11 places for the perfect (very) late-summer getaway

Summer is winding down and the kids are heading back to school, it’s true. Yet you shouldn’t let the imminent arrival of Labor Day stop you from dreaming of that last-minute escape. And acting very fast to make it happen.

It’s important to remember that summer isn’t officially over until the end of September. And indeed, those late-summer September weeks (and those in early October) are a fabulous time to score a travel deal, as flights and hotel prices descend from their summer peaks. As long as, that is, you’re flexible about where and when you travel in the coming weeks. Count on some research (the fun part!), set some alerts – then be prepared to book at any moment.

Just setting up a few Google Flights alerts won’t cut it; you’ll need to pull the trigger literally the minute the right price lands in your inbox. I know this from experience: with my mom’s birthday coming up, and her endless, unsubtle hints about wanting to go to Hawai‘i, I monitored flights for two weeks before snagging a sudden $500 deal on Delta. Just days later, the prices went way up.

So when you see the deal you’ve been waiting for, pounce on it. Consider it a way of keeping the spirit of summer 2025 spirit alive and kicking.

1. The Island of Hawai‘i, Hawai‘i, USA

Best for lush vistas and fabulous hotels

While getting to the biggest island of the Hawai‘i archipelago is a haul for even West Coasters, it’s well worth the time in the air. For landing at Kaiulua-Kona airport (book a window seat) is like arriving in another world, as you look out at crystal-clear water juxtaposed with nearly-black volcanic rock against a backdrop of mountains and lush green vegetation. Step off the plane and get in your rental car (you can Uber to your hotel, but you’ll need a car to explore the island) to continue the feeling of being somewhere completely different. No trip to the island is complete without a visit to Hawai’i Volcanoes National Park; if you’re very fortunate, you can see lava spew from Kĩlauea (check the website for the latest bulletins).

It always feels a bit like summer in Hawai’i; temperatures usually hug the mid-80°F range, especially in early September. You’ll find a variety of accommodation options for all budgets – many about 20 minutes from the airport, along the Kohala Coast – though for a true splurge, Four Seasons Resort Hualalai is justifiably and consistently one of the island’s top-rated luxury stays. 

2. Anchorage, Alaska, USA

Best for independent shopping and natural wonders

Enveloped by the extraordinary peaks of the Alaska Range on the northern horizon, the Chugach Mountains on its eastern doorstep and the Gulf of Alaska’s Cook Inlet to the south and west, Anchorage is an American city like no other. While the natural beauty here dazzles, the city’s built environment tends toward strip malls – albeit ones packed with locally owned, independent businesses running on the state’s free-spirited nature.

Explore the city itself for a day or two, getting your fill of crab Benedict (!!) at Snow City Cafe before heading on a cycle tour of the Tony Knowles Coastal Trail. (You can either rent your own bike or book a day tour with Alaska Trail Guides to soak up the scenery at a leisurely pace.) Beyond the city limits, you can book a “flightseeing” tour of Denali, or hop on a train for a delightful ride through the wilderness to this stunning mountain and national park, adding optional overnight stops. Alternatively, if you’re looking to get up close and personal with some sea creatures, head to Seward for an overnight stay and boat tour of Kenai Fjords National Park. 

3. Bozeman, Montana, USA

Best for crowd-free hiking and fly fishing

This mountain town hits a travel sweet spot – and in September and October it really puts on the shine. In this ideal travel window, the days are warm, the evenings crisp and the air blissfully mosquito-free – making for an optimal moment to take to the (crowd-free) trails. Not far from downtown, the College M is an easy hike offering superb views; it’s a daily ritual for many Bozemanites. Anglers (or mere wannabes) will find September the perfect time to book a fly-fishing excursion: the cooler temperatures make the brown trout particularly aggressive, giving you a better chance to snag a trophy. Afterward, grab a craft beer at one of the many area brewpubs; our favorite is Bozeman Brewing. 

4. Austin, Texas, USA

Best for live music and Tex-Mex queso

With airfares to Austin currently less than some people’s fall wardrobe budgets, now might be the perfect time to explore this state capital with a small-town heart. This fast-growing but ever-quirky Texas city draws visitors thanks to its incredible music scene, culinary prowess and whip-smart locals with a sociable streak impossible to resist. September cools things down a bit in Austin, but things remain hot enough to chill at Barton Springs and see the bat colony under Congress Avenue Bridge. And fall is when the music scene in Austin really starts to heat up, with Austin City Limits happening over two weekends in October. If all else fails, you could always taste every queso in town. 

5. Athens, Greece

Best for urban strolls and fewer crowds

Since there’s always something going on in Athens, it would be silly not to take advantage of lower post-summer airfares to the Greek capital. What’s more, September and October in the Greek capital are like gifts from Zeus. Mild temperatures make exploring easy, with summer crowds having waned enough to give you some elbow room at all the famous sights. Things really perk up in Athens in these early-fall months, with locals back from their island vacations and ready to jump into the joys of city life.

