Winter Holidays In The Americas


With winter right around the corner and snow already falling in some cities, I thought some of you might be already thinking about some winter holidays. I asked some other writers about what their favorite places are to visit in the winter.

Some of them are winter wonderlands, while others are for those who like sun holidays. I had a massive response to the question, so I decided to divide the answers up into continents.

So, this first one is for those looking for a winter break and perhaps not traveling too far. For everyone who is looking for a little winter sun in the Americas, hopefully, these places will inspire you when planning your winter vacation.

If you want to go somewhere else, I will be posting about other winter vacation ideas in Europe and the UK. It will be followed by winter sun holidays in Asia and after that will be winter sun destinations in the Oceanias. Lastly, winter holiday destinations in Africa.

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Within the Americas, I think the best winter vacations are ones that include warm places in December through March. The top of my list is where I used to live - Costa Rica.

Kauai, Hawaii. United States

Written by LeAnna Brown from Economical Excursionists.


Kauai has this magical sort of feel to it. It is “American” enough to not feel overwhelming to many travelers but has its own Hawaiian culture to give it a slight “exotic” feel to it.

Add in some of the world’s most stunning beaches, top-notch winter surfing, and endless activities to keep you busy if beach lounging isn’t your thing, and you’ve got yourself an ideal winter getaway.

If you love surfing, head to the North Shore of Kauai for some of the best waves you can find anywhere.

Winter months are perfect for ideal swells! Of course, if you love diving, head to the South for great tunnel and volcanic dives.

Or go snorkel and see how many sea turtles you can spot (we counted 11 in one hour!). Why not get in some hikes in between your beach days as well to round it all out!?

The best part is, while Hawaii can seem expensive for some, there is some phenomenal camping in Kauai that can help ease the burden on the wallet. Alternatively, you can choose to enjoy posh resorts.

The point? There is absolutely something for everyone for a winter escape in Kauai!

Palm Springs, California, USA

Written by Dhara from It’s Not About the Miles. Follow Dhara on Instagram here.


Palm Springs, California, is the perfect destination if you’re looking to escape winter! With daytime temperatures in the 70-75°F (21 – 24°C) range, the weather is ideal for exploring the southern California desert. And with plenty of sunshine, you can really enjoy being outdoors!

Whether you are looking for an active sun vacation, or just want to chill and be pampered, there are lots of things to do in Palm Springs and the neighboring desert communities.

Play a round of golf at one of the famous courses in the area. Or lounge by the pool or book a pampering treatment at an upscale spa.

If you enjoy art, you’ll find it everywhere in the region, not just in the museums. Every community in Greater Palm Springs showcases public art, whether it be sculptures or murals, or fountains.

If architecture interests you, go on a self-guided tour of the famous mid-century modern buildings in Palm Springs. One of them is the home where Elvis honeymooned!

For the outdoor enthusiast, visit nearby Joshua Tree National Park for the day. With its massive boulders and quirky Joshua trees, the park is fun to visit. You can also go hiking in one of the many desert trails in the area.

You can even take the tram up to the top of Mount San Jacinto, but you’ll need to bundle up for sure!

Whatever you choose to do in Palm Springs, one thing is guaranteed: you’ll have a fabulous time!

Playa Mujeres, Mexico

Written by Jen Brommer from Travel With A Plan.


Sunshine, sand, and tranquility will greet you in the beautiful Caribbean coastal community of Playa Mujeres, Mexico.

As one of the top winter escape destinations, Playa Mujeres has so much to offer in terms of both a fun and relaxing winter getaway.

Located 26 miles/12.6km north of Cancun, Playa Mujeres is a 35-minute drive via shuttle from Cancun International Airport.  There are direct flights from major cities like Minneapolis, Atlanta, Phoenix, New York, and Toronto, so getting there isn’t hard.

Along with its convenient seaside location, another great thing about Playa Mujeres is that it is an entirely gated community. Security measures are taken before vehicles are allowed to enter the city, with additional safety measures taken at each resort.

