Select Page

Your 20s are all about coming into your own. It’s a time to actually leave the house instead of watching someone else’s Coachella videos. A time to get life experiences that will become more valuable than your beer pong record. And a time to visit these 20 unique cities that will teach you things you’ll carry well into your 30s and beyond.

How did these cities make our list? Check out our criteria below:

  • Cities with an equal balance of stunning natural scenery (#nofilter) and bustling concrete jungle streets
  • Cities with high populations of coming-of-age twentysomethings like yourself, looking for life’s next amazing Snapchat story
  • Cities so incredible they make you question if this is real life


1. What Happens in New Orleans Goes Home with You

New Orleans, Louisiana

“The Big Easy” is sometimes characterized as having four seasons: summer, winter, hurricane, and Mardi Gras. You can’t go through your 20s without attending one of the greatest parties on earth. But before you join the festivities along Bourbon Street and enjoy a Sazerac at Jean Lafitte’s Old Absinthe House, make a pit stop at the New Orleans Historic Voodoo Museum—the only one of its kind on either side of the Mississippi. Cast a curse on the ex who wronged you back in college.


2. Relive the Glory Days of College in Texas’s Capital

Austin, Texas

Nothing says living it up in your 20s like taking a trip to this college town that also doubles as the state capital. From taking selfies in front of the trippy Baylor Street Art Wall to cruising down 6th Street looking for the best place to enjoy drinks in the evening, you won’t have a problem finding something fun to do. And before you leave town, be sure to enjoy a meal at Stubb’s Bar-B-Q. It might be the best meal of your life.


3. Skiing and Snow Bunnies Go Hand in Hand in This Mountain Town

Park City, Utah

Don’t you dare get to the big 3-0 without taking a proper ski trip with your fraternity brothers. And this ski town in the Wasatch Mountains is hard to beat. Hit the slopes at Canyons Village and then stop in the No Name Saloon & Grill for a No Name sour and the buffalo nachos. When night comes along, catch a show at the historic Egyptian Theatre. This is one of the theaters used for the Sundance Film Festival and it might just give you the acting bug.


4. Put That Twentysomething Body to the Test

Moab, Utah

Trade your skis for a mountain bike and put that twentysomething body to the test on the insane rock formations of Moab. With nearby Arches and Canyonlands National Parks providing some of the greatest trail riding in the United States, knocking these two off your list should be a top priority during your energized 20s. If you want to get a sense of what this place is all about, check out the Museum of Moab before pedaling off for the ride of a lifetime.


5. Line Dancing Until the Sun Comes Up

Nashville, Tennessee

Do you hear that? It’s the sound of country music and you need to point your car in its direction until you get to “Music City.” Whether you’re 20 or 29, spending all night in a honky-tonk saloon listening to live country music is a rite of passage. Spend a few hours exploring the Country Music Hall of Fame and head over to the Nashville Municipal Auditorium for a Nashville Rollergirls match. Maybe it’ll inspire you to pursue a career bashing bodies on the roller rink.


6. Trade House DJs for House Sax Players

Kansas City, Missouri

This city on the confluence of the Kansas and Missouri Rivers is far from a sleepy Midwestern town. From the unbelievable eats at Arthur Bryant’s Legendary Kansas City BBQ (it’s time to retire the insta-ramen) and the nightlife in the Power & Light neighborhood to the jazz clubs, nothing says living it up in your 20s like dancing the night away to the sweet sounds of jazz in the historic 18th and Vine District of KC.


7. Start Your Run for POTUS Right Here

Alexandria, Virginia

We know you were in high school just a few years ago, but it never hurts to get up close and personal with your American history. As you walk down the cobblestone streets of Old Town Alexandria, you’ll feel like you’re back in the 1700s. Especially when you take an Alexandria Colonial Tour. Come back to the present day by exploring the Torpedo Factory Art Center. The knowledge you’ll gain by visiting this town will have you wise beyond your years.