While we still recommend booking tickets to top sights in advance (especially the Parthenon), we’d also recommend – heartily – a day to wander slowly through the city. How does a morning at Monastiraki Flea Market, an afternoon wander through the National Garden and a finale of a sunset seen from Fillopappou Hill, sound to you?

6. Rome, Italy

Best for world-famous sights and tourist-free neighborhoods

Flights to Italy never go out of style – and right now they seem to be more reasonable than ever. Connected by air to countless cities around the world, Rome offers a sui generis mix of haunting ruins, awe-inspiring art and vibrant street life – a blend that makes it one of the world’s most romantic and charismatic cities.

While September and October are still considered high season and can bring both high temperatures and hordes of people, you can count on walking just three or four streets away from major tourist attractions to find the crowds disappear, as if by magic. By all means, don’t skip Rome’s world-famous sights. But count on balancing the chaos with visits to quieter neighborhoods (might we suggest Trastevere?) to enjoy an intra-city escape.

7. Vienna, Austria

Best for high culture and romantic walks

Some very-well-priced airfares place this alluring and multi-dimensional European city within reach – and September in Vienna is a wonderful time to experience the city’s fabled culture. While folks are settling back into their routines after summer holidays, there is ample time to relax at one of the city’s centuries-old coffee houses (you can’t go wrong at Prückel), or admire the endless collections of art and artifacts collected by the Habsburgs. 

This is a city that stays with you – and with those you love. On a romantic weekend getaway, you can hold hands while you walk along the Danube and sip wines from urban vineyards (10er Marie is the oldest Heuriger, or wine tavern, in town). Plus, the start of October features the annual Long Night of the Museums, during which popular museums and galleries across the city stay open after dark, as they beckon visitors with music and special treats. 

8. Barcelona, Spain

Best for fall festivals and local flavor

Barcelona is popular – so popular that it makes headline after headline for ranking among the most touristed cities in the world. And for good reason: it’s amazing. But the peak-season crowds are a lot. Which means that when you visit in September, after the summer crowds have returned home, you’ll experience a whole new city. Hotel rates drop, and you’ll find a relaxed atmosphere that lasts until the end of the month. At that point, a party atmosphere picks up in the streets with the approach of La Mercè, a festival honoring the city’s patron saint. 

The temperatures do start dipping a bit come October – but with fewer crowds in the streets and on the beach, this is a great moment to enjoy the sunshine, tour Gaudì’s famous buildings and snack your way through Mercat de la Boqueria.

9. Mexico City, Mexico

Best for savory street food and national celebrations

With spring-like temperatures year round and a constantly churning cultural scene, there’s never a bad time to visit CDMX. But the post-summer-vacation moment, when Mexicans are back from the beach, and the streets buzz once again with students, office workers and shoppers, offers an extra dose of excitement in an always-exciting place.

Arrive without an agenda to stroll Mexico City’s picture-perfect neighborhoods. Get lost in the city’s many bustling markets, gorging yourself on drool-worthy street food along the way. Up your cultural quotient by visiting the city’s stunning museums; the National Anthropology Museum and Museo Frida Kahlo (reserve tickets well ahead) are both musts. And for a truly local (and, well, national) experience, celebrate Mexico’s Independence Day on September 16 by joining the throngs in the Zócalo to watch historical reenactments, a military parade and spectacular fireworks.

10. Seoul, South Korea

Best for indulgent beauty treatments and religious festivals

It always seems too good to be true when the price of flights to Asia drops to within reach. But those current promotions are very real – making right now the right moment to snatch up a last-minute deal to Seoul, South Korea. This sprawling, ultra-modern city remains at the cultural vanguard, with K Pop everywhere, beauty treatments on the cutting edge and architecture that keeps reaching new heights.

You can also join the celebrations for South Korea’s September harvest holiday, Chuseok, paying homage to the gods of earth and grain during the 50-minute procession of Sajik Daeje that winds its way through the capital near Gyeongbokgung station.

11. Mumbai, India

Best for a bucket-list getaway

If a major getaway has been on your list for a while now, pull the trigger and (finally!) book that trip to India. To start in Mumbai is to throw yourself right into the frying pan of this one-of-a-kind, continent-scale country. The city is big. It’s full of dreamers and hard laborers, starlets, gangsters, fisherfolk and millionaires – and lots and lots of other people. Prepare yourself: the energy can be a lot for visitors.

But, man, is this city filled with amazing things to see and do. Take afternoon tea at the Taj Mahal Palace, one of the world’s grandest hotels and a marvel of Indian luxury, and admire the view of the Gateway of India, just next door. Follow the pilgrims to the holy shrine of Haji Ali Dargah, which floats like a mirage in the Arabian Sea just off the coast. And dig into Parsi cuisine in the Fort neighborhood – try the berry pulao (rice) at Brittania & Co. before grabbing some takeaway bread with khamir yeast from Yazdani Bakery.