The 10 Best Trips to Take in Your Twenties

Your twenties are a decade all about exploring, having fun, and finding yourself. You graduate college (with a degree you may or may not end up using), find a job (that you may or may not like), move to a new city (where you may or may not know anyone), change jobs, become more financially stable, find your calling (or wonder when the heck you’ll find your calling), go out with your best friends (a lot), date around (thanks Bumble), and eventually find a partner who you want to spend the rest of your life with (ideally).

It’s the most chaotic, most stressful, most challenging, and most invigorating decade of our lives. And what better way to make the most of it than traveling the world in your twenties? Although you may not be luxe-ing it up in the Four Seasons just yet (you can save that for your honeymoon one day), there are some epic trips to take with friends in your 20’s that you’ll remember for a lifetime. So whether you want to travel with a couple girlfriends on a girls trip, with a bunch of guys on a boys trip, or head out on a group trip with a mix of friends somewhere exotic around the world, these are my top choices for the 10 best trips you must take in your twenties


Is there anywhere more iconic and known for exploration and finding yourself as Bali is? Bali is ideal for a fun or relaxing group trip (and is best experienced with a mix of both!!) and will be the vacation you and your crew will remember for a lifetime. 


Bali’s mix of one-of-a-kind culture with it’s gorgeous beach clubs, stunning landscape, and amazing food and bar scene make it a perfect (and easy!) group trip. Did I mention it’s one of the most affordable places to travel in the world? You can eat dinner in Bali for about $5 USD. And drink Bintangs on the beach for about $1.

You’ll spend your days in the jungle exploring the beautiful rice fields of Ubud, at the beach clubs in Uluwatu, or shopping around Canggu and getting massages (about $10 for an hour, and the best massage you’ll ever have), or your group can head out on a ferry to some of the world’s most beautiful islands and most world-renowned party spots like the Gili Islands. Whatever you do, don’t miss a sunset at Single Fin, or a day at Sundays Beach Club in Uluwatu.


I know, I know, “Europe” is entirely too generic. But a girls trip to Europe or a friends euro trip is basically a right of passage for anybody in their 20’s. Depending on what you and your friends are looking for, I’d recommend Barcelona for the going out scene (and the bottomless Sangria), Paris for the history, eating, and shopping, the South of France for the chic beach clubs, Iceland for an epic adventure, and the Greek Islands for a beachy summer trip. 

Las Vegas

Wherever you’re coming from around the world, Las Vegas is synonymous (or should we say Sin-onymous) with wild times and party vibes. A weekend trip to Vegas in your twenties with your girls or your guys, is a MUST

Spend your mornings popping mimosas in bed at a chic hotel like the Wynn or the Aria, then head to a pool party for the day.

Break for a change into your going out outfits and then start your night with a fancy dinner (I love Estiatorio Milos), and head out to the clubs or the casino. Rinse and repeat the next day, and have yourself a weekend to remember (or forget). 

The Virgin Islands

The Virgin Islands is one of the most beautiful, and most fun, areas of the world. Sailing the BVI’s is one of the best trips you can take at any age, but especially fun in your twenties when hangovers don’t exist and Painkillers are your breakfast (the most popular cocktail in the Virgin Islands is called the Painkiller)

Stay on St. Thomas or rent an epic group house in St. John , both are on the USVI side so it’s easy to. From there, rent a sailboat for the day (or heck, stay a few nights on a sailboat sailing through the BVI – you can read more about how to do that here!) and island hop. Each island in the Virgin Islands is filled with fun, funky beach bars, and there’s even a pirate ship bar called Willy T’s that you have to boat to get to. 

When to travel to the USVI / BVI: The weather is great year round, but I’d avoid hurricane season (Summer and Fall). The best season is US Winter – when it’s dry, warm and sunny in the Virgin Islands.

