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When You’re Turning 21 

Birthdays seemed a lot simpler when we were kids. Your parents threw you a party, you were ecstatic about growing a year older, and you could eat all the pizza and cake you wanted. Just cause you’re an adult and perhaps bemoaning calling attention to your age doesn’t mean you should skip a birthday party—especially when you’re hitting a milestone year or kicking off a new decade. There’s no better celebration than grabbing your closest friends or family members for a group trip. And when you have a party in a hotel suite, you don’t have to clean up—talk about a birthday gift to yourself! We found the perfect destination for every milestone birthday and, if you’re bringing the family, check out our guide on traveling with the kids.

Viva Las Vegas 

Alcohol, gambling, recreational marijuana—when you’re 21, you can partake in all Las Vegas has to offer, but maybe not all at once. Pacing yourself is key to having a great birthday trip in this city and, if you don’t believe us, check out these Reddit stories on the craziest birthday parties gone sideways in Vegas. Mark the occasion by booking an incredible only-in-Vegas hotel suite with connecting rooms, so you and your friends (or family, if you dare) can stay together and still have privacy. With four rooms, five beds, and your very own pool table, Nobu’s penthouse + Two King Rooms + Double Queens Room creates such an epic party atmosphere that you’ll never want to leave. Figure out your favorite cocktail before you go out on the town in Park MGM’s Nightingale Queen Suite + Park MGM Queen Room, which has a wet bar and plenty of room to entertain. Double the fun in The Palazzo Resort Hotel & Casino’s Luxury 2 Queen Suite + Luxury 2 Queen Suite and stretch out among two generously-sized living rooms, four queen-sized beds, and two full-sized sofabeds.

Pro tip: Hit up one of Vegas’ legendary pool parties—check out 10 of our absolute favorites.

Sip Manhattans in Manhattan

If New York City never sleeps, perhaps it’s because the bars and clubs don’t close till 4 a.m. You’ll need a strategy to make it to last call, so be sure to take a late afternoon nap after a long day of sightseeing and museums. Stay in the heart of the action and have plenty of space for your friends in the Knickerbocker’s Corner Junior Suite + Premier Guestroom Two Queens, where Times Square’s neon lights glow just outside your window (black-out drapes ensure a restful sleep). Steps from the coolest shopping and hippest nightlife, the James New York in Soho has chic suites that feel like you’re living in a beautifully-designed apartment. In Tribeca, the connected Corner Suite and Superior Double Room at the Duane Street Hotel has some of the best views of the city.

Pro tip: In between bar hopping, make a late-night stop at the Empire State Building, which most people don’t know is open till 2 a.m. every day, including all holidays. The lines to catch the view from its 102nd floor observation deck are remarkably chill after 11 p.m., but get there before 1:15 a.m., which is the last elevator up.

Bienvenidos a Miami

Miami’s South Beach is a spectacle for the eyes and ears with its glistening white beaches a stone’s throw away from 24/7 clubs blasting everything from cabaret tunes to EDM and Latin beats. Just a block away from the beach, Boulan South Beach’s Deluxe Suite offers ocean views and easy access to nightlife. Relax on your own private roof deck with a 54" TV in the Dream South Beach's opulent Guesthouse + Silver Deluxe King, connected rooms that sleep up to four. Not far from South Beach but out of the fray, downtown Miami’s more relaxed vibe is ideal for sipping craft cocktails with twelve of your dearest friends, all of whom can stay with you in these three connected rooms, VIP Suite + Standard Double Room + Standard Double Room, at the Hyatt Regency Miami.

Pro tip: Devour Miami’s foremost hangover treat, the Cubano sandwich, a savory combination of roasted pork, ham, swiss cheese, pickles and mustard on toasted Cuban bread. You’ll find Cubanos all over the city, from the iconic Versailles in Little Havana to the hole-in-the-wall Las Olas Cafe in South Beach. Check out more of our favorite spots in Miami.

