Trip Ideas grass outdoor sky mountain Nature leaf wilderness ecosystem autumn hill highland rural area tundra field landscape tree fell national park biome canyon meadow escarpment mount scenery temperate broadleaf and mixed forest grassy grassland shrubland ecoregion Farm grass family hillside lush surrounded
Trip Ideas

8 Vacations We’ll Be Taking This Fall

As we bid adieu to another fast and furious summer, we've started to think about all the fabulous trips we'll be taking this fall. Here are 8 enticing getaways on our radar from Vancouver and the Berkshires to Melbourne and Hong Kong.

A Brooklyn-based writer and editor, Chelsea's work has appeared in Matador Network, The Huffington Post, the TripAdvisor blog, and more. When not planning her next trip, you'll usually find her drinking way too much iced coffee (always iced—she’s from New England) or bingeing a Netflix original series.

See recent posts by Chelsea Stuart

Bedroom Hotels Trip Ideas indoor wall room window floor property ceiling Living bed estate Suite home living room hotel real estate condominium interior design Villa nice cottage apartment mansion furniture decorated
Food + Drink Hotels Pool Scenic views Trip Ideas sky outdoor leisure swimming pool walkway estate vacation reflecting pool Resort dock reflection Lake boardwalk park
Exterior Food + Drink Hotels Mountains Trip Ideas building mountain tree grass outdoor Town historic site house neighbourhood estate human settlement residential area Village rural area aerial photography château monastery bird's eye view mansion cityscape old stone Garden
Dining Trip Ideas indoor table floor window ceiling room restaurant estate interior design Resort meal Bar furniture Island area dining room
Dining Patio Scenic views Trip Ideas tree table meal water feature Resort Drink
Trip Ideas tree grass outdoor sky botany Garden plant path woody plant woodland flower botanical garden autumn shrub waterway plantation park lush surrounded

Douro Valley, Portugal

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.

See All Portugal Hotels
Hotels Trip Ideas wall indoor bed room floor property Bedroom home pillow cottage real estate interior design white furniture apartment
Hotels Trip Ideas red indoor bowl food close up macro photography produce dessert Drink glass flower
Trip Ideas building outdoor Architecture facade wood window interior design chapel ancient history place of worship synagogue palace stone
Trip Ideas person indoor girl Beauty lady black hair human darkness long hair scene fun brown hair model
Budget Trip Ideas outdoor ground crowd person people public space City market human settlement group crowded several
Budget Trip Ideas food dish sandwich produce cuisine vegetable half close meat

New York, New York

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).

RELATED: The 10 Best Hotels in New York City

See All New York Hotels
Trip Ideas sky outdoor water reflection City leaf tree cityscape skyline Nature morning Lake River shore bank evening landscape real estate wetland plant dawn reservoir line distance
Trip Ideas tree outdoor water plant leaf waterway Nature autumn woody plant reflection River Canal spring bank landscape maple tree pond recreation branch deciduous leisure maidenhair tree traveling
Trip Ideas table food dish fork meal cuisine produce breakfast vegetable meat soup
Trip Ideas sky water outdoor Sea horizon body of water Ocean cloud calm shore Sunset evening sunrise reflection dusk Coast coastal and oceanic landforms morning dawn Beach wave River afterglow bay landscape dock vacation
Trip Ideas outdoor scene way urban area City metropolitan area sidewalk Town street metropolis infrastructure neighbourhood road Downtown pedestrian sky cityscape building tower block daytime skyscraper lane tree condominium pedestrian crossing facade day
Trip Ideas indoor floor room restaurant interior design estate lighting wood Bar counter meal Design long several dining room

Vancouver, British Columbia

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.

See All Vancouver Hotels
Trip Ideas food plate bowl dish meal produce set different variety several arranged
Hotels Trip Ideas window indoor Living chair room living room property wall interior design home furniture condominium window covering Design wood table seat sofa
Trip Ideas building place of worship altar shrine temple
Trip Ideas color red flower spring event Christmas carnival festival chinese new year colorful plant decorated colored
Trip Ideas building swimming pool property Pool leisure condominium Resort leisure centre estate blue real estate Villa swimming
Trip Ideas color night amusement park carnival Resort festival colorful colored

Hong Kong

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.

