10 Super-Chill Vacation Destinations for Millennials

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A group of millennials sit around in a coffee shop while on vacation.

Millennials are always in the headlines. They really want this product (avocado toast), or they’re being blamed for that societal issue (a housing crisis), or they post too many Instagram photos (#foodporn). 

Another reason they’re in the news: Travel. 

Millennials love to travel, and who can blame them? As a generation, they prefer experiences over products, and value the personal fulfillment that a trip provides. Now those are some headlines we can actually get behind! 

At Wanderu, we do our best to empower people to go on adventures by offering the cheapest bus, train and plane tickets through an easy-to-use booking platform. The only thing we can’t do is tell you where to go — but we’re happy to offer suggestions. 

The best places in the U.S. for millennials balance a few different factors: They’re affordable, they have an inviting nightlife scene, and they offer some sort of artistic, cultural or outdoorsy experience to complete a well-rounded vacation. The destinations below are fantastic spots to bring your friend group, and are also friendly enough to hit up with a significant other or Solo Dolo. 

So, stop thinking about work for a weekend (that means taking your work inbox off of your Gmail app), rally your group text, and hop on a bus or train to one of the following millennial hotspots.

1. Atlanta, GA

Photo of the Atlanta skyline.

BEST TIME TO VISIT: Spring brings the most comfortable temps and best prices.

TOP ATTRACTIONS: Centennial Olympic Park, Piedmont Park, World of Coca-Cola.

WHY YOU SHOULD VISIT: A premier urban center in the South, Atlanta plays host to festivals like Music Midtown Festival and the Atlanta Pride Festival, with many of its largest gatherings occurring in the sprawling Piedmont Park. You can also pay your respects at the Martin Luther King Jr. National Historical Park

Nightlife is buzzing in the ATL. Try out something a little different with a visit to the first virtual reality bar in the entire U.S. 

During the day, mix a suicide in the tasting room and learn about Coke’s journey from being just a fizzy drink to one of the most ubiquitous brands in the world. Then visit Centennial Olympic Park, where the 1996 Summer Olympics helped revitalize the city center. 

Finally, you should stretch your legs on the Atlanta BeltLine, 22-miles worth of defunct railroad that has been reworked into trails for hiking, biking and rollerblading.

2. Chicago, IL

Photo of a Chicago theater in the downtown Loop.

BEST TIME TO VISIT: Shoulder seasons (avoid the dead of winter at all costs).

TOP ATTRACTIONS: Activities in and around the beaches on Lake Michigan; the Willis Tower Skydeck; the Field Museum

WHY YOU SHOULD VISIT: Downtown in the Windy City is a bit touristy and overpriced (although an architectural boat tour on the Chicago River is a truly worthwhile endeavor), but neighborhoods like Pilsen, West Loop/Fulton Market and Old Town offer plenty of great food options, bars and things to do. Meanwhile, Wrigleyville is one of the ultimate millennial destinations in the country when it comes to cheap(ish) beer, revelry, and the Chicago Cubs.

Warmer months mean volleyball courts open on the beaches, and foliage in Grant Park flourishes in the midst of skyscrapers (hello, Lollapalooza during late summer). Find a friend (or make a new one) who has a boat to get access to the lusted-after lounge spot called the Playpen, a section offshore where you can drop an anchor, crack your (spiked) seltzer of choice, and gawk at the skyline.

3. Austin, TX

BEST TIME TO VISIT: Shoulder seasons; summers can be scorching if you’re not used to the climate.

TOP ATTRACTIONS: Zilker Metropolitan Park; Texas Capitol; Lady Bird Lake.

WHY YOU SHOULD VISIT: A more recent hotspot for incredible food (tacos, anyone?) and music (Austin City Limits, anyone?), Austin is the cool cousin when it comes to the Texas metropolis scene.

Cruise on Lake Travis or Lake Austin, with or without alcohol, and check out the sunset on Mount Bonnell — the highest point in town, which is also one of the most Instagrammable locations in the area (and free to visit).

