Portland Oregon
Trip inspirationTips and adviceFood and drinkHistory, art and cultureShows and events
Lyndsey Fish

Best Vacation Spots for 20 Somethings - 5 U.S. Cities Everyone in Their 20's Should Visit

We love traveling, we work at Go City® – the two go hand in hand. We love hearing about people's favorite experiences and places to visit so naturally, we took a poll in the office asking employees to name 5 cities that they've been to that they think everyone in their 20's should visit.

Why 5 cities, why 20-somethings?

We whittled our list down to five U.S. cities (as opposed to say, 20) because visiting 5 U.S. cities in your 20's is totally doable, and we figured that 5 cities could illustrate how diverse U.S. cities are. 

What makes a city great for twentysomethings to visit? A unique mix of the following characteristics: an active nightlife scene, unique-to-the-city culinary creations, a culturally diverse population, a landscape conducive to outdoor activities, and a few more intangible feel-good characteristics that make us want to cancel our return flights and move there when we visit. 

The 5 U.S. cities everyone in their 20's should visit are... 

1. Portland, Oregon

Portland, Oregon

Why it made the list 

Portland O. is like the Portland M. of the West; it gets overlooked because it's a little out of the way, but once you're there, you'll be pleasantly surprised by the city's creativity, chill vibes, and appreciation for bicycles. Portland, Oregon is also the micro-brewery capital of the nation with more breweries than any other city in the world. That's what we call a "beertopia". 

What to do when you visit 

See a live show at Holocene

This place offers a variety of free live music every Sunday and hosts lots of other art and music events throughout the week. You can sit outside on their large patio or dance inside what used to be an old Best Auto Parts warehouse. 

Get a Voodoo Doughnut

This place constantly makes the cut on 'best doughnut shop' articles year after year. Maybe it's because they offer nearly 100 different varieties, all with funny names that will put a smirk on your face, OR it could be the fact that they hold legal wedding ceremonies here. Whether you're a doughnut lover or not, it's a must-see! 

Voodoo doughnuts

2. San Francisco, California 

San Francisco Golden Gate Bridge

Why it made the list 

This city was made for 20-somethings with lots to offer foodies, micro-brew enthusiasts, activity and adventure-seekers, wine lovers, and more. Visiting San Francisco quickly turns into wanting to move to San Francisco. Its geographical location is one of its most desirable traits. With its consistently fair weather and close proximity to wine country, Lake Tahoe, Muir Woods, the Pacific Ocean, and more, there's plenty for visitors to see and do. 

What to do when you visit

Visit Wine County

Some of the best wines in the world come from Napa Valley and Sonoma, so get somebody else to do the driving and enjoy the scenery and samples. Spend the day learning about the history of California's wine industry and sample wines as you visit multiple vineyards. Take some time to relax and soak up the sweeping views of the picturesque vineyard settings while sipping on a newfound favorite. 

Insider tip: Lots of vineyards can arrange to ship your favorite finds to your home. They make great souvenirs and gifts!

Napa valley wine

Muir Woods

Go on a tour of Muir Woods in the picturesque seaside/mountainside Marin County area. Hiking enthusiast? Turn your visit to Muir Woods into a day of pleasant hiking. Rent a car and head to Mount Tamalpais, hike down to Muir Woods, and then back up to where you parked your car. The drive on the way takes you through beautiful Marin County with lots of places to pull over for unbelievable views of downtown San Francisco from atop Mt. Tamalpais.

Cross the Golden Gate Bridge

Whether you go by car, foot, or bike, crossing the Golden Gate Bridge is a San Francisco must-do. Best way to explore? Rent a bike for the day and go on a self-guided tour (moderate ride).

Recommended route: Past Crissy Field, where you can stop for photos and the best views of the bridge.

Then, follow the path to the Golden Gate Bridge, cross over, and continue to the quaint oceanside town of Sausalito where you can stop for a waterfront lunch or poke around the shops. From there, you can either turn around and head back the way you came, take the ferry back to Fisherman's Wharf, or continue to Tiburon where you will have the same options for your return.

En route to Tiburon, you'll cover long stretches of bayside parks and bike paths. From Tiburon, riders can stop for refreshments, explore the shops, and then turn around and head back or hop on the Ferry to Fisherman's Wharf.

Bike tour across Golden Gate bridge

Eat like a local

Tacolicious: Get the fish tacos (we don't think they make 'em better anywhere in the world), street corn, and a passion fruit margarita.

Bi-Rite Creamery: For completely original ice cream flavors like balsamic strawberry, lavender, and Sonoma honey, salted caramel, and more, head to one of Bi-Rite Creamery's locations. Even if you know which flavor you want to get, ask for a sample of something unique.

Tartine: Suggested by pretty much anyone who's lived in SF, Tartine is worth the block-long line you'll see during peak hours. This cafe offers a wide selection of authentic French pastries and breakfast bites. Croque monsieur, Croque madame, almond croissant (as you can see from the picture, we couldn't choose just one).

Tour a brewery: San Francisco is home to an up-and-coming craft brewery scene. Check out Anchor Brewing for one of the best brewery tours (and tastings!), like ever. Make a reservation as soon as possible, due to popularity, these tours fill up faster than you can book a plane ticket.

