10 Trending Destinations to Put on Your Fall Travel List

Highlights at a Glance

• One US mountain town saw a 92% jump in searches on Expedia

• A Portuguese island was named Tripadvisor’s #1 trending destination for 2026

• One Japanese island is seeing a 71% surge in Expedia searches

• One Mediterranean island saw Expedia searches jump 63%

• One colorful city was named the #1 city in the world by Travel + Leisure readers

• Several warm-weather favorites get noticeably quieter once summer ends

• Fall brings everything from grape harvests and foliage to beaches and Día de los Muertos celebrations

1. Madeira, Portugal

Madeira has officially gone from under-the-radar island escape to one of the biggest destinations of 2026. Tripadvisor ranked the Portuguese archipelago #1 on its global Trending Destinations list, and with volcanic cliffs, waterfalls, natural pools, mountain trails, and dramatic coastline packed onto one island, it is pretty easy to see why.

Fall is a particularly nice time to visit. September and October still bring plenty of pleasant days, but with fewer visitors than the summer months. Fly into Funchal Airport (FNC) and consider renting a car if you want to explore beyond the capital.

Hikers should plan ahead. As of 2026, Madeira’s classified walking trails require advance timed reservations, and the general visitor fee is €4.50 (or $5.25).

2. Big Sky

Apparently, the secret is officially out on Big Sky. Searches for the Montana mountain town jumped 92%, the biggest increase on Expedia’s 2026 Destinations of the Year list.

Fall brings a much quieter version of this famous ski destination. The aspens turn gold, summer crowds thin out, and hiking, wildlife watching, scenic drives, and trips toward nearby Yellowstone are still on the table. September in particular is one of the area’s sweet spots before winter settles in.

Fly into Bozeman Yellowstone International Airport (BZN) and drive south to Big Sky.

3. Tbilisi, Georgia

Tbilisi feels like one of those cities everyone suddenly starts talking about at once. Georgia’s capital landed at #2 on Tripadvisor’s global Trending Destinations list, with its colorful Old Town, sulfur baths, food scene, and centuries-old wine culture giving travelers plenty of reasons to take notice.

Fall adds another reason to go. Georgia’s traditional Rtveli grape harvest begins in September, with the famous wine region of Kakheti kicking off the season before harvests continue across the country.

There are no nonstop flights from the US, so expect a connection, but once you arrive, Tbilisi makes an easy jumping-off point for exploring more of Georgia.

4. Sardinia, Italy

If you love the idea of an Italian beach vacation but not the idea of fighting peak-summer crowds for every inch of sand, Sardinia deserves a look. Expedia saw searches for the Mediterranean island jump 63%.

Fall arrives late here. Temperatures can stay pleasantly warm, particularly in early fall, and the sea holds onto much of its summer heat. By October, the biggest crowds have disappeared, making it a great time to explore both the coast and the island’s quieter inland towns.

Fly into Cagliari (CAG) for the south or Olbia (OLB) for the northeast.

5. Chicago

One of the world’s hottest destinations for 2026 happens to be right here in the US. Chicago ranked #3 on Tripadvisor’s global Trending Destinations list.

The timing is especially fun because Route 66 turns 100 in 2026, and Chicago is where the legendary road trip officially begins, so there is a little extra reason to visit this year. Fall is already one of the city’s best seasons, with crisp weather, colorful trees, and fewer summer crowds. Add in the lakefront, incredible museums, iconic architecture, and one of the best food scenes in the country, and Chicago makes a pretty convincing fall getaway

6. Milan

Milan is having a moment of its own in 2026, landing at #6 on Tripadvisor’s global Trending Destinations list. Between its fashion scene, striking architecture, world-class museums, and some of Italy’s best people-watching, it makes an easy fall city break.

Autumn suits Milan especially well. October can still be mild, while parks like Parco Sempione begin turning gold and the city settles into peak café, aperitivo, and hearty northern Italian food season.

Fly into Milan Malpensa (MXP), Linate (LIN), or Bergamo (BGY) depending on your route and fare.

7. Okinawa

Tokyo and Kyoto may get most of the attention, but travelers are increasingly heading much farther south. Expedia searches for Okinawa jumped 71%, making it one of the biggest movers on its 2026 list.

This is a very different side of Japan, with turquoise water, coral reefs, beaches, historic Ryukyu sites, and a culture distinct from the mainland. October averages around 79°F during the day, and many beaches remain open for swimming.

