Cheaper Stays & Festive Streets: One Of America’s Most Charming Cities Is The Perfect Winter Escape

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Ever been to Europe?

There’s something almost indescribable in regard to wandering timeless streets mesmerized by centuries-old architecture and simplistic lifestyles.

Then we come back home dying to be first in line for the latest cell phone, video games, and whatever that whole NFT craze was.

Savannah, GA riverfront

Well, unlike the U.S., which is generally depicted as just wide open spaces, bougie beaches, and sky-high modernized metropolises, there are still plenty of timeless cities to enjoy, especially during the holiday season.

Perhaps the best area for such places is the South from New Orleans, Charleston, and one of America’s most charming cities, Savannah, Georgia.

This winter, discover cheaper stays and festive streets perfect for a winter escape in a city known for ‘southern hospitality’, old-timey plazas, and a springboard to a blissful side of the Atlantic coastline.

Winter In Savannah: Enjoy Less Crowds & Cheaper Costs

River Street in Savannah at dawn

There’s many reasons to visit Savannah, but this historic city was just crowned #1 on Southern Living’s new ’10 Winter Vacation Ideas’ list primarily due to crowd-free streets and the affordability factor this time of year.

There’s really not a bad time to visit Savannah unless you’d like to avoid the humidity. In that case, a summer trip may not be for you.

Wintertime brings more splendid weather, consistently in the 60s, great for venturing out to nearby islands, perusing cobbled streets, or hopping aboard a scenic river cruise like Savannah Riverboat Cruises (where they ‘guarantee the lowest prices’!).

Riverboat in Savannah skyline under full moon

Savannah is a popular getaway year-round, but winter is the best time to take advantage of the least of amount of crowds for easier navigation and better photo-ops.

Perhaps more importantly, you can typically score cheaper stays and even airfare on occasion, according to Southern Living.

If you prefer luxury over boutique stays, check out the following 3 hotels with great rates in December and January (including Christmas!):

  • Hotel Indigo Savannah Historic District – $99
  • Aloft Savannah Downtown Historic District – $136
  • The Westin Savannah Harbor Golf Resort & Spa – $155
St John's Episcopal Church in Savannah

For comparison, the above hotels are all deep into the $200’s in summer, proving your bank account will thank you this winter.

Savannah’s architecture is to die for with well-preserved rows of a variety of styles from Georgian (of course!) and Greek Revival, among others.

There’s plenty of vacation rentals and converted hotels too, like the Olde Harbour Inn for true Savannah stay.

Savannah’s Festive Streets

There’s definitely a European vibe in Savannah and even more so come winter when the popular Savannah Christmas Market arrives (Nov. 21 – Dec. 31)

Christmas decor in Savannah City Market

It’s not only the market that’s festive, however. The main parts of the city, such as always bustling River Street, are decked to the gills with holiday decor to set the mood for the ‘most wonderful time of the year’.

The Historic District is already teeming with charming streets, historic homes, and the unmissable Gothic-style Cathedral Basilica of Saint John the Baptist, which of course, is even more incredible to visit with the magical ambiance of Christmas.

One unique event that’s a must-see is the Holiday Boat Parade of Lights (November 30th) showcasing a dazzling display of synchronized lights.

Christmas decor on historic home in Savannah

While the Christmas Market takes a page out of Europe’s playbook, the Boat Parade is true Savannah through and through along the Savannah River. and always draws a crowd.

A Multi-State Coastal Escape: Seaside Bliss Is In Close Reach

Even though Georgia borders Florida, it’s actually the Georgia-South Carolina line that’s one of the best beach spots.

While you won’t find Caribbean-esque sun this time of year, walks on the beach, kayaking, surfing, and simply finding a nice beachfront restaurant is always enjoyable.

Beachgoers walking on Tybee Island

One such place to check off all these boxes this winter is Georgia’s Tybee Island, roughly 25 minutes from Savannah.

Across the Savannah River, however, is the South Carolina state line with its own set of beautiful islands like the hidden gem of Daufuskie Island, popular vacation spot Hilton Head, and one of our Editor, Tyler’s favorite beach getaways, Fripp Island.

