The fall season ushers in the full spectrum of emotion: mourning for summer’s end, excitement for apple pies, anticipation (or trepidation) for the coming school year—and for most, a healthy dose of nostalgia as we recall jumping in leaf piles, carving pumpkins and traversing apple orchards. But fall is not the same around the world, and with reduced crowds and a break in the heat, it is one of the best times to enjoy the cultural and natural gems of destinations around the world, from the stargazing festivals of Alberta to the harvest in the Italian countryside and the dizzying fall colors of Tokyo. This year, as everyone returns to travel, it is especially important to book early to ensure the best guides and experiences. Read on for why these 15 destinations are ideal for fall trips (plus where to stay in each).
Contact Indagare to book your fall vacation. Our team of expert trip designers can recommend the best hotels, restaurants, activities and more just for you.
Foodie & Film Buffs: Italy
Why Go Now: Harvest season in Italy is a magical time, bringing wine, oil, chestnut and truffle festivals to many of the country’s sprawling regions. This year, Piedmont’s Alba White Truffle Festival is back Saturdays and Sundays (October 9-December 5) and includes meetings with chefs, tastings, wine courses and more. But while the leaves are turning in the north, Rome stays warm and green often until mid-October, which is also the time when filmmakers and actors from around the world—including plenty of Hollywood royalty—descend on the Eternal City for the Rome Film Fest (October 13-23). Screenings and red-carpet events will take place at the Parco della Musica.
Where to Stay: Those seeking a jump into the past will find their ideal Piedmont home base at Castello di Guarene, an 18th-century Palace atop a charming village, while those who enjoy more contemporary accommodations and resort-like amenities will prefer Casa di Langa. In Rome, we recommend sister properties Hotel de Russie, offering enviable panoramic views from the rooftop, and Hotel de la Ville, set above the Spanish Steps.
The Cultural Island Getaway: Oahu
Why Go Now: The month-long Aloha Festivals in Oahu (beginning on September 10) celebrates the state’s history, as well as local music and dance traditions. One of the highlights is the Waikiki Ho’olaule’a (September 17), an enormous block party with four concert stages and vendors selling all manner of local dishes and artisan crafts. Other notable festivals include the Hawaii Food & Wine Festival (October 20-November 6) where chefs from across the islands travel to Honolulu and the 50th annual Kona Coffee Cultural Festival in Kailua (November 4-13). Plus, though the state is busy year-round, October is one of the least touristed months, making it a great time to enjoy all the hiking, snorkeling and beach time that Hawaii has to offer.
Where to Stay: The nine-story Espacio in Waikiki, offering guests an exclusive experience that includes a two- or three-bedroom suite per floor with butler service, a balcony complete with a Jacuzzi, marble bathrooms with deep soaking tubs and a state-of-the-art kitchen.
For the Starry-Eyed: Alberta
Why Go Now: Calling all stargazers—whether you love the stars for the romance, science or spiritualism, this province in western Canada offers it all. Come mid-October, the Jasper Dark Sky Festival (October 14-23) in Jasper National Park is in full swing, with stargazing events, a photo workshop, outdoor symphony performances, traditional Cree celebrations, speakers (including an astrophysicist, aquanauts and an astronaut candidate) and more. Plus, in nearby Banff, the nine-day Banff Centre Mountain Film and Book Festival (October 29-November 6) features screenings of films about mountain sports, culture and the environment, as well as appearances by renowned mountaineers, climbers and other adventurers.
Where to Stay: Located about an hour south of Jasper and 2.5 hours north of Banff, Glacier View Lodge offers an all-inclusive experience. Visitors can take an evening tour of the Athabasca Glacier, stargaze from a viewing deck, enjoy a three-course dinner and stay in a cozy-chic room with either a view of the mountains or the glacier.
A Quintessential Greek Getaway: Crete
Why Go Now: Enjoy fewer crowds, milder temperatures and a longer beach season on Crete, where the water stays relatively warm even into October. Pair your beach days with exploration of the island’s varied landscapes, with hikes up Mount Ida, treks into the gorges, tours of the Knossos Palace and ventures into Psychro Cave. Shopaholics will want to visit in September and October when souvenir shops, fashion stores and markets experience a dip in prices, allowing travelers to procure signature leather goods and quality products like olive oil, wine and cheese at reduced cost. And while the rains do start to pick up in October into November, those who stay can get a dose of culture through rakokazana, an annual tradition in which brewers turn their fermented grapes into raki, a traditional alcoholic drink that is coupled with ample feasting. Note: Avoid staying over the 28th, when the crowds come out for Oxi Day, one of the biggest national holidays in Greece.