The ‘small town’ feel here is a welcome addition when looking for a winter escape.

Resort options in Playa Mujeres include luxury golf and spa resorts, family-friendly all-inclusive resorts, and several adult-only properties, all of which are highly rated.

A unique feature of Playa Mujeres is its proximity to the magnificent and secluded island of Isla Mujeres. This gorgeous Mexican island is known for its white coral beaches, scuba diving, and sea turtle sanctuary.

It is very popular for visitors staying in Playa Mujeres to take a day trip via ferry here for which you will experience an incredibly different experience than that of at your resort.  (Visiting here feels like you are getting two vacations wrapped into one!)

Grab your beach bag, swimsuit, and sunglasses if making Playa Mujeres your winter escape destination.  Tropical vibes await!

New York City – USA

Written by Michele DeBella from From Inwood Out. 


The good news about winter in New York City is that prices fall right alongside the temperatures. Once the peak holiday season passes, visitors will find a city that’s a little less crowded yet still packed with things to do.

In January and February, take advantage of Restaurant Week by sampling special Prix Fixe menus from the trendiest restaurants in town, or see a stretch of plays and musicals during 2-for-1 Broadway week.

Winter is also the best time to take in New York City museums. Check out the newly expanded galleries at the Museum of Modern Art or hop on a subway and head to the Brooklyn Museum for the French artist JR’s first major exhibition in North America.

The best part about winter in the Big Apple—aside from watching the snowfall amidst twinkling city lights—is the many ways to warm up. Take a spin under the famous skyline at one of the ice skating rinks around the city, then go on a hot chocolate crawl and decide who makes it best.

City Bakery even holds a Hot Chocolate Festival every February, when they roll out their most unique flavors. If spirits are more your style, there are plenty of bars in NYC with fireplaces to cozy up to.

Finally, what better way to warm up inside and out than by pampering yourself at a spa? Lounge in the various warm baths inside a restored textile factory at AIRE Ancient Baths in TriBeCa or, for a totally different experience, head to Spa Castle in Flushing, Queens.

Soothe your muscles at the water therapy stations in the large heated outdoor pools and then indoors, hop from sauna to sauna to complete a day of utter warmth and relaxation.


Trinidad Cuba

Written by Sarah Carter from ASocialNomad. 


Trinidad is the pastel-painted, cobblestone streeted UNESCO World Heritage City in central Cuba.

The city has an awesome mix of history, classic cars, and colonial architecture. Best of all, the nearby village of La Boca is a fabulous place to stay in a local casa and enjoy the beach vibe when exploring the city.

Trinidad owes much of its history to the sugar plantations – and the colonial elegance of the architecture comes from that money and the unique cocktail, the Canchanchara has its base in sugar cane too.

There are hikes nearby – to Radio Tower Hill, where you’ll get a great view of the city and surrounding area, and gorgeous beaches at Playa Ancon. The musical heritage of Trinidad is in evidence at the Casa de la Musica, where you can dance all night while drinking rum with the locals.

There’s a kind of decrepit elegance to Trinidad, many of the colonial buildings are in need of maintenance, but still look glorious in a faded sort of way. What is in evidence, though, is the warmth of the welcome of the Cuban people.

Enjoy the sunny days, the warm sultry nights, and the laidback atmosphere of a Cuban winter break in Trinidad.

Runaway Bay, Jamaica

Written by Nicole Fiorante from The Passport Kids


A glorious place to escape the cold, dark, and snowy winters is to fly to Jamaica! Runaway Bay in Jamaica is the perfect place for you to soak up the sun, relax on the white sand beaches, and defrost your bones from the cold weather.

Swim in the clear turquoise water and relax with lazy days on the beach at any of the resorts along the water.

Runaway Bay beach resorts cater to fun in the sun and all the activities that go along with relaxing at the beach or pool. Be sure to have some of Jamaica’s famous Jerk Chicken, rice, and plantains! If you are looking for a bit of adventure on the island, you can explore Dunns River Falls, go snorkeling off of a catamaran, cool off at a waterpark, or play golf at several courses around the area.