See All Hong Kong Hotels
Deck Elegant Exterior Garden Grounds Inn Nature Outdoors Patio Romantic Terrace Trip Ideas grass tree sky outdoor park estate lawn residential area backyard landscape architect yard stone lush
Drink Elegant Inn Romantic Trip Ideas indoor wall furniture room shelf shelving product cabinetry table interior design chest of drawers several
Trip Ideas water tree sky reflection Nature leaf Lake outdoor wilderness autumn River pond reservoir biome mount scenery landscape bank larch temperate broadleaf and mixed forest evening computer wallpaper calm Forest wetland surrounded
Trip Ideas grass outdoor sky mountain Nature leaf wilderness ecosystem autumn hill highland rural area tundra field landscape tree fell national park biome canyon meadow escarpment mount scenery temperate broadleaf and mixed forest grassy grassland shrubland ecoregion Farm grass family hillside lush surrounded
Trip Ideas Nature rock outdoor water Waterfall rocky creek body of water stream wilderness watercourse River water feature rapid Forest wasserfall autumn woodland rainforest
Trip Ideas tree outdoor Nature leaf tower landmark autumn woody plant sky stately home estate City grass plant national trust for places of historic interest or natural beauty campus lawn tourist attraction mansion real estate university Garden building château palace facade landscape house spring spire steeple medieval architecture landscaping old tall place of worship Church government building surrounded

The Berkshires, Massachusetts

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).

RELATED: 8 Great Weekend Getaways in New England

See All Berkshires Hotels
Trip Ideas furniture table chair product design seat wood product
Trip Ideas person photograph standing event brunch fun lunch Drink meal recreation Party ceremony rehearsal dinner taste bridal shower
Trip Ideas plate dish food vegetarian food cuisine recipe soup
Australia Hotels Melbourne Romance Trip Ideas floor property chair City condominium Architecture estate real estate interior design plaza home outdoor structure headquarters apartment window covering furniture area
Trip Ideas person outdoor fun girl human glasses smile event crowd
Trip Ideas person outdoor event Entertainment festival crowd people public event fête recreation computer wallpaper

Melbourne, Australia

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.

See All Melbourne Hotels
Trip Ideas person building outdoor crowd marketplace public space people City market fête tourism block party festival fair recreation
Trip Ideas plate food table meal dish indoor breakfast dessert brunch full breakfast cuisine fried food american food pancake flavor sliced
Trip Ideas building outdoor road transport neighbourhood City urban area Town brick street house Downtown human settlement Architecture residential area facade
Trip Ideas person public space food market local food marketplace produce product preparing
Trip Ideas natural foods produce local food food marketplace market outdoor fruit vegetable public space person vendor greengrocer whole food floristry City plant leaf vegetable selling fresh sale variety
Trip Ideas water sky outdoor skyline skyscraper City cityscape geographical feature horizon metropolitan area landmark human settlement urban area Downtown metropolis tower block reflection dusk Harbor panorama Sea Island

Boston, Massachusetts

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.

RELATED: What to Do in Boston: The Perfect 3-Day Itinerary

See All Boston Hotels
Trip Ideas outdoor sky Town landmark City tourism human settlement flower vacation River waterway Village travel Garden cityscape old stone
Trip Ideas tree outdoor Resort restaurant Village sign area several
Arts + Culture Fall Travel Festivals + Events Offbeat oktoberfest Trip Ideas person table Drink alcohol sense distilled beverage
Offbeat Trip Ideas person crowd people outdoor colorful audience event festival bazaar market fair chinese new year colored auditorium
Trip Ideas tree grass outdoor habitat plant park green woodland autumn leaf season field sunlight grove Forest woody plant deciduous branch maidenhair tree lush wooded
Trip Ideas outdoor sky building skyline cityscape landmark City Boat metropolis urban area Town skyscraper human settlement spire tower cathedral tourism Downtown place of worship panorama tours Church

Munich, Germany

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.

See All Munich Hotels

Want more?



All products are independently selected by our writers and editors. If you buy something through our links, Jetsetter may earn an affiliate commission.