Sip Your Way Through Tuscany & Umbria: A September & October Wine Travel Guide 🍷

If you’re dreaming of an Italian wine vacation, September and October are the best months to visit