Explore Ochos Rios, which is the birthplace of Bob Marley, and enjoy some of the reggae musical atmospheres on the island. There is so much to do in the Runaway Bay area in Jamaica, so it will just be up to you on how much you want to do or just lay by the pool and beach to enjoy the sunshine! Life slows down in Jamaica, enjoy the people, the sun, the water on the island.

Kihei Maui, USA

Written by Sam Wilbur from Worldwide Wilbur.


On the sunny south shore of Maui, the town of Kihei is one of the very best winter escape destinations in the US. It has a dozen golden sand beaches, where the warm Pacific waves never get below 70°F (20°C).

You can surf in the morning, and snorkel with sea turtles in the afternoon. There are also many guided ocean activities to enjoy like paddle boarding, outrigger canoeing, and kayaking.

Unlike crowded Oahu or Bali, it’s still possible to find a completely empty stretch of sand to lay on and forget about everything for a while. But keep your eyes on the horizon, wintertime is whale season in Maui, and it won’t take long before you’ll spy a humpback flapping his tail at you.

Apart from the fine beaches, Kihei also boasts many opportunities to experience real Hawaiian culture.  From the lady selling fresh-cut coconuts on the roadside to the guy who carves tiki statues in the Kihei Marketplace, and the nearby Te Au Moana lu’au. You are never far from Hawaiian life in Kihei.

If you like seafood, Kihei boasts several world-class sushi restaurants like Sansei, Sushi Paradise, and Miso Phat.  The cultural melange of resident chefs from Polynesia, Asia, and the mainland U.S. results in some fantastic culinary creations.



Dreaming of white sandy beaches and deep blue waters while surrounded by the reality of falling leaves and snow? Aruba is the perfect destination for North American travelers. At under six hours of flight time from most East Coast or midwest airports, and with many direct flights, Aruba lends itself to a long weekend getaway.

Sun worshippers rejoice! This desert island experiences less than 20 inches of rain a year, so even non-sunny days don’t see a lot of the wet stuff.

The average daily temperature year-round is 80 degrees, but the winds make it seem much more tolerable. So be sure to wear sunscreen!

With some of the world’s best beaches, like Palm and Eagle Beaches, visitors can choose to layout under a palapa where drinks are brought by the resort’s wait staff. Snorkeling and windsurfing are also popular activities. Due to the small size of the island, getting from point to point is fairly easy and ATVs serve as popular rentals.

As an island, seafood dishes will be the most affordable, while imported items cost substantially more. Try the local lager, Balashi, for a refreshing alternative. Foodies can enjoy local fare like pastechi (a hand-held pastry) and funchi (polenta) to the first-class cuisine offered at some of the island’s fine resorts.

So whether you want to enjoy duty-free shopping, eating delicious food, or just soaking up the sun, Aruba is the perfect winter blues-busting destination. Read about some more Sightseeing in Aruba here.

Grand Cayman, Cayman Islands

Written by Laura Wilkens from Adrift Aesthetic. Follow Laura on Instagram here.


Many would agree that the perfect winter escape vacation means heading to the Caribbean.

However, not everyone considers the Cayman Islands when they are making their plans and booking their winter travel. Made up of three islands in the Caribbean, Grand Cayman is the largest and most activity-filled spot in the Caymans.

Grand Cayman’s port city of Georgetown is a popular cruise-ship stop. Unlike the rest of the island, Georgetown can be a bit touristy, catering to those who only have a few hours to explore the island before they set sail again.

However, by staying for an extended period on Grand Cayman, you can experience all that the island has to offer. Go swimming with stingrays on a sandbar 25 minutes from shore, meet sea turtles up close at the Cayman Turtle Farm and Conservation Center, or tell your friends you’ve literally “been to Hell” in the kitschy town of Hell, Grand Cayman.

But what is the ideal way to escape the winter blues? Sipping a frozen cocktail on a gorgeous white sand beach with crystal-clear turquoise water at your feet. Luckily, Grand Cayman has Seven Mile Beach, one of the highest-rated beaches in the world.

