Whether you’re into hearts, candy, and flowers (heart-shaped candy flowers?) or secretly anti-Valentine’s Day, travel is one gift everyone can agree on. Let’s be honest: in the middle of cold, gray February, we could all use a vacation.
We’ve zeroed in on some of most romantic cities in the country, with swoon-worthy attractions and intimate tables for two—plus cozy, affordable vacation rentals to woo that special someone. Enjoy the privacy of your own place and a full kitchen for whipping up a romantic dinner or thoughtful breakfast in bed.
From the Deep South to California Wine Country, each of these destinations makes for a dreamy getaway. Use our Valentine’s Day ideas guide to plan the perfect trip (and avoid the dog house!) on February 14th. And for a few extra brownie points? Skip the box of chocolates and upgrade your stay by booking a rental on TripAdvisor.
What to Do: Whether you decide to explore this enchanting port city by land or by sea, you’re in for a romantic adventure. Book a private carriage ride with Palmetto Carriage Works for a tour highlighting Charleston’s lavish mansions and gardens, or take in historic landmarks from the water as you circle the harbor with Charleston Sailing Charters. Step back in time with a tour of Magnolia Plantation & Gardens, one of the city’s most iconic plantation homes. Don’t miss the heritage camellia collection—one of the best in the world!—which blooms during the winter.
Where to Eat: At Charleston Grill, intense flavors meet live jazz for a sophisticated dining experience. Given the incredible menu, it’s no surprise that the restaurant has received both an AAA Four Diamond Award for food excellence and a “Best of Award of Excellence” from Wine Spectator. Also ideal for a dinner date? Circa 1886, located in the carriage house of the Wentworth Mansion. You’ll fall head over heels for the original architectural details and creative take on Lowcountry cuisine.
Where to Sleep: See all 470+ rentals in Charleston!
What to Do: “E komo mai” means “welcome” or “come in” in Hawaiian, and if you’re looking for the perfect paradise getaway, you’ll feel right at home in Maui. Set aside a day to follow the legendary Road to Hana along Maui’s northeastern shore. The famous stretch of highway—52 miles between Kahului and Hana—winds past breathtaking beaches, gardens, and rainforests, with plenty of photo ops along the way. Prefer to observe the scenery from above? Take a helicopter tour over west Maui for striking views of hidden waterfalls and dormant volcanoes, or soar above the trees on the Skyline Haleakala zipline tour.
Where to Eat: A trip to Hawaii wouldn’t be complete without a luau, and the Feast at Lele promises both Polynesian fare and an unforgettable performance featuring traditional Samoan, Tahitian, and Hawaiian dances. Up the romance factor with an intimate table for two overlooking the Pacific at Mama’s Fish House. The old Hawaiian decor and lavish flower arrangements set the stage for a memorable meal of fresh, local fish.
Where to Sleep: See all 2,880+ rentals in Maui!
What to Do: Get swept off your feet by vibrant details in the Big Easy, from historic streetcars to hidden-gem alleyways. Spend the morning at the Sydney and Walda Besthoff Sculpture Garden, located next door to the New Orleans Art Museum. The setting—winding footpaths through live oaks and magnolias—is ultra-romantic (not to mention completely free). If you love fine arts, make time for the superb collection at the NOMA; if not, sign up for a hands-on cooking class at the New Orleans School of Cooking instead. Cap off the afternoon with a ride on the Steamboat Natchez, which offers daily jazz cruises on the Mississippi River.
Where to Eat: Set the tone for a lively evening with a stop at Bacchanal Wine (“NOLA’s backyard party”) in the Ninth Ward, a spot known for its Old-World wine shop and live music in the courtyard. For a meal that captures the flavors of New Orleans, look no further than GW Fins. The restaurant boasts a spectacular view of the French Quarter, and reviewers rave about the locally sourced seafood and extensive wine list.
Where to Sleep: See all 1,250+ rentals in New Orleans!
