My Favorite Winter Getaways + Real Tips to Survive and Enjoy your Travels
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Hi Friends!
Winter trips don’t have to be boring or freezing. You don’t have to hide inside the whole time. I’m talking real adventure, cozy vibes, and moments that’ll make your family talk about the trip for years. Snow-covered forests, crackling fires, or even sunny beaches, yeah, winter can do that too. So if you want to plan a getaway that feels like a warm hug and a thrill all at once, keep reading.
Winter Hobbies:
Skiing and Snowboarding:
Skiing and snowboarding aren’t just for pros! Beginner lessons and rentals make it easy to join the fun. Plus, nothing beats gliding through snowy mountain views while getting your cardio on!
Ice Skating:
Ice skating is a classic winter activity that is perfect for all ages and a great way to spend time with loved ones. Some ice rinks even offer special events like ice shows and ice discos, adding to the fun and excitement.
Spa Day:
A more relaxed winter activity is a spa day, and many hotels and resorts offer spa packages with massages, facials, and other treatments, perfect for unwinding after a busy holiday season!
Winter Destinations:
When planning a winter getaway, the destination can make or break your vacation, so consider your interests, budget, and preferred weather conditions to ensure an unforgettable and enjoyable experience.
If you're a winter sports enthusiast, check out winter resort recommendations like Mont-Sainte-Anne, just outside Quebec City, Aspen, Colorado, or anywhere in New Hampshire for their family-friendly cold weather travel, unparalleled skiing and snowboarding opportunities, as well as other winter activities like ice skating, snowmobiling, and snowshoeing.
Why Le Château Frontenac Is More Than Just a Hotel to Me
Winter escapes are the perfect way to shake off the monotony of daily life and create lasting memories. And what better place to indulge in a winter getaway than the iconic Le Château Frontenac, nestled just outside Quebec City? This stunning architectural masterpiece is a hotel and a historic landmark that has played a significant role in my family's story.
My grandma was a total boss, the first woman in her city to own a car, and she even swam across the fierce Saint Lawrence River. My mom told me that my grandparents’ love story kicked off right outside Le Château Frontenac, after an ice-skating date. I got a mini souvenir there when I was 12, and it still feels like a warm hug from my family history. It’s the kind of place where magic happens, perfect for making your own winter memories!
What Makes Steele Hill Resort a Family & Couples Dream
Winter escapes can be the perfect way to recharge your batteries and take a break from the hustle and bustle of everyday life. And what better way to do this than by retreating the mountains?
For my family, our usual winter cabin stays around North Conway were found on Craigslist, a far cry from our current options. However, we decided to switch things up one winter and booked a stay at Steele Hill Resort. It was a new and luxurious experience that added a touch of pizzazz to our usual mountain escapades.
Years later, my then-boyfriend, now-fiance, planned an anniversary getaway, and he chose Steele Hill again without knowing I had been there as a kid. It was a happy coincidence because we had such an incredible experience during our stay together. When we came home, and I was raving about it, my Dad reminded me and showed me pictures from my childhood!
Our view from Steele Hill Resort in the summertime.
This time, Jon and I’s room featured an in-room jacuzzi, and as hot tub enthusiasts, we couldn't resist soaking in warm bubbles while surrounded by the beauty of the New Hampshire mountains outside our windows.
Steele Hill Resort surprised us. It was the perfect mix of luxe and cozy, and our in-room jacuzzi? We were obsessed. Two indoor pools with waterslides, outdoor pools, and killer mountain views made it feel like a little winter paradise. Whether you’re with family or just your bae, there’s something for everyone to love.
Steele Hill Resort's real star is its breathtaking views, though. The resort overlooks Lake Winnipesaukee and Winnisquam, framed by the Belknap and White Mountains. It's a winter wonderland that offers a dreamy setting for a wedding!
Steele Hill Resort encapsulates the essence of New Hampshire's Lakes Region, a perfect blend of relaxation, adventure, and nature. Whether seeking a family-friendly retreat, a cozy romantic escape, or even contemplating it as a wedding venue, Steele Hill Resort offers something genuinely enchanting!
Orlando: Hilton Tuscany Village
When winter gets too cold, we escape to Hilton Tuscany Village in Orlando. This place is a stunner — think sunny pools, a heated hot tub perfect for chilly evenings, and a vibe that made us feel like we were in Mexico (hello, Instagram-worthy moments!). Plus, it’s close to the airport and shopping outlets, making travel and retail therapy a breeze. Oh, and the nearby Universal Studios and Voodoo Donuts? Total cherry on top. Read more about it here: TRAVEL TIPS & INSPO: WINTER ESCAPE IDEAS
The resort is nothing short of stunning. Our balcony overlooked the heated pool and hot tub, aka my favorite hangout. There’s nothing like soaking in warm bubbles while a soft Florida breeze hits your face.
