If you’re in need of a winter vacation, but the cost is a deciding factor, consider one of these more affordable destinations around the world where the currency conversion is in your favor and your dollar will go the furthest. Here are some of our favorite winter holiday destinations!

Awesome Winter Holiday Vacation Destinations

The Florida Keys

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The Florida Keys are a string of tropical islands connected by US Highway 1 that stretch about 120 miles off the state’s southern tip. While Florida is home to a variety of affordable winter destinations, Key West is popular with partiers as well as those who love beautiful beaches and sunsets, art galleries and water sports. Parrot Key Hotel & Resort offers a great value in a recently revamped destination resort that feels like an old-fashioned beach community, complete with picket fences and porches, but if resorts and hotels in Key West are a bit too pricey for your tastes, consider staying on one of the Keys farther north like Marathon or Islamorada, which tend to be cheaper. Lime Tree Bay Resort is known as one of the best affordably-priced resorts in the Keys. Set along a palm-shaded, sandy beach, it offers all sorts of activity options, including kayaking onsite, swimming in one of two pools, soaking in the hot tub and lounging in a hammock.

Puerto Rico

There’s no need for a passport to visit Puerto Rico, but you’ll be able to enjoy a tropical, exotic island just the same. From a beach that glows in the dark, the pink sands of Isla Verde, outstanding diving and snorkeling to delicious cuisine, salsa dancing the night away and waking up with incredible Puerto Rican coffee, there are many reasons to travel here. You’ll also find lots of small independent hotels that are very budget friendly, like the Villa Montana Beach Resort, a full-service hideaway on the sea, located just a few miles from the airport. The Copamarina Beach Resort in Guanica is an oceanfront resort stretching across 20 acres of lush tropical gardens offering seclusion and upscale amenities.


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Few people put Panama on their list of places to travel during the winter, but it not only offers an ideal destination for warm weather and sunshine but accommodations that run only around $40 a night. It will cost you a bit more to get there due to the lesser demand, but unlike high-traffic destinations such as Cancun, once you get there it’s not only a lot more economical, it’s less likely to be overrun with tourists.

Bocas del Toro, situated on the northwestern Caribbean coast, is an archipelago of nine tropical islands where you’ll find some of the best scuba diving and surf breaks in the country. The orange-tiled roofs and Spanish colonial architecture of old town Panama City offer a striking contrast to the skyscraper skyline across the bay, and in Casco Viejo, after dark music pours onto the street from every alley and corner. By day, you’ll find this area ideal for sipping coffee at Plaza Bolivar, browsing the markets and watching the sunset from just above Plaza Francia.

Las Vegas, Nevada

Sin City is a popular destination year-round, but it offers an especially ideal spot for warming up in the winter while enjoying sizzling entertainment at an affordable cost. In fact, some say it’s the very best wintertime bargain in the U.S. While room rates for some of the very best rooms are around $200 a night, if you’re willing to go a little off the Strip, you can find lodging for less than $50 per night in addition to a collection of unique attractions. In addition to all of the shows and gambling opportunities, visitors enjoy everything from a peaceful gondola ride at the Venetian to heart-pounding thrill rides at the Stratosphere.

San Diego, California

San Diego is renowned for its year-round pleasant weather and a multitude of attractions. While it may not be warm enough for swimming in the winter, the mild temperatures are perfect for taking part in all sorts of other activities, while hotel prices are at their lowest. Enjoy taking a stroll on the beach while watching for whales as winter also happens to be whale migration season. Mission Beach is the hot spot for soaking up some rays, while La Jolla draws surfers with its great waves. Of course, you won’t want to miss a trip to the San Diego Zoo – and, you can save on attractions too by purchasing combo tickets that will get you into the zoo as well as museums and other parks. Pearl Hotel, a hip boutique hotel is not only stylish, but it’s also a steal, with rooms at less than $100 per night.

5 More Awesome Winter Holiday Destinations

Caladesi Island, Florida

Caladesi Island has been called one of America’s top “secret islands.” It stays warm all year long and boasts three miles of white, sandy beaches scattered with seashells. In fact, you’ll find some of the best shelling on the Gulf of Mexico right here. There are no hotels and no cars on the island – you’ll have to take a ferry and then explore it on foot. Walk the boardwalk nature trail where you’ll pass stands of mangroves, sand dunes, and possibly even a rare gopher tortoise. Rent a kayak and paddle around the bay side of the island where you’ll have the chance to glimpse herons, ospreys and other birds that live in the sea-grass flats too.