When You’re Turning 30

Go big in the Big Easy

Your dirty thirties were meant to be kicked off with a refreshing Hurricane sipped in the cobblestone streets of New Orleans. It’s legal to carry an alcoholic beverage out in public in NOLA as long as it’s not in a glass container, so grab a roadie and revel in all the city has to offer. If you’re combining your birthday trip to New Orleans with a major event such as Mardi Gras or Jazz Fest, you’ll want to book well in advance. Stay near the French Quarter, but away from the chaos and debauchery at one of these three hotels. Located on historic Magazine Street in a former 19th-century newspaper office, the Eliza Jane has excellent connecting room options like the Editor's Suite Two Queen Beds + Editor's Suite King, which sleeps up to 10 guests. Relax in old-world style at the Roosevelt New Orleans, a Waldorf Astoria Hotel, where the One King Bed Waldorf Suite + Queen Superior adjoining rooms feature an elegant dining room with a crystal chandelier, living room with tufted armchairs, and even a half bath for guests. Families love the free hot breakfast at the Homewood Suites by Hilton New Orleans and two-bedroom suites like the 1 King 2 Queen Beds 2 Bedroom, which boasts three beds plus a sofabed.

Pro tip: All of the above hotels are a short walk to Cafe Du Monde, the famous beignets spot in the French Quarter that’s open 24/7. Lines can be long, so late-night is a great time to scarf down these puffy donuts covered with powdered sugar and soak up all that alcohol.

Find your happy place 

Thirty is the perfect age to reconnect with your inner child at one of Orlando’s theme parks and, if you have kids, it’s the ideal family vacation. With eight theme parks to choose from, pick a hotel that’s convenient to where you want to go. Stay near the Happiest Place on Earth at the Hilton Orlando Lake Buena Vista — Disney Springs™ Area, which offers connecting rooms like the Two Double Beds Junior Suite + King Standard Room that sleeps seven. There are also plenty of options if you aren’t traveling with kids; Universal’s Hard Rock Hotel® features an adults-only jacuzzi and massive adjoining rooms with five beds like the King Suite ＋ Pool View Queen ＋ Pool View Queen.

Pro tip: Before Orlando’s theme parks existed, Gatorland entertained families with its park full of alligators and crocodiles, from babies to 14-foot adults. In addition to tours and shows, you can zipline through the park and fly above a marsh filled with 130 giant alligators.

When You’re Turning 40

Do-si-do in Music City

Two step into your 40s in Nashville, where there’s live music and delicious food around every corner. While the city is known as the Country Music Capital, you’ll also hear plenty of bluegrass, Americana, rock, jazz, and hip-hop. In between sets, make a reservation at one of Nashville’s thriving chef-driven restaurants. Stay at the Hilton Nashville Downtown to be near historic lower Broadway aka Honky Tonk Highway, a cluster of bars that have live music every day, and relax in a Two Double Beds One Bedroom Suite that sleeps six. Don’t miss Music Row, the heart of the city’s music industry, where the One King Bed Junior Suite at the Hilton Garden Inn Nashville Vanderbilt offers a spacious separate living area.

Pro tip: Carve out a few hours to visit the Country Music Hall of Fame, where you can admire the guitars, cars, clothes, handwritten lyrics, and more that belonged to the most influential artists in American music.

Brews, buds, and the great outdoors

Your days of taking birthday shots are likely over by 40, so how ‘bout a flight of craft beer and a toke of premium cannabis? If that’s your speed, Denver’s the spot to do it, where there’s a brew pub on every corner, often right next to a recreational cannabis dispensary. There are also plenty of outdoor adventures to keep you busy, from whitewater rafting to ziplining through the Rocky Mountains. Host 25 of your closest friends in the massive Aspen Suite at the Hyatt Regency Denver at Colorado Convention Center, which has breathtaking views of Denver and sits one block from the 16th Street Mall. Large groups will love the connected rooms at the Hilton Denver City Center, where the Junior King Suite + Two Queen Beds has more than 1,000 square feet to sprawl out in.

Pro tip: No one has to be the designated driver at My 420 Tours’ Buds & Beers: A Grow & Brewery Tour, a cannabis-themed beer tour that invites stoners to blaze on a party bus and drink at one of Denver’s must-visit microbrewies. 

Lions, tigers, and bears, oh my!

It’s okay to let the kids crash your 40th birthday trip. In San Diego, you’ll have the best of both worlds—zoos and theme parks for the kids and sunset walks on the beach for you and your partner. Enjoy day and evening childcare and close proximity to LEGOLAND at the Omni La Costa Resort & Spa, where family-friendly connected rooms like the La Costa Suite with Signature 2 Queens have three beds plus a sofabed. Wake up on your birthday with a view of the Pacific Ocean at the Beach Village at The Del, Curio Collection by Hilton, which has gorgeous beachfront rooms that connect to sleep large groups like the Beachfront Cottage Suite + Beachfront Cottage Room, which accommodates up to eight. Be within walking distance of cool sites like the USS Midway Museum at the Andaz San Diego, where adjoining rooms such as the Andaz Extra Large Loft + Andaz King offer sweeping city views and a spacious living room. 