8. Sand, Sun, Art, and Seafood—Oh My

Provincetown, Massachusetts

Driving the length of Cape Cod with a car full of friends and not a care in the world will make any summer vacation complete. Get your hands on the Provincetown Gallery Guide and explore the many art galleries that line the streets. Hey, it’s never too early to appreciate the finer things in life—your older self will thank you. But as much as this place is known for its artsy stuff, it’s even more known for the seafood. Get a big table at the Lobster Pot and have yourself a good ol’ time sucking down oysters and cracking lobster claws.


9. The Future is in the Hands of Silicon Valley

San Jose, California

Silicon Valley is full of young professionals vying to climb to the top of the newest tech company. And before you join the rat race—you will one day—check out the Tech Museum of Innovation. After geeking out for a few hours, take care of that growing appetite at San Pedro Square Market. Get yourself a carnitas taco from Loteria Taco Bar and wash it down with a locally brewed beer and plan how to become the next Mark Zuckerberg.


10. Trade Desert Casinos for Lakeside Casinos

Lake Tahoe, California

Would you like to try your chances at the gambling tables without spending a boat load of cash? Trade Las Vegas for the shoreline of Lake Tahoe and enjoy all the pleasantries that come with being in your 20s. It’s just as glorious and glamorous as that neon paradise in the desert, but you get the added luxury of lush forests and sparkling waters. Start your morning at Lakeside Inn with blackjack and some of the best steak and eggs in either state. Then zip around the lake during the day with a rental boat. Finally, spend the night dancing at MontBleu and tossing dice at Harrah’s. And because you’re in your 20s, you’ll have plenty of energy for it all and more.


11. The Quintessential College Town

Madison, Wisconsin

Relive the glory days of college in this university town. After leaving the rental car at your hotel, go for a stroll down State Street and pick out a bar to visit later in the evening. But before the sun tucks itself in for the night, wander through the exhibitions at the Madison Museum of Contemporary Art or go for a walk through the incredibly scenic botanical gardens. Want food and drinks with a view of the capitol? Get a table at The Old Fashioned and experience something other than a dive bar.


12. The Big House Without the Inmates

Ann Arbor, Michigan

Via Ann Arbor Area Convention and Visitors Bureau

If you want to see a football game in a stadium nicknamed “The Big House” while 100,000 twentysomethings cheer wildly, Ann Arbor, Michigan, should be at the top of your list. Start your morning with a local delicacy called a “fragel” from MD Bagel Fragel and then treat yourself to a self-guided walking tour of town. Make your Instagram followers jealous with pictures of Main Street, where coeds flock day and night. You’ll be looking for an excuse to go back to grad school after a few days here.


13. A Desert Oasis of the Highest Caliber

Palm Springs, California

Nonstop sunshine. Awesome pools. Golf courses as far as the eye can see (Escena Golf Club in particular is perfect for practicing your swing for future company fundraisers). Palm trees taller than most buildings. All that and more is on offer when you exit Interstate 10 for Palm Springs. The pool parties here rival the ones in Vegas, but aren’t nearly as pricey. And events like Splash House are unbelievable. What’s Splash House? It’s a weekend of DJs and pool parties that don’t stop until early Monday morning. And don’t be nervous if you’re under the age of 25; you’re still allowed to rent a car at this age in California and cruise along the palm trees in style.


14. Vacation Like the Boss

Asbury Park, New Jersey

Why Asbury Park? Because during his 20s, Bruce Springsteen came of age along its famous boardwalk and it’s always good to reconnect with classic rock’s most legendary figures. You can almost hear him belting out the words to “Thunder Road” as you relax on the beach. After you’ve gotten properly bronzed, access your inner child and play a game or two of pinball at the Silverball Museum. But the main reason you came here is to see a show at The Stone Pony. Who knows, maybe The Boss will show up for an impromptu jam session.


