reference Portland’s Indigenous community and heritage. The PaliSociety’s Hotel Grand Stark is even more impressive — doubling down on the midcentury vibe of the city’s industrial-era buildings with interior design that could be set dressing for an early season of Mad Men. The whole property leans heavily into jade green and feels like a memory of Portland that I never actually experienced firsthand but still somehow know (plus the beds are extremely comfortable).

It’s true, Portland may not be polished the way it once was. And the extremist violence is genuinely troubling, make no mistake. But seeing a place with clear eyes is always more authentic than viewing it through rose-colored glasses. There’s no ignoring social issues in Portland right now, nor is there a desire to. And that’s a good thing. Being willing to face the reality of the situation in the places you visit is the core difference between “travel” and “tourism.”

So yes, go to Portland. But not just for the famous food carts and pods or the new hotels or the many many bars or the dance clubs like Holocene and CC Slaughters or the endless live music options or the comedy scene or the city’s prominent LGBTQI community or the commitment to public art or the fact that it was named America’s Best Pizza City a few months ago or because it’s home to one of the largest urban forest reserves in the nation or those incredible donuts or… those elements were all in place in some form pre-pandemic, pre-protests, and pre-extremist violence. Go to witness a city that features all of those incredible attributes and is also in the midst of the biggest transition it’s seen in more than 25 years.

Go to be part of the city’s new era. An era that’s sure to be more inclusive and progressive than those that preceded it. Go to support new development and fresh ideas. Go to bear witness to the creative minds like Bertony Faustin who are helping get P-Town back on track.

“Don’t write this city off,” Faustin says. “Portland thrives as an underdog. Give it a chance and it’ll surprise you.”

WHY IN 2021:

Don’t visit Portland expecting glossy perfection. Visit ready to wrestle with some of the tough issues the city is facing and with the attitude that your tourism dollars can help aid in the Rose City’s reblossoming.

Check Portland’s COVID guidelines here.

We’d like to acknowledge and honor the original peoples of this land, the Confederated Tribes of Siletz Indians, the Confederated Tribes of Grand Ronde, the Multnomah nation, and the Stl’pulmsh (Cowlitz) nation.

Greenville, SC used to be an overlooked city that most people breezed by on the way to or from the popular and well-known Asheville, NC. Lately, however, it’s creating quite a buzz with its 18-plus breweries, thriving food scene, and many options for adventurous types.

You can’t go wrong with anything Birds Fly South. known for their saisons and farmhouse ales, keep your ear to the ground for their limited beer releases which tend to really pop. Another favorite brewery in Greenville is Fireforge. Dogs are welcome in their Biergarten as long as they don’t run away with the corn-hole bags. If you’re there mid-week, Wednesday is pitcher night on all of their taps so settle in for a long night of fun, food, and brews.

In addition to the numerous brewery options in Greenville, there’s a whole host of awesome places to get a bite, too. When you make it to Greenville, head to Gather GVL. This shipping container community space is comprised of 13 restaurants including the very delicious HenDough (that’s right, fried chicken AND doughnuts). The whole place doubles as both an entertainment venue, and, as the name suggests, a social gathering place.

All this being said, don’t stuff yourself to the point that you just want to lay down and take a nap. There’s a ton of outdoor adventures to be had in this city, including riding your bike or walking along the Swamp Rabbit Trail, exploring Falls Park on the Reedy, and the shot of adrenaline otherwise known as BMW’s Performance Driving School where you can learn how to corner from the pros and experience your very own ‘Hot Lap.’ Trust me on this one, this is one of the most hair-raising and exhilarating experiences you’ll ever enjoy.

WHY 2021:

Go now before everyone else realizes how cool it is. Perfect for a trail-to-town adventurer who doesn’t want to fight big crowds.

Check Greenville’s COVID guidelines here.

We’d like to acknowledge and honor the original peoples of this land, the ᏣᎳᎫᏪᏘᏱ Tsalaguwetiyi (Cherokee, East) nation.

The big story for much of the US National Park system in 2021 has been overcrowding. People are traveling in extremely high numbers across the United States to see the nation’s iconic park vistas for themselves. So it’s surprising to find a park that most people have never heard of, much less visited.

A park that still feels a little wild. Because it is.

That park is Cumberland Island National Seashore. As the largest and southernmost barrier island in Georgia, the park offers more than 17 miles of secluded white, sandy, and completely undeveloped beaches. Wild horses and ample wildlife (sea turtles!) roam freely across the island’s shores and interior.

You can only reach Cumberland by ferry or private boat. Once on the island, the only commercial establishment is the all-inclusive Greyfield Inn, which is only accessible to guests. You can stay at the inn or camp — but you must pack everything in and out. After getting settled, you can hike, rent a bike, or book the one motorized tour (which travels down the one dirt road) operating on the island.

Want to keep up with social distancing? This is your spot.

