For an autumnal turn in Europe you could do worse than to start with Tuscany, where the hills come alive each autumn with a feast of fall festivals timed to coincide with the harvests. Pick your pleasure among the region's countless hillside towns: Bagnone honors the humble chestnut, Castiglione d'Orcia uncorks its extra virgin olive oil, and San Miniato's famous truffles are shoveled onto area dinner plates. Rich, hearty meals are a staple of the season, and in most towns, a tasting tour goes hand in hand with all the revelry. Fall also heralds the start of the local hunting season; expect to see wild boar on most menus as you make your way across the countryside. For a postprandial nap, curl up on the couches at the intimate Campo Regio Relais. Sitting in scenic Siena, the Campo has just six rooms in sight of the city's Duomo, and makes a convenient, cozy base for exploring the region.

For more information: Campo Regio Relais

Berlin's art scene might be the hottest in Europe, but don't plan on doing much gallery-hopping during the dog days of August. With most of the city's trendiest spaces taking a summer break, a stroll through red-hot 'hoods like Mitte and Brunnenstrasse offers more fizzle than sizzle. It's not until fall that the buzz comes back to Berlin. In October, Art Forum Berlin—a four-day festival of contemporary art—sets the pace for what promises to be a busy season, with a host of new galleries crowding their way onto an already-crowded scene. Channel your art smarts at the stylish Arte Luise Kunsthotel, where each of the edgy rooms was designed by a different artist. Housed in a former 19th-century palace, it's a hip hideaway that's fit for framing.

For more information: Arte Luise Kunsthotel

Though Lugano says "arrivederci" to summer with its annual fall festival, autumn is a fine time to visit the city tucked into the southern Swiss canton of Ticino. Mild Mediterranean weather graces the southern side of the Alps, where charming villages ring the shores of Lake Lugano, and a hike between towns takes you through colorful vineyards and thick forests of chestnut trees. The celebration of the fall harvest means hearty dishes of the region's Italian-infused cuisine: Think creamy risotto, pork loin stuffed with Mortadella—and of course wine. Butterfield & Robinson, specialists in hiking and biking tours of Europe, organize week-long walking tours of Ticino and the northern Italian Lakes, complete with luxurious accommodations and special bespoke trips with personalized itineraries.

For more information: Butterfield & Robinson

Hundreds of killer whales arrive off the coasts of Norway each fall for a feeding frenzy that lasts throughout the winter, offering a stirring spectacle for visitors traveling to the country's rugged north. Up-close encounters with Orca Tysfjord's "whale safaris" bring you nose to snout with the behemoths by boat, inflatable dingy—or even by dipping into the water for a swim. As a bonus, Norway's Northern Lights begin to show their colors in early autumn, promising a spectacular show come nightfall.

For more information: Orca Tysfjord

In vino veritas: No truer words were ever spoken, and no place truly knows how to celebrate the fall harvest like La Rioja. The Spanish wine region is famous for its fine vintages, sprawling vineyards, and medieval villages which celebrate the annual harvest with flair. The party kicks off on the feast day of San Mateo, when the first taste of the new harvest is offered up to the patron saint of Rioja. Luckily, the Virgin of Valvanera doesn't horde it all for herself: Around the region, you'll be able to sample some of the fall's best offerings—and bring a few bottles back as a souvenir. If all that grape-crushing has you pining for some pampering, check into the stylish Hotel Marques de Riscal. The Frank Gehry-designed hotel offers Spain's first "wine therapy" spa, where vine and grape seed extracts are used in the treatments.

For more information: the Hotel Marques de Riscal

The famous fungi of France and Italy are no strangers to gastronomes around the globe, but Croatian connoisseurs know their sumptuous subterranean treats are just as pleasing to the palate. It's hard to argue with the offerings in Istria, where the world's largest truffle—weighing in at nearly three pounds—was discovered in little Livade, and where the town of Buzet has proclaimed itself Grad Tartufa—"the City of Truffles." Decadent dishes laden with white truffles are an alluring reason to visit, but rummaging through the forest behind a pack of snuffling dogs is what makes a truffle hunt so unforgettable. Afterward unwind in the charming Hotel San Rocco, whose stone walls and wooden shutters evoke the pastoral pleasures of village life. Tucked away in the tiny town of Brtonigla, the hotel overlooks wooded hills and flower-filled meadows.

For more information: Thomson Holidays

Kilts, castles, and Highland culture take center stage during the Doric Festival, an annual celebration on the outskirts of Aberdeen for those whose tastes run toward the tartan. The fortnight fete features food, song, dance, and colorful competitions that will, among other things, make you see (or hear) the fiddle in a whole new light. Take advantage of the surroundings with a walk on the Malt Whiskey Trail, then retire from the revels at the regal Meikloeur Castle. The opulent estate sprawls across 40 manicured acres and sleeps 18—the ideal place to make like a monarch for a few days with the royal retinue (or the kids). A private, nine-hole golf course is part of the package, though some of Scotland’s most celebrated courses are just a short drive away.

For more information: Homes Away

No one will dispute Prague’s proud musical pedigree, but fall in the Czech capital offers a chance to soak up the city’s eclectic—and eccentric—music scene. From the lofty strains of the Strings of Autumn to the best of Bollywood to the colorful cacophony of the Stimul Festival—a celebration of electronica and noise music—the fall festival calendar is a chance for the Czech Republic’s oddball and offbeat to shine. Of course, if your musical tastes are more Mozart than Massive Attack, the stately Estates Theater offers an aural counterpoint to all that noise. Catch Don Giovanni on the stage where Mozart debuted it more than 200 years ago; for a coda, unwind at the music-themed Aria Hotel. With each of the luxury hotel’s 52 rooms dedicated to a different musician or composer, the hotel hits the right note for music-lovers.

For more information: The Aria Hotel

With vibrant colors cascading down the hillsides and farmers working their fields to take in the fall harvest, there’s no better time to tour Burgundy. Gentle terrain and temperate fall weather are ideal for exploring by bike, with paths wending through the vineyards or along the winding Burgundy Route des Grands Crus. DuVine Adventures offers award-winning bike tours through the region’s vineyards and villages, with frequent stops to explore old churches and charming chateaux—or to dig into the delectable dishes for which Burgundy is famous.

For more information: DuVine Adventures

The White Nights might light up St. Petersburg during the long days of summer, but most of the city’s top theaters and opera houses go dark until the fall. Come October, the curtain rises at the majestic Mariinsky Theater—historic home of some of St. Petersburg’s premier performers and prima donnas. Tchaikovsky, Rimsky-Korsakov and countless others debuted their ballets and operas at the city’s grand dame. Catch Swan Lake on the Mariinsky’s main stage, then play swan with a graceful glide over the canals of the “Venice of the North.” To get in touch with your inner czar, check into the regal Kempinski Hotel Moika 22. With 197 opulently appointed rooms and picture-perfect views of the Winter Palace, it’s the sort of place Peter the Great himself would be proud of.

For more information: The Kempinski Hotel Moika 22