Where to Have a Romantic Retreat This Valentine’s Day
It’s time to plan a special trip to celebrate Valentine’s Day together, even if this year’s destination is just a few hours away.

Departures is published by Meredith Corp. and owned by American Express. While American Express Card Member benefits are highlighted in this publication, including through the links indicated below, the content of this article was independently written by the editorial staff at Meredith. Other Departures content paid for by American Express is explicitly marked as such.
Travel may have changed in 2020, but getting away together is still a great way to celebrate the holiday and experience the intimacy of exploring a new locale or returning to a favorite destination. You don’t have to travel far to enjoy the benefits of a trip together, and the fun starts with the planning.
Related: Valentine's Day Gift Ideas for Her
We’ve taken a look around the U.S. from east to west and north to south to come up with ideas that will offer romance and a change of pace for couples with tastes ranging from warm weather relaxation to wintery excitement. Big cities, small towns, wine country, and destination resorts are all options for a Valentine’s Day trip.
Active couples may want to consider snowy fun in the Catskills of New York, while the beaches of Lanai, Amelia Island, and Santa Barbara will appeal to others. Las Vegas and New Orleans guarantee a lively atmosphere, and Savannah, Bluffton, and St. Michaels offer their own style of charm. Big city fans might consider Dallas or Chicago.
Related: These Are the Most Romantic Restaurants in America, According to OpenTable
The fun can begin even before February rolls around. A cocktail or glass of wine and a few snacks will create the perfect atmosphere for browsing websites and brochures to plan your romantic Valentine’s Day trip. Here are some suggestions to get you started.

Santa Barbara, California
Sandy beaches, the blue Pacific, and rugged hills as a backdrop make Santa Barbara one of California’s most beautiful locales. A stroll along the shore, a harbor cruise, or a hike to enjoy the views and get a workout at the same time—perfect ways to spend a day together on the American Riviera. Browse through downtown to dine, shop, or taste local wines, and when the day is over, head to one of the area’s luxurious hotels. The Belmond El Encanto, an American Express Fine Hotels & Resorts property, high in the hills overlooking Santa Barbara, offers individual bungalows set among winding paths and secluded gardens. Dining on the terrace with a view of treetops and the sea in the distance is lovely, or for total privacy, couples may opt in-room dining. The oceanfront Rosewood Miramar Beach—also an American Express Fine Hotels & Resorts property—is another elegant option, with a variety of accommodations that include guest rooms, beach-view suites, garden bungalows, and private residences. Guests can enjoy a cocktail at the Miramar Beach Bar or dine at Caruso’s for Southern Italian dishes.

Chicago, Illinois
If big cities, sophisticated hotels, and top restaurants are your choice as a couple, a trip to Chicago might be the best way to celebrate. Sure, it’s chilly in winter, but indoor activities are plentiful. Browse the exhibits at the Art Institute of Chicago where there’s something for every taste, from ancient to modern, sculpture, paintings, and artifacts. The Museum of Science & Industry is another place to spend a fascinating day. Bundle up for a stroll along Chicago’s Riverwalk or a trip to Millennium Park for a photo in front of the gleaming stainless steel Cloud Gate sculpture. See Chicago from 1,000 feet above famed Michigan Avenue for views of the lakefront and skyline from 360 Chicago or thrill to a ride on TILT from the 94th floor observation deck. For luxurious surroundings, stay at The Langham, with views of the Chicago River and Lake Michigan or consider The Peninsula, another five-star property with traditional Asian hospitality—both American Express Fine Hotels & Resorts properties. The Ritz-Carlton, on Chicago’s Gold Coast, offers a spa, indoor swimming pool, and Torali, an Italian-inspired steak restaurant.

St. Michaels, Maryland
A small, historic town might be your ideal getaway, especially if waterfront restaurants, Chesapeake Bay oysters, and hot steamed crabs sound appealing. St. Michaels dates back to the mid-1600’s, and you can spend days exploring its maritime museum, antique shops, galleries, and vintage neighborhoods. In the evening, head for your plush suite with views of the Miles River, sip a cocktail in a cozy pub, and enjoy a romantic private dinner with a secluded table for two. The Inn at Perry Cabin offers all this plus golf, tennis, spa, and sailing. Originally built in the early 19th century, the Inn combines its vintage atmosphere with modern conveniences and is within driving distance from most east coast cities. Also, if your pooch is part of the romantic getaway plans, you’ll be glad to know that dogs are welcome and totally pampered at the Inn, with an assortment of treats and a special menu.