When you’re not enjoying the sun, make sure you taste all the local foods. Often made with jerk seasonings, it’ll warm up your insides and make you forget the weather back home. With sun, sand, and a Rum Punch made from local Caymanian liquor, there’s no better place to go to escape winter than Grand Cayman.

Sedona, Arizona, USA

Written by Allison Boyle from She Dreams of Alpine.


Sedona, Arizona is an adorable desert town in the United States that is known for its mesmerizing red rock buttes, relaxing getaway vibes, and easy-to-access adventure. The town also has a lot of great shopping, art galleries, and spas, which make it a popular place to visit if you’re looking for a chill-outdoor retreat.

There is no bad time to visit Sedona, Arizona because the weather is great year-round. However, it’s a fantastic place to visit in the winter since Sedona is in the desert, and there are fewer crowds.

While the evenings can get down to the mid-30°F’s (2°C)in the winter, the afternoons are sunny with an average of high 50°F’s (13°C) and 60°F’s (18°C) around December and January, which make for amazing temps to get out and explore everything Sedona has to offer.

From relaxing in one of Sedona’s well-known day spas to exploring the area via jeep tours, and hiking some of Sedona’s best hiking trails, Sedona is a great place to both relax and play in the wintertime.

Hike the iconic Devil’s bridge trail, for a relatively easy 2-4 miles roundtrip hike with amazing views, or spend the day relaxing and getting a massage at one of Sedona’s best spas.

Whatever you decide to do here over the winter, you’ll be looking forward to planning your next visit to this vibrant, adorable desert wonderland.

Tulum, Mexico

Written by Ioana Stoica from The World Is My Playground.


Mexico has long been known as a perfect winter escape destination. In a sea of well-established getaway possibilities within the country, Tulum is essentially the new kid on the block. Formerly considered a hidden gem, Tulum’s popularity has risen dramatically in the last four years.

That’s largely due to the popularity of the Tulum Ruins (thanks, Instagram!), and the development of the Tulum Beach Strip, a small road parallel to the Tulum Beach that’s packed with hotels, restaurants, beach bars, and Instagram-worthy photo opportunities.

You’ll have no shortage of restaurants and cafes to choose from, and you can’t go wrong with either. For the tried and tested, get your morning coffee at Coco Tulum, head to Raw Love for a delicious lunch, catch a sunset dinner at the Real Coconut further south down the beach.

You’ll also find that as you venture further south the strip and you’ll find smoother beaches and more luxurious hotels, each picture-perfect in their own way.

The Tulum Ruins, found just north of the strip, are an exquisite example of Mayan culture and the only Mayan Ruins of their kind in the Quintana Roo region.

Perched on a seaside cliff, the ruins aren’t only full of history, they also serve one of the best views in Tulum. Leave yourself extra time, bring a bathing suit, and head down to the small beach below for a truly unbelievable day.

The best time to see Tulum is during the dry season between December and April. If you’re looking for a less touristy experience, consider going in November or May, just outside of the rain season.

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  1. That was a great post by the way. Have been to kauai, maui and sedona and looking forward to go there again.

    1. Sally Pederson says:

      Thank you. Yes, there are some great places to go. I have been to Maui a few times, it has always been great.

    1. Sally Pederson says:

      I also think it is a great time of the year to visit.

  2. Hawaii sounds like a nice sunny getaway!

    1. Sally Pederson says:

      Hawaii is a wonderful place. It is very beautiful.

    1. Sally Pederson says:

      I feel the same way. That is why I try to get to sunny beach places during winter. However, I know some people that enjoy winter.

  3. Great list! I would love to go to Playa Mujeres, Mexico one day. Sedona, Arizona also looks adventurous. Thank you for the information.

    1. Sally Pederson says:

      Yes, I think they both would be great places to visit in the winter. Sun and warm weather is what I love.

  4. Restaurant week in NYC is my favorite time of year haha but Fall is my favorite season. Love this roundup of places!

    1. Sally Pederson says:

      Glad you enjoyed the list of places.