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Colombia’s Undiscovered City: Swap Medellin’s Chaos For Timeless Streets & Authentic Culture

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At this point, everyone already knows about Medellin. It’s been taken over by digital nomads and is popular among solo travelers too.

With that comes a lot of chaos that you don’t necessarily have to deal with to check Colombia off your list.

People walking through Popoyan, Colombia

Is Medellin old news? No, not necessarily.

But don’t sleep on Colombia’s hidden gems.

While you may want to avoid visiting Bogota for more than a layover, and Medellin has its own set of issues we reported on earlier this year, there’s so much more to explore in this fascinating country.

Whether it’s beaches, ancient sites, or the timeless streets of Popayan, Colombia’s undiscovered city, it’s time to swap the chaos of Medellin for a more authentic experience amongst some of the country’s most picturesque surroundings.

Colombia’s Little Known Slice Of Spain

White buildings of Popyan, including church

I get it. Saying there’s a ‘slice of Spain’ in the middle of Colombia might seem a bit dramatic, but what else do blocks and blocks of captivating whitewashed buildings remind you of?

Santorini perhaps? Now that would be a stretch!

With no blue trim and endless gleaming white structures, Spain is the best comparison since there’s no other place like this in the nation.

Plus, centuries ago, for better or worse, Popayan was on the Spanish conquistador’s trading route through South America, and the preservation of their lasting marks is incredible to visit.

Church of San Francisco in Popayan

How such a beautiful city has flown under the radar for so long is baffling, but it’s probably because Colombia has so many other popular destinations.

Popayan also has no international airport (which only serves a few domestic flights), so getting here is more of a trek than getting to Medellin, Cartegena, or Cali.

Speaking of, Cali is the most convenient gateway into Popayan by bus unless you connect by flight through Bogota via Avianca or Clic.

Upon arrival, you’ll be welcomed by stunning colonial architecture, historic cobbled streets, and virtually no tourists – but don’t worry; it’s safe here!

Safe And Insanely Budget-Friendly

Whitewashed buildings in Popayan

Colombia’s white city, as it’s known, ticks all the boxes many travelers seek when venturing to this side of the world.

First, unlike Medellin, where it’s almost guaranteed you’ll have some sort of unfortunate run-in the longer you stay, Popayan is widely regarded as safe.

The only issue you’ll want to be aware of is that you may stand out like a sore thumb, being one of few tourists in the entire city of nearly 320,000 residents.

Furthermore, you can stay for cheap in one of the numerous beaming white buildings, whether a boutique hotel, hostel, or rental.

Elderly locals of Popayan, Colombia

For example, you can stay at Hotel Dann Monasterio, a former 1500s monastery turned ritzy hotel for only $41 on Priceline.

Airbnbs on the other hand offer similar rates and more space than a traditional hotel room, so you have plentiful options at hand.

Monthly stays are even better, so those Medellin digital nomads tired of keeping their head on a swivel could definitely opt for Popayan for super cheap – think nice apartments for $300 – $450 per month.

Where do I sign up?

Calling All Foodies! UNESCO’S First ‘City of Gastronomy’

Restaurant in Colombia

Oftentimes, UNESCO designated specific sites or regions to protect cultural heritage and encourage education.

But did you know they also do the same for food?

While it’s completely different than receiving Michelin stars, it still shows how incredible a place can be to indulge in local cuisine.

While Colombian restaurants aren’t as popular as they should be in the States, Colombian cuisine goes well beyond savory empanadas.

Food prep of fresh ingredients in Popayan

Popayan was the first ‘City of Gastronomy‘ recognized by UNESCO, particularly for its rich fertile soil resulting in fresh ingredients, whether it be locals’ favorite beverage chicha or corn pancakes.

Culinary traditions are well-preserved here thanks in part to UNESCO and partly due to the community’s’ sense of pride showcased at numerous restaurants here, where traditional methods are still used, such as esamargados (fruits and zest marinade).

While UNESCO doesn’t give restaurant recommendations per se, TripAdvisor sure does. Check out these 3 top-rated restaurants:

  1. Restaurante Carmina (perfect rating!)
  2. Mora Castilla
  3. La Cosecha Parrillada Centro

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