Where to Stay: An opulent resort known for its luxurious seaside villas, Elounda Beach Hotel and Villas is a great home base on the eastern side of the island. For a stylish, family-friendly retreat on Crete’s western side, head to Ammos within easy access of the Old Town of Chania and plenty of beaches and hikes. Both close October 30.
A Springtime Dream: Argentine Patagonia
Why Go Now: While the north slinks towards winter, the southern hemisphere is just coming to life. Their spring is one of the best times for spotting Patagonian wildlife like puma, foxes, condors and a plethora of birds—this is also when whale watching is at its peak (September and October) and the penguins return to the coast for breeding. Travelers who visit early enough may be able to squeeze in some spring skiing in Bariloche, but for the rest of the season, hiking the mountains and valleys is a wonderland of color, especially in the north, where the country is awash with lupine in shades of purple, red and orange.
Where to Stay: Eolo, a 17-room luxury lodge with panoramic views of the Patagonian steppe and an extensive activities menu, including bird watching, ice trekking, horseback riding and more. In between the activities, guests can relax at the indoor pool and sauna or out on the deck overlooking Lago Argentina.
Cozy Cabins and Fiery Foliage: Rural New England
Why Go Now: From Maine’s rugged coast to the Berkshires in Massachusetts, nowhere does fall like New England, where maple trees transition from green to yellow to crimson on rolling hills interrupted by quaint towns and stately farmhouses. This is a part of the country that takes fall seriously and as such is characterized by a smattering of harvest, Octoberfest and foliage festivals and fairs, many of which are returning for 2022. New Englanders will also preach the beauty of hiking and biking—and they aren’t wrong. Peak leaf season varies by the year and the latitude (and altitude), but usually you can find it between late September and mid-October when the weather is mild and great for outdoor activities.
Where to Stay: Twin Farms, in Central Vermont, is a perennial favorite, but fills up early. Another option we love is Hidden Pond, a relaxed resort with standalone cottages in the woods near Kennebunkport, Maine. The adults-only bungalows are removed from the larger, kid-friendly two-bedroom houses, though both areas showcase classic Maine touches like stone fireplaces and spacious porches.
A Cultural and Culinary Adventure: Spain & Portugal
Why Go Now: At the southwestern tip of Europe, Spain and Portugal offer an intoxicating mix of dynamic cities, fascinating histories and beautiful scenery. Enjoy the thriving arts and culinary scenes in Lisbon, Madrid or Barcelona, and head to the Atlantic or Mediterranean coasts for charming towns and some off-season beach time. (In southern Spain, temperatures hit the seventies well into November, so sunbathing and swimming is possible late into the fall.) Both countries have unique architecture and cuisines that vary region to region, making them ideal for both deep-dive trips to single-destinations or longer itineraries that showcase the breadth of the Iberian Peninsula.
Where to Stay: Most trips to Spain will—and should—include at least a few days in its capital, Madrid, where a 121-million-dollar renovation at the Mandarin-Oriental Ritz Madrid has brought the city’s most iconic hotel (built by César Ritz) back to its original 1910 glory. In Lisbon (another must see) make your home base at the Verride Palácio Santa Catarina, a palatial boutique hotel with panoramic city views and an exquisite fine-dining experience.
Related: Top Trips to Take with Dad
The Exotic Wildlife Trip: The Galápagos
Why Go Now: In the Galápagos, September to November is the driest, coolest season, when daytime temperatures drop to the mid-70s, rainfall is virtually nonexistent and the Humboldt current is at its peak, bringing colder, nutrient-rich waters to the archipelago. What that means for visitors: swimming and snorkeling might warrant a wetsuit, but this is also the best time of year for seeing marine life like green sea turtles and endemic penguins, sea lions and seals. On land, bird-watchers will be able to see nesting blue-footed boobies and albatrosses.