Pro tip: Hit up one of San Diego’s many tiki bars, where parents can sip an adult beverage while flaming drinks (including those without alcohol), wild decor, and food keep the kids captivated. We love False Idol in Little Italy, not far from downtown.

When You’re Turning 50

Hang ten while you can still hang

Embark on a spiritual awakening on Oahu, the most group-friendly island because it has something for everyone. Culture vultures can tour historic homes, like Shangri La, now a museum of Islamic art, and beach bums can chill in Waikiki or escape the crowds on the North Shore. Dine on fresh poke at a beach barbecue, hike Diamond Head, or take a surf lesson, but above all, relax. With three beds and a mid-century aesthetic, Hyatt Regency Ambassador Suite provides the perfect group vacation hideaway. Gather eight of your favorite people in the spacious Grand Wailea, A Waldorf Astoria Resort in the Napau Club Royal Suite + Napau Ocean View 2 Queen and take in spectacular views.

Pro tip: Discover the mystical heart of the island at the Mermaid Cave, a haunting formation that sits in a pool of blue water littered with seashells and coral on the west side of the island, between the Kahe power plant and Nanakuli Beach Park. 

Hit the highway 

There’s nothing like a road trip with friends to clear your head and reset your mind for a new year. Start in Los Angeles where you can cruise the Sunset Strip and stay in a hotel worthy of a rock star. Once home to Robert Plant, Jim Morrison, and Little Richard, the Andaz West Hollywood offers a relaxing retreat for groups with connecting rooms like the Deluxe View Suite + Two Queen Beds Sunset Boulevard View that sleep up to seven. Or head to the beach and stay three short blocks from the Santa Monica Pier at the DoubleTree Suites by Hilton Santa Monica, where adjoining rooms like the One King Bed One Bedroom Suite + Two Queen One Bedroom Suite can accommodate up to eight people. Take the Pacific Coast Highway to Long Beach and, if you’re really feeling adventurous, keep going south all the way to Palm Springs.

Pro tip: California’s recreational marijuana laws forbid driving under the influence, but there’s no law against smoking a doobie while watching the sunset over the great Pacific. We found the best spots in Los Angeles to smoke legal cannabis.

When You’re 60 & Beyond

Soak up architectural gems and waterfront views

For a busy metropolis, Chicago is a surprisingly easy city to navigate thanks to a robust mass transit system and walkable neighborhoods laid out in a simple grid. Stay in the heart of the city’s architectural gems in the Loop, an area south of the Chicago River that’s brimming with photo ops like 19th-century Art Deco buildings, The Bean sculpture in Millennium Park, and the Willis Tower—Chicago’s tallest skyscraper. In the Magnificent Mile neighborhood, north of the Chicago River, the recently renovated Conrad Chicago boasts lavish connecting rooms with spa-like bathrooms such as the Royal Suite + Two Queen Beds Superior Room, which sleeps up to eight.

Pro tip: Learn the history behind Chicago’s most iconic buildings aboard the Chicago Architecture Center’s river cruise, a relaxing 90-minute ride that departs from downtown multiple times a day.

Wear flowers in your hair

If you were too young to experience the Summer of Love, but old enough to long for the flower power days, you can commune with its spirits in San Francisco. Though the city has changed a lot since the 60s, it’s still a rebel in its own right. After legalizing recreational marijuana in 2018, San Francisco quickly became home to the most cannabis consumption lounges in the United States—meaning you can buy and smoke marijuana in the same shop like they do in Amsterdam. Put yourself at the center of it all by staying in Union Square, where shopping and nightlife are steps away. Enjoy amazing city views from the Corner King One Bedroom Suite at the Hilton San Francisco Union Square at the Grand Hyatt San Francisco.

Pro tip: Located approximately 90 minutes from San Francisco, Napa Valley and Sonoma grow some of the best wines in the country. Don’t miss the hamlet of Yountville as you cruise through Napa Valley, which thanks to Thomas Keller’s French Laundry has more Michelin stars per capita than any town in the world.

Updated 4/8/23