Trip Ideas

The Best Places to Travel This September

Crisp autumn air, leaves crunching underfoot, and festivals aplenty—September is the perfect time to plan a fall getaway. Whether you're seeking cultural cachet, excellent restaurant scenes, or outdoor adventures (or all three), these nine destinations check all the boxes.

An avid Italophile, Laura is always on the hunt for the next great travel trends, luxury hotels, best places to eat and drink, and hidden gems. Her writing has appeared in dozens of publications. She also co-wrote "New York: Hidden Bars and Restaurants," an award-winning guide to the city's speakeasy scene.

See recent posts by Laura Itzkowitz

Girl & The Goat, Chicago
Queen bedroom at the Chicago Athletic Association
Suite bedroom at Chicago Athletic Association
Living room in a suite at the Chicago Athletic Association
Bridge in Lincoln Park Neighborhood of Chicago

Chicago, IL

Aside from pleasant weather, there are plenty of reasons to visit Chicago in September. This month welcomes the city’s major art fair, EXPO Chicago, which draws legions of artists and collectors to the historic Navy Pier. The Windy City’s food scene is also hotter than ever, with new must-visits like the breezy, California-inspired Pacific Standard Time; chef CJ Jacobson’s trendy Israeli restaurant Aba at Fulton Market; and the upscale Bellemore (which has been conquering Instagram with its decadent caviar-topped oyster pie) joining dependable favorites like award-winning chef Stephanie Izard’s Girl & the Goat. The Peninsula Chicago, with its classy rooftop Z Bar, is EXPO Chicago’s official hotel partner, but there are plenty of other great places to stay, too, like the gorgeous Chicago Athletic Association Hotel—home to one of the best rooftop bars in the country. We’re also digging the St. Jane Hotel in the Art Deco-era Carbide & Carbon building, whose moody interiors (black walls, herringbone stone floors, gold fixtures) nod to its Jazz Age roots.

Marina Bay Sands Hotel
Marina Bay Sands Hotel


The runaway success of Crazy Rich Asians, which hit number one at the box office following its blockbuster debut, has thrown Singapore into the limelight. There’s plenty to love about this dynamic city-state, from its over-the-top hotels (we’re looking at you, Marina Bay Sands, with your gravity-defying 57th-floor infinity pool) to its incredible food scene. You could easily spend a week eating your way through the city's hawker stalls and upscale restaurants like Violet Oon, exploring the diverse neighborhoods of Chinatown and Little India, and shopping at the boutiques on Haji Lane. The iconic Raffles Singapore just remerged from a sweeping renovation; for something a little less classic, check out the industrial-chic Warehouse Hotel on the banks of the Singapore River.

RELATED: Live Like "Crazy Rich Asians" in Singapore at These 7 Real-Life Film Locations

Ischia Island, Italy
Monastero Santa Rosa Hotel, Amalfi Coast
Monastero Santa Rosa Hotel, Amalfi Coast
Monastero Santa Rosa Hotel, Amalfi Coast

Amalfi Coast & Ischia, Italy

Italy’s glittering Amalfi Coast is typically cast as a summer destination, but if you want to avoid the crowds and enjoy lower airfares and hotel rates, fall is the best time to go. In September, it’ll still be warm enough to swim in the Mediterranean and hang out at the area's famous beaches. With the money you'll save on flights, might we suggest splurging on a room at Le Sirenuse in Positano, Palazzo Avino in Ravello, or the Santa Caterina in Amalfi? All three are members of Leading Hotels of the World and bookable via its Leaders Club loyalty program, which offers the chance to earn complimentary nights, room upgrades, and more. You can also catch the ferry to Ischia (where HBO filmed its TV adaptation of Elena Ferrante’s bestselling Neapolitan Novels) and explore the island by boat or vespa.

See All Hotels on Italy's Amalfi Coast
The Siren Hotel, Detroit
The Siren Hotel, Detroit
The Siren Hotel, Detroit

Images Courtesy of Christian Harder

Detroit Institute of Arts
Skyline view of Detroit

Detroit, MI

All September long, the Motor City will be celebrating Detroit’s Month of Design with a series of events including the popular Market After Dark, which is expected to draw 20,000 people to Eastern Market to see murals, hear music in the streets, and eat great food. If you’ve been curious to experience Detroit’s comeback, this is the time to go. Check into the beautiful Siren Hotel, which features an eight-seat tasting menu counter by award-winning chef Garrett Lipar in addition to a bubblegum-pink Candy Bar, Populace Coffee Roasters in the lobby, and a restaurant by acclaimed chef Kate Williams. Before you leave town, be sure to visit the Detroit Institute of Arts to see Diego Rivera’s monumental murals and stroll the Belt, a public alley covered in street art.