Sonoma County, California
Wine lovers can’t miss with a trip to northern California’s wine country, for visits to tasting rooms, delicious dinners prepared with farm fresh local ingredients, and drives among rolling hills and picturesque vineyards. More than 400 wineries, 60 miles of coastline, and nearly 50 miles from north to south provide much to see and do. Wine might be at the top of the list, but Sonoma is also home to breweries and distilleries for a change of pace. Drive along the coast, bike through rows of grapevines, or stop at a farmers’ market for ripe fruit and locally made cheese. At the recently renovated MacArthur Place Hotel & Spa in the town of Sonoma, you can book the Chef’s Cottage with a cozy wood burning fireplace and private patio, firepit, and outdoor shower. In the charming town of Healdsburg at the other end of Sonoma County, the Montage Healdsburg offers exquisitely appointed suites with floor to ceiling windows looking out over vineyards or oak forests, as well as furnished terraces with outdoor fire pits. Their Spa Montage features dedicated treatment rooms for couples and signature experiences for two.

Bluffton, South Carolina
In South Carolina’s Lowcountry, this historic area features a variety of activities, ideal for couples who enjoy being outdoors during the day and then settling in for a luxurious dinner and a comfortable place to spend the night. Extensive bike trails—perfect for strolling too—meander among huge oaks draped with swaying Spanish moss. There’s boating, fishing, golf, stand up paddle boarding, and horseback riding. Sporting clay shooting at the Palmetto Bluff Shooting Club is fun as well. When the busy day is done, the American Express Fine Hotels & Resorts property Montage Palmetto Bluff offers a collection of guestrooms, suites, cottages, and vacation homes, designed and decorated in classic Southern style. Their charming cottages provide a romantic setting, with a choice of forest, river, or lagoon views. Gas fireplaces, private screened-in porches, steam showers, and soaking tubs complete the picture. Dine at Octagon for classic Carolina cuisine, at a casual outdoor spot, or opt for room service for a private couples’ dinner.

Amelia Island, Florida
In its early days, this small barrier island off the coast of northeast Florida was a lively seaport, and today, its Victorian homes, cottages, shops, and colorful Fernandina Beach downtown tell the story of those days. Self-guided walking tours are available for couples who want to explore in more detail or visit the historic 1829 lighthouse. Scenic biking and hiking trails, beaches, and thirteen miles of coastline provide daytime activities, and boating, kayaking, and fishing in the surrounding sea are other options. Many of the historic homes, some listed on the National Register of Historic Places, have been converted to bed and breakfast inns. For a luxurious stay, the Ritz-Carlton Amelia Island features guest rooms and suites with expansive ocean views and private balconies, indoor and outdoor pools, championship golf course, and full-service spa with special couples’ treatments. Dine at Salt for fine coastal cuisine, where foodies have the option to arrange “Dine with the Chef” for a close-up view of the action in the kitchen. A private sunset cruise would be a romantic way to end a day on Amelia Island.

Savannah, Georgia
Considered one of the country’s most romantic cities, Savannah offers walkable places to explore, delicious food, history, art, and Southern hospitality. Stroll hand-in-hand among Savannah’s 22 squares—landscaped, with displays of statues, memorials, and historic plaques—and spend some time at famed Forsyth Park, home of the iconic fountain designed to resemble the one at the Place de la Concorde in Paris. Spanish moss-covered oak trees, flowers, and monuments, along with the fountain, make this one of Savannah’s most popular sites. Along the way, you’re sure to spot some of the city’s many murals, perfect places for selfies to remember your getaway. If it doesn’t seem like a vacation unless there’s a beach involved, Savannah’s Tybee Island is just twenty minutes away, with Atlantic Ocean breezes, fresh seafood, and Georgia’s oldest lighthouse. Back in town, stay in luxury at the Perry Lane Hotel, play pinball in the arcade, relax in the library, or enjoy cocktails and dinner with a view from the rooftop Peregrin.

