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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.


20. Surf’s Up in Surf City

Huntington Beach, California

If one of your goals during your 20s is to learn how to hang ten, then you’ve come to the right place. Nicknamed “Surf City, USA,” this Southern California beach town is one of the best cities for millennials and a paradise for twentysomethings. Check out the exhibits at the International Surfing Museum before heading over to The Bungalow for some tropical cocktails. This chic beachside bar has twentysomething-millennial written all over it. But you can’t leave this place without surfing, so sign up for a lesson with Banzai Surf School. People might start mistaking you for local surfing hero, Brett Simpson.


19. College Life is Alive and Well

Boulder, Colorado

Do you miss college life? If so, a visit to Boulder, Colorado, will have you right back in the thick of it in no time. Start your “trip back in time” in The Hill neighborhood. There are a variety of restaurants, shops, and bars to explore that are loaded with people looking to have a good time like yourself. Eventually, wander down to the Boulder Theater and catch a live show. However, a trip to Boulder isn’t complete without hiking the famous Flatirons.


18. Bourbon + Live Music = Fun

Louisville, Kentucky

Beer and wine trails are awesome, but Louisville’s Urban Bourbon Trail puts this city on any list of cool places to travel. You’ll start by picking up an Urban Bourbon Trail passport before departing on this unique adventure. There are 44 bars and restaurants that take part on the trail, so the options are endless. After a few around town, make your way to Fourth Street Live!. This massive entertainment and retail complex plays host to all sorts of live events, but the music acts are where it’s at. National acts like Eric Church, O.A.R., and Jason Aldean have all rocked there. But before you leave, be sure to set aside a day to explore the Louisville Mega Cavern. It’s exactly what it sounds like.


17. You Betcha!

Rochester, Minnesota

Welcome to Minnesota’s third-largest city. Before you do anything in this town, get a bite to eat and a margarita at Hefe Rojo. This place puts a creative twist on traditional Mexican fare like tortilla soup and enchiladas. After you’ve fueled up, rent a canoe from Silver Lake Fun and paddle around Silver Lake for the afternoon. Bring a rod and reel and see if you can bag a famous Minnesota walleye. If you’d like to mingle with locals in your age group, head to one of the local breweries like Forager Brewery. Cheers to your 20s!


16. 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.


15. 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 dips in the Barton Springs Pool 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.


14. 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 craddled in the Wasatch Mountains is hard to beat. Hit the slopes at Park City Mountain and then stop in the No Name Saloon & Grill for a whiskey 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.


13. 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.


12. 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 the legendary Arthur Bryant’s Barbeque (it’s time to retire the insta-ramen) and the nightlife in the Power & Light District, 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.


11. 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.


10. 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 bigwig in technology.


8. Trade Desert Casinos for Lakeside Casinos

Lake Tahoe, California

Would you like to try your chances at the gambling tables without spending a boatload 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 Resort Casino & Spa and tossing dice at Harrah’s Lake Tahoe. And because you’re in your 20s, you’ll have plenty of energy for it all and more.


7. 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 there for the taking 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.


6. 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.


5. 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.


4. 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 road trip. 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 nearby 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.


3. 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 County, 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.


2. 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 walking tour. Since you’re in your 20s, it’s about time you became a foodie.


1. “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 any twentysomething.

You may think the 10 years between the ages of 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!
Q. Have any other questions?
A. Check out our Ultimate Car Rental Guide!

Header image via Soloviova Liudmyla’/

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