20 Best Winter Break Vacation Ideas for Holiday Memories
- Park City, Utah offers a premier skiing experience with a vast terrain suitable for all skill levels and local hot springs for relaxation.
- Hawaii, specifically the Big Island, is a fantastic destination for whale watching, providing warm weather and clear ocean views.
- Steamboat Springs, Colorado combines hot springs, scenic views, and skiing opportunities, perfect for those looking for a unique winter getaway.
- Cocoa Beach, Florida allows visitors to watch rocket launches while enjoying mild weather and beach activities, making it a great alternative to traditional winter vacations.
- Gatlinburg, Tennessee’s Winter Magic Celebration features stunning light displays throughout the town, creating a festive atmosphere ideal for family outings.
20 Best Winter Break Vacation Ideas for Holiday Memories
Looking for winter break vacation ideas? Here are 20 of our favorites, from skiing in Park City and soaking in Steamboat hot springs to watching a rocket launch in Cocoa Beach and whale watching in Hawaii. Whether you want snow or sunshine, there's something here for your crew.
Tis the season! When winter break rolls around, you're probably dreaming of escaping the routine and bundling up for a cozy mountain retreat or soaking up some warm sunshine.
So, whether you want to try night skiing in Park City, looking for some small-town festival magic, or chasing the sun on the best Big Island beaches, picking the right destination makes all the difference.
And to help you plan your next great escape, we've rounded up the 20 best winter break vacation ideas! From snowy getaways to sunny hotspots, here is your ultimate guide to planning an unforgettable winter trip.
1 | Hit the Slopes in Park City | If you've got snow on the brain, start here. Park City is one of the biggest ski areas in the country, with runs for both total beginners and those who like to show off.
And after a long day on the slopes, enjoy a gondola ride above mountain tops, hit one of the hot springs in Park City that locals love, or just enjoy an afternoon of sipping cocoa and seeing the lights on Main Street.
-
Insider Tip: Westgate Park City Resort & Spa makes a great HQ for your ski adventure. It sits at the base of Canyons Village, so you're steps from the lifts; plus the resort has a spa, on-site dining, and is located close to Main Street for easy access to downtown festivities.
Where: 3000 Canyons Resort Dr, Park City, UT 84098 | Who: (435) 655-2240
RELATED ARTICLES:
Have an Adventure-Filled Vacation With These 11 Park City Winter Attractions
10 Things to do in Park City, Utah in Winter Without Spending a Dime
2 | Check Out the Chicago Christkindlmarket | Think of this as a holiday market with a lot of snacks.
Grab some hot cider and explore rows of wooden stalls selling ornaments, handmade gifts, pretzels, and German-style treats, and it all sets up right downtown.
-
Insider Tip: Go on a weekday afternoon. Weekend evenings get packed, and it's hard to enjoy a pretzel when you're getting elbowed.
Where: 50 W Washington St, Chicago, IL 60602 | Who: (312) 494-2175
3 | Snorkel Reefs in Bimini | How about the opposite of a snow day? Winter in Bimini means warm days, fresh seafood, and snorkeling the day away in some of the clearest waters around.
From snorkeling the famous SS Sapona shipwreck and feeding wild stingrays at Honeymoon Harbour, there are plenty of exciting things to do in Bimini during the winter months.
-
Insider Tip: Consider Westgate Bimini Bay for your stay! Just steps from white-sand beaches, the property is newly renovated and centrally located, making it super easy to get around the island.
Where: Bailey Town, Bahamas
4 | Chase the Northern Lights in Fairbanks | Seeing the aurora is a bucket-list thing for a lot of people, and Fairbanks is one of the best places to try. Winter nights are long, dark, and cold, which is exactly what you want.
For an extra unique experience, head to Chena Hot Springs, about an hour outside of Fairbanks. Soaking in a hot spring while the sky does its thing is hard to top.
-
Insider Tip: The lights never come with a guarantee, so plan for a few nights. Dress in way more layers than you think you need, and bring a thermos of something hot.
Where: 17600 Chena Hot Springs Rd, Fairbanks, AK 99712
5 | Wander Gatlinburg’s Winter Magic Celebration | Every winter, Gatlinburg covers the downtown strip, trails, and the iconic Anakeesta in twinkling lights. It's cozy, it's festive, and it's very easy to do with kids and grandparents.
Walk the lights at night with a hot drink in hand, then check out a few of the shops and snack stops along the way.
-
Insider Tip: Warm up after a cold day with a stay at Westgate Smoky Mountain Resort & Water Park! Enjoy cozy cabin rooms, an indoor water park, spa, and a variety of on-site dining that specializes in comfort food.
Where: Old Mill Ave, Pigeon Forge, TN 37863
6 | Go Dog Sledding in Ely, Minnesota | Ely is basically the dog sledding capital of the Midwest, and it's a seriously fun way to see the winter woods.
