We're thrilled to kick off our new Jetset Journeys series, where we turn the best U.S. cities to explore this year into our own personal playgrounds. This is not just a travel guide but a way to spark your creativity and your wanderlust for weekend and week-long travel. Pack your bags , join us here every week, and get jetsetty this summer.
When you think of romantic destinations, you probably envision secluded beach getaways, remote mountain cabins with a roaring fire, or luxurious suites in a historic Parisian hotel. These options definitely qualify as romantic, but the truth is that most of us can’t travel into quite such another world on a regular basis… much less within a two-day timeframe.
Photo by Andres Ayrton
Exploring a new city stateside can be uber romantic, if you know what to do with your time. Here are our top five cities for a romantic couple’s getaway closer to home, one that’s sure to be just as exciting and intimate as any dreamy honeymoon-esque destination.
Chicago
Photo by Aveedibya Dey on Unsplash
A fantastic city for old-fashioned American romance is Chicago. With its sweeping architecture, beautiful parks and lakefront views, this city is not to be underestimated if romance is your goal.
Photo: Beatrix
Start your first morning off at a classic brunch destination like Beatrix or The Bongo Room, both of which are sought out weekend after weekend by Chicago couples.
Art Institute of Chicago | Photo: Shutterstock
Next, take a stroll along Chicago’s Riverwalk, where you’ll find yourself gazing up at the incredible skyscrapers for which the Chicago School of architecture is known. If you’re really into history and design, the Chicago Architecture River Cruise Tour is not to be missed - you’ll float down the Chicago River (yes, drinks are available), and gaze up at the city from the center of its famous waterways.
Next, check out one of Chicago’s many amazing museums. The Museum Campus, located right along the lakefront, is home to the world-famous Art Institute of Chicago, the Shedd Aquarium, and the Field Museum. Oh, and did we mention the Adler Planetarium, where you can cuddle up and gaze up at the stars together?
Photo: Alinea
For dinner, make a reservation at one of the city’s best restaurants, like world-famous Alinea or celebrity chef Stephanie Izard’s Girl & The Goat.
Photo: The Violet Hour
Finish off your day with a stroll along Navy Pier, where you can kiss atop the Ferris Wheel while taking in breathtaking nighttime views of the city.
Spend your second day touring Chicago’s most interesting neighborhoods on foot. Head to Old Town for gorgeous historic homes and a super-walkable, classic city vibe, or opt for Logan Square if hipsters and arcade bars are more your speed.
Round off your weekend with cocktails at one of the city’s trendy speakeasies, like The Violet Hour or The AviarySan Francisco
Photo by Taryn Elliott
San Francisco’s natural landscape and architecture, with its rolling hills and European-feeling streets and architecture, makes it a serious contender for the most beautiful city in the U.S.
Photo: Amy Holt for Tartine
Start off your first day with a pastry from Tartine, or grab a meal at a charming cafe like Mama’s on Washington Square. San Francisco’s food and wine scene is truly its own culture, so don’t be surprised if you grab some extra items to-go.
Next, head to the Embarcadero and take in the waterfront views, or hit up the iconic Golden Gate Park for a classic attraction you won’t want to miss. Spots like the Japanese Tea Garden, Conservatory of Flowers, and Stow Lake serve up beauty and romance in heaps.
Japanese Tea Garden | Photo by Enric Cruz López
While you’re on foot, enjoy a picnic in the park. SF is the kind of city where you can easily grab fresh bread, deli meats, gourmet cheeses and snacks from your pick of local artisan markets with superb offerings.
That night, enjoy a romantic dinner at a waterfront restaurant along the Embarcadero, such as the Spanish-inspired Coqueta at Pier 5 or The Franciscan Crab Restaurant at Pier 39 for fresh seafood and stunning views of the Bay.
Photo: 15 Romolo
The next morning, take a walking tour of North Beach, often referred to as San Francisco's Little Italy. Grab brunch at Caffe Trieste and/or drinks at 15 Romolo, then explore the area’s historic streets and many local boutiques.
To cap off your trip, take a romantic sunset cruise on the San Francisco Bay. Sail past iconic landmarks like Alcatraz Island while sipping Champagne and enjoying hors d'oeuvres.
Boston
Shutterstock
Boston is arguably the country’s most historic city, and its charming architecture, beautiful streets, and fantastic dining scene are perfect for a couple’s escape.
On your first day in Beantown, start your morning off with breakfast at a charming cafe like Tatte Bakery & Cafe or Thinking Cup. Go for a walk along the Charles River Esplanade, enjoying the scenic views of the river and the Boston skyline.
