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Warm Weather Winter Retreats

Montego Bay, Jamaica

Montego Bay, Jamaica

Once you set foot on the sands of Montego Bay, you will immediately understand why the Beach Boys weren’t singing about Omaha, Nebraska. One of the most affordable vacations on this list, Jamaica is easily accessible to travelers on any budget. Plus, at no point during the year does the temperature drop below 70°F.

Honolulu, Hawai'i

Honolulu, Hawai'i

Whether you are working on your tan on Waikiki Beach, taking a hike at Diamond Head, or remembering a solemn piece of American history at Pearl Harbor, you are sure to create memories that will last a lifetime on this island that is practically crafted from your fantasies. Who needs snow while you are inhabiting this slice of heaven?

Islands of Greece

Islands of Greece

This pocket of the world is known for its romantic views and vibrant nightlife. With a chain of over 200 islands, Greece offers visitors more choices than they will ever be able to take advantage of in a single trip. A great place to start would be Mykonos, home to world-famous beaches.

Hoi An, Vietnam

Hoi An, Vietnam

Not that long ago, a story that started with “When I was in ‘Nam…” was usually not very pleasant. That is certainly not the case anymore. With temperatures that don’t leave the '70s and gorgeous beaches, this hidden treasure on the country’s central coast is perfect for any traveler. Enjoy the wonderful Vietnamese food that keeps visitors coming back again and again.

Palm Springs, California

Palm Springs, California

Palm Springs is a desert oasis that is typically popular in the summer. However, in the summer the heat can be downright scorching, so the best time to go is actually in the inter. You can still enjoy all the same amenities at any one of their luxurious hotels but at a temperature that is a lot more comfortable – only around 75 degrees during the day. In many cases, hotels are available for under $100 during the off-season.

Puerto Vallarta, Mexico

Puerto Vallarta, Mexico

Our neighbor to the south is a favorite destination for American travelers. This west coast city gives visitors an authentic piece of Mexican culture while also providing the security and comfort of a luxury resort. It is also very affordable with many hotels under $75 per night.

Costa Rica

Costa Rica

Discover why this Central American country always finds its way onto the lists of happiest places on earth. With breathtaking sunsets and lush rainforests, it is easy to see why the atmosphere takes a much slower pace in this seaside nation.

Havana, Cuba

Havana, Cuba

When you are looking for some relaxation, and a great drink, Havana, Cuba has just what you are looking for. Enjoy a wide variety of authentic Cuban dishes while sipping some exquisite Cuban rum.  Hotels are available in the area for as low as $45. There's a ton of options available in that price range or you can splurge on something a little higher-end. Temperatures typically reach the high 70s from December through February.

Fort Myers, Florida

Fort Myers, Florida

Fort Myers has stopped being one of Florida’s best kept secrets and has transformed into the idyllic travel destination that its picturesque landscapes demand it to be. Take an afternoon trip to nearby Sanibel Island, and walk along the shell-covered beaches. Also, traveling in the winter helps to avoid the rains that plague this area through much of the summer.

Antigua and Barbuda

Antigua and Barbuda

Antigua and Barbuda is one of the most affordable of the Caribbean islands. This European-influenced retreat has 365 beaches with plenty of British forts to explore. Round-trip flights are available for as low as $300 and hotels as low as $60 in many cases. In the winter, the temperature can be as high as 80 degrees.

Fiji

Fiji

Simply looking at pictures of this tropical paradise may be enough to cure your winter blues. Have fun island hopping, or just lie on the sand soaking in the ocean air. Either way, you are sure to come home feeling invigorated.

San Diego, California

San Diego, California

Less secluded than the other stops on this list, San Diego holds all of the exciting opportunities of a big city, while still maintaining absolutely perfect weather. While you can still find beautiful beaches, the city is also known for its lavish animal displays. The San Diego Zoo and SeaWorld each pull in millions of visitors every year.

Amalfi Coast, Italy

Amalfi Coast, Italy

There are countless scenic trips that could be made to Italy, but the Amalfi Coast, situated on the Tyrrhenian Sea, makes for an ideal escape from winter. It won’t take long to discover why residents have developed such a laid back attitude toward life. Also, be sure to take an afternoon trip to the ruins of Pompeii or the unforgettable Blue Grotto.

Cabo San Lucas, Mexico

Cabo San Lucas, Mexico

A flight to Cabo San Lucas in Mexico is under three hours from LAX, which means that you don't have to travel far to get to paradise. The temperature typically reaches a high of about 80 degrees Fahrenheit in January. Located at the tip of Baja California, Cabo San Lucas features an exotic landscape and offers a ton of luxurious hotels where you can pamper yourself. It’s a cherished spot for celebrities, but you don't need to be rich and famous to retreat here. There are plenty of hotels available for under $100 per night. 

Peru

Peru

There's a ton of things to love about Peru in the winter but the biggest thing is that in Peru, winter is actually summer there. The average temp is around 77 degrees. However, while it is warmer, you'll have to deal with the occasional shower as it is rainy season. On the upside, hotel stays are as low as $30 per night and you can get a ticket to Lima for under $400. Explore the rich culture Peru has to offer and discover the Sacred Valley – where you'll find the famous Machu Picchu.

Cayman Islands

Cayman Islands

If you are looking for white-sand beaches, crystal-clear turquoise waters, and a pleasantly warm temperature of around 80 degrees, the Cayman Islands are the perfect retreat for you this winter. Bathe in the sun or engage in numerous water sports like sailing, scuba diving, kayaking and much more. Flights can typically be found for around $300 and a hotel for around $100 per night early in the year.

Key West, Florida

Key West, Florida

Key West is another incredible Florida retreat with not one - but two – coastlines: along the Atlantic Ocean and the Gulf of Mexico. If you love beaches, you'll find plenty of them here, which means it should be easy to find a secluded spot where you can get some peace and quiet. The Ocean Key Resort and Spa is just one luxurious retreat where you can wind down after the hectic holidays. Enjoy the perfect fusion of Caribbean and American cuisine.

Seville, Spain

Seville, Spain

Seville, Spain is one of the most breathtaking sights in Europe. A mix of Moorish and Spanish architecture, the city is over 2,000 years old. It has a unique culture with the perfect mix of traditions and artistic influence. Usually, the city can be quite expensive to visit but around February, you'll find the cheapest flights under $500 and hotels as low as $50. In March, Seville can get as high as 90 degrees!

Bermuda

Bermuda

Winter temperatures in Bermuda are in the low 70s, which is just about the most perfect temperature you could ask for. Bermuda offers gorgeous pink sand beaches that are unlike anywhere else and other natural wonders like crystal caves. The colonial architecture provides a distinct character to the island and recalls British settlement as far back as the 17th century. It can still be a little pricey during the winter, with hotels around $150 or up to $500 per night.

Negril, Jamaica

Negril, Jamaica

Negril is another terrific retreat in Jamaica. Experience the unique, lively Caribbean culture with great food, music and plenty of fun activities. Engage in watersports like diving and on-land activities like dancing. Temperatures in the winter go up in the 80s. If you want to let loose this winter, Negril is easily one of the best places to do it. And we aren't saying you should get blackout drunk…but we are just saying that there are certain resorts like Sandals where you hypothetically could – because drinks are all included with your stay.