15. The Oldest City Will Keep You Young at Heart

St. Augustine, Florida

Just because this is “America’s Oldest City” doesn’t mean it’s not suited for a twentysomething like yourself. Downtown is packed with fun restaurants and bars catering to the young and hip, and the historic walking tours will transport you back in time. Want to see what the oldest masonry fort in the country looks like? Explore the grounds of Castillo de San Marcos and be impressed. All the while, you’ll be getting the best tan of your life.


16. A 10-Gallon Cowboy Hat to Go with Your Skinny Jeans

Denton, Texas

On the outskirts of Fort Worth and Dallas is a town at the tip of the “Golden Triangle.” Denton, Texas, is perfect for galivanting during your 20s because of the ridiculously fun Downtown Square. Get yourself an ice cream cone at Beth Marie’s Old Fashioned Ice Cream—the banana split is ridiculous. And when you’re ready to get your hipster vibe on, shop your way through Recycled Books, Records, & CDs. Nothing says being in your 20s than having a few Bruce Springsteen vinyl’s in your collection.


17. Spring Break Like You Never Left College

Biloxi, Mississippi

There you are, sitting around with your friends wondering where in the world you guys should go on your next getaway. Well, the coast along the Gulf of Mexico in Biloxi, Mississippi, is a great place to start. Lather up with high SPF sunscreen and hit the sand of Gulf Islands Seashore. When your appetite comes calling, suck down a dozen or so oysters at the Half Shell Oyster House. You might not be able to get away with driving along the Gulf Coast during spring break with a belly full of oysters in your 30s.


18. Where to Refine Your Taste for Fine Wine

Sonoma, California

You’re getting older. Wiser. Which means you’re beginning to enjoy the finer things in life. Like a meat and cheese platter paired with a beautiful bottle of wine at a fancy winery in Sonoma, California. Make your way to Chateau Diana that’s located among the rolling hills, where rows and rows of perfectly manicured grape vines stretch as far as the eye can see. Select one of the many vineyards in the area and take a bottle home. For dinner, take a cooking class at Ramekins and learn the culinary skills you’ll need later in life.


19. Art Districts Are Your New Norm

Asheville, North Carolina

Plop down your credit card for a rental car and take a scenic drive through the mountains until you get to the lovely city of Asheville, North Carolina. A great way to get the lay of the land is to take a Gray Line Trolley Tour through town. And since you’re becoming wiser with age, trying to interpret the fantastic pieces of art in the River Arts District is a must-do. When you get hungry, but have no clue where to eat, sign up for an Eating Asheville Tour. Since you’re in your 20s, it’s about time you became a foodie.


20. “The Big Apple” Still Has Some Hideaways

Queens, New York

Every twentysomething who wants to become a big shot heads to the glitz and glamour of New York City. But before you plant a seed in the concrete jungle that is Manhattan, take a self-guided driving tour through one of its most unique boroughs. Everything from exploring the Queens Botanical Garden and Gantry Plaza State Park to eating a meal at Park Side Restaurant makes this place a perfect destination for anyone between the ages 20 and 30.


You may think the 10 years between ages 20 and 30 is a long time, but it will blow by you faster than a New York City subway train. Don’t let that happen without treating yourself to time away in these 20 fantastically unique places. We can’t wait to hear all about it.

Car Rental Tips for Twentysomethings
Q: How old do you have to be to rent a car?
A: These days, most companies require a driver to be 21 or older, but they’ll have to pay an underage fee. This is how companies like Enterprise operate.
Q: How do you rent a car with a debit card?
A. Most companies accept both debit and credit cards, as long as the card is in the renter’s name.
Q: How do you rent a car with multiple drivers?
A. For most companies, anyone who wishes to be an additional driver must be at the rental counter with a credit card and driver’s license and pay an extra fee.
Q. How do you rent a car with cash?
A. Companies that allow you to rent with cash require that you show proof of residence and a verified identification card.
Q. How do you rent a car from the airport?
A. Go to the car rental counters and viola!


Going to Orlando?

Book the perfect car to see St. Augustine