Americans Can Fly Nonstop To These 4 Cultural Beach Destinations In The Caribbean

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The Caribbean may be the number one destination for Americans going on a sunny break in winter, but for some, it’s not without its downsides:

Cancun, Punta Cana, and the like are all primariliy resort destinations you go for relaxing, taking a breather, and some week-long pampering, and though they are indisputably incredible on the luxury tourism front, the cultural offer is infamously lacking.

Fortified City Walls Of Old San Juan, Puerto Rico

With a growing number of U.S. passport holders now actively seeking cultural immersions when away from home, as opposed to lounging by the pool all day, the usual beach hotspot may not exactly fit their criteria for a more meaningful experience.

There are plenty of exceptions to the rule, of course, with incredible Caribbean destinations boasting not only palm tree-lined sands and turquoise seas but also mind-blowing sights.

If we may add, they’re all a short 2-4 hour flight away from major U.S. hubs like Atlanta (ATL), Chicago-O’Hare (ORD), Houston (IAH), New York (JFK), Newark (EWR), and others:

San Juan, Puerto Rico

Colorful Houses In Old San Juan Puerto Rico

The bustling capital of Puerto Rico, an unincorporated U.S. territory U.S. citizens can travel to passport-free, San Juan is a cultural treasure dating back to the time of Spanish rule, which, similarly to Santo Domingo, has retained much of its Old World allure.

The main attraction here is Old San Juan, a maze of cobble-covered streets and tree-shaded plazas flanked by brightly-colored edifices that will make you feel more like being in Southern Europe, proper, than somewhere in the Caribbean.

Cobblestone Alley Lined With Colorful Houses In Old San Juan, Puerto Rico

The towering Bautista Cathedral serves as the final resting place for Juan Ponce de León, a renowned Spanish explorer, and the Old Town is still surrounded by city walls, making San Juan one of a handful of colonial cities in the Americas to have this feature.

Needless to say, there are countless beaches and swimming spots within a short distance of the picture-perfect historic center, with a sandy Condado Beach, lined with restaurants and high-rises, and El Escambrón, a well-frequented snorkeling area, to name a couple.

Santo Domingo, Dominican Republic

Tourist woman appreciating the beauty of the colonial city of Santo Domingo, Dominican Republic

The often-overlooked capital of the Dominican Republic, Santo Domingo is the oldest European city in the Americas and a bustling metropolis best known for its cobbled Zona Colonial, with buildings dating as far back as the 1500s, surrounded by UNESCO-listed ramparts and towers.

Its towering cathedral is the first built by the Spaniards upon their initial incursion into the New World, while Plaza de España is the city’s colonial centerpiece, housing a monumental Alcázar de Colón palace and a number of casual, charming cafes.

Old Spanish Ozama Fortress In Santo Domingo, Dominican Republic

Minus the buzzing traffic, exotic smells emanating from the stall-lined Mercado Modelo, and the fact it’s a little rough around the edges, you could easily be led to believe Santo Domingo is just another postcard town in Spain, but that’s not to say old stones is all it has to offer.

With up-and-coming Boca Chica and its largely undeveloped, sun-kissed shores being a short half-hour drive from the historic center, where beachfront stays start from $63, it is a budget-friendly alternative to a pricey Punta Cana or increasingly expensive La Romana.

Cartagena, Colombia

Historical City Center In Cartagena, On The Caribbean Coast Of Colombia, Mexico, South America

Lining the sun-drenched Caribbean shores of Northern Colombia, Cartagena ticks all the boxes for what makes a culture-infused sunny break great: it has the postcard-ready colonial core, the inviting street food scene, and even pristine islands just off its mainland.

If you’re going to Cartagena this winter, you should take your time strolling its monument-packed fortified Old Town, filled with 16th-century squares, street food stalls strewn along cobblestone alleys, and ornate Baroque churches, as well as walking the impressive ramparts.

Woman Walking Down the Street in Cartagena

Thanks to its tropical weather, Cartagena is great for water-based activities, and one could argue no visit is complete without an island-hopping adventure: in that case, this 5-island boat tour around the Rosario archipelago is a must-do, costing only $75.66.

Now, if you’re keen on seafood, you can’t miss out on Pezetarian‘s sushi tacos: not exactly traditional, but one of Cartagena’s culinary highlights, nonetheless; as for authentic Colombian food, Reina Arepa probably serves the yummiest arepas in town, starting from a single dollar.

Tulum, Mexico

A Father And His Son In Tulum Ruins, Mexican Caribbean, Mexico, Latin America.jpg

A trendy resort town straddling the turquoise Mexican Caribbean, Tulum may be best known for its luxury hotels, party scene and shop-bordered Quinta Avenida, but if it’s ancient culture you’re coming all the way down to Mexico for, then it’s ancient culture you’ll get:

It is home to the sprawling, 13th-century Tulum National Park, an archeological zone comprising the iconic cliffside Castillo, a Mayan watchtower overlooking the Caribbean, and many smaller temples, including the landmark, mural-clad Templo de las Pinturas.