Napa Valley

A group trip to Napa Valley is ALWAYS a good time. When I was living in San Francisco, we would organize party buses to Napa / Sonoma for the day which was always so much fun. You can combine this trip with a night or two in San Francisco, or I recommend getting a group house in Napa for the weekend for the ultimate experience. I have a ton of recommendations on the best wineries for groups in Napa on this blog post here

Yacht Week

The Yacht Week is an epic annual trip where tons of groups of friends sail – and party – for 7 days straight (usually in Croatia, or the BVI) and anchor together for a rager in a new destination every single day. There are themes, and groups will dress up in themes, bringing matching swimsuits in the same print, matching Hawaiian shirts, having ‘white nights’ and more. It’s not for the faint of heart (or liver) but if your crew is game for the absolute most FUN week ever, there’s nothing quite the Yacht Week for a friends trip to take in your twenties. (By the way I also have friends who met their husbands and wives on The Yacht Week!!! Nothing like an all day and night 20-something rager in the middle of the ocean to find love, right?)

Photo via @RuthieSchorr and @ECKoehler

Photo via The Yacht Week


Whether your group’s idea of a South American vacation is sipping the world’s best coffee on a bougainvillea-laced balcony and taking chic instagram photos in the Cartagena streets, drinking cocktails on a lush tropical island, or salsa-dancing until 6am in one of Colombia’s famous nightclubs (My favorites are La Movida, Alquimico, La Jugada, or Cafe Havana in Cartagena), Colombia has a ton to offer every type of group.

Start your trip by staying in one of my favorite Airbnbs for Groups in Cartagena, which are all conveniently located in Old Town (the safest, easiest, and best area to be in Cartagena) then take a hopper flight to Medellin for a few nights in Colombia’s coolest city. You’ll want to make time to get to the outskirts of the city and spend a day in Guatape or Jardin, and if you have time, you’ll want to head over to Santa Marta to hike Parque Tayrona as well! The possibilities for a trip to Colombia are endless, and it’s sure to be you and your friend’s favorite adventure of all time. 

The California Coast (Highway One Road Trip)

Start in San Francisco and head down South on Highway One. Take in the views of the world-famous coastal highway, and stop to explore Big Sur (and go glamping for a night!). Spend a couple days in Santa Barbara, or go wine tasting in Paso Robles.

Finish your road trip in Malibu and Los Angeles, or keep going even further to San Diego. Don’t forget to stop at In n’ Out (duh). 

The South of France

Now I know we already talked about Europe, but the South of France deserves its own spot in the top 10. This was hands down my favorite trip I took with my girlfriends in my twenties. From the beach clubs of St. Tropez (literally the best days of our lives), to exploring the Lavender Fields of Provence, to dancing the night away in Monaco and Cannes, and ending up on yachts, there’s just nowhere like the South of France for a girls getaway.


Southeast Asia

From Thailand, to Bali, to Cambodia, to Singapore, and everywhere in-between, a Southeast Asia trip with friends is one of the most fun trips you can take in your twenties. Hit up the full moon party in Thailand, do a layover in Singapore, and get to Bali, too!


Whether you explore the cenotes of Tulum, or rent a massive villa Cabo San Lucas, a Mexico getaway with friends is one of the most fun fiestas you can have – whether it’s a Mexico bachelorette party, or just a random weekend in the sol. 

Wherever you travel with your girlfriends or guy friends in your twenties, make it one for the books. These memories will last a lifetime and I can’t imagine if I didn’t fully live up my twenties traveling as much as I possibly could. You’ll only regret the trips you don’t take.

My best friend and I in Uluwatu, Bali in 2016

Remember that, and try not to say no to your best friend’s crazy trip idea, like when my best friend suggested we should travel to Bali on a whim in 2016 — because you never know where that trip might lead you.

For me, that one trip to Bali led to me quitting my job, starting my business, falling in love, getting engaged and never looking back.

My fiance Kenny and I in Uluwatu 2 and a half years later.

Check out these other blog posts!

Where to travel in the USA

What to pack for a tropical vacation

25 things I’d tell my 25 year old self

The best girls trip destinations

Miami travel guide

The best airbnbs in Cartagena for groups

The Ultimate Key West Travel Guide

The best airbnbs in Joshua Tree

how to sail the British Virgin Islands


The Best Austin Airbnbs For Groups


Bali is Opening to Tourists in 2021 - Here's Everything You Need to Know


Christina is a leading luxury lifestyle and travel blogger with over 2 million readers. Follow her on instagram @jetsetchristina.