  5. This is a great list of places to visit. I think my favorite in the winter is NYC. Even if it is bitterly cold that city is still alive and booming.

    1. Sally Pederson says:

      I’ve not spent winter there, but I’m sure it is wonderful…. as long as you bundle-up.

  6. I would love to visit Palm Springs some day. I’ve been all over California but never there.

    1. Sally Pederson says:

      It is a great place to go to escape cold winters in other cities.

  7. thanks for sharing this, very beautiful winter experience as a great reference for me as am always facinating a winter holidays. cheers, siennylovesdrawing

    1. Sally Pederson says:

      Glad you like it. Hopefully, it gave you some great ideas for your next winter holiday experience.

  8. Those places are included in my bucketlist! Will definitely go to one of these places one day!

    1. Sally Pederson says:

      Glad you included them and hopefully you can start going to them soon.

  9. There are so many wonderful places here! A tropical getaway is always so nice during the winter months.

  10. I would like to be able to take a nice warm vacation during the winter. I am so terrified of winter. I live in a wooded mountain side in PA where it gets really cold.

    1. Sally Pederson says:

      I always want to go somewhere warm. I hate being cold and therefore, not a fan of winter.

  11. So many beautiful places to visit! Looking forward to visiting the US

    1. Sally Pederson says:

      I’m sure there are many more places that people love for winter holidays. This is just a shortlist that will hopefully inspire some vacations.

  12. I’ve always wanted to go to Hawaii, but after seeing all those other beautiful places you posted I can’t decide which I’d like better.

    1. Sally Pederson says:

      Yes, it can be a tough decision. However, you can never go wrong with a trip to Hawaii.

  13. I haven’t been to the US yet so this list is super helpful for me to plan my next winter vacation ? I am also waiting for your UK list!

    1. Sally Pederson says:

      There are many great places in the US. The Europe and UK article has just been posted. I hope it doesn’t make your list of places too long. 🙂

  14. The last few days have been cold and rainy here in Texas. All of the locations you mentioned look warm and inviting!

    1. Sally Pederson says:

      Chicago has not been great weather either. It has been making me think about some warm destinations.

    1. Sally Pederson says:

      Hawaii is a wonderful place to visit. I’m sure you would love it any time of the year.

  15. I think that kissing under the ball-drop event at New York will be my ultimate go-to on the bucket list for winters! Such a fun list of ideas though. I’m a huge fan of Aruba and Cayman Islands, can’t wait to go there as well. 🙂

    1. Sally Pederson says:

      Yes, kissing under the ball-drop would be unforgettable. I haven’t been to Aruba or the Cayman Islands yet, but hopefully, I’ll get there someday soon.

  16. I’ve never spent Christmas Holidays away from home–except when home was in London when my dad was assigned there. I’ve always dreamt of spending Christmas Holidays elsewhere. Perhaps in cold place where it snows everyday and I can spend my days snuggling beneath thick coats.

    1. Sally Pederson says:

      You could still spend Christmas at home, then go somewhere right after. Most flights and hotels are cheaper after the 3rd of January.

  17. Jimmy John says:

    I could jump through the screen right now to escape this dreadful cold!

  18. I love it being winter for the holidays but definitely love getting away to somewhere warmer. We plan to travel to Hawaii soon! Never thought about going in the winter though!

  19. I would be ok with just about any of these vacation spots! I’ve been to Maui before but I would love to visit Kauai, too. The only other one I’ve been to before is Grand Cayman on a cruise. I never really thought about taking a vacation there during the winter months, though. I hate the cold, so I am good with a warm sunny winter vacation.

  20. Heyyyy I am Sedona based, it truly is a great place to visit any time!!! This is giving me the travel itch! I have never been to Hawaii somehow and NYC is so special during the Holidays.

  21. I love Kauai! Kauai is Hawaii’s fourth-largest island and is sometimes called the “Garden Island,” which is an entirely accurate description.

  22. My favorite spot is by far Tulum! It’s so gorgeous with all the cenotes!

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