Where to Go in September 2025: The Most Beautiful Places to Travel During Shoulder Season
Where to go in September isn’t just a question for the hyper-organized traveler — it’s the holy grail for those in the know. This month sits in the rare sweet spot: after the chaos of summer but before the full swing of fall. The crowds thin, the temperatures mellow, and destinations that felt overrun just weeks earlier return to themselves — quieter, calmer, and somehow more magical. It’s a time when Tuscany tastes richer, the Greek islands breathe deeper, and California sunsets stretch longer. Whether you’re looking for the final golden light of summer, harvest-season culinary escapes, or a sophisticated Mediterranean retreat, these are the destinations that shine the brightest in September. Here are the best places to go in September 2025 — and where to stay when you get there.
Tuscany, Italy – For Wine, Villas, and a Softer Side of Summer
Average Temperature: 27°C high / 17°C low
Season: Late Summer
Italy in July is for the rookies. Tuscany in September is for travelers who know what they’re doing.
The fierce sun has eased just enough to make strolling through Florence or hiking vineyard-covered hills completely pleasurable. Harvest season is beginning — which means fresh figs, grape festivals, and truffle menus that haven’t even hit Instagram yet. Art lovers, wine drinkers, and countryside romantics, this is your moment.
Where to stay: Book a cypress-lined villa with Haute Retreats — full of rustic elegance, private pools, and vineyard views. Villa Busini and Villa Pesa are perennial favorites.
Lisbon, Portugal – For a City Break With Soul
Average Temperature: 26°C high / 17°C low
Season: Early Autumn
Where to go in September if you want both culture and coastline? Lisbon is calling.
September here feels like a sigh of relief. Locals return from the Algarve. The air smells like grilled sardines and sea salt. And the city, with its trams, tiles, and twilight fado music, exudes a kind of melancholy charm that’s best enjoyed in a slower season. Bonus: cultural season is kicking off — from art exhibitions to food festivals.
Where to stay: Think rooftop terraces, restored villas, and walking distance to every miradouro worth photographing.
👉 Browse Villas in Portugal by Haute Retreats
Santorini, Greece – For Fewer Tourists, Same Famous Sunsets
Average Temperature: 26°C high / 20°C low
Season: Autumn
Everyone talks about Santorini in the summer. But the best time to go? September. The light is softer, the crowds have thinned, and the water is still warm enough to lure you in every afternoon.
Expect quieter streets in Oia, easier reservations, and sunsets that still stop you in your tracks. And while the island feels more relaxed, it hasn’t lost an ounce of its postcard-perfect drama.
Where to stay: A cliffside cave villa with a private plunge pool and uninterrupted caldera views — trust us, there’s no better wake-up call.
Provence, France – For Late Harvests and Slower Days
Average Temperature: 26°C high / 15°C low
Season: Early Autumn
Dreaming of where to go in September for sun, style, and soft Provençal romance? Provence is your answer.
Post-summer, the region slows to a languid pace. Village markets brim with late-summer produce. Sunlight filters through vineyards as grapes ripen for harvest. And charming towns like Gordes and Lourmarin finally feel like the villages they were meant to be — serene, sleepy, and bathed in gold.
Where to stay: Haute Retreats offers villas that feel like the pages of a Peter Mayle novel come to life — stone facades, poolside rosé, and kitchens made for making something delicious with those just-picked tomatoes.
👉 Discover Luxury Villas in Provence
Ibiza & Mallorca, Spain – For Sun-Soaked Days and Slower Nights
Average Temperature: 27°C high / 19°C low
Season: Autumn
The White Isle and its Balearic sister are famously buzzy in July and August. But in September, Ibiza and Mallorca hit their stride.
Temperatures are still warm, the water even warmer, and the vibe transitions from peak-party to effortless elegance. Day clubs slow down. Beach restaurants are no longer reservation nightmares. And the coastal villages — think Deià or Santa Gertrudis — are at their most soulful.
Stay here: Choose a luxury villa with sea views, daily breakfast by your private chef, and plenty of space to do absolutely nothing.
👉 Explore Villas in Ibiza & Mallorca
Ibiza Villas by Haute Retreats
Malibu, California
Temperature in September: 30°C high; 19°C low
Season: autumn
Yes, Los Angeles is still hot in September — but Malibu feels just right.