3. New York City, New York

New York

Why it made the list

Going to New York City just to get a view of the skyline is a perfectly legitimate reason to justify your plane ticket. Other acceptable reasons to justify your airfare are the amazing food, the late-night culture, the world-class museums, the Statue of Liberty, people-watching, and just to immerse yourself in a city so romanticized by movies and pop culture.

New York City has something to offer everyone (couples, nerds, etc.). Avoid the tourist traps and explore some of the unique, cutting-edge culture the city is famous for.

What to do when you visit

Scope out the best skyline views 

No visit to New York City is complete without an Instagram showcasing a sweeping view of the city skyline. Head to one of our top 4 places to go for a view of the Manhattan skyline.

Rooftop bars with views to die for:

SixtyFive Bar & Cocktail Lounge: With views that rival the Top of the Rock itself, this recently re-opened bar has surprisingly managed to stay under the radar a bit. Head up here for the views, a great wine selection, and delicious appetizers (we recommend the sliders and fries!)

Blue Ribbon Beer Garden: Go here to see and be seen. We're not sure which is better, the open atmosphere, Indian spice market-esque décor, ping pong tables, or the frozen foam-topped beers that are the perfect refreshment on a hot summer day.

Meander around world-class museums

Whether your main reason for heading to The Met is for the view, or to see historically significant art from around the world in person, don't leave NYC without browsing through at least one museum.

Check out masterpieces such as Vincent van Gogh's The Starry Night, Claude Monet's Reflections of Clouds on the Water-Lily Pond, or Andy Warhol's Campbell's Soup Cans at the MoMa. Or, admire the architectural wonder by Frank Lloyd Wright that is The Guggenheim, home to famous works by some of the greats, including Cézanne, Manet, Monet, Picasso, Pissarro, and Renoir.

Guggenheim

Sample a selection of New York's best eats

The Meatball: With six locations and counting, it's safe to say that The Meatball craze in NYC is going strong. The visionaries behind The Meatball have taken these Italian classics to a whole new level their creative, gourmet renditions.

Lois: Wine enthusiasts will enjoy the carefully selected wines on tap and seriously, well-crafted bites. Insider tip: if they have the avocado arepa or pork rillettes on the menu, GET THEM. 

Treat House: Forget cronuts. Indulge your sweet tooth (and your inner 4-year-old) with gourmet rice crispy treats. They're almost too pretty to eat but impossible to resist.

4. Austin, Texas

Austin, Texas

Why it made the list

If you haven't already been, Austin is unlike anything you would imagine Texas to be. The city's motto: "Keep Austin weird" is an indication of what you can expect from the laid-back and friendly locals. Austin has also claimed its name as "the music capital of the world." Absolutely one to experience for yourself.

What to do when you visit

Go for a swim in Barton Springs

This year-round, 70°F/21°C natural spring is located right at Zilker Park. Splash around in the large pool or venture out onto Barton Creek where you can swim, hike, bike, sail, paddleboard, take a boat tour... you get the drift!

Barton Springs

See some live music

Live music can be found on any day or night of the week in Austin upholding its title as music capital of the world. There's even a live band that plays in the airport. You can find all of Austin's music events here.

Stop by Torchy's Tacos

If there were a national food truck competition going on, Austin would win. You can find a multitude of awesome food truck options downtown Austin but Torchy's Tacos was our favorite. They've got wild options like fried chicken and chili or blackened salmon. Located at 1311 S. 1st Street, Torchy's Tacos may not necessarily be traditional, but it's certainly delicious! See the menu.

5. Chicago, Illinois

Chicago skyscrapers

Why it made the list

Chicago has it all. Besides being known as the "second city" for it being the second to reach the highest population in the U.S. after New York, it perfectly mixes the big city feel with mid-western small-town friendliness. You can find anything and everything here, from great food, to bars and live music, and free events all summer. Chicago also takes great pride in its public parks, artwork, and architecture. Visiting Chi-Town is a must in your twenties!

Lake Michigan

The Lakeshore in Chicago is 18 miles long and a big part of what makes the city so awesome. There are trails for running, cycling, or taking a stroll. You'll also find some great restaurants/bars along the way. We highly recommend making a stop at Castaways, a beachside party spot with delicious drinks and fun vibes.

Lake Michigan

The Hideout: This secret spot may not be so secret anymore but it's worth seeing. They've got a different themed event happening every night of the week such as Blue Grass Tuesdays and Epic Dance Party Saturdays.

Millennium Park: This popular tourist destination is one of the most photographed places in the country for a reason The park is constantly hosting live entertainment such as music shows, art exhibitions, local vendors, and fairs. Not to mention it's home to the infamous "bean"; the large reflective sculpture that looks like a giant... bean.

There's also an entertaining, somewhat creepy/cool "Crown Fountain" that spits water at you between May and October (think great people watching). 

So there you have it, young wanderlusters

We hope this inspired your next trip! Don't forget, at Go City® we can help you save up to 50% with our travel passes compared to buying individual entry to everything you want to do - winning! 

🌏 Explore our destinations 🌏 

Love this article? Why not share it:

Buy with confidence

Free cancellation

Plans can change, we get it. All non-activated passes are eligible for a refund within 90 days from your purchase date.

Find out more

We're kind of popular, but don't just take our word for it.

Have a 5% discount, on us!

Sign up to our newsletter and receive exclusive discounts, trip inspiration and attraction updates straight to your inbox.

  • Thick check Icon