After the sun dips below the Texas horizon, head to South Congress Bridge (leave your squeamish friends at home), and watch as some 1.5-million bats flap out from the bridge’s nooks and crannies and into the glowing sky. To see exact time estimates for your visit, click here.

4. Toronto, ON

Photo of the Toronto skyline, including the CN Tower.

BEST TIME TO VISIT: Late spring and early fall.

TOP ATTRACTIONS: CN Tower; Royal Ontario Museum; Casa Loma.

WHY YOU SHOULD VISIT:  To most Americans, Canada seems like a faraway land with lots of snow and neighborly manners. And while they certainly get loads of snow and many Canadians are quite polite, the part about it being far away just isn’t true — especially Toronto. 

Just a four-hour drive from Detroit and under two hours from New York state, Toronto is perfectly pleasant, climate-wise, during shoulder seasons. It’s also home to the Royal Ontario Museum, the largest museum in Canada. You can try poutine, walk through the Hockey Hall of Fame, experience a thriving theater scene, and get out of town with a day-trip to Niagara Falls.

5. San Luis Obispo, CA

Photo of the beach in San Luis Obispo, California.

BEST TIME TO VISIT: The weather is pleasant pretty much year-round, but January is one of the quietest tourism months — which means cheaper accomodations and fewer crowds! 

TOP ATTRACTIONS: Downtown San Luis Obispo Farmers’ Market; Bubblegum Alley; Mission San Luis Obispo. 

WHY YOU SHOULD VISIT: A hub for art, a wonderful farmers’ market scene and Spanish history, San Luis Obispo will broaden your idea of California outside of L.A. and S.F. You’ll also find yourself spending way less money than in the state’s largest urban centers, while still having access to beaches, kayaking, paddleboarding and more.

Mondays are special in SLO: From 4 p.m. to 7 p.m., Baywood Park becomes Beer at the Pier, with live music, food, drinks and dancing. Enjoy happy hour, then walk through an iconic alleyway with chewed gum blanketing the walls on either side of you … if you want. At Bubblegum Alley you can even leave your own mark on the walls! Just, for our sake, please wash your hands afterward.

6. Milwaukee, WI

Photo of the Milwaukee, Wisconsin skyline, along the coast of Lake Michigan.

BEST TIME TO VISIT: Late spring or early fall.

TOP ATTRACTIONS: The Milwaukee Art Museum; a 30-plus brewery scene; the Harley-Davidson Museum.

WHY YOU SHOULD VISIT: About a two-hour bus ride up Lake Michigan from Chicago is Milwaukee, an integral hub in the American brewery landscape. Yes, there’s a reason their MLB team is known as the “Brewers,” as the city houses over 30 breweries amidst a population of less than 600,000 (including the historic Pabst Blue Ribbon). 

The Milwaukee Art Museum is an astounding physical building in and of itself, and holds more than 25,000 pieces of art — making it one of the largest museums in the country. The biggest city in Wisconsin is also home to the Harley-Davidson Museum, a completely different exhibition of art in its own right, while the Pabst Theatre is a beloved spot to go see the country’s top entertainers as they breeze through town.

7. Nashville, TN

Photo of a honky-tonk sign in downtown Nashville.

BEST TIME TO VISIT: April through October.

TOP ATTRACTIONS: Grand Ole Opry; the Parthenon; the Country Music Hall of Fame.

WHY YOU SHOULD VISIT: Save a horse, ride a bus on over to Nashville — where you and your friends can lean into the enchanting live-music scene and consume some delicious food.

You could truly spend a long weekend — or even a full week — eating, drinking and head-bobbing your way through venues like the Ryman Auditorium, the Grand Ole Opry, or smaller venues like 3rd and Lindsley and The Basement

The odd Parthenon replica in Centennial Park is worth getting outdoors for, especially if you’re walking off some hot chicken from a spot like Hattie B’s.

8. Miami, FL

Photo of a lifeguard hut in Miami.