The beaches are quieter post-Labor Day, the Pacific is at its warmest, and the sunsets seem custom-ordered. Hike Solstice Canyon in the morning, sip Syrah in the afternoon at a local vineyard, and wrap your day with a seafood dinner overlooking the water. It’s laid-back luxury at its finest.
Stay here: Forget hotels. A private cliffside home with a pool, outdoor shower, and ocean soundtrack is the only way to do Malibu in style.
Umbria, Italy – For Soulful Italy Without the Crowds
Average Temperature: 26°C high / 15°C low
Season: Early Autumn
When Tuscany feels just a bit too known, Umbria steps forward with a quieter kind of charm. Often called “Italy’s green heart,” Umbria in September is where you go when you want medieval towns without the tour groups, olive oil straight from the press, and slow, deeply satisfying days.
The weather? Still warm. The hills? Rolling and vineyard-draped. The mood? Completely serene. Picture long lunches in Spello, afternoon strolls through Assisi, and hilltop wine tastings in Montefalco. September also brings harvest festivals across the region — from porcini mushrooms to truffles and grapes — all of it celebrated with the kind of low-key joy you’ll remember long after you’ve left.
Where to stay: Think converted monasteries turned luxury villas, complete with stone walls, private chefs, and views that stretch across golden farmland. Haute Retreats has a handful of secluded gems that make you feel like you’re in on Italy’s best-kept secret.
👉 Discover Villas in Umbria by Haute Retreats
Lake Como, Italy – For Glamour, Stillness, and That View
Average Temperature: 25°C high / 15°C low
Season: Late Summer / Early Autumn
Yes, it’s famous. Yes, George Clooney might casually cruise by. And yes, Lake Como in September is just as fabulous as you’re imagining — only without the August madness.
This is where to go in September if you want luxe lakeside living with space to exhale. By now, the crowds have thinned, but the lake is still warm enough for boat days, aperitivi on the dock, and a lazy paddleboard before lunch. Bellagio, Varenna, and Menaggio shine in the late-summer light, their cobbled streets less crowded and more local.
The vibe is ultra-chic, but never rushed. Fashion editors, discreet billionaires, and honeymooners alike quietly float between villas and vintage wooden boats, sipping espresso under wisteria-covered terraces.
Where to stay: This is where Haute Retreats brings its A-game — lakefront villas with private docks, plunge pools overlooking the water, and in-villa chefs serving pasta fresca under the stars.
👉 Explore Lake Como Villas by Haute Retreats
Where to Go in September – The Traveler’s Sweet Spot
The best places to go in September aren’t just about catching good weather — they’re about catching destinations at their most authentic. When locals linger a little longer, service slows down (in a good way), and prices haven’t caught back up to high season levels just yet.
So go now. Go somewhere unexpected. Go somewhere you’ve always wanted to experience without the summer surge.
And if you’re looking for a stay that matches the magic of the destination? Haute Retreats has the keys.
👉 Start Planning Your September Escape
❓ Frequently Asked Questions: Where to Go in September
1. Is September a good time to travel to Europe?
Yes — and for many savvy travelers, it’s the best time. September brings warm weather, fewer tourists, and often lower rates. Destinations like Tuscany, Provence, Santorini, and Lake Como are at their most enjoyable, with outdoor dining, cultural events, and golden light you won’t forget.
2. What are the best warm destinations in September for beach lovers?
If you’re chasing sun and sea without summer crowds, head to Ibiza, Mallorca, Santorini, or Malibu. These destinations still offer swimmable seas, warm temperatures, and a more relaxed, refined energy. Want something tropical? Try Koh Samui, Thailand, or Bali during their dry season.
3. Is September considered high or low season?
September is typically shoulder season — that dreamy sweet spot between high and low. You’ll enjoy better availability, fewer tourists, and more personalized service at luxury resorts and villas. Flights and accommodations may also be more affordable than in July or August.
4. What’s the best way to book a luxury villa for September travel?
We always recommend working with a trusted travel advisor or curated platform like Haute Retreats. Villas book up fast in iconic locations (even in shoulder season), and an experienced concierge team can secure the best properties, handle logistics, and tailor every detail — from private chefs to wine tours and yacht days.
