Love Is In The Air: The Most Romantic Cities In The U.S

The United States might not be a top destination for luxurious, dreamy romantic trips filled with flowers and wines like Paris, but these romantic cities are the perfect and affordable choices for you and your loved ones.
December 20, 2021 | 13:46

Compared to luxurious romantic places such as Venice or Paris, these romantic getaways in the United States are much cheaper and easier to get access to. From cuddling up in cozy mountain B&Bs to relaxing on the beach while watching the sunset, these romantic U.S. cities have everything you and your partner need for a love-filled weekend!

1. Aspen, Colorado

Photo:  Inspirato
Photo: Inspirato

Around every corner in Aspen lies beautiful architecture, which is home to all sorts of fine shops, restaurants, and lodges. There are very few towns that are known for upscale, sporty fun like Aspen. Located adjacent to some of the most beautiful mountains in the state, Aspen is an outdoor paradise. It’s urban yet secluded, with plenty of wilderness to explore.

The Roaring Fork nearby provides an opportunity for cliff jumping. It’s also known for decadent restaurants, family-oriented ski lodges, historical sites, and many different local arts attractions. Aspen is home to Sport Obermeyer, a historic outdoor clothing maker.

Like much of Colorado’s westward mountain expansion towns, Aspen’s origins are strewn throughout the ashes of the once-thriving Colorado silver mining industries. But Aspen has always had something special about it. It’s not just another pioneer town peppered with colorful mining history.

Instead, Aspen has evolved from being a settlement of miners ignoring warnings of potential conflicts with the Ute tribes of the area, to the United State’s most productive silver-mining region in the early 1890s. Over the course of the next 130 years, Aspen’s rollercoaster history led it to its current state, where according to Zillow the average home price is around $2.2 million.

Soar above the Rocky Mountains with a private hot air balloon experience available year-round—or attend the Snowmass Balloon Festival in the fall, where you can watch balloon launches while enjoying a hard cider. Take a snowmobile or hike the trails to Maroon Bells to discover breathtaking views of wine-colored peaks. Get tickets to Ullr Nights during the winter for a nighttime wonderland of live music and snuggling by the campfire with s’mores. Take your taste buds on an adventure with libations from accomplished winemakers and delicious food samples from celebrity chefs at the Food & Wine Classic in June. Or make reservations for a snowcat to take you up the mountain for a romantic dinner at Cloud Nine Alpine Bistro, where you can indulge in a four-course meal and the finest wines.

2. Chicago, Illinois

Photo:  Jefferson Lines
Photo: Jefferson Lines

"It is hopeless for the occasional visitor to try to keep up with Chicago – she outgrows his prophecies faster than he can make them," wrote Mark Twain in "Life on the Mississippi." Although Twain made up his mind about the Windy City before it even reached its 50th year, his impression of Chicago has proven long-lasting. America's third-largest city has been described in a myriad of ways throughout its lifetime. When Thomas Edison and Nikola Tesla were competing for the right to use their forms of electricity to illuminate the 1893 World's Columbian Exposition (also known as the Chicago World's Fair), Chicago was known as a city of industry. When Prohibition set in, notorious mobsters like Al Capone transformed Chicagoland into their own dangerous playground. And intense immigration surges throughout the 20th century brought a host of new identities to the Windy City, including Greek, Polish, Italian, Irish and Jewish.

Considered the birthplace of the skyscraper, there’s a reason why Chicago often gets voted the city with the best skyline since there are plenty of picture-perfect rooftops that make for prime proposal spots. Take your pick of ways to eye the views opting between a boat on the Chicago River or an observatory deck on one of the skyscrapers themselves. Once you’ve checked the Wrigley Building and Frank Gehry’s Pritzker Pavilion off your sightseeing list, eat your way around town at one of the city’s many-starred restaurants like Alinea, where chef Grant Achatz’s 18-course, the multi-sensory menu is as artfully curated as Chicago’s world-class museums.

3. Charleston, South Carolina

Photo: Britannica
Photo: Britannica

While Charleston has its centuries-old cobblestones and horse-drawn carriages, the city is far from stuck in the past. Creativity and innovation are as synonymous with Charleston as the humidity and Spanish moss. Yes, you'll find Southern staples (Rodney Scott's James Beard award-winning whole hog barbecue is a must) and the views Charleston is famous for (the Pineapple Fountain in Waterfront Park), but it's also home to a variety of new sites and up-and-comers that have made names for themselves in the past few years. Stop by Babas on Cannon, just a block off King Street, for European-inspired dishes, espresso, and maybe an aperitif or two. If you've reached the point where you can't eat another bite—which isn't hard to do in a town like this—venture to Mount Pleasant, where Charleston Artist Collective houses art by a number of local talents across a range of price points, according to Travel + Leisure.

Spend the day lounging on a blanket and watching the waves roll in at Sullivans Island, or head out on the water for romantic Moonlight Sail aboard the Schooner Pride. Walk through the butterfly house, see where movies like The Notebook were filmed, or take a torchlit boat ride through the swamp at Cypress Gardens. Go on a brewery tour, dance to live music, and enjoy a Bearded Tiger Cream Ale and Poutine at Rusty Bull Brewing. Make a reservation with Palmetto Carriage Works for an intimate carriage ride through Downtown Charleston. Experience full-body relaxation and rejuvenation at The Spa at Belmond Charleston Place.