The history of the park is absolutely fascinating. Once owned almost entirely by the Carnegie families (along with Rockefellers and Candlers of Coca-Cola), there is no shortage of Gilded Age intrigue and colorful stories to learn. The families fought to keep the park wild, too — all of the remaining family homes and one commercial inn all have agreements to eventually donate the buildings back to the Park Service, so that the island can be entirely wilderness. In fact, Cumberland is so undeveloped and remote, JFK Jr. was famously able to marry Caroline Bisset on the island without anyone in the media knowing until after they had already departed for home.su Rumor on the island is that he would run on the long beach during his visits and said it was the only place he could truly escape the paparazzi.

WHY 2021:

With National Parks booming, this is a US NPS unit that is both undeveloped and under-visited. A place to truly escape into the wild in 2021.

Check Cumberland Island’s COVID guidelines here.

We’d like to acknowledge and honor the original peoples of this land, the Mvskoke (Muscogee / Creek) and Timucua nations.

St. Lucia is back, and it’s a whole lot more than a honeymoon destination. Having visited over the summer, I can vouch that there’s no rule saying you need a ring to travel to the island nation — despite its long-standing reputation as a favorite island for newlyweds. Besides, lovers make for good people watching at spots like the widely-beloved Falco’s Bar.

During the height of the pandemic, St. Lucia’s adventure guides turned their attention from the sea to the island’s dramatic labyrinth of mountainous rainforests, rivers, and waterfalls. Local tour guides like Island Routes swapped scuba tanks for machetes as they forged paths up St. Lucia’s largest peak, the 3,100-foot Mount Jimmy, and began searching for hidden waterfalls in the jungles.

That doesn’t mean diving the idyllic island ended, though. Dive operators are returning to form and beginners can get PADI certified while gliding across St. Lucia’s bountiful reefs and shipwrecks. Meanwhile, experienced divers are sure to appreciate the wonder of plunging beneath the volcanic spires of the incomparable Pitons.

WHY NOW:

East Coast crowds descend on St. Lucia from December until early April. Shoulder season is just starting, and while it comes with an increased chance of rain, a little rain won’t stop you from having an amazing time hiking up to the waterfalls, diving beneath the surf, or lounging with a drink in hand. Full-service resorts typically book from the top down, leaving entry-level and mid-tier rooms — that still include unlimited diving, food, drink, and adventure tour access — ripe for the picking at much more reasonable rates for travelers looking for an escape.

Check Saint Lucia’s COVID guidelines here.

We’d like to acknowledge and honor the original peoples of this land, the Kalinago (Island Carib) and Taino nations.

New York was hit hard when the pandemic arrived in the U.S. early in 2020 — with tremendous loss of life, the collapse of businesses, and an exodus of its population. What’s left, in my experience, is a tale of two cities. This city is experiencing a renaissance of its underdog energy. For the third of the population who left, almost that same number have moved in and taken their place, breathing life into the cultural capital of the world and supporting those who stayed put.

Because New York was so affected by the pandemic, it has been the most diligent in safety, COVID testing, and vaccine rollout, hitting a key vaccine threshold early on June 15th with 70 percent of New Yorkers having at least one vaccine shot. Currently, the city 9and the state) sit well above the national average for vaccination rate. That collectivist approach was celebrated with a fireworks show and in the months since, I’ve witnessed what feels like a re-awakening after almost 15 months of being cooped up in notoriously tiny New York City apartments.

New Yorkers have invested their time and money in outdoor spaces and public parks: Mr. Sunday dance parties at Nowadays; Cuban salsa dance parties in Far Rockaway Beach; free events by BRIC Celebrate Brooklyn! Festival, Summerstage, and the Downtown Brooklyn Partnership; Lincoln Center’s Restart Stages, including transforming its iconic plaza into The GREEN, as well as adding nine other outdoor performance and rehearsal stages; outdoor artist residencies and free events in Brooklyn Bridge Park; NYC’s Open Culture program which transforms streets and open spaces into ticketed, socially distanced outdoor venues; the opening of Little Island at Pier 55; open-air art at the Industry City creative hub in Sunset Park; and I could keep going… The theme for the city’s next chapter in its transformation is clearly more space plus more art.

As outdoor spaces became essential during the pandemic, the city now wants to make them more permanent. NYC’s Open Streets program prioritizes pedestrians and cyclists by transforming driving streets into public spaces. Entire blocks are closed off to cars, allowing small businesses and local communities to use the space for spillover and for safe gathering areas. Think of them as hundreds of block parties sprinkled throughout the five boroughs from Harlem to Manhattan’s Chinatown and Little Italy to Little Caribbean, in Brooklyn.

Restaurants and bars were the most impacted economically, and unfortunately, many of New York’s institutions have shuttered their doors for good in the past year. Those that survived, were buoyed by the city’s Open Restaurants outdoor dining program, allowing roadway and sidewalk seating. The city’s landscape is transformed with beautifully decorated pop-up patios that extend from the brick and mortars, adding a new vibrancy to the city. This program is so well-received, it was extended through the end of this year with a permanent program currently in development. From that, a volunteer neighborhood-recovery effort grew — The Neighborhood Curbside Canvas Project — which unites local artists with struggling New York City restaurants to transform these “streeteries” into street art.