BEST TIME TO VISIT: Spring — it has the best weather, it’s the end of tourist season, and is a time of year that doesn’t see hurricanes. 

TOP ATTRACTIONS: South Beach; Vizcaya Museum & Gardens; Ocean Drive. 

WHY YOU SHOULD VISIT: Party! On! The! Beach! You can be buzzed on any beach, but there’s a certain level of bravado that comes with partying in Miami, and the weather here will rarely do you dirty.

Of course, this doesn’t have to be a spring break sort of trip. Calle Ocho in Little Havana is where you can come face-to-face with the strong Cuban influence on the city (and chow down on a Cuban sandwich), and the mansion at Vizcaya will mesmerize you with its grandeur. Art is also a huge part of the community, whether it’s the contemporary showcase at Pérez Art Museum Miami, or taking a casual stroll through Wynwood to admire the graffitied walls.

The best part: You’re never that far from the ocean (and beautiful white sand), and one of the most important (and only) rules of this place is to apply (and reapply) that sunscreen.

9. Philadelphia, PA

Photo of Independence Hall in Philadelphia.

BEST TIME TO VISIT: Spring for the fewest crowds, most mild weather and cherry blossoms.

TOP ATTRACTIONS: Liberty Bell; Philadelphia Art Museum; Benjamin Franklin Parkway.

WHY YOU SHOULD VISIT: Philly is home to many artifacts of early America, such as the famed Liberty Bell and the Second Bank of the United States. History buffs can tour Independence Hall (where a certain Declaration was signed), or several other Revolutionary War sites.

History or not, you simply must try a Philly cheesesteak (they say Delessandro’s is #1). And for non-meat eaters, there are endless options at Reading Terminal Market, which is actually America’s oldest farmers’ market. Benjamin Franklin Parkway, modeled after Paris’s Champs Elysees, features several fabulous museums and institutes, and a day is done and dusted after a walk down to the inviting Delaware River waterfront and piers. (For even more free things to do in Philly, check out our guide.)

10. Williamstown, MA

Photo of an old church in Williamstown, MA.

BEST TIME TO VISIT: June to August.

TOP ATTRACTIONS: Mount Greylock; pubs in town; the Clark Art Institute.

WHY YOU SHOULD VISIT: A quaint town nestled in the picturesque Berkshires, Williamstown is surprisingly versatile — largely due to its dual role of liberal arts college town and alluring vacation destination.

The town is close to Mount Greylock, a hiking and skiing hotspot that also happens to be the highest point in Massachusetts. And make sure you get your artistic fix at the Clark Art Institute, or Williams College’s own Museum of Art. You’ll find paintings pair well with that fresh mountain air.

The downtown area of Williamstown is thick with charm, and includes friendly haunts like Purple Pub and Water Street Grill. A slice of New England all to yourself, this is a place to kick back, take it easy, and not have to pay $21 for a good drink.

Whether it’s your new group of co-workers or your pals from middle school, millennials can swing an exciting (or relaxing) trip to any of these 10 destinations without paying a 🤴‘s ransom. 

Other ideas to stay under budget: Bunk up in an AirBNB, plan to use public transit (or at least opt for an UberPool), and cook as many of your own meals as you can. And, of course, use Wanderu to book your travel: The simplest way to compare buses, trains and flights, all in the same search! Just download the Wanderu app or visit Wanderu.com to start your search.

So, get out there, you little avocado-toast gobbler. And once you’ve got the lighting right on that Portrait Mode photo, put the phone down for a bit and remember why you went on vacation: To think of more ways to thwart Boomers, of course

Travel Safely

At Wanderu, we want to make sure you are equipped with all the information you need to plan a safe trip. Please visit our COVID-19 Travel Guide for the latest tips & advisories.

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About the author
Karl Ortegon

Karl Ortegon

Karl studied abroad in Stockholm, Sweden, where he became infatuated with meatballs and fika (though he didn't care for the sun setting before 4pm). He's down to go on a trip at a moment's notice, and he has previously written for travel guide website iExplore.

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