One thing to keep in mind: typhoons can still occur in October, so keep an eye on the forecast if you are planning a beach-heavy trip.

8. The Peloponnese

If Santorini and Mykonos feel a little too obvious, head south from Athens instead.

Condé Nast Traveler included the Peloponnese among its Best Places to Go in Europe in 2026, highlighting everything from its ancient history to its growing trail network and connections to Christopher Nolan’s The Odyssey.

Think ancient ruins, seaside towns, mountain villages, sandy beaches, and the rugged Mani Peninsula. Fall gives you a chance to explore after the crush of peak summer, making this an especially good pick for a road trip.

Fly into Athens (ATH), rent a car, and head south.

9. San Miguel de Allende

San Miguel de Allende is one of those cities that looks almost unfairly pretty in photos, and apparently travelers agree.

Expedia saw searches rise 30%, while Travel + Leisure readers named San Miguel de Allende the #1 city in the world in the 2026 World’s Best Awards.

Fall is one of the most atmospheric times to visit, especially as October gives way to Día de los Muertos celebrations. Expect cobblestone streets, colorful architecture, rooftop restaurants, galleries, and plenty of reasons to wander without much of an agenda.

Fly into Guanajuato International Airport (BJX) or Querétaro International Airport (QRO).

10. The Cotswolds

Sometimes the trip you need is less sightseeing marathon and more stone cottage, country walk, and pub fireplace.

Expedia searches for the Cotswolds jumped 39%, putting the English countryside favorite firmly on its list of destinations having a moment in 2026.

Fall may also be the region at its coziest. Expect changing leaves, honey-colored villages, cooler walking weather, and plenty of excuses to stop for a long pub lunch. Popular stops include Broadway, Stow-on-the-Wold, Bourton-on-the-Water, and Bibury, but half the fun is simply seeing what you find along the way.

Where Will Everyone Be Traveling This Fall?

If these travel trends tell us anything, it’s that people are still dreaming about places like Italy, Japan, Greece, Mexico, and the UK, but they’re looking a little beyond the usual favorites.

Instead of Amalfi, there’s Sardinia. Instead of Tokyo, there’s Okinawa. Instead of Santorini, there’s the Peloponnese. And fall might be the perfect time to see them, when the biggest summer crowds have cleared out but the weather is still working in your favor.

So if one of these places has been sitting on your travel wish list, this could be the season to finally make it happen.

Frequently Asked Questions: Fall Travel in 2026

What are the best fall travel destinations in 2026?

Some of the biggest trending destinations for fall 2026 include Madeira, Big Sky, Tbilisi, Sardinia, Chicago, Milan, Okinawa, the Peloponnese, San Miguel de Allende, and the Cotswolds. The list includes everything from warm-weather islands and European city breaks to mountain escapes and fall road trips.

Where is the best place to travel in October 2026?

It depends on the kind of trip you want. Madeira and Sardinia are good picks for lingering warm weather, Milan and Tbilisi are ideal for a fall city break, Big Sky brings mountain scenery and foliage, and San Miguel de Allende begins gearing up for Día de los Muertos celebrations toward the end of the month.

Where is warm in October for a fall vacation?

Madeira, Sardinia, Okinawa, and parts of the Peloponnese can all stay pleasantly warm into October. Okinawa can still have beach weather, while Madeira and Sardinia are particularly appealing if you want sunshine without peak-summer crowds.

What are the best fall destinations in the US?

Big Sky, Montana and Chicago are two trending US destinations to consider in 2026. Big Sky is best for mountain scenery, hiking, wildlife, and fall foliage, while Chicago offers a classic city break with cooler temperatures, lakefront views, museums, and Route 66 centennial events.

What are the best places to visit in Europe in the fall?

Madeira, Sardinia, Milan, the Peloponnese, and the Cotswolds all work particularly well for fall travel. Travelers can choose between Mediterranean warmth, Italian city breaks, Greek road trips, Portuguese hiking, and cozy English countryside escapes.

What are the best fall beach destinations in 2026?

Sardinia and Okinawa are two of the strongest beach options on this list. Sardinia holds onto much of its summer warmth into early fall, while many Okinawa beaches remain open for swimming in October. Typhoons are still possible in Okinawa at that time of year, so travelers should keep an eye on the forecast.

Where should I go for fall foliage in 2026?

Big Sky is one of the strongest choices on this list for traditional fall color, with golden aspens appearing around the Montana mountains. The Cotswolds also make a beautiful autumn escape, with changing leaves surrounding its villages, walking trails, and countryside.