Extend Your Summer: Where to Travel in September & October
Summer's end needn't mean the end of vacation. With kids back at their desks, early autumn is often the quietest season abroad - ideal for travelers craving a little peace. And while temperatures may be dropping at home, for those hoping to squeeze in a little more beach time, the Mediterranean holds its warmth well past August. Or, if you’re in the camp that can’t wait to break out the sweaters, you can fast forward into full fall during these months as well - this is the time of year when auburn maple groves from Maine to Japan turn entire cities into their most photogenic selves. Harvest festivals take over, with Italy's wine and olive oil season chief among them, while hiking trails and harbors feel far more inviting without the midsummer heat. From warm mornings on turquoise water to breezy evenings with spiced cider among crimson orchards, we've gathered a list of destinations for anyone lucky enough to take advantage of this quietly perfect season.
Mykonos, Greece
FALL HIGHLIGHTS
Harvest Festival
September 13, 2026
Mykonos Running Festival
End of September 2026
Mykonos is more than the 4am dance parties it's known for - it's blue-domed chapels and cobalt shutters, whitewashed lanes and riots of ivy. And as August winds down, so does the crowd that usually overshadows all of it. Champagne spray gives way to salty ocean mist and menus turn toward lighter seafood dressed with fresh figs and pomegranate but the turquoise coves still hold onto the summer's warmth. As September progresses, the island returns to itself, as locals return to the narrow streets, the meltemi winds ease, and evenings turn balmy rather than blustery. There are cool-morning hikes to Ano Mera, catamaran runs out to Rhenia's clear waters, unhurried wanders through the ruins of Delos, and golden hour in Little Venice at its most photogenic. If Mykonos's summer reputation feels a bit too intense, September is its quieter, more delicious rebuttal.
Where to Stay:
Fouquet’s Mykonos
Fouquet’s has arrived on Mykonos and is the belle of the ball. The hotel, which opened this past June, is set on a secluded stretch of the island's rocky coastline. Guests have easy access to the pristine sands of Paraga and Paradise beaches, along with exclusive boat transfers to Scorpios and Nammos for those chasing a livelier scene. Each room and suite is built around sea views, and dressed in cream furnishings with terracotta accents and rustic wooden touches. The resort's refined dining rooms open onto the same panoramic horizon; if you need a retreat from the sun, the cutting-edge Rock Spa offers a slate of soothing treatments, as well as a indoor pool and a basketball court carved directly into the rock. Tempted? The resort closes for the season September 27, so how does this weekend sound?
Milan & Lake Como, Italy
Women’s Spring/Summer 2027 Fashion Week | Milan
September 22-28, 2026
Tremezzina Gastronomica | Lake Como
Beginning early October
September in Milan begins as the city's own private season, unhurried and ideal for wandering beneath the Duomo's spires or through the boutiques of Via Montenapoleone, before Fashion Week arrives late in the month and the whole city shifts into a higher gear, runway energy spilling onto every street corner. By October, that intensity fades into cooler air, quieter piazzas, and a local rhythm built around risotto, truffle season, and long dinners rather than front-row seats. Either version of Italy’s fashion capital is a fitting prelude to Lake Como, an hour north, where autumn settles over the water in soft shades of gold. The crowds that fill Bellagio's docks and Varenna's lakeside cafés all summer thin considerably, leaving ferries half-empty and villa gardens blissfully quiet. Start the day with an espresso on a terrace overlooking the lake as the morning mists dissipate; then, hike into the hills for a view worth the climb. The two make an a perfect pair any time of year, but early fall, when one feels urbane and electric, and the other still and golden, it’s proof that Lombardy's best season might not be summer at all, but the weeks that follow.
Where to Stay:
Mandarin Oriental, Milan &
Mandarin Oriental, Lago di Como
Mandarin Oriental, Milan sits a few steps from the Duomo and La Scala, whose season kicks off in September. With its lush courtyards and elegant Italian design, it is an ideal base for a few days of Fashion Week energy and al fresco dining. Interiors are warm, with tailored, art-filled rooms built for a city with serious design bonafides. Then, an hour north, Mandarin Oriental, Lago di Como unfolds across Villa Roccabruna, an eighteenth-century estate once restored by the opera singer Giuditta Pasta into a neoclassical manor, its gardens tumbling down toward the water. Over nine buildings, the resort's 75 rooms, suites, and two private villas are anchored by a floating pool with jacuzzis set right into the lake. Plus, there are perks to combining the two into a perfect getaway.