Museum of Fine Arts | Photo: Shutterstock
The Museum of Fine Arts isn’t to be missed, as it houses one of the most comprehensive art collections in the world.
Next, have a romantic lunch at a cozy bistro in the Back Bay neighborhood, such as Deuxave or Mistral. For dinner, enjoy a romantic meal at a waterfront restaurant in the Seaport District or the North End. Legal Harborside boasts delicious fresh seafood in a modern environment, while Ristorante Lucia offers a super romantic aesthetic.
After dinner, take a sunset cruise on Boston Harbor. Relax aboard a sailboat or yacht while taking in the breathtaking views of the city skyline and the harbor lights.
Swan Boats | Photo: Shutterstock
The next day, head to a historic diner like The Paramount or Mike's City Diner for breakfast or brunch. You’ll need sustenance for all the must-do activities in Boston, which include exploring the historic Freedom Trail, starting at Boston Common and ending at the USS Constitution Museum in Charlestown.
Next, enjoy each other’s company and conversion as you stroll through the beautiful Boston Public Garden. Enjoy the lush greenery, colorful flowers, and the iconic Swan Boats on the pond.
For dinner, try a romantic dinner cruise on the Charles River. Enjoy a gourmet meal and live music while cruising along the river and admiring the city lights. After the cruise, take a romantic walk along the historic streets of Beacon Hill. Admire the charming brownstones, gas lanterns, and cobblestone streets as you stroll hand in hand.
New York City
Photo by Samson Katt
New York City is for lovers and always has been. Start your first day off with a cozy breakfast at the NYC staple Sarabeth’s, which boasts a killer location just south of Central Park. Next, stroll hand in hand through the park as you digest. For bonus romance points, you can even rent a rowboat and paddle around the lake, taking in the urban beauty around you.
Photo: Cynthia Ortega Espinosa
Visiting the Metropolitan Museum of Art is a great way to spend your afternoon, and you can take in even more of the iconic experience by heading up to the Met’s rooftop garden for stunning views of NYC. Another great place for walking? The High Line, a converted rail line that’s now an elevated park perfect for strolling and taking in the city’s views.
Photo: One if by Land, Two if by Sea
Grab dinner at a romantic spot that boasts some more killer views. Some of your best options include The River Café for waterfront dining or One if by Land, Two if by Sea for a historic atmosphere and plenty of romance.On your second day in town, explore the more creative neighborhoods of NYC. Start your morning off with breakfast at a trendy spot like Jack's Wife Freda or Buvette, then stroll through Greenwich Village, SoHo, or Brooklyn’s Williamsburg, taking time to stop at every cute little boutique that captures your interest.
Austin
Photo by Tomek Baginski on Unsplash
Keep Austin weird for sure, but also embrace its youthful energy and fresh, creative environment.
Start your romantic trip to Austin with breakfast at a cozy cafe like Elizabeth Street Café or Paperboy. Then take a stroll around Lady Bird Lake, enjoying the scenic views of downtown Austin and the Colorado River.
That afternoon, take a dip in the Barton Springs Pool, a natural spring-fed pool located in Zilker Park. After you’ve worked up an appetite, enjoy a romantic picnic lunch in the park as you take in the natural scenery.
Photo: Perla's Seafood & Oyster Bar
As far as cuisine is concerned, Austin’s foodie scene is ever growing and expanding. Enjoy a romantic dinner at a restaurant with outdoor seating, such as Uchi or Perla's Seafood & Oyster Bar. Savor delicious cuisine and cocktails while soaking up the ambiance of Austin's vibrant nightlife.
After dinner, take a moonlight stroll along South Congress Avenue. Explore the eclectic shops, street art, and live music venues that make this area so unique.
Photo: Josephine House
On your second day in town, have breakfast at a trendy brunch spot like Bouldin Creek Café or Josephine House.
After filling up, explore the vibrant East Austin neighborhood on foot or by bike. Visit local art galleries, boutique shops, and coffee shops.
Photo: Viva Day Spa
Next, get out of the city for the afternoon and take a scenic drive to the Texas Hill Country. With a plethora of wineries and or breweries to visit, you won’t regret going just a little bit off the beaten path around Autin. Consider destinations like Duchman Family Winery or Jester King Brewery for a romantic afternoon sampling local wines or craft beers.
Not interested in getting out of town? Stay in Austin and spend the day relaxing together with a couples' massage at a spa like Milk + Honey or Viva Day Spa.
For dinner, indulge in a romantic meal at a cozy restaurant with a farm-to-table menu, such as Lenoir or Olamaie.
Main image: Taryn Elliott
Follow along for all your travel needs with our Flights of Fancy series and Jetset Journeys series.
