Fall invites us to pause, to linger a little longer around the table with the ones we love. As the air cools and the crowds thin, cities around the world come alive with festivals, harvest celebrations, art fairs, and culinary rituals. For curious couples and culturally inclined travelers, it’s the perfect season to embrace the art of slow travel—especially when there’s something delicious waiting at every stop.
From wine festivals in castle courtyards to couscous celebrations on Sicilian beaches, here’s your guide to some of the most flavorful fall events happening across our Context cities. Pair them with one of our expert-led food or wine tours for a true immersion into the culture and cuisine of your destination.
Italy:
Couscous Fest
When: Sept 19-28, 2025
Where: San Vito Lo Capo,
What: A Mediterranean celebration of unity through cuisine. Chefs from around the world, guests and artists descend on San Vito Lo Capo in Sicily for ten days of events, cooking challenges, tastings and cultural meetings. Be sure to catch the couscous championships, which compare dishes from Italian and international chefs.
Tour Pairing: Head to nearby Palermo to sample traditional dishes and street food on our Palermo Food Tour.
Milano Fashion Week
When: Sept 23-29, 2025
Where: Milan
What: Milan Fashion Week blends creativity, craftsmanship, and Italian culture. The event is one of the Big Four (Paris, London, New York are the others) and is one of the most important fashion shows in the world.
Tour Pairing: Pair couture with cuisine when you book your spot on the Aperitivo in Navigli tour.
Venice Biennale
When: May through November, 2025
Where: Venice
What: The Venice Architecture Biennale has been curated by Carlo Ratti and explores how architecture can adapt to global challenges by leveraging various forms of intelligence. Visitors will notice an emphasis on the need for collaboration, inclusivity, and experimentation to find innovative solutions. The event has also transformed Venice into a "Living Lab," with installations and prototypes scattered across the city.
Tour Pairing: After exploring the exhibits, get a lay of the land at the Rialto Market.
Fra Angelico Exhibition
When: Sept 2025-Jan 2026
Where: Florence
What: This extraordinary exhibition is dedicated to Fra Giovanni da Fiesole, a key figure of Quattrocento art in Florence. Across two venues, Palazzo Strozzi and the Museo di San Marco, guests can explore the production, development, and influence of Fra Angelico’s work in dialogue with painters such as Lorenzo Monaco, Masaccio, and Filippo Lippi, as well as sculptors like Lorenzo Ghiberti, Michelozzo, and Luca della Robbia.
Tour Pairing: Get out into the countryside and find your own inspiration in the glasses poured on our Half-Day Tuscany Carmignano Wine Tasting Tour from Florence.
Greece:
Ifestia Festival
When: Sept 20
Where: Santorini
What: Santorini’s fiery celebration of its volcanic heritage. Fireworks erupt over the caldera while locals host cultural performances and festivities throughout the island.
Tour Pairing: Get a better understanding of the city of Santorini on the Santorini Highlights Full-Day Tour with Wine Tasting experience.
Turkey:
Istanbul Biennial
When: Sept 20–Nov 23
Where: Istanbul
What: One of the world’s leading contemporary art events, the Biennial fills Istanbul’s galleries and public spaces with bold, thought-provoking works.
Tour Pairing: Head to the Istanbul Grand Bazaar and Spice Market with a local who can help you connect with the local culture.
Akbank Jazz Festival
When: Sept 28-Oct 13
Where: Istanbul
What: For more than 30 years, this festival has brought Turkish and international jazz greats together for concerts in venues across the city, while also providing opportunities for emerging artists. Get your tickets!
Tour Pairing: Take a break from the music and dive into the melodies found in the shouts and clamor of the Spice Bazaar and Kadikoy Market.
France:
Paris Design Week
When: September 4-13
Where: Paris
What: Paris’ premier design showcase spreads across the city with exhibitions, pop-ups, and showrooms—perfectly paired with wine and cheese in Saint-Germain.
Tour Pairing: When you've had enough of the city, get out into the countryside for a visit to local champagne houses on our VIP Full-Day Champagne Tasting Tour.
John Singer Sargent at the Musée d’Orsay
When: Sept 25, 2025-Jan 11, 2026
Where: Musée d'Orsay, Paris
What: This retrospective celebrates the legendary painter’s luminous portraits and landscapes in the grand halls of the Orsay.
Tour Pairing: Head across the Seine and sample delightful bites from local specialty shops in the Marais after you've explored the halls of the Musée d'Orsay.
Germany
Berlin Food Week
When: October 6-12
Where: Berlin
What: The German capital’s celebration of culinary creativity brings together pop-up kitchens, tastings, and sustainable food initiatives.
Tour Pairing: Can't get enough? Grab a spot on our Berlin Food Tour and explore German traditions and immigrant influences that shape Berlin's culinary culture today.
Vienna Design Week
When: Sept 26-Oct 5
Where: Vienna
What: The Austrian capital’s largest design festival highlights innovative architecture, interior design, and urban planning through exhibitions and city tours.
Tour Pairing: Whet your appetite for Viennese cuisine and cakes worthy of an emperor with an exploration of essential Austrian Cuisine.
Spain
La Mercè
When: Sept 19–24
Where: Barcelona
What: A citywide celebration of Catalan identity with parades, human towers, concerts, and pyrotechnic displays that light up the city.
Tour Pairing: All of that excitement can make you hungry. Satisfy your sweet tooth with a Barcelona Chocolate Tour.
Mexico
Día de Muertos
When: Nov 1-2
Where: Mexico City
What: Celebrate and honor the dead, taking in some of the biggest and most elaborate decorations and celebrations, including arts installations in the main square, elaborate decorations in museums and galleries, and enormous celebrations surrounding cemeteries. Don't miss the iconic parade along Paseo de la Reforma.
Tour Pairing: Dive into the origins and ingredients of Mexico's cuisine in an authentic food and flower market at the Jamaica Market.
Pair Your Travel With Something Flavorful This Fall.
Whether you’re planning around a festival or simply craving a slower, richer journey, fall offers the perfect canvas for connection. Across our cities, the season brings markets spilling over with ripe produce, culinary traditions passed down through generations, and cultural celebrations that only locals know best.
Join one of our expert-led food and wine tours to uncover the stories behind each dish this season.