Douro Valley, Portugal
Festa das Vindimas - Lamego
September 11 - 13, 2026
Douro Harvest Experiences
September 10 - October 5, 2026
Portugal’s Douro Valley offers spectacular views year-round, but photos taken here in the fall have a way of convincing friends and family you've been dropped into a postcard. UNESCO named the Alto Douro Wine Region a World Heritage Site back in 2001, citing the nearly 25,000 hectares of terraced slopes shaped by the Douro River and its tributaries. Early autumn brings perfect temperatures; it is also harvest season, when the valley's star red grapes Touriga Nacional and Touriga Franca, along with Tinta Roriz and Tinta Barroca, are picked and pressed into celebrated wines, including ruby, tawny, and vintage Ports, plus the increasingly acclaimed Douro DOC reds and whites. We recommend pairing a glass with seasonal staples like roasted chestnuts, hearty stews, slow-roasted lamb, and local olive oil. In between tastings, enjoy a private charter along the Douro River, cool breeze at your back, or take the historic rail line out of Peso da Régua to Pinhão, where the station's azulejo tiles depict the valley's winemaking history in full. Douro casts its spell in every season, cool months included.
Where to Stay:
Six Senses Douro Valley
A restored 19th-century manor overlooking the valley, the 19 acres of vibrant vineyards that comprise Six Senses Douro Valley are hard to beat. The hotel’s suites are minimalist in design, with earthy tones, stone walls, and warm wooden accents, and they’re all offset by panoramic views of the surrounding estate. Before it became a resort, the Six Senses was a working wine estate, which explains why its cellar and seasonal dining have earned such acclaim. With a spa spanning eleven treatment rooms and experiences ranging from forest treks to cooking classes (complemented by wine, of course), we’re tempted to order another bottle - and stay another night or two.
Kennebunkport, Maine
Kennebunk Artisans Marketplace
September 12, 19, & 26, 2026
Holiday Trolleys
September 25 & October 23, 2026
HarvestFest
October 19, 2026
Maine is having a moment. The Northeast’s casual and breezily chic aesthetic is at its most photogenic here, and as fall approaches, things only get more idyllic. Autumn colors typically peak between mid- and late October, but until then, it’s sweatshirt and shorts weather, with warm afternoons and crisp evenings. When we want to feel like we’re living in a Nancy Meyers movie, our pick is Kennebunkport - a charming small town where, once summer winds down, so do the crowds. Scents of apple and pumpkin drift through Dock Square, the brick-lined shopping and dining hub, but freshly caught lobster remains the main draw along the shore, pulled straight from the harbor at Cape Porpoise. Early October brings the Kennebunk Harvest Fest, with its costume parade, craft fair, and pumpkin decorating downtown, while nearby orchards like Spiller Farm and McDougal Orchard open their fields for apple and pumpkin picking.
Where to Stay:
White Barn Inn
There's a reason this shingled sanctuary has held court on the Maine coast for over 150 years: White Barn Inn does New England hospitality like nowhere else. Decor is classic with a wink - plaid throw blankets and wicker chairs flirt with animal print details, offset by framed mallards and marble. Come fall, when foliage blankets Kennebunk in amber and rust, the whole place slows down, a pace perfect for a morning beach ride on one of the property’s electric bikes, and an afternoon river stone massage at the spa. The season peaks with Oktoberfest Weekend, kicked off by the annual Lowering of the Pumpkin. Our favorite place to stay is one of the new houseboats - Cora, Nettie, Grace, and Ivory - which float alongside the resort’s dock and each have their own private roof deck. Book midweek for the same golden light with even fewer crowds.