What to Do: Get acquainted with America’s Sailing Capital on a Main Street stroll from Church Circle to City Dock. With its cobblestone side streets and colorful row homes, the city’s historic downtown is a superb spot for people-watching. Once you’ve explored the boutiques and galleries near the harbor, join a seafood crawl to sample a few local specialties. And after sunset, enjoy drinks and a show at Rams Head on Stage, a hidden-gem venue where well-known bands play to a smaller, more intimate crowd.
Where to Eat: Take the water taxi to Carrol’s Creek Cafe, an Eastport restaurant long-favored by locals for its quality seafood and waterfront views. Craving something rich and creamy? Satisfy your sweet tooth with a visit to Annapolis Ice Cream Company, where the butterfat (17%) is a decadent special ingredient. Signature flavors include Apple Pie and Peanut Butter Oreo.
Where to Sleep: See all 110+ rentals in Annapolis!
What to Do: Kick off your Seattle getaway by kicking back with a complete spa experience at the Spa at Willows Lodge. Book a couples package and splurge on a massage, facial, or scrub in a treatment room for two. If you have a weakness for vino, do a tasting at one of the vineyards in Woodinville Wine Country before returning to downtown Seattle. Spend an enchanting afternoon gazing up at the suspended sculptures at Chihuly Garden and Glass, then hop on the Seattle Great Wheel as night falls for a dazzling view of the city lights.
Where to Eat: Savor Alaskan salmon and Pacific Northwest oysters at Salty’s on Alki Beach, a classy eatery known for its stunning views of Elliott Bay and the Seattle skyline. Don’t skip town without stopping at Fran’s Chocolates for a Gold Bar and a box of their bestselling caramels. One reviewer writes, “This is one of those places that every chocoholic has to make a pilgrimage to.”
Where to Sleep: See all 870+ rentals in Seattle!
What to Do: An early-morning hot air balloon ride with Napa Valley Aloft is the perfect introduction to Wine Country. Float above rolling hills and lush, green vineyards before returning to earth for a post-flight breakfast. The Downtown Napa Winetasting Card is your ticket to trying fine artisanal wines from all over the valley. Discover a new favorite and buy a bottle to enjoy at Skyline Wilderness Park. On a clear day, the ridge trail promises views of San Francisco Bay.
Where to Eat: Take a tour of the historic caves at Schramsberg Vineyards to discover how they produce their world-class sparkling wine. Interested in tasting some limited production wines? Sign up for the Reserve Wines & Cheese Pairing experience. Of course, after a day of vineyard-hopping, you’ll need more than just cheese in your stomach, which is why you should head to Celadon for a quaint and cozy meal featuring the flavors of the Mediterranean, Asia, and the Americas.
Where to Sleep: See all 70+ rentals in Napa Valley!
What to Do: Spend a morning with Old Savannah Tours to get your bearings in Georgia’s charming capital city. Take the Historic Overview trolley tour for an entertaining history lesson full of colorful anecdotes, or opt for a slower-paced walking tour instead. Savannah’s 22 historic squares and Forsyth Park (a 30-acre park in the historic district) are iconic attractions in their own right. Pack a picnic and eat beneath Spanish moss-draped oaks before making your way to City Market. This lively cluster of restored warehouses, which displays work from dozens of artists, is a brilliant place to hunt for the perfect souvenir.
Where to Eat: Elizabeth on 37th is a primer on Southern hospitality, and the location—a Victorian District mansion—sets an elegant tone. Try the chef’s tasting menu for a fresh take on Southern Coastal cooking. Also redefining “down-home” comfort food? The Olde Pink House, where new Southern cuisine is served up in an 18th-century mansion. Whether you sit in the historic dining room or cellar tavern (think exposed brick and live music), you’ll be smitten with the setting.
Where to Sleep: See all 330+ rentals in Savannah!
What to Do: The windswept beaches of the Cape are a bit chillier (but no less beautiful!) this time of year. Bundle up for a bike ride along one of many Cape Cod Trails, or visit Cape Cod National Seashore to walk the shoreline and admire the views. Warm up at Pairpoint Glass Company’s factory shop, where you can browse heirloom-quality products and watch from above as artisans shape glass on the factory floor. Round out your visit with a trip to Cape Cod Museum of Art, a small museum with revolving exhibitions and a splendid permanent collection.
