Fall’s Most Romantic Destinations (And What to Pack for Each)

In autumn, most of the summer crowds have dissipated and flights are generally more affordable, making it the perfect time to take a romantic getaway.

Every swoon-worthy travel destination needs a set of romantic getups to go with it. If you're the kind of person who waits until the last minute to pack, Trunk Club should be your wardrobe go-to. With both online and in-person styling services, it's never been easier to curate your look and wow your partner in the process. Here are seven destinations—and outfits—on our radar this season.

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Berkshires outfit collage

The Berkshires, Massachusetts

When it comes to a quintessential romantic getaway, the Berkshires have it all, from stunning fall foliage to bountiful apple picking and iconic art galleries like the Norman Rockwell Museum. Ladies, slide on some comfortable mules for a drive down the area's winding mountain roads and be sure to pack some effortlessly cool wide-leg trousers—they'll take you seamlessly from outdoor exploration to indoor relaxation. For men, short-sleeved henleys layer well under denim or field jackets. Plus, they're perfect for nailing that ruggedly handsome look that’s oh-so-perfect for a Massachusetts fall.

Book Hotels in the Berkshires
portofino outfit collage

Portofino, Italy

Cheerful pastel homes and a relaxed coastal vibe make this Italian resort town a dreamy seaside getaway for Europe-bound couples. Ladies, it's time to flaunt your most stylish swimsuit—try a chic one-piece in a fun print—and break out your espadrilles, so you can easily sidle up to the bar for a post-swim limoncello. Men, opt for swim trunks in an unexpected pattern (and don't forget to bring a collared shirt—Italians are known for their impeccable style, after all).

Book Hotels in Portofino
Prague outfit collage

Prague, Czech Republic

As the historical capital of Bohemia, Prague is romantic at any time of the year. During the fall, however, when summer's typical throng of tourists have long gone, you’ll have ample room to take in the city's many fairytale-like Baroque and Gothic buildings. Colder temperatures tend to set in around mid-October, so ladies should be sure to bring layers like a leather jacket or textured button-downs in materials like denim or chambray. For men, smart jackets, dark denim, and leather boots provide warmth but still keep you looking sharp.

Book Hotels in Prague
Tofino outfit collage, what to wear in tofino

Tofino, British Columbia

Situated on the edge of Canada’s west coast, Tofino is a small surfing town with vast beaches, old-growth forests, and incredible seafood. Autumn is an especially magical time to visit: the beginning of storm-watching season means high winds and crashing waves—the perfect excuse for cuddling up inside with that special someone. Make sure to pack warm layers like knitted sweaters and light, waterproof jackets. If you're a bit more on the adventurous side and eager to venture out onto the beaches, brightly-colored rain boots are a must, and a quilted jacket keeps you warm while still looking Pacific Northwest-chic.

Book Hotels in British Columbia
joshua tree outfit collage, what to wear in joshua tree

Joshua Tree National Park, California

The desert has some of the best sunsets around, and Joshua Tree National Park, where the Colorado Desert meets the Mojave, is no exception. Late fall is a fantastic time to visit, when the season's soft light illuminates the vast landscape and rock formations. Plan a stay at one of the many homesteader cabins situated in the middle of the desert and hunker down with your romantic partner. The weather begins to cool down by October, so for men, breathable layers like cotton and linen are ideal. For women, a patterned dress paired with a denim jacket or light sweater is romantic and ranch-ready.

Book Hotels in Nearby Palm Springs
aix en provence outfit collage, what to wear in provence

Aix-en-Provence, France

The south of France is a magical place come fall. Not only are the open-air markets brimming with fresh herbs, fruits, and vegetables, but it's also the height of wine harvest season—what more could you ask for on a romantic getaway? Because the weather in this part of the world is still delightfully warm, you'll find plenty of locals and visitors hanging out in the vineyards or at sidewalk cafés. Ladies, you'll feel right at home relaxing in a printed dress; pair it with a straw bag and you're set to sip wine and collect fallen fruit in style. For men, short-sleeved button-downs in stripes or muted colors and light khaki trousers achieve a certain je ne sais quoi.

Book Hotels in Aix-en-Provence
savannah outfit collage, what to wear in savannah

Savannah, Georgia

If a warm, southern autumn is what you're dreaming of, look no further than Savannah. Aside from its beautiful willow trees and historic landmarks, Savannah is known as one of the most haunted places in the United States—and what better excuse is there to get close to your partner than on a ghost tour? Whether you're here to ghost-hunt or attend a free outdoor concert, women should pack accordingly with simple-but-stylish pieces like chic white blouses, flowing midi skirts, and elegant leather loafers. A plaid sport coat and colored trousers is perfect for the fellas (and will make those mint juleps look right at home in your hand).

Book Hotels in Savannah

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