RELATED: A Local's Guide to Detroit with Gallery Co-Founder Anthony Curis

The "Old Town" in Aarhus
Aarhus in Denmark
Aarhus, Denmark

Aarhus, Denmark

Danes are known for making the most of the good weather when they have it, so fall is a fantastic time of year to visit. Though Copenhagen usually steals the spotlight, Aarhus has been gaining recognition since it was named the 2017 European Capital of Culture. For a small city, it punches above its weight in cool things to do. Be sure to visit the ARoS art museum to see Olafur Eliasson’s extremely ‘grammable Rainbow Panorama and installations by Portuguese artist Joana Vasconcelos, American photographer Robert Mapplethorpe, and other leading artists. From August 30 until September 8, the annual ten-day Aarhus Festival will celebrate art, culture, and music with more than 1,000 events, while the Food Festival (which claims to be the “biggest food festival in Northern Europe”) will host tastings and workshops with a focus on Nordic cuisine.

Book Hotels in Aarhus
Faena Hotel, Buenos Aires
Faena Hotel, Buenos Aires

Buenos Aires, Argentina

The Argentine capital’s reputation as South America’s most important art city was cemented last year when Art Basel launched its Cities program, a week-long event curated by artistic director Cecilia Alemani (who previously brought her expertise to New York's High Line and the Italy pavilion at the Venice Biennale) and included work by world-renowned talents like Italian sculptor Maurizio Cattelan and American mixed-media artist David Horvitz. Although the event is taking place in Miami Beach in 2019, a visit to Buenos Aires proper is a must. Our favorite place to stay is the Faena Hotel, which ushered in Puerto Madero’s renaissance with its theatrical design by Philippe Starck, excellent restaurants, and the best tango show in the city. Buenos Aires is also known for its incredible shopping—head to the vintage markets in San Telmo for unique finds and hit up the indie boutiques in Palermo to discover emerging Argentine designers.


Tivoli Avenida Liberdade
Tivoli Avenida Liberdade
Tivoli Avenida Liberdade

Lisbon, Portugal

Is there ever a bad time to visit Lisbon? We think not—but September is especially great. The city starts to cool off after the hot summer and music festivals like LISB-ON and Nova Batida heat up the party scene. Check into the luxurious Tivoli Avenida Liberdade, which debuted an Eastern-influenced Anantara Spa after a multi-million-dollar renovation; the hotel is the perfect base for exploring the vibrant Chiado neighborhood, which is full of boutiques like A Vida Portuguesa and Livraria Bertrand, the world’s oldest bookstore. Combine Lisbon with a trip to nearby Sintra, a fairytale village where Portuguese royalty built their castles. You can even stay overnight in one of them at the Tivoli Palácio de Seteais, which is housed in a UNESCO-listed 18th-century fortress complete with manicured gardens and frescoed guest rooms.

RELATED: Lisbon for Food Lovers

Four Seasons Vancouver
Four Seasons Vancouver

Vancouver, British Columbia

Vancouver is often hailed as one of the world’s most livable cities. Nature buffs will love exploring Grouse Mountain, Vancouver Harbor, and Stanley Park, a 1,000-acre park surrounded by water on three sides that’s home to the seawall—the world’s longest uninterrupted waterfront pathway. There’s plenty for culture vultures to do, too. This September, the Westward Music Festival will animate several downtown music venues with performances by over 100 artists, while the Vancouver International Film Festival is set to kick off on September 26 with an exciting roster of screenings and events spotlighting Canadian filmmakers. Check into the luxurious Four Seasons Vancouver overlooking the skyline and take advantage of the indoor-outdoor pool.

Great Barrington, MA - October 17, 2016: Traditional Brick Buildings with Colourful Shops and Restaurants along Railroad Street. Great Barrington, located within the valley of the Housatonic River, is both a summer resort and home to Ski Butternut.
Traditional American White Church with a high Steeple in Williamstown, MA, on a Clear Autumn Day
Autumn fog in the village of Tyringham in the Berkshires region of Massachusetts

The Berkshires, MA

Ready to savor some crisp mountain air and feel autumn's leaves crunching underfoot? Plan a getaway to the Berkshires in western Massachusetts, home to the highest mountains in the state. Long a destination for artists and writers like Edith Wharton (whose mansion you can visit) and Norman Rockwell (who has a dedicated museum in the area), the Berkshires is as much a cultural destination as it is a beautiful one. MASS MoCA, a contemporary art museum set in an industrial mill complex in North Adams, has nearly doubled its size over the last few years and added new long-term installations by the likes of James Turell and Jenny Holzer. Rest your head at TOURISTS, a minimalist boutique hotel in a revamped motor lodge that’s become the area's new creative hangout.

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