All orders qualify for free returns. Free shipping is automatically applied to orders over $50. Want to enjoy free shipping on every order? Join Routefinders Rewards for free.

Free shipping is not available for pro deal members unless otherwise stated.

Your Guide to Tropical Adventure: Where to Escape Winter This Winter

In the legendary words of House Stark, “winter is coming.” And when it does, what will your adventure of choice be? Skiing in the Mountain West? Ice fishing in the Midwest? Snowshoeing in the Pacific Northwest? 

If none of these snowy (not to mention westerly) adventures quite strike your fancy, then fear not. There’s a sun-soaked, surf’s-up, waterfall-filled alternative: tropical adventure. 

That’s right: when winter’s stranglehold sets in, it’s easy to forget just how easy it is to reach some genuinely stunning tropical destinations from major American travel hubs. 

Here, we’re highlighting a few of the must-visit tropical destinations within a 5-hour flight of key US flight centers. What each of these places has in common is a few things: they’re (relatively) easy to reach, they’re perfect for a long weekend winter migration, and they’re true outdoor and eco-adventure epicenters.


Waimoku Falls, along the famous Road to Hana. Photo by Bryan Woolbright(Se abre en una ventana nueva)


Just a 5-hour flight from Los Angeles and San Francisco—and 6 hours from Seattle and Portland—Hawaii has long been a lauded winter escape for West Coasters. Arguably the toughest thing about visiting Hawaii is deciding which island to visit. Do you opt for the cosmopolitan Big Island? Or the Jurassic cliffs of Kauai? Answer: Maui. 

Maui is, in many ways, like the Goldilocks choice of Hawaii travel. It’s got enough in-town flavor to keep you entertained with great food (all the fish) and great drinks (all the craft beer). But it’s also a true outdoor mecca home to killer surf, world-class hiking, one of the most iconic drives in the world, and 10 of the world’s 14 climate zones—from tropical rainforests to desert grasslands. 

Because Maui is blessed with such a dizzying mix of ecosystems, it’s understandably got a ton of adventures to match. Some absolute musts include: 

The Road to Hana

This 64-mile drive is legendary. Sure, it can get crowded. But this day trip is the living embodiment of “it’s not about the destination, it’s about the journey.” If you go in with that mindset, no amount of stop-start traffic will put a dent in what’s truly one of the most scenic drives on the planet. With hundreds of worthy pull-offs—including roadside waterfalls, cliffside ocean views, rainbow cypress trees, and even dozens of food stands with Huli-Huli chicken, fresh banana bread, fruit smoothies, and more—cruising the Road to Hana is a must for any Maui trip.

Haleakalā National Park

Hawaii, or Mars? Photo by Jeff King(Se abre en una ventana nueva)

Sprouting up from the center of Maui like a teenager’s growth spurt (aka all sprout, no stout), the dormant Haleakalā Volcano(Se abre en una ventana nueva) is a 10,003-foot behemoth. Reaching its summit (either by car or by bike for the brave of heart) takes you from sea level to… well… 10,003 feet above the clouds. Along the way, you’ll pass through an incredible array of ecosystems—pine and cypress forests, long-grass pastures filled with horses and cows, windswept chaparral, and then sprawling, Mars-like barrenness above the treeline. The sunset views (not to mention the starry ones come nightfall) from the Observatory at the summit are some of the best in the world.


Located in the northwest corner of Maui, the old whaling town of Lahaina is a launchpad for a variety of fun experiences. First, the Old Town itself is great to stroll through, with dozens of excellent bars, restaurants, and shops tucked in quaint historical structures from the 1800s and nestled amongst enormous shade-giving banyan trees. Second, while “whaling” is thankfully a thing of the past in Lahaina, whale watching is still very much alive. Taking a chartered boat from Lahaina in winter will yield countless views of breaching humpbacks. Finally, you can’t visit Maui without surfing. And Lahaina offers a great break for beginners and seasoned surfers alike.

Puerto Rico

Exploring the fortress of Old San Juan. Photo by Zixi Zhou(Se abre en una ventana nueva)

Getting to Puerto Rico from pretty much anywhere on the East Coast is about as easy as deciding to go to Puerto Rico in the first place. AKA, it’s very easy! 