Kyoto, Japan
Seiryū‑e (Blue Dragon Festival)
September 15, 2026
Jidai Matsuri Festival
October 22, 2026 (day)
Kurama Fire Festival
October 22, 2026 (night)
Though it’s Japan’s cultural gem year-round, Kyoto bursts into color each fall. Known as the aesthetic and spiritual heart of Japan, the city retains an extraordinary share of the country's pre-modern temples, shrines, gardens, and traditional architecture. It’s home to over 1,600 Buddhist temples and 400 Shinto shrines, with the Golden Pavilion (Kinkaku-ji) and the wooden temple of Kiyomizu-dera topping must-visit lists. Autumn is the ideal season to visit, thanks to momiji - the term for Japan's fall foliage, which literally means "red leaves" - when maple trees bordering each temple and on every scenic corner burst into deep reds and burnt oranges as though on cue. Peak color tends to arrive later in the season (think mid-to-late November), but each month here has its own appeal. September, still warm, is quietest, making for peaceful, unhurried temple visits. By October, the air turns crisp, the first warm hues begin creeping in, and it becomes prime season for kaiseki dining and matcha tastings. November brings the most dramatic foliage of all, but really, any stretch of weeks just after summer offers Kyoto at its best. We’re already dreaming of an evening stroll through Gion, its lantern-lit streets glowing in the autumn dusk.
Where to Stay:
Capella Kyoto
Capella Kyoto opened in March of 2026 in the historic Miyagawa-chō district, just steps from the city's Zen temples and geiko and maiko theaters. The four-story hotel holds 89 spacious rooms and suites arranged around a tranquil bamboo courtyard and pond, drawing on classic Kyoto townhouse architecture. Inside, calming design, Japanese artwork, and refined textures create a holistic, soothing atmosphere that has earned universal raves from every Local Foreigner guests lucky enough to visit. Guests can unwind in private onsens, take in immersive cultural experiences, visit the signature spa, or settle into refined dining - this is a hotel built for travelers who want to move through Kyoto with intention.
Istanbul, Türkiye
Istanbul Coffee Festival
September 10 - 13, 2026
Akbank Jazz Festival
September 26 - October 11, 2026
Republic Day
October 29, 2026
Istanbul is split by the Bosphorus Strait, with one foot planted in the ancient world and the other in the modern one. The city's storied sights, including the Hagia Sophia, the Blue Mosque, Topkapi Palace, and the labyrinthine Grand Bazaar, date back thousands of years, but Istanbul is just as defined these days by its art scene and the bohemian corners of historic neighborhoods. In Karaköy, the Renzo Piano–designed Istanbul Modern anchors a growing cluster of galleries, while nearby Balat's rainbow houses and umbrella-lined stairways draw photographers to its historic narrow alleyways. Across the water on the Asian side, Kadıköy attracts artists and night owls to enjoy vintage stalls, waterfront buskers, and the easy, unhurried pace. Early September is still warm enough for a dip in the Bosphorus or a swim off the Princes' Islands, but by October, a soft autumn haze settles over the city and the crowds thin considerably; queues at Hagia Sophia and Topkapi shrink, and temperatures cool. Whether you choose to explore on foot, by car, or by boat, Istanbul's architecture rewards being seen from every angle. Lovers of history, culture, and shopping will find themselves entirely in their element here, and a fall visit only sharpens the city's charm.
Where to Stay:
The Peninsula Istanbul
Housed within a cluster of restored early-20th-century maritime buildings on the Bosphorus waterfront in Karaköy, The Peninsula Istanbul pairs that history with interiors by acclaimed designer Zeynep Fadıllıoğlu, threading early Turkish detail across its 177 rooms and suites, many opening onto sweeping water views. Dining spans two registers: The Lobby, with its soaring ceilings and garden terrace, is perfect for afternoon tea and Sunday brunch, and the rooftop GALLADA, where two-Michelin-starred chef Fatih Tutak serves Turk-Asian cuisine beside the nautical Topside Bar. For getting out onto the water itself, the hotel's private 16-metre motor yacht, PEN 1, offers custom charters along the Bosphorus, while the Peninsula Spa and Wellness Centre rounds things out with eight treatment rooms and traditional hammams. Sultanahmet's landmarks sit a short tram ride away, but most guests leave talking about one thing above all: the exemplary service, polished since the hotel's 2023 opening.