A Young Woman Smiling For A Picture At The Ancient Ruins Of Tulum, Mexico, Latin America.jpg

The Tulum Ruins ranks among the most popular in the Yucatán Peninsula for tourists to immerse themselves in the region’s rich past, though they’re not the only ones accessible from Tulum: for instance, the equally-beautiful Cobá is a 45-minute drive inland.

This winter, Americans flying directly to Tulum Airport can use the opportunity to board the newly-launched Teen Maya, a scenic train traveling on a loop around Yucatán and calling at Tulum to discover many more Mayan sites, undisturbed native settlements, and colonial towns.

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Experience Cultural Delights & Affordable Luxury In The Southwest’s Most Underrated City

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If you’re over mainstream news (and who wouldn’t be by now?), then there’s one remarkable city that always seems to slip through the cracks as more than just a pass-through city.

Chances are, if you’ve ever taken a road trip on I-10, then you’ve passed through one of the Southwest’s top hidden gems, yet nearly 700,000 people call it home.

Socorro Mission in El Paso

Largely ignored even by its own state, with locals commonly mislabelling it as “Mexico” and misinformed characterizations since it’s lined by “the wall”, fellow Texans and general travelers have long been missing out on the cultural delights and affordable luxury of El Paso.

Yes, El Paso – the one often portrayed as a run-down desert town and unsafe hub for illegal migrant crossings.

As a former resident, I can attest that, yes, there are occasional border issues, but one small sub-section of a city shouldn’t represent the masses when there’s astounding nature, prideful, friendly locals, and an ever-changing downtown district beginning to buzz again.

The Forgotten City Of Texas

El Paso skyline at twilight

Despite breaking tourism records in 2023, El Paso still flies well under the radar except when talking heads spew negative depictions of what’s actually an awesome city to visit.

Even if you haven’t brushed up on Rosetta Stone lessons lately, you can probably surmise El Paso translates to “The Pass” in English, and that’s largely how El Paso has been visited – just a stayover on to somewhere else.

But El Paso deserves to be your next weekend getaway, at the very least. If you enjoy phenomenal Mexican food ranging from classic hole-in-the-walls and cart vendors to high-end Michelin-worthy eateries, El Paso has you covered, and it exudes authenticity, unlike that other record-breaking Mexican-influenced city.

Rolled tacos at Elemi in El Paso

No offense, San Antonio, but El Paso’s food is unmatched, and one hike in the Franklin Mountains puts your “river” to shame.

Despite many Texans pretending the Lone Star State’s southwest tip doesn’t exist, popular Texas publication Texas Monthly had the huevos to recognize two El Paso restaurants with the best tacos in the state:

Of course, indulging in local cuisine is great way to experience any destination, this is only a tidbit of El Paso’s cultural delights.

Not Just Margs & Tacos: Discover Historic Neighborhoods & Important Landmarks

San Elizario Presidio Chapel

You’ll find every legitimate Mexican dish under the sun in El Paso, with a special emphasis on Southwestern and Chihuahua influence, given the close proximity to Ciudad Juarez.

Texan and Mexican history blend timelines, and there’s no better place to experience the best of both worlds than a plate served in El Paso, but to witness the history itself is another story, and you can do that too.

One overlooked gem, even for locals, is in the next town over, Socorro. Here, you’ll find the El Paso Mission Trail home to an immaculately preserved glimpse of the past, with stunning historic Missions playing a significant role in a former trade route spanning from Mexico City to Santa Fe.

Sunset Heights mural in El Paso

Make sure to check out all 3 missions, each with their own unique relevance:

  • Ysleta Mission
  • Socorro Mission
  • San Elizario Presidio

In El Paso proper, the beauty of exploring the city’s historic neighborhoods is you never know what you’ll find.

Check out Sunset Heights, Manhattan Heights and my old stomping grounds, Segundo Barrio, for rows of streets oozing timeless charm and hidden gems like my favorite restaurant you’d otherwise never know about, Jalisco Cafe (only open on weekends).

Free Public Transit & Affordable Luxury

El Paso trolley passing street mural showcasing local heritage

Downtown has continued to undergo a mass transformation since the pandemic’s ghost town vibes.

As WinterFest recently transformed downtown into a desert’s version of a winter wonderland, there are also many new bars, restaurants, cafes, and the city’s first-ever capsule hotel, breathing new life into formerly barren streets.

Getting around in El Paso’s splendid winter weather is easy, but if you plan to visit in the scorching summer, you may want to take advantage of the city’s free Streetcar connecting downtown to the high West Side.

Downtown is likely where you’ll want to make your base no matter the season. With a plethora of upscale hotels and rooftops with sweeping views, you’ll be shocked by how nice El Paso really can be – a far cry from its reputation as a bland desert town.

Plaza Theater and Plaza Hotel in El Paso

My favorite is The Plaza Pioneer Hotel (commonly referred to as “The Plaza”), recently awarded a Michelin Key and can be booked in the low $100s.

These 5 hotels offer affordable luxury in downtown El Paso: (under $150 per night)

  • Hotel Paso Del Norte (check out the European-esque Dome Bar)
  • The Plaza Pioneer Hotel
  • DoubleTree By Hilton Hotel El Paso Downtown
  • Hotel Indigo El Paso Downtown
  • Aloft El Paso Downtown
Dome Bar at El Paso's Paso Del Norte Hotel

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