The Bahamas are not only just a hop, skip and a jump from Florida, but hotels here start at around $100 a night. Considering the flights run as little as $300 roundtrip from the east coast and about $500 from the west, it’s easy to put together a fairly affordable trip to the islands and their wonderfully warm surrounding waters where you can indulge in fun activities like swimming, snorkeling, sailing, windsurfing and a myriad of other water sports. Chez Pierre on Long Island features doubles with its six bungalows that are spread across a wide crescent beach, each with a screened porch that overlooks the water. Bikes, a catamaran, and kayaks are all available and no charge.

Catalina Island, California

If you want to go snorkeling or diving without flying all the way to the Caribbean or another tropical locale, Catalina Island is a great option for a more affordable vacation. Located about 20 miles off the Southern California coast via a one-hour boat trip from Long Beach, you can enjoy swimming through the clear waters that are filled with a diverse array of marine life. Lover’s Cove has been ranked among the top ten best spots in the world for snorkeling with sea stars, octopi, Garibaldi fish, eels and anemones just a few of the creatures you’re likely to encounter. Sea lions and dolphins are frequently spotted too. The Hermosa Hotel makes an ideal place to base your stay with incredibly reasonable rates during the winter.

Montego Bay, Jamaica

While much of the Caribbean is expensive in the winter, Montego Bay in Jamaica is one of the few reasonably priced places to visit during high season, from about mid-January through early April. While the flight will set you back about $500, accommodations can be as low as $30 a night and the weather during this time of year just doesn’t get much better. You’ll also find several high-quality all-inclusive options that offer a very good value. The Iberostar Rose Hall Beach is an upbeat, all-you-can-drink mega-resort that crushes its competition with better food, liquor, service, and activities (including free scuba tours), for less. No matter where you stay in Montego Bay, in addition to relaxing on the sand, you’ll find plenty of water sports and other activities to keep you busy.

Tulum, Mexico

While December and January tend to be popular months for visitors to Tulum, you can find some good deals on hotels and flights throughout February and into early March. Mexico has long been known as an affordable paradise for escaping the chill of winter, and in Tulum, you’ll find as much, or as little, to do as you like. This seaside community on the Yucatan peninsula is famous for its picture-perfect Caribbean beaches with giant sea turtles that roam the sand as well as being the site of pre-Columbian Mayan ruins, including temples and castillos dating back to the 13th, 14th, and 15th centuries. While some of the area’s most famous resorts run around $500 a night, there are plenty of more affordable options too.

5 More Awesome Winter Holiday Destinations


Getting to Barbados is more affordable than ever, thanks to JetBlue’s new direct route from Boston, which has decreased airfares to the island. Flights are under $400 roundtrip after the holiday season from the east coast, and reasonable resort rates can be had too, including Bougainvillea Beach Resort, a Mediterranean-style resort on the south coast. All rooms have either a kitchen or kitchenette, making it easy to save on meals, or guests can dine at one of two eateries along the water. It also boasts a fitness center, spa, kids’ club, and water sports. While the winter months attract more visitors, the island is rarely overcrowded.


Costa del Sol, Seville and Barcelona all make fantastic winter destinations since the weather is quite a bit warmer than most of the rest of Europe. The more favorable exchange rates this winter make it even more affordable too. Costa del Sol in the winter enjoys average temperatures in the lower 70s. At popular resorts like Marbella, you can enjoy soaking up the sunshine on one of 24 beautiful beaches, sipping cocktails in the elegant marina and indulging in retail therapy in the trendy boutiques. In Barcelona, take a stroll around the dramatic Gothic quarter and visit the magnificent cathedral, or walk down Las Ramblas, the city’s main strip to watch street performers, dine in numerous tapas eateries and check out La Boqueria, one of the best markets in Europe’s.

Punta Cana, Dominican Republic

The Dominican Republic is popular with snowbirds and other travelers seeking an inexpensive destination for fun under the sun. At its far eastern edge, you’ll find the collection of beaches towns that are collectively referred to as Punta Cana. Unlike most of the other Caribbean islands, there are lots of massive beach hotels with 1,000 rooms or even more. That allows them to offer some of the best rates in the Caribbean – NH Punta Cana is a colorful resort on Bavaro Beach with lots of modern amenities, including satellite TV and free Wi-Fi. While you’re here, in addition to all of the usual beach activities, you can take a day trip to Indigenous Eyes Park, a private nature reserve and jungle park with waterfalls and lagoons for swimming, explore the Cordillera Septentrional Mountains, or soak up some history at Casa Ponce de Leon, a museum dedicated to the explorer.