Where to Stay: With a chic, minimalist design, the lava-built Pikaia Lodge offers unparalleled comfort with a conservationist focus on Santa Cruz island. For those looking to maximize their time at sea—yachts are the way to go. Indagare has several favorite operators for both private and semi-private sailings.
A Fall Fairytale and Outdoor Playground: The Scottish Highlands
Why Go Now: The Scottish Highlands are mesmerizing enough—jagged rock fixtures spearing up through the plains, glistening lakes and deep serpentine valleys guarded by castles. Now imagine that same dramatic landscape painted in sunset hues. That is the beauty of Scotland in the fall, when the crowds are thinner, the weather is cooler and the hiking and biking is post card picturesque. And if you happen to be there anyway, add a little magic to your journey with the Enchanted Forest (September 29-October 30) in Pitlochry, a woodland sound and light show that is celebrating its 20th anniversary—a great add-on for families, especially with younger kids.
Where to Stay: The Gleneagles Hotel, a playground for children and adults alike where days are spent fishing, hiking, learning falconry, playing golf and horseback riding (there are even two miniature ponies for young riders). Or, for a more old world experience, head to Inverlochy Castle where active days are complimented by exquisite food and 19th-century décor in a lakeside castle.
A Coastal Retreat: Rhode Island
Why Go Now: Salty sea breezes, the soothing rhythm of crashing waves, cedar-shingled cottages overlooking grassy dunes… coastal Rhode Island is just as enticing in the fall as it is in the summer. This is the time for biking by the shore, a day trip to Newport to explore a historic mansion or a leisurely brunch in Watch Hill or Weekapaug followed by an afternoon spent curling up with a good book. The weather stays pleasant through October, making boating, hiking and, of course, long walks on the beach, perfectly lovely—and for the bird lovers among us, this is also when Rhode Island birding is at its peak. You may even sneak in a spontaneous beach day or two, a picnic (or both).
Where to Stay: The majestic Ocean House hotel, notable for its iconic yellow facade and wrap-around porch and spectacular sea views and beach access. Fall is a great time to take advantage of Ocean House’s considerable amenities, including wine and cooking classes at its Center for Wine & Culinary Arts, indulging in treatments at the 12,000-square-foot spa or hitting the fitness center, indoor pool and squash courts.
A Food and Art Lover’s Escape Down Under: Sydney
Why Go Now: A true foodie city with a penchant for the arts, fall brings no shortage of activity to Sydney. In October, travelers can feast on all manner of Asian street food during the Night Noodles Market (October 4-9) in Hyde Park. There are also plenty of new restaurants in town, including the Turkish plant-based Maydanoz and Gildas, chef Lennox Hastie’s soon-to-open Spanish wine bar, a spinoff from the ever-popular Firedoor. Turning to art and culture, Sydney Fringe Festival is back through the month of September with art shows, music performances, cabaret and film premiers, as is Sculpture by the Sea (October 21-November 7), the world’s largest free sculpture exhibition with 100 sculptures set up along a two kilometer stretch between Bondi and Tamarama Beach.
Where to Stay: The Langham, the stylish boutique property in the Rocks historic area, home to Kent Street Kitchen, a unique fine dining meets buffet experience (we recommend trying for a seat at the exclusive Chef’s table).
Flowers, Fields and Foliage: Tokyo
Why Go Now: Spring may have cherry blossoms, but autumn brings with it koyo, or fiery colored leaves. Starting late September, you can day trip from Tokyo to Hakone to view the silver-gold waves of pampas grass, while back in the city, mid-October brings the Koizumi Cosmos Festival, when the pink cosmo flowers are in bloom in Show Kinen Park. Late November (the peak for fall foliage) is the time to visit Rikugien, the traditional Japanese garden in Tokyo where vibrant leaves are lit up nightly until early December. Plus, you can pair a trip here with a visit to Kyoto, an easy train ride away.
Where to Stay: The Tokyo Edition opened in Fall 2020 and now that the country has reopened, it is finally available to international tourists. Inspired by Buddhist temple layouts, this 206-room hotel at the top of the Tokyo World Gate skyscraper uses greenery and wood accents to create a serene retreat in the bustling city.