4. Nantucket, Massachusetts

Photo:  Conde Nast Traveler
Photo: Conde Nast Traveler

Nantucket is an idyllic island paradise—except instead of tropical paradise vibes, you'll find Vineyard Vine-clad gentlemen and mansions with gray, natural wood shutters. Nantucket is the epitome of summer New England life, though, unfortunately, it means much of the island shuts down in the colder months. Boasting the highest concentration of pre-Civil War homes in the country and 82 miles of pristine coastline, Nantucket is a postcard come to life.

From charming Nantucket hotels to five-star restaurants to the prized Nantucket beaches, this town comes alive in the warmer months. It's a destination that thrives on outdoor dining (think: lobster rolls on the water), boutique shopping, and picturesque walks through town. And certainly, there is no shortage of things to do in Nantucket, whether you're partial to walking the beach at sunset, biking to pick up your latte in the morning, or ordering up a dozen oysters with a bottle of good Champagne.

Rent a bike for two at Young’s Bicycle Shop and head to Jetties Beach for a relaxing swim or to look for sea glass. Hit the water and go on a sailing excursion or cross “learn to surf” off your bucket list with your partner at Nantucket Island Surf School. Watch humpbacks whales soar out of the water by day or go on a romantic sunset cruise at night with Shearwater Excursions. Explore the beautiful Greek Revival mansion and Victorian garden at the historic Hadwen House. Make your way out to Brant Point Lighthouse for great views of the island and the Nantucket Sound. Head to Cisco Brewers Nantucket for a vineyard, brewery, or distillery tour and stay for live music and eats from food trucks.

5. New Orleans, Louisiana

Photo:  Universal Commercial Capital
Photo: Universal Commercial Capital

New Orleans is an over-the-top experience for the senses, a city filled with vibrantly colored streets, soul-filled rhythm and blues, and memorable flavors. The coastal Louisiana enclave is the culinary heart of creole and cajun food, and beyond delicacies from gumbo to shrimp and grits, it's the city that brought us the muffuletta, beignets, and char-broiled oysters.

New Orleans, nicknamed "The Big Easy," is a town of jazz kings and queens, iconic architecture, the New Orleans Saints, and perhaps the most spirited street in America—Bourbon Street. It's also one of the only cities in America where you can legally drink on the street, which only adds to the lively nature of NOLA nightlife. Comedian and actor Hannibal Burress famously said of the Big Easy that "for $300 you can have your own parade on a day's notice," and if that doesn't beautifully encapsulate the glory of New Orleans in one sentence, we don't know what does.

The Big Easy may be known for its nonstop nightlife (this is the town famous for Bourbon Street, after all), but one stroll along Frenchmen Street will have you instantly swooning—and swaying—over New Orleans’ signature jazz music. Roll along the Mississippi on a jazz cruise or catch a show in one of the iconic music clubs like The Spotted Cat. If you’d rather cozy up in your hotel, you can still hear music streaming from the street below on your wrought iron balcony in the oldest stretch of the city, the French Quarter.

6. Milwaukee, Wisconsin

Photo:  Two Drifters
Photo: Two Drifters

Sometimes derisively called “Chicago north,” Milwaukee is just two hours from Chicago by car, bus or train, and makes for a great weekend (or even long day trip) from the city. Home to Miller-Coors and several other breweries, it’s a haven for beer lovers. But this small city is coming into its own in other ways too, with new developments, a lively public market, a world-class art museum, and a revitalized historic district.

Milwaukee is another great Midwest weekend destination, offering lots to see and do for both kids and adults. The city was once a great center for industry in Wisconsin, and at one time it was home the number one beer producing city in the world (it was home to four of the world’s largest breweries – Schlitz, Blatz, Pabst, and Miller), before it began to decline in the 60s and 70s. Now the city is experiencing a mini-Renaissance, restoring historic districts and luring tourists with the promise of family fun, history, and of course, lots of beer.

The Milwaukee Public Market is the perfect place to grab a quick bite, stock a picnic lunch, or enjoy some fresh but cheap eats. Open daily from at least 10 am to 6 pm (with longer hours on Saturday), it’s home to dozens of vendors selling everything from cheese curds to sushi to soup to pasta to sandwiches to wine and dessert, all of which is ready to eat, according to Free Fun Guides.

7. Savannah, Georgia

Photo: Hotels
Photo: Hotels

Savannah, with its Spanish moss, Southern accents, and creepy graveyards, is a lot like Charleston, South Carolina. But this city about 100 miles to the south has an eccentric streak. Savannah College of Art and Design students mix with ghost hunters and preservationists, while Southern restaurants share street blocks with edgy cafes and restored theaters. The quirky characters in the true crime story, "Midnight in the Garden of Good and Evil," say it all. Yes, eccentricity is the name of the game, but if that's not your "box of chocolates," as Tom Hanks famously said in the Savannah-filmed "Forrest Gump," maybe history or nightlife is.

Savannah's antebellum past seeps from nearly every corner – it's home to one of the oldest Black churches in North America and Fort Pulaski acted as a safe haven for enslaved people to escape to freedom. But regardless of if you're in town to immerse yourself in history, see the sights, sample the tasty Southern cuisine or spend a few nights bar-hopping, Savannah knows how to show visitors a good time.

Have a picnic under a shady tree, take a walk around the 150-year-old fountain, or listen to live music in the amphitheater at Forsyth Park. Head to Chippewa Square to catch a play or walk the trails to see the bench where the opening scene of Forrest Gump was filmed. Stop to smell roses while strolling through 12 different gardens at Coastal Georgia Botanical Gardens. Get your heart pumping with a private carriage ride ghost tour. Venture to Tybee Island to watch the sunset on the pier or take a dolphin cruise. Board the Georgia Queen for the seasonal Valentine’s Day dinner cruise or for brunch.

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