Cartagena, Colombia

January is when Colombia, home to sandy beaches, vast rainforests, beautiful snow-capped mountains, fantastic coffee, and charming colonial cities, gets its very best weather with average high temperatures at 85 degrees, and average lows of 75. It’s sunny and warm but not too hot, and, it’s far cheaper than any other spot in the Caribbean. High season ends in mid-January, so the already affordable hotel rates will be even less expensive from mid-January through the end of February. Cartagena, a city on the northern coast facing the Caribbean, features impressive mangroves, powdery beaches and brilliant coral reefs along with a historic old town surrounded by the city wall.  The 500-hundred-year-old coral stone forts and much of its walled city are admirably intact. They also represent some of the finest examples of civil and military architecture of the Spanish colonial times.

Bariloche, Argentina

As January is the height of summer in South America, many of its major cities are not only quite warm but also overcrowded. Bariloche, a mountain resort town in the country’s southern region, offers milder, more pleasant temperatures, for a perfect break away from the crowded, sizzling hot cities along the coast. This town situated in the foothills of the Andes is surrounded by lakes that provide a great opportunity for water sports, while the mountains are popular for trekking and climbing. Bariloche is also renowned for its Swiss-like atmosphere and fabulous chocolate boutiques. Even during high season, prices are lower than what you’ll find in places like Buenos Aires, making it a bargain for most foreign visitors.

3 More Awesome Winter Holiday Destinations

Boracay Island, Philippines

If you’re looking for affordable prices, the sun without the crowds and access to all sorts of amenities, you might be surprised to find that Boracay Island in the Philippines offers all of that and more. While it’s no longer considered a hidden gem, this small island with gorgeous sugar white beaches still doesn’t draw massive crowds. By going after the holidays, from mid-January through the end of February, even the busiest beach on the island is likely to have only some scattered sunbathers and swimmers.

You can also enjoy horse riding on the sand, diving, snorkeling, cliff diving and parasailing, or join an exploration trip to a remote cove with a turquoise water-filled lagoon. While there are no super cheap places to stay, mid-range Boracay hotels (some as low as $70 a night), tend to offer a great value with nearly all accommodations located just steps away from the beach. Plus things like food, drinks, excursions, and massage tend to be very reasonably priced.

Chiang Mai, Thailand

While the touristy beach areas in the southern region of Thailand like Krabi and Phuket are pricey, by heading north on the overnight train from Bangkok to Chiang Mai, you’ll not only enjoy a more authentic experience, but cheap accommodations as well as the chance to enjoy the area’s magnificent mountains, vibrant hill tribes and a more relaxed vibe. In fact, Chiang Mai may be the best winter travel value around. The weather is ideal, with warm sunny days and mild nights, while rustic but clean, comfortable and private rooms can be had for under $10 a night. This historic former capital is also home to many temples, and you can enjoy cheap multi-trips to nearby forests and other temples too.

Venice, Italy

As temperatures in Venice during the winter aren’t exactly warm, that means that by bundling up you can enjoy this romantic city without the crowds. In fact, locals say that it’s actually even prettier with a dusting of snow. Plus, as this is the low season, airfare and hotel rates are the lowest they’ll be all year. If you’re looking for more excitement, plan to arrive between January 23 and February 9. This is when the Carnevale di Venezia festival, one of the most famous carnivals in Europe, takes place.

If you’d rather skip the crowds completely, you can by going mid-week during this time or heading there before or after it takes place. Going out of season also means you’ll benefit from shorter lines while having a better opportunity to experience the “authentic” Venice that most high season visitors miss. The thick mist that often settles atop the canals also makes for especially beautiful, atmospheric photos, though you may not be able to get that perfect view from the top of St. Mark’s Basilica. You can still enjoy the gondolas – they run year-round and when it’s chilly out the gondoliers will provide you with blankets.

Next Steps for an Awesome Winter Holiday Escape

When you’re ready to explore your options and book a trip, make sure to get in touch with the Travel Beyond Limits team!

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