The spa's serene ambiance, combined with the skillful hands of the masseuse, will make you forget all your worries. The well-equipped fitness center is perfect for fitness enthusiasts who want to maintain their routine while on vacation.
The resort's two beautiful pool areas offer ample opportunities to soak up the Florida sun. I enjoyed lounging by the larger pool, sipping on a refreshing drink from the adorable pool bar. It felt like a scene from a Jimmy Buffet music video, with an added touch of luxury.
The resort's wooden bridge over its picturesque pond was a perfect setting for romantic evening strolls and a couple of pictures. The resort's being so close to the airport also made our travel experience hassle-free!
Of course, no vacation is complete without indulging in some delicious food. My fiance Jon and I decided to treat ourselves to classic burgers, fries, and a flatbread pizza while washing it down with a refreshing hurricane at the pool bar.
And ooh! The little lizards!
Practical winter escape tips:
Waterproof, insulated boots are a must.
Hand warmers? Stick ‘em in your pockets.
Portable charger for your tech, cold kills batteries.
Warm, moisture-wicking socks keep feet dry and happy.
Warm Weather:
Lightweight, breathable clothes that let your skin breathe and block the sun.
Reusable water bottle + cooling towel = survival kit.
Moisture-wicking underwear keeps things comfy.
Light jacket or shawl for cool nights.
General Tips:
Know local customs so you don’t look like a tourist mess.
Prep for delays and pack meds for colds/allergies.
Consider investing in travel insurance to cover unexpected situations, make copies of important documents, and have a backup credit card.
Finally, stay flexible and open to changes in your itinerary due to weather or other factors.
❄️ FAQs That’ll Help You Plan the Trip (Not Just Daydream)
How early should I book a winter resort?
If you're going anywhere even remotely popular between mid-December and early January, book 3–6 months in advance. But book activities and spa treatments when you book the room. Otherwise, you’ll get there and everything’s “fully booked” except a 9 a.m. couples massage next to the ice machine.
What’s the worst mistake people make on winter getaways?
Not factoring in travel delays. Winter trips are cute until your flight’s stuck in Chicago for 8 hours and you lose a whole day.
Pro tips:
Book early morning flights (less risk of delays)
Always pack one full outfit in your carry-on
Skip tight connections, it’s not worth it in winter
Are all-inclusive resorts worth it in the winter?
It depends. For warm-weather destinations, yes, food, drinks, and activities are bundled and easy. But for cold-weather resorts, “all-inclusive” usually just means overpriced buffet and one sleigh ride. You’re better off choosing a place with à la carte add-ons and paying for what you want.
What should I look for in a winter resort if I have dietary restrictions?
Call ahead, don’t rely on the website.
Ask:
Do they use seed oils?
Can they accommodate allergies without cross-contamination?
Is there a microwave or fridge in-room if you bring your own food?
This matters way more in small ski towns where grocery options are limited.
Should I rent a car or use Uber?
If you're going somewhere snowy, rent a car with AWD and a heated steering wheel. Uber is unreliable in remote areas, especially after dark. Also, parking costs add up fast in resort towns. Ask about that when booking. Some places charge $40 a night just to park.
What’s the one thing people always forget to pack for a winter trip?
Something cozy for indoors that still looks cute. You’ll spend more time in loungewear than you think. You need a pair of chic PJs or a matching sweatsuit that makes you feel like a 10 while drinking hot chocolate by the fire. Also: lip balm, blister patches, and moisturizer that works in dry air.
When is the cheapest time to go on a winter vacation?
Early December and mid-to-late January are the best-kept secrets. Everyone’s too busy before Christmas or recovering from New Year’s. Resorts slash their prices, but the weather’s still good, and everything’s decked out in lights. It’s also the best time to get an upgraded room or a last-minute spa opening.
Are kid-friendly resorts a nightmare if you’re traveling without kids?
They can be! Read the reviews and filter by “couples”. Some “family resorts” do a great job of separating adult and kid spaces, while others feel like a daycare with cocktails. If you want quiet, look for places that say “adults-only pool” or “spa wing.” If they don’t mention it, assume it’s chaos.
Is it better to book through a third-party site or directly with the resort?
Here’s the deal: third-party sites might get you a better price, but they won’t help you if something goes wrong. Booking directly usually gets you:
Priority for upgrades
Better room location
Easier cancelation policies
Pro tip: use a third-party site to find deals, then call the resort and ask if they’ll match it.
Should I plan every day or leave it open?
Leave at least one full day unplanned. Winter weather messes with everything, and your energy level will surprise you. You’ll thank yourself for that flexible day when you're either snowed in or just want to binge-watch holiday movies in a robe and order room service.
Sharing is Caring!
Tag your winter trip buddy and save this for your next cold-weather escape!
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Warm Wishes,
Kacie