Where to Eat: Although the Belfry Bistro occupies a converted church, this unconventional restaurant is anything but stuffy. From the beautiful stained-glass windows to the confessional behind the altar—now home to the wine collection—the architectural details are a key part of the quirky-chic vibe. For an intimate, white-tablecloth dinner, make a reservation at Captain Linnell House. The three-course prix fixe menu, available now through June, boasts entrées like grilled Atlantic swordfish and pan-seared breasted duck.
Where to Sleep: See all 3,140+ rentals in Cape Cod!
What to Do: Given Miami’s reputation as an architectural destination, it’s no surprise to find a gem like Vizcaya Museum & Gardens just a few minutes from downtown. Time stands still in this Mediterranean-style mansion, home to 2,500 art objects and ten acres of formal gardens. Afterward, enjoy an Island Queen sightseeing cruise and a performance by the New World Symphony. (Pro-tip: Visit the New World Building’s rooftop garden during intermission for a fantastic view of the Art Deco skyline.)
Where to Eat: You can’t visit Miami without exploring the Design District, and Michael’s Genuine Food & Drink is the place to stop for a bite. With its laid-back atmosphere, outdoor courtyard, and creative comfort food, you’re in for a delicious meal. If the modern vibe at Michael’s isn’t quite your style, try Old Lisbon, a Miami staple known for its traditional open kitchen and gourmet Portuguese menu. One reviewer writes, “I wish I lived in Miami so I could go back and become a regular!”
Where to Sleep: See all 680+ rentals in Miami!
What to Do: One of Newport’s top attractions, the Cliff Walk runs for 3.5 miles along a stunning stretch of coastline. The trail boasts views of the Newport Mansions, once owned by wealthy families including the Astors and Vanderbilts. (Three of the most popular “summer cottages”—The Breakers, Marble House, and The Elms—offer self-guided audio tours during the winter.) Finish the walk and find your zen at Bodhi Spa, modeled after a European bathhouse. You can’t go wrong with a Swedish couples massage or the full hydrotherapy package.
Where to Eat: For fresh seafood cooked just the way you like it, there’s no better place to indulge than at Scales & Shells. The blackboard menu presents items like grilled swordfish and dayboat scallops alongside preparation options. If you love historic homes, you’ll fall head over heels for The White Horse Tavern, one of the oldest tavern buildings in the US. Built in 1673, this cozy spot is one worth fitting into your itinerary.
Where to Sleep: See all 80+ rentals in Newport!
What to Do: Perhaps one of San Antonio’s best-kept secrets, the Japanese Tea Garden feels more like a movie set than a public park with its stone bridges, shady walkways, and 60-foot waterfall. It’s the perfect spot for a quiet morning stroll before heading downtown to the River Walk, which winds through the city center for easy access to museums, shops, and restaurants. Hop on a flat-bottomed boat and catch a ride to the Pearl Brewery District, a revitalized destination located on the site of Pearl Brewing Company. Eat your way through the neighborhood on a walking tour, which stops at four different restaurants over the course of two hours.
Where to Eat: Enjoy brunch on the patio at The Guenther House, located in a beautifully restored home that once belonged to the owner of the adjacent flour mill. Reviewers rave about the biscuits, pancakes, and tortillas, all made on-site from flour ground at the mill. Bliss, a chef-owned spot south of downtown, is making serious waves with its rich flavors and elegant presentation.
Where to Sleep: See all 300+ rentals in San Antonio!
What to Do: Art lovers, serious shoppers, and beer nerds will feel right at home in Portland’s Pearl District, and a brewery bike tour is a fun way to explore downtown and enjoy some fresh brews on the side. Brush up on the city’s past at Pittock Mansion, a historic house museum set 1,000 feet above the city’s skyline, then take in the sunset at Skidmore Bluffs.
Where to Eat: The rooftop bar at Departure Restaurant and Lounge might be one of the most romantic places to sip a cocktail in the entire city. (The incredible small plates and top-notch service at this Asian fusion spot definitely don’t hurt.) For a delicious traditional turkey dinner, visit Huber’s Cafe, the oldest restaurant in the city.
Where to Sleep: See all 450+ rentals in Portland!