An Exotic Hideaway: Maldives
Why Go Now: Rainy season in the Maldives extends through October, but that shouldn’t stop you from heading to this cluster of more than a thousand tiny islands off the southern tip of India. Fleeting storms usually pass by quickly—and actually create optimal conditions for surfing—and both air and water temperatures hover at an idyllic 80 degrees. Although the visibility underwater is slightly diminished due to plankton at this time of year, snorkeling and diving in the Maldives never disappoints, and out of the water, days can be spent lounging seaside, traversing the islands and sailing.
Where to Stay: We love LVMH’s Cheval Blanc Randheli, with 45 ultra-chic villas designed by Jean Michel Gathy on the Noonu Atoll. And, says Indagare’s Sasha Feldman, “snorkeling and scuba diving in the nearby reefs feels like The Little Mermaid come to life.”
Disconnect Up North: Alaska
Why Go Now: Alaska is at its most dramatic in the fall, when the leaves change colors—blueberry bushes transform into a red carpet; birch trees fade to gold; the tundra turns a russet brown—and the Northern Lights begin their dance across the night skies. Wildlife-viewing is excellent this time of year as well, as it’s migration season for a diverse group of fauna including caribou, beluga and gray whales and many species of birds, including cranes.
Where to Stay: Accessible only by helicopter, Sheldon Chalet is a stylish, five-bedroom retreat on the only privately owned land in the mountains of Denali National Park. Panoramic windows provide unobstructed views over the national parkland, and guests are able to be wholly present in the unique Alaskan wilderness—no WiFi means no distractions here. And instead of scrolling on their phones, visitors enjoy activities like glacier trekking, crevasse exploring, mountain climbing and snow-cavern spelunking.
Late Fall Beach Holiday: Caribbean Islands
Why Go Now: For any traveler looking for an endless summer, the Caribbean is the closest, most convenient option—and perhaps most gorgeous, too. Hurricane season peaks in September (and extends into November), but mid-October can be a lovely time of year to visit the Caribbean. This is when the water is at its warmest, the air is balmy but not oppressive and resorts usually have increased availability (the entire region is effectively sold out between Thanksgiving and Easter). Of course, having booking flexibility is key, on the off chance you need to alter dates due to storms.
Where to Stay: The Caribbean’s myriad islands are each unique, and a beach vacation here can lean cultural, culinary, sceney, escapist and adventurous depending on travelers’ preferences. Discover the 10 hotels that earned spots in the Indagare Index. And if you’re looking to see more than just one island, a Caribbean yacht charter is an ideal way to explore.
Extended Summer and Sunsets: Tel Aviv
Why Go Now: Come September, the crushing heatwaves of Tel Aviv begin to break, making way for temperatures in the high seventies and low eighties—perfect for some fall beach time. With the decrease in tourists, the fall is also a great time to enjoy sites like the historic city center and Tel Aviv port, as well as the country’s delicious cuisine with classics like falafel, shakshuka and sabich. And in September, after a day of lounging or exploring, head to Gordon Beach, Old Jaffa or the port for what many claim are the best sunsets of the year. Note: Unless you are traveling for religious reasons, it is best to avoid Tel Aviv during Rosh Hashanah and Yom Kippur due to increased airfare prices and restaurant and shop closures.
Although the state department has issued a warning against travel to Jerusalem, Tell Aviv remains at a Level 2 Travel Advisory.
Where to Stay: The Jaffa, a chic city spot for couples and families alike where travelers have a choice between the sleek lines and modern lighting of the Contemporary Wing and the stone facades and high ceilings of the Historic Wing.
Bonus: Blackberry Mountain, Tennessee
Why Go Now: For another dose of brilliant fall foliage coupled with the ultimate outdoor adventure, wellness and culinary hotel experience, head to Blackberry Mountain in the Great Smoky Mountains of Tennessee. A destination in itself, the 10,000-acre property offers ample space for hiking, kayaking, fly fishing, archery and wheel-thrown pottery, and the mild temperatures in the sixties and sunny days makes for beautiful weather to do it all. The indulgent seasonal culinary program and charming country-esque cottages and villas also make it ideal for couples and families seeking a one-stop fall getaway.
Contact Indagare to book your fall vacation. Our team of expert trip designers can recommend the best hotels, restaurants, activities and more just for you.