Vintage Vacations Are Trending - Here’s Where to Time Travel in Style

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In a world obsessed with what's next, the next flight, next TikTok, next place to check off the list, a growing number of travelers are looking backward, not in regret, but in curiosity. They're swapping modern distractions for a sense of nostalgia, diving into curated experiences that feel like stepping into a different decade, or even a different century.

Welcome to the trend of Time Tripping, where travel isn't about how fast you get somewhere or how far you go. It's about reconnecting with the soul of a time long gone, and maybe with yourself in the process.

From Old West adventures and 1920s speakeasies to glamorous 1950s resorts and stargazing under analog skies, here are five standout destinations that let you hit rewind. 

In an age of fast-paced getaways, the Rusty Parrot Lodge & Spa offers a timeless escape. Tucked away in the heart of Jackson, Wyoming, this family-run lodge blends luxury with the rugged charm of the Old Wild West. From handcrafted furnishings and western art to the warmth of a crackling fire after a day in the Tetons, it's a place where modern comforts meet frontier nostalgia.

For those looking to dive even deeper into the spirit, the lodge's Cowboy Concierge is your personal guide to the Wild West - whether it's lining up horseback rides through scenic trails, booking an Old Time Photo Shoot, or uncovering hidden gems only the locals know. The Rusty Parrot lets you slow down and reconnect with a simpler time and with yourself.

Secret passwords behind hidden doors, evoking classic Prohibition vibes with bites and libations to match. A whimsical cocktail menu with drink names like "Smoke & Mirrors" and "Last Word" is complemented by decor that throws it back to the roaring 1920s —  bookshelves lined with vintage titles, a record player, plush velvet furniture, inspired playlists, antique artifacts, and artwork.

Welcome to Room Nine01 at Hyatt Centric Las Olas, a private experience by reservation only for up to 12 guests. The nostalgia of exclusivity and secrets awaits behind the room door.

Step into the glitz, glam, and tropical swagger of the 1950s at the legendary Caribe Hilton - the very first international Hilton hotel, famously dubbed the "Gateway to the Americas." Since opening its doors in 1949, this Latin icon has played host to a dazzling list of stars and starlets, from Sophia Loren and Rita Moreno to Iris Chacón, who famously performed at the hotel's buzzing Julianna's nightclub.

Elizabeth Taylor even honeymooned here. A Caribbean and pop culture institution, Caribe Hilton is also the birthplace of the piña colada — arguably the most famous cocktail of the century — invented at the hotel's Beachcomber Bar in 1954. Now, fresh off its 75th anniversary, the hotel continues to blend timeless appeal with just the right dose of tropical nostalgia. This is where Old San Juan meets old-school glam. 

Before apps told us where to look or when to sleep, we looked to the stars, and Hotel Rangá invites guests to return to that slower, more wondrous time. Tucked along Iceland's remote South Coast, this family-owned lodge is one of the best places in the world to stargaze. The experience is elevated with their Ultimate Star Bath: a private astronomy session under Iceland's pristine night skies, complete with cozy blankets, an astro-inspired cocktail, and a personalized star map.

For those wanting to disconnect from the digital age fully, the hotel's Analog Menu takes guests even further back — with disposable cameras, a deck of cards, folklore-themed coloring books, and a hand-drawn map of the region. A handwritten postcard, mailed from the front desk, seals the experience.

For those who yearn for those good ol' days before you could post about your travels all over the Gram, back in a time when you could only share your adventures by sending off a cute postcard from every stop on your trip, then you have to head to the Galapagos for a little nostalgic magic. A trip to one of the world's most protected destinations can almost feel like traveling back in time when you stop at the iconic Post Office Bay – a centuries-old sailor barrel where pirates and sailors once left letters for others to carry home, truly an OG mail delivery system!

Today, travelers can still sift through postcards to find one addressed near their town so they can pay it forward by hand-delivering it upon their return home, keeping the tradition alive. Guests aboard Ecoventura's luxury 20-passenger mega-yacht are given beautiful custom postcards to address and leave behind in the barrel in return, so that you can send a message to a loved one back home and tell them about your epic trip of a lifetime! Overall, the experience is a heartwarming reminder that in our modern world, the best travel souvenirs are still often the ones you pass along with love by hand.