7 Romantic Winter Getaways Across America

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Winter is in full swing, which means a weekend getaway is in order. I’ve rounded up 7 road trip ideas from major cities across the country. Of course, these picks are all based on my personal opinion and experiences but feel free to add your own ideas to the mix!

7 Dreamy Weekend Getaway Ideas for Every Travel Style

Happy trails all!

New York –> The Finger Lakes for wine tasting ?

It might have taken me 5+ years of living in New York to finally experience the Finger Lakes but better late than never! This past Spring, my husband and I headed to Aurora to witness the wedding of two of our dearest friends. While we fell in love with this small, dollhouse-looking town, there are lots of other cities to explore in the Finger Lakes, too.

For wine tasting, you’re best bet is to is to tailor your trip to a wine trail. There’s the Cayuga Lake Wine Trail, the Keuka Lake Wine Trail and the Canandaigua Wine Trail to choose from, so take your pick. If you’re on a time crunch, consider heading to Seneca Lake, which is home to more than 30 wineries plus several breweries and even a meadery.

Travel expert tips to the Finger Lakes

DC –> Middleburg for the not-so-wild West ?

I’m from the DC area so I may be a little bias with this one but aren’t we all when it comes to our hometown? Middleburg, VA is my absolute favorite weekend getaway and for good reason. For one, the tiny town is the complete contrast to the bustling District; instead of grand office buildings there are horse stables and independent designer boutiques.

Having grown up horseback-riding, I immediately gravitated toward the city’s horse-themed shops and restaurants. From the National Sporting Library and Museum that pays homage to iconic mares and stallions to equestrian-themed artwork seen throughout the Salamander Resort, you’ll feel like you’ve entered the wild, wild West, albeight much more refined.

Travel expert tips to Middleburg

Baltimore –> Annapolis for historic sights ⚓️

Annapolis might be home to the United States Naval Academy, but there’s a lot more to this charming city than meets the eye. Budget-wise, you’re in luck, as many of the top attractions are free, including the narrow waterway called Ego Alley and the Maryland State house that boasts architecture exhibits. Then there are the many shops and stops along Main Street.

For me, the best part of Annapolis isn’t what you’ll see indoors—although there is a lot of interesting history attached to the city—but the unspoiled nature outside. Quiet Waters Park is a dream all four seasons while the William Paca House and Garden is the gorgeous 18th-century Georgian mansion you never knew you needed. Don’t forget your camera!

travel expert tips to Annapolis

San Francisco –> Carmel for California charm ?

During our brief stint living in San Francisco, we only took a few weekend getaways but we definitely found our favorite retreat. Carmel-by-the-Sea is a picturesque beach town that boasts the best of both words—a sunny and sandy beach coupled with top-notch farm-to-table restaurants, all within walking distance of each other. Go for the day or spend the entire weekend away.

If you’re making the trip to Carmel, you’re in for a real treat. It’s part of Bug Sur, which is ranked among the top driving destinations in the country thanks to lush landscape and idyllic coastal views. Once there, indulge at one of Carmel’s cozy but upscale restaurants and maybe even splurge on a glass of rosé. Then, take a well-deserved nap on the beach.

travel expert tips to Carmel by the Sea

Charleston –> Isle of Palms for beach bumming ?

Some of my best childhood memories are those from our summer trips to Isle of Palms, a beach bum paradise just outside of Charleston. For the most part, we spent our days building sand castles on the beach and our nights watching TV and dreaming up our next scheme. As I grew older, those days and nights graduated to fine-dining and bottles of wine.

In my opinion, Isle of Palms is a much calmer, more sophisticated beach getaway than, say, Miami. Rent a set of bikes and tour the island, taking in some of the island’s grandest and most colorful homes. Later, you can swing by for a flavorful scoop (or three!) of ice-cream or a fancy cocktail at the bar. When you’re all “beached” out, Charleston is only 12 miles away.

travel expert tips to Isle of Palms

SLC –> Park City for snow sports & skiing ❄️

I visited Park City for the first time this year and wow, did it blow me away! We stayed at the ornate Washington School House boutique hotel and ate to our heart’s content at the nearby High West Distillery & Saloon. If that’s all you accomplish on your trip, consider yourself a champ. Bonus points if you spot the Banksy piece just outside of the hotel.

Still, there’s a lot more to Park City than the downtown shops and restaurants. If you visit during the winter season, you’ll have quite the ski adventure. The Park City Mountain Resort is a popular spot for both skiing and spa treatments, and with 7300 acres of terrain, you’ll become a ski pro in no time. Classes are also available, should you want to up your game.

travel expert tips to Park City

Houston –> Galveston for foodies ?

While I’ve only seen Houston on my way to Galveston, I can attest that the two have very little in common, of course, making for the perfect weekend getaway. Galveston has many faces, each one more surprising than the next. There are historical homes that double as museums, a Pleasure Pier with thrilling amusement park rides and even a haunted manor.

For me, Galveston is best experienced through food. Head to Farley Girls Cafe for comfort food battered in grease or sample the local flavors at Little Daddy’s Gumbo Bar. Keep in mind that the phrase, “everything is bigger in Texas” also applies to the food. The servings are quite large, so make sure you’ve worked up quite an appetite before dining.

travel expert tips to Galveston

What’s your favorite nearby weekend getaway? Tell us in the comments below!

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