Book a guided trip with a local outfitter and get ready to ride along, or take the runners yourself, while a team of very excited huskies does the work.
-
Insider Tip: Trips depend on snow, so check conditions before you lock anything in. Also, wear snow boots, not sneakers. Trust us on this one.
Where: Various excursions available in Ely, Minnesota
7 | Soak in a Steamboat Springs Hot Spring | Want to feel like you're living in a snow globe? Steamboat Springs is full of cozy, small-town charm, plus natural hot springs, and a ski scene that will make the whole trip feel like a movie.
Hit the slopes in the morning, then end the day at Strawberry Park Hot Springs surrounded by falling snow.
But don’t let the quaint village vibes deceive you; between rodeos and hot air balloon rides, there are plenty of exciting things to do in Steamboat Springs for the whole family!
-
Insider Tip: If you’re looking to stay close to the mountain, consider The Village at Steamboat. It’s located in the heart of the town, giving you easy access to local dining and attractions.
Where: 44200 Co Rd 36, Steamboat Springs, CO 80487 | Who: (970) 879-0342
8 | Watch a Rocket Launch from Cocoa Beach | Yes, you can watch a rocket launch from the beach. It's loud, it's bright, and it's the kind of thing kids (and adults) will talk about for years.
And if you think the beach and winter don’t mix, you’d be wrong! The weather is mild, and the tourists have thinned out, making it the perfect time to spend a day exploring Cocoa Beach Pier.
-
Insider Tip: Launches get delayed all the time, so build in a flexible day or two and keep an eye on the schedule. And for easy beach and pier access, make Westgate Cocoa Beach Resort your vacation launch pad.
Where: 401 Meade Ave, Cocoa Beach, FL 32931
9 | Ride a Snowmobile Through Yellowstone | Yellowstone in winter feels like you’ve stepped into a completely different world. It's quiet, it's covered in snow, and you can see steam rising from the geysers in the cold air, along with bison, elk, and breathtaking frozen landscapes
Or, take a guided snowcoach tour of Old Faithful and let someone else handle the driving, while you sit back, relax, and enjoy the views.
-
Insider Tip: Park access is limited during winter months, and tours book up months in advance, so book ASAP.
Where: Yellowstone National Park, WY | Who: Multiple excursions available
10 | Step Back in Time at Silver Dollar City | Silver Dollar City is already a must if you’re visiting Branson, but during the holidays, it’s nothing short of magical.
Think millions of twinkling lights, carolers, craft demos, and a lot of hot cocoa – it's one of the best things to do in Branson during the holidays.
-
Insider Tip: Pair your old-timey adventure with a cozy cabin stay at Westgate Branson Woods Resort in the heart of the snow-covered Ozarks.
Where: 399 Silver Dollar City Pkwy, Branson, MO 65616 | Who: (417) 336-7100
11 | Kick It in New York City | Catch the Radio City Christmas Spectacular with the Rockettes, then lace up some skates at one of the city's outdoor rinks. This one is a classic, but for a reason!
Skate at Bryant Park's Winter Village, then wander the holiday shops and ogle at the spectacular window displays. Rockefeller Center's rink and tree are a bucket-list stop, too, but they get packed.
-
Insider Tip: Staying central is key. Westgate New York Grand Central puts you right in Midtown, which makes using public transportation and getting around the city one less thing to worry about.
Where: 1260 6th Ave, New York, NY 10020 | Who: (212) 465-6000
12 | Ring in the New Year on the Vegas Strip | If your winter break lines up with New Year's Eve, Vegas is hard to beat. The Strip puts on a huge 8-minute fireworks show over the city, and there’s no bad view.
Grab an early dinner, then find a spot to watch the fireworks go off over the Strip. Keep your plans simple that night, because walking is the main way to get around.
-
Insider Tip: Avoid extra chaos with a stay at Westgate Las Vegas Resort & Casino. It’s just off the Strip, but still connected via the Las Vegas Loop, so you can be in the middle of the action and still have a quieter place to come back to.
Where: Las Vegas, NV
13 | Explore History in St. Augustine, Florida | St. Augustine hosts Nights of Lights, one of the most spectacular holiday light displays in the world, illuminating the whole of historic downtown with millions of white lights.
Just a few hours away, this is one of the best day trips from Orlando if you’re looking for a break from the theme parks.
-
Insider Tip: Get into the holiday spirit(s) by adding a ghost tour to your visit! As the nation's oldest city, St. Augustine has a long and fascinating history that comes alive when the sun goes down.
Where: 170 St George St, St. Augustine, FL 32084
14 | Go Whale Watching in Hawaii | Trade snow for sand with a tropical getaway! Humpback whales spend the winter in Hawaii's warm waters, so why not join them?