New Orleans, Louisiana
Live music, historic neighborhoods, the French Quarter, Mississippi River, and the festive atmosphere make New Orleans a favorite of many couples. Ride a streetcar, cruise the river, enjoy a delicious dinner, and end the day with a beignet from Cafe du Monde or another NOLA bakery. It’s a fine way to start the day too. Many couples love visiting the above-ground cemeteries, taking a haunted tour or walking among the headstones and memorials—an excuse to hold each other a bit tighter. Music clubs on Frenchmen Street, Bourbon Street, and most any street for that matter create the soundtrack for late nights and fun. When it’s finally time to rest, choose from a variety of hotels that fit your style. Steps away from the French quarter, the Ritz-Carlton, New Orleans is set within a 1908 Beaux-Arts building. Newly opened, The Chloe is a 14-room boutique housed in a 19th century Uptown mansion. The Roosevelt New Orleans, another historic property, offers elegant guest rooms, suites, rooftop pool and bar, and the classic Sazerac Restaurant.

Lanai, Hawaii
This unspoiled tropical paradise is the smallest of Hawaii’s inhabited islands. Secluded beaches, red lava cliffs, forests, rugged landscapes, and abundant marine life combine with luxurious resorts to create a perfect romantic getaway. Adventurous couples can explore in a four-wheel drive vehicle to find hidden shoreline spots, Shipwreck Beach, and Sweetheart Rock (Pu’u Pehe) or take a short hike from the Four Seasons Resort Lanai up a rocky path to Pu’u Pehe for romantic sunset views over the bay. The oceanfront Four Seasons Resort offers luxurious rooms, exceptional dining, lagoon-style pools with tucked away cabanas, spa, golf, and exquisite service. At Sensei Lanai, a Four Seasons Resort, newly renovated and set in lush hills and art-filled spaces, guests can choose a personalized wellness experience, fitness classes, spa treatments, and dining at Nobu. From Honolulu, Lanai Air provides luxury air service to the island of Lanai, a special way to begin your visit to the island. (optional with a stay at Four Seasons Resort Lanai; included with a stay at Sensei Lanai)

Las Vegas, Nevada
Some couples love the excitement and variety of Las Vegas as well as the fine dining, luxe hotels, gaming, and entertainment. Attractions like the High Roller, the world’s tallest observation wheel, the Big Apple Coaster, and Big Shot at the STRAT attract thrill seekers, and others will head for the Fountains of Bellagio or the Conservatory & Botanical Gardens. Downtown, the Fremont Street Experience features a spectacular light show, zipline, and outdoor entertainment. The hotel buffets of the past have been replaced by chef-helmed dining spots attracting foodies to restaurants like Wolfgang Puck’s Cut, Thomas Keller’s Bouchon, Lorena Garcia’s Chica, and David Chang’s Majordomo Meat and Fish. If a trip to Italy is not in the plans right now, perhaps it would be fun to pretend a bit on a gondola ride at the Venetian Resort where you can even stroll through St. Mark’s Square and browse boutiques while enjoying a gelato. For many, a trip to Las Vegas is a temporary escape from reality, perhaps not a bad idea at all.

Catskill Mountains, New York
What could be more romantic than snuggling indoors when it’s cold outside? Or perhaps for some couples, getting out and playing in the snow and then warming up together in front of a fireplace or in a hot tub. The new Urban Cowboy Lodge, set on 68 acres, is a historic structure turned luxury hotel—the place for both indoor and outdoor fun. Many rooms feature clawfoot bathtubs for two and potbelly stoves, and their Walden Forest Bathing Suite also has an outdoor heated Japanese cedar soaking tub on a private deck. For another Catskills option, couples can indulge their favorite fantasies in one of the Tower Cottages at The Roxbury, with a choice of the Superhero Suite, Dracula’s Fangs, or Terraza of the Titans, among others. All are decorated and accessorized to perfection to create the desired atmosphere. Mansion rooms also follow a theme and offer a glimpse into the hotel’s history. Is something a bit more rustic your style? Consider luxe glamping in a Scandanavian-style cabin at Eastwind Hotel & Bar.
Become a DEPARTURES VIP
Join our Weekly Newsletter