TRAVEL INSPIRATION
Best Places to Visit in the Fall in 2026
By The Kensington Content Team
TRAVEL INSPIRATION
By The Kensington Content Team
The summer crowds have thinned, the air is crisp and fresh, leaves change to bold reds and golds, and the world seems to slow down—inviting you to savor the moment. Whether you’re chasing peak foliage, more intimate, authentic moments away from the crowds, or a bucket list experience, the best places to visit in the fall are waiting for you.
Kensington crafts personalized journeys that turn seasonal travel into something extraordinary. Our team of Destination Experts know their regions inside and out, and tailors your fall adventure perfectly to the places, experiences, and meals you’re dreaming of.
Are you ready for your fall getaway? We’ve rounded up some of the best places to visit in the fall as a starting point to tailor a trip to your specific dreams. Let the season inspire you.
Amanda Wells' love of travel started when she grabbed her backpack and a one-way ticket. What was supposed to be a six-month solo trip after graduation turned into a three-year adventure across Australia, Southeast Asia, and Thailand. “I was absolutely amazed at the kindness of other people, how they wanted to learn about you, your culture and your country. And they wanted to teach you about theirs as well. That's what made me fall in love with travel.”
Today, Amanda works as Kensington’s Director of Product – Europe, drawing on her deep local knowledge to go far beyond the guidebooks. Her passion lies in uncovering hidden gems and designing experiences that feel personal, meaningful, and just a little unexpected.
“I think travel is my love language,” she says. “It brings joy at every stage: dreaming, doing, remembering.” Having explored all seven continents, Amanda brings a truly global perspective to every itinerary she helps shape, ensuring each trip is as enriching as it is unforgettable.
Amanda is ready to take you to the best places to visit in fall, “The weather is crisp and sunny, there are fewer crowds, and you get to enjoy things with a bit more space.”
This self-guided adventure through Western Canada is designed for travelers who crave wide-open roads, iconic landscapes, and the flexibility to explore the best places to visit in the fall on their own terms.
“This is the classic Canadian road trip,” says Amanda. “It hits all of the key highlights in Western Canada and does a really beautiful job of blending independent travel with guided experiences.”
Starting in Calgary, you’ll make your way through Banff, Jasper, and Lake Louise, each destination a showstopper in its own right. “Lake Louise is still unmatched as one of the most beautiful places I’ve ever been in the world,” Amanda shares. “If people have the chance to go there, how lucky.” You’re free to pull over for a spontaneous picnic or take in the turquoise shimmer of Lake Louise framed by fall foliage, while not having to worry about the details along the way.
Fall is a spectacular time to visit: crisp mountain air, vibrant leaves, and fewer crowds make every stop even more magical. Pair that with iconic stays like the Fairmont Chateau Lake Louise, and you have a road trip that’s wild, flexible, and unforgettable.
This journey is a love letter to Scotland. “In most itineraries, Scotland is thrown in with England or Ireland. It's not treated as its own unique, special destination,” says Amanda, “But it absolutely is. And here you get nine days of pure Scotland.”
This packed trip is ideal for travelers who love to road trip and combine history with activity. “You get to explore a different part of the region, every single day.”
With a private driver and guide, you can roam the storied streets of Edinburgh, Glasgow, and Inverness, experience scotch distilleries throughout the region, and even enjoy a Scottish safari. “Climb aboard a private 4x4 Land Rover with cameras and binoculars, and journey through the Scottish Highlands, steeped in breathtaking views,” says Amanda.
“You’re going on hikes that mirror historical moments, learning in an experiential way.” Experience Glencoe Valley, Edinburgh Castle, Cairngorm National Park, and so much more. It’s Scotland the way it deserves to be experienced: untamed, immersive, and unforgettable.
Portugal in the fall is full of golden vineyards and harvest celebrations along the Douro River. This itinerary blends city discovery with serene river cruising, making it ideal for travelers who want a slower, more scenic way to experience the country. “For guests who aren’t into car transfers, this is a really beautiful way to discover Portugal,” says Amanda.
Your journey begins in Lisbon, one of Europe’s most dynamic capitals. With a private guide, you’ll explore iconic sites like Sintra and Pena Palace at just the right time to grab the perfect shot. “It’s this colorful palace up in the hills that has become an Instagram sensation,” Amanda explains. “The architecture is striking, but you can wander beautiful gardens, or head into Sintra, a cute little village where you can spend a day getting lost, trying some local dishes.”
The round-trip river cruise from Porto is ideal for ease and indulgence: gourmet meals, daily excursions, and uninterrupted vineyard views. Fall is harvest season in the Douro Valley, bringing wine festivals, local celebrations, and the region’s best flavors to your plate. With Kensington, you can customize the experience to match your pace. Whether you want to relax on the boat, or head out for an e-bike ride, explore the vineyard-terraced town of Pinhão, or taste wine at the historic Morgadio da Calçada manor house, the choice is all yours.
For travelers who’ve fallen in love with France and want to go deeper, this itinerary offers a rich, refined blend of wine, food, culture, and coastal charm. “France is my favorite place in the whole wide world,” says Amanda. “And Bordeaux is one of my favorite cities. It’s like a mini Paris, and so often overlooked.”