Book a whale-watching boat tour, and keep an eye out for splashes, spouts, and tail slaps. You can also spot them from shore on a good day, so keep your eyes on the horizon during beach time.
Insider Tip: When you’re looking for the best hotel in Hawaii for your stay, remember to book early if you want to stay beachfront.
15 | Ride the Polar Express Through the Smokies | The Great Smoky Mountains Railroad in Bryson City, North Carolina, runs a licensed THE POLAR EXPRESS™ Train Ride every November and December.
You ride out to the North Pole with hot chocolate and holiday stories, and Santa comes through each car on the way back to hand every kid a gift.
If you’ve got the time, get to Bryson City early so you've got time to wander the shops and grab some fudge before you board.
-
Insider Tip: Wear pajamas for a one-of-a-kind photo op! Lots of families do, and it's half the fun.
Where: Old Mill Ave, Pigeon Forge, TN 37863
16 | Jazz up the Holidays in New Orleans | New Orleans brings its unique culture and festive spirit to the winter season with incredible food, holiday concerts, and caroling in Jackson Square.
Enjoy world-class jazz performances in the historic French Quarter, warm up with steaming bowls of gumbo and beignets, and walk through City Park illuminated by millions of dazzling lights.
-
Insider Tip: Go “hotel hopping.” Walk through the lavishly decorated lobbies of iconic hotels like The Ritz-Carlton and enjoy the free and absolutely gorgeous holiday displays.
Where: City Park, New Orleans, LA
17 | Saddle Up at River Ranch | Take the time to slow down and enjoy the simple life with a country Christmas!
Winter in Central Florida is mild and sunny, so it's the perfect time for some outdoor fun with camping, horseback riding, or a rodeo.
-
Insider Tip: If you enjoy the great outdoors but still want to sleep indoors, glamping at Westgate River Ranch Resort & Rodeo is the best of both worlds!
Where: 3200 River Ranch Blvd, River Ranch, FL 33867 | Who: (863) 692-1321
18 | Ski Heavenly and Ride the Gondola in Lake Tahoe | The village of Heavenly sits right on the California-Nevada state line, and the views of the lake from up high are truly… heavenly.
Ski or snowboard in the morning, then ride the gondola up for the lake views. If you're not a skier, there are still plenty of things to do in Lake Tahoe in winter to enjoy the season, including a mountain roller coaster!
-
Insider Tip: Can’t decide between staying in California or Nevada? Kingsbury of Tahoe is a good home base; it’s on the Nevada side but close enough to the state line that you can easily visit both.
Where: 4080 Lake Tahoe Blvd, South Lake Tahoe, CA 96150
19 | Ride the Palm Springs Aerial Tramway | Here's a fun one. You start in the warm desert, hop on a rotating tram car, and about 10 minutes later you're up in the mountains, where it can be snowy.
Ride up for the views, then take a short walk or hike at the top. You can see for miles on a clear day.
-
Insider Tip: Bring a real jacket; even if it's 75 degrees at the bottom, it’s a good 30 degrees cooler at the top.
Where: 1 Tramway Rd, Palm Springs, CA 92262 | Who: (888) 515-8726
20 | Do the Holidays at Orlando's Theme Parks | Orlando's theme parks go all out for the holidays, with decked-out streets, special shows, festive treats, and a lot of lights. It's an easy pick if you've got a group with different interests.
-
Insider Tip: Whether you’re park hopping or just visiting your favorite, Westgate Orlando has resorts on International Drive, Kissimmee, and Lake Buena Vista, so you’re never far from where you need to be.
Where: Orlando, FL
YOU MAY ALSO LIKE:
15 Best Things to Do in Lake Tahoe in Winter
12 MUST-TRY Things To Do in Branson in the Winter
10 Things to Do at the Beach in the Winter
Icy Winter Fun in Your Future!
Whether you want to ski down a mountain, snorkel a reef, or just sip hot cocoa under a million twinkling lights, your perfect winter wonderland is out there waiting for you.
Ready to start planning your adventure? From deciding where to stay to what to do, and everything in between, visit our Westgate Resorts Travel Blog for travel tips and vacation inspo!
35 Best Black Friday Gift Ideas for Savvy Savers and Travelers
At Westgate Resorts, when you Check In, there’s a LOT to Check Out! Your vacation awaits! Start planning your next vacation today or talk with a vacation planner at 888-852-2959 or 407-355-2690.
* Westgate Resorts is in no way affiliated with the attractions featured in this article. Items or places listed are current as of the publishing date of this article. Please call or visit the respective website for the most up-to-date offerings and details.
When You Check-in, There's a Lot to Check Out
Sign up for our newsletter and check-in to great offers, secret stuff, and special events.