8 Vacations We’ll Be Taking This Fall

Portugal was one of Europe’s undeniable hotspots this summer, but moving into autumn, we’re still riding the Iberian wave in anticipation of Douro Valley’s magnificent foliage. Witness the region’s transition from the Six Senses, a 19th-century manor house (restored in 21st-century style by New York-based firm Clodagh Design) with enviable views of the sun-drenched, vineyard-swept mountainsides and majestic Douro River. When you’re not unwinding with vinho-focused treatments in the spa, go for a tour and tasting at Pinhão’s nearly 1,500-acre Quinta das Carvalhas vineyard.

Full disclosure: yes, NYC is always on our list regardless of season, but we think it earns its perennial status. The end of summer saw the introduction of Smorg Square—a SoHo outpost of Brooklyn-fave Smorgasburg and Brooklyn Flea. Indulge in churro ice cream sammies and wood-fired pizzas on Fridays, Saturdays, and Sundays, but take the 6 uptown to tuck in for the night at the HGU New York Hotel in buzzy Nomad. The glamorous Beaux-Arts boutique secures its own quiet slice of the city on 32nd between Park and Madison Avenues. Dinner is to be had at intimate Restaurant at Rose Hill (we love the Fiji apple salad and wild snapper ceviche), and then it's off to the new rooftop bar which is within spitting distance of the Empire State Building. Looking to feel cultured? Stop by the 55th New York Film Festival for films from Richard Linklater (Last Flag Flying), Todd Haynes (Wonderstuck), and Woody Allen (Wonder Wheel).

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The 2010 winter Olympics effectively established Vancouver as Canada’s cool kid. But the city was quick to prove it’s got staying power as it hasn’t stopped pumping out sidewalk cafes, design-driven boutiques, and indie galleries since. This season, follow cinephiles into town for the Vancouver International Film Festival (that’s VIFF, for short), and drop your bags at The DOUGLAS, a brand new Autograph Collection hotel that’s set to open in September. This year, the two-week fest will screen films from directors Mina Shum (Meditation Park), Todd Haynes (Wonderstruck), and Melanie Wood (Shut Up and Say Something), among others. As for eats, we could rattle off a George R.R. Martin-length list, but we’ll spare you and just go with Cafe Medina, a Mediterranean-style brunch spot that delivers some of the city’s best waffles—think milk chocolate lavender and pistachio rosewater—courtesy of chef Adam Perrier.

HK is no stranger to festivals, but autumn sees more than ever. Plan a trip for September or October, and you’ll basically be able to hit a street fair, parade, or celebratory event every day. First, stow your things at the Cordis, Hong Kong, a plush Kowloon high-rise with a two-Michelin-starred Cantonese restaurant and renowned spa. As for what’s happenin’ fest-wise, there’s the Hungry Ghost Festival—in which festival-goers “feed” restless spirits to their ancestors; the Mid-Autumn Festival—a harvest celebration full of paper lanterns and lion dances; and the Monkey God Festival—an event that observes the revered, mystical monkey god with lots of incense and magic acts.

New England may be all but ignored for three-quarters of the year, but each fall it gets its due recognition as leaf peepers infiltrate every corner of the region’s six tiny states. In western Massachusetts, the Berkshires present a near-perfect bucolic escape with pint-sized hamlets, historic Main Streets, and family farm stands. Check in at Lenox’s Kemble Inn, a Colonial Revival style estate with homey suites (think: wood-burning fireplaces, four-poster beds, and mountain views) and an in-room spa menu. City slickers will want to make time for leisurely hikes through hemlock-forested Bash-Bish Falls, and a trip to Bartlett’s Apple Orchard and Farm Market. The family-run affair offers apple picking, fresh apple cider, and every essential New England baked good one could want (see: cider donuts, apple muffins, tunovers, and more).

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Hipster Melbourne has long held onto its “culture capital of Australia” crown, and this fall, a slew of food, film, art, and heritage festivals speak to why. Drop your things at QT Melbourne, a cutting-edge, industrial-chic boutique—with timber floorboards, naked cement walls, bespoke furnishings, and tongue-in-cheek art— in the heart of the city. Then, draft an agenda that includes Melbourne Fringe—a 35-year-running, multi-artform fest that makes space for diverse expression; the Melbourne Festival—a 17-day international art festival that will be premiering Terrence Malick’s Voyage of Time (three decades in the making) as accompanied by the Melbourne Symphony Orchestra and Chorus; and Taste of Melbourne—an annual, 4-day feast held in Yarra Park.

Boston may not be a “big city” in the eyes of New Yorkers, Chicagoans, and Philadelphians, but that doesn't mean New Englanders will ever stop singing its praises. Come fall, Beantown strikes a perfect balance between quaint and cosmopolitan with brisk temperatures and its own small swaths of foliage (check out the Boston Common and Garden). Make like Tom Brady and Gisele Bundchen and make historic Beacon Hill your home base by checking in at the Beacon Hill Hotel & Bistro. Cobblestone streets, Federal-style brick row houses, and tiny boutique shops make the neighborhood one of Boston’s most picturesque. Brunch at The Paramount (literally 100-feet from the hotel) before heading to the South End’s SoWa Open Market (similar to the Brooklyn Flea) to shop handmade goods from New England artisans. Once you’ve secured some impulse buys and tucked into Boston’s best food trucks, end your afternoon on the Charles River Esplanade. Grab an Adirondack chair on one of the docks for a people watching session, or just enjoy the breeze and Cambridge views across the water.

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This may be somewhat of a given, but Munich’s popularity surges every September as it kicks off its world-renowned, 18-day Oktoberfest which attracts more than 6 million beer lovers and sees nearly 8 million sudsy liters served. More interested in bottles and barrels than steins and kegs? The Bavarian city has that covered too. Wurstmarkt—the world’s largest wine festival—also takes place in September in the spa town of Bad Dürkheim, about a 3-hour drive northwest of Munich. Good news is it can be reached via the Deutsche Weinstrasse, AKA the German wine route, which runs through the Palatinate wine region along the French border. FYI: Chardonnay, Sauvignon Blanc, and sweet Weiß-und Spätburgunde are the area’s best offers, so go for those at dinner.