From NYC to San Juan, for example, is a manageable 4-hour flight that has the added bonus of frequently being pretty inexpensive (i.e. rarely over $300 round trip, often closer to about $100). And let’s face it: between bone-chilling winds ripping through your winter coat on Broadway or a snorkeling excursion among dazzling reefs in impossibly crystal clear waters, there’s an obvious winner here. 

What’s more is that, like Maui (obviously), you don’t even need a passport to visit Puerto Rico, since it’s an American territory. A simple state-issued ID will do. Just another notch in the “hassle-free” belt of visiting Puerto Rico. 

Some musts in Puerto Rico:

Old San Juan

If you’re flying into San Juan (which you likely will be since it’s the largest city), be sure to find lodging accommodations in Old San Juan. This 16th Century National Historic Site, encircled by old fortress walls and brimming with brightly colored houses and cobblestone streets is like something straight out of an Iberian postcard. Exploring these colorful streets, getting lost among its alleyways and then found within labyrinthine bars, like La Factoria(Se abre en una ventana nueva), is a major part of what makes Old San Juan such a special place to visit. Not to mention, beaches abound nearby!

Vieques & Culebra

The stunning waters of Culebra. Photo by Juan Burgos(Se abre en una ventana nueva)

The outer islands of Puerto Rico are simply stunning. Vieques is famous for Mosquito Bay, the brightest bioluminescent bay in the world. Not to mention dozens of breathtaking beaches and undeveloped coves. Culebra is similarly off-the-grid yet on-point when it comes to snow-white sands and beautiful turquoise waters. Reaching these outer islands can be done via jumper plane, ferry, or catamaran snorkeling tours(Se abre en una ventana nueva). The latter takes you to Flamenco Beach—once ranked Discovery Channel’s best beach in the world—and allows you to snorkel among some seriously showstopping waters and beautiful reefs.

Costa Rica

The looming summit of Arenal Volcano in La Fortuna. Photo by Cosmic Timetraveler(Se abre en una ventana nueva)


When people think “tropical adventure,” they’re often thinking of Costa Rica. In recent years, this Central American paradise has become synonymous with “ecotourism” at a “Pura Vida” pace. In other words, between the lush jungles, towering volcanoes, hidden beaches, world-class surf breaks, and incredible biodiversity, Costa Rica is—well—kind of a nice place to visit. 

From Dallas or Houston (or even Atlanta), flights to Costa Rica’s capital are less than 5 hours nonstop. From more wintry cities like Denver or Chicago, you can still reach this tropical oasis in about 7 hours. 

Some iconic experiences to have once you’re there:


Monteverde’s Cloud Forest Reserve(Se abre en una ventana nueva) is every eco-tourist’s dream come true. This verdant jungle high in the Cordillera de Tilarán mountains is a place where tranquil beauty meets thrilling adventure. Come for the deliriously robust lineup of flora and fauna diversity. Stay for the suspension bridges swaying through treetops, the ziplines plunging through the clouds, and the world-famous Tarzan Swing(Se abre en una ventana nueva).


Located on the Osa Peninsula—which is uncannily shaped like a whale’s tail and which is also unironically a great place for whale watching—Uvita is an off-the-grid paradise of the highest order. Howler monkeys outnumber people. Jaguars lurk among the verdant jungle. Yogis bend and bind in mahogany tree houses. And surfers take advantage of the consistent waves and safe conditions. It’s no wonder this region is so renowned for turning travelers into ex-pats.

La Fortuna Waterfall in all its glory. Photo by Etienne Delorieux(Se abre en una ventana nueva)

As the gateway to Arenal Volcano National Park(Se abre en una ventana nueva), it’s no wonder La Fortuna is such a popular destination. Nestled at the base of the looming (and active) 5,436-foot Arenal Volcano, La Fortuna has it all: strenuous hikes to volcano craters, plunging waterfalls, magma-heated hot springs, green lagoons, and denser-than-dense jungle forests. 

In sum, if you’re looking for a little less winter this winter, you can find it in these tropical paradises (among many others throughout Central America and the Caribbean).