Begin your journey in Bordeaux, where Amanda recommends a visit to La Cité du Vin, a cutting-edge, interactive wine museum with panoramic views and tastings from around the world. “You can easily spend half a day there,” she says. “And to finish your day at the top, sampling wines, it’s perfect.”
Across the rest of the journey, you’ll enjoy the medieval streets of Saint-Émilion, the bold culinary creativity of San Sebastián, strolling through Gothic cathedrals, and sipping cognac by the sea. Make the most out of harvest season, when vineyard visits include seasonal pairings and Basque towns like Biarritz shine with local festivals.
This trip is ideal for culture seekers and food and wine lovers. Deep dive into the spirit, and spirits, of this stunning region.
This is Tuscany at its most luxurious: a private villa, rolling vineyards, and a weeklong stay that blends touring with true relaxation. Designed for families, couples, or groups of friends, this trip pairs total privacy with full-service luxury. “You have one home base for the entire time,” says Amanda. “And you’re going to have good food and every need taken care of, without having to worry about it.”
With a private chef on hand, daily housekeeping, and concierge-style support, every detail is managed for you. Spend your days however you choose: touring medieval towns, wine tasting in Chianti, or lounging poolside with a glass in hand. In the fall, truffle season adds something truly magical. “Being able to go into the woods with a professional truffle hunter and their dog, learn the tradition, catch your bounty, and then cook with it,” Amanda says.
You can even explore vineyards on horseback, enjoy farm-to-table meals in the hills, or simply soak in the serenity of villa life. With its perfect pacing and bespoke experiences, this retreat is the ultimate way to settle in, slow down, and savor the richness of Tuscany.
This nine-day culinary journey through Milan and Turin is designed for travelers who’ve already visited Italy a few times and are ready for a deeper, more immersive experience.
You’ll ease into Italy’s elegant north with a coffee in hand, exploring the quiet beauty of historic bars and stylish cafes. Then, in Turin, you’ll discover a city separate from the typical tourist hotspots, “It offers a different side of Italy that most people don't get to explore.” Explore the city’s tree-lined streets and stunning views of the Alps.
Fall is an ideal time to visit Northern Italy. With plenty of time in Turin and Milan, you can work with Kensington to tailor the trip to match the season, and your bucket list, choosing activities like truffle hunting with a private guide and chef, visiting a chocolate festival, or just savoring a glass of wine at a local restaurant.
“This itinerary does such a beautiful job of balancing culture and exploration, but giving you time to breathe,” Amanda explains. This is Italy for the connoisseur.
This 14-day journey proves that Switzerland is one of Europe’s most majestic destinations, especially for fall foliage train rides. Traveling through Zurich, Lucerne, Lugano, St. Moritz, Zermatt, Montreux, and Geneva, this immersive itinerary is perfect for both seasoned travelers and those new to the region. “What’s really beautiful about this itinerary is it’s literally the best of Switzerland,” says Amanda. “Everything that you need to do is beautifully packed into a 14-day experience.”
You’ll explore fairytale castles, glide across lakes, and coast through the peaks aboard the iconic Glacier Express, one of the world’s most scenic railways. “It’s one of those trains where the journey is the highlight, it is all open and glass” Amanda notes. “Sit back, look at all the beautiful scenery, and enjoy a drink as the beauty of the world rolls by.”
Fall brings a quieter magic: golden leaves drifting outside Château de Chillon, fewer crowds, and cool days perfect for lakeside sunset cruises. With thoughtful touches like white-glove service between hotels, you can relax completely and take it all in. From Mediterranean-flavored Lugano to the snowy summits of St. Moritz, this is Switzerland at its most spectacular, tailored to your rhythm, and unforgettable at every turn.
This nine-day journey is perfect for the first-time visitor to Japan who wants to see a unique blend of highlights, including iconic sites, rich culture, and jaw-dropping autumn landscapes. While many travelers aim for cherry blossom season, Amanda encourages heading to Japan in the fall instead. “Fall is just as beautiful as cherry blossom season, if not more,” she says. “The foliage is out of this world.”
Private guides will help you explore Tokyo, Kyoto, and Osaka; explore modern skyscrapers and Tokyo’s oldest temple, Sensoji Temple, venture into stunning nature in the stunning bamboo forests of the Arashiyama Bamboo Grove, and enjoy a first-class fall foliage train ride across the country.
“This one hits all the cultural moments, the castles, the shrines, the street food, and the mix between modern and traditional,” Amanda explains. For active, curious travelers seeking a thoughtfully curated introduction to Japan, fall is the perfect season to go.
Fall has a way of bringing out the best in a place. The crowds thin, the colors deepen, and there’s space to breathe, to linger a little longer at lunch, to follow your curiosity down a side street, and to feel the rhythm of local life. It’s the perfect season to travel with intention.
Whether you want to board one of the world’s most scenic fall foliage train rides through the Swiss Alps, sip wine in the Douro Valley during harvest season, or balance urban adventure and wilderness escape in Japan, your itinerary is shaped around you. With Kensington, every trip is crafted around your style, your dreams, and your idea of a perfect day. Let us handle the details, so that you can fully immerse yourself in the best places to visit in fall.
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