The outer boroughs are getting their time to shine right now, and some restaurants have even opened in the middle of the pandemic, including Ayat’s home-cooked Palestinian recipes in Bay Ridge’s Little Middle East. Venture off to East Williamsburg/Bushwick (depends who you’re asking) to get a spectacular view of the entire city at Llohi Bar, a modern, sleek rooftop bar with craft beers, cocktails, food, and live music. Head up to The Bronx to visit Bronx Native, a store that boasts Bronx pride while also acting as a community hub for open mics, DJ sets, and educational workshops. Long Island City in Queens is a hot spot for brewery buffs and a destination for artists, including the live, outdoor performance space at Culture Lab LIC. Of course, we’re all excited about Broadway reopening again fully by September, with already a handful of shows running, including Springsteen on Broadway.

WHY 2021:

Now is the time to come to New York City. Support its recovery, celebrate what’s new, cherish what stands the test of time, and be reminded — 20 years after 9/11 — that this city is nothing if not resilient.

Check New York City’s COVID guidelines here.

We’d like to acknowledge and honor the original peoples of this land, the Munsee Lenape, Canarsie, Wappinger, Matinecock, and Lekawe (Rockaway) nations.

After more than a decade of topping “must-travel” lists, many Iceland adventures still play a little one-note. Instagram is full of the same waterfalls, the same lagoons, the same geysers, which, while undeniably stunning and beautiful, are far from all the country has to offer. It’s time to venture beyond Reykjavik, the Golden Circle, and the Ring Road and head to the Westfjords — the country’s westernmost region — which is woefully underrated.

Tiny, tucked-in towns dot the various fingerlike fjords of this peninsular region. The largest, with a population of 2700 people, is Ísafjörður, but Patreksfjörður, Hólmavík, Reykhólar, and Flateyri are all homey and cozy and sure to prove fascinating to the American traveler. The Sea Monster museum in Bíldudalur is an interactive way to become immersed in mythological aspects of Iceland’s culture, while the Arctic Fox Center in Súðavík is an excellent place to become familiar with Iceland’s only native mammal.

The Westfjords are an incredible, rugged nature destination. Arctic foxes are seen regularly in the Hornstrandir Nature Reserve and Atlantic puffins (among other avian species) abound at the bird cliffs of Látrabjarg. Like so many other parts of the country, the Westfjords are full of natural hot springs and cascading waterfalls, like the impressive Dynjandi. Secret perk: in this area, the arresting smell of sulfur is nowhere to be found.

The recently constructed Dýrafjarðargöng tunnel, lying between Arnarfjörður and Dýrafjörður, now links the north and south parts of the Westfjords, making travel through the region easier than ever, especially during the winter when driving through snow is to be expected. So go now, when the whole area is “just accessible enough” but not overrun.

WHY 2021:

There’s no shortage of adventure, culture, and mythological mysteries to uncover in the Westfjords. But if the trends seen in the rest of the country continue, soon it will be just as popular as the sights around the rest of the island nation.

Check Iceland’s COVID guidelines here.

The first time I visited Savannah, Georgia was on accident. I was road-tripping with friends from Washington, D.C. down to Florida on college spring break and we stopped in town to stretch our legs and grab a quick lunch. I was instantly taken by the charming vibe of the city, which was wholly unique from anything I’d experienced before.

Over the years, I’ve made a point to return to Savannah several times, and am thoroughly convinced that one day I’ll attempt to purchase property there. Why? Each visit has brought something new, delightful, and unexpected as I stroll along the water on sunny days, listen to musicians play the violin in Forsyth Park, and down beers at the supposedly haunted Moon River Brewing.

While the city has no shortage of fascinating history — like the oak-shaded Wormsloe Historic Site, the spooky and scenic Bonaventure Cemetery, and the rosy-hued Olde Pink House (a restaurant operating within a 245-year-old home) — it also continues to move toward the future. For one, Savannah’s dining scene has become more exciting over the years, thanks to innovative chefs like Mashama Bailey at The Grey and restaurant group Ele and the Chef, which has brought Asian cuisine to the forefront with spots like Madame Butterfly and Flock to the Wok.

WHY 2021:

Along East President Street, development is currently underway on a $600 million mixed-use project that will soon bring a brand new Thompson Hotel, an apartment building, a public park, retail, restaurants, and more to that once desolate area of the riverfront.

A city that combines past, present, and future in a seamless and always intriguing way, Savannah is a domestic travel destination that commands your attention—almost as much as the ghosts that haunt it, always trying to sneak in your selfies.

Check Savannah’s COVID guidelines here.

We’d like to acknowledge and honor the original peoples of this land, the Yamassee and Mvskoke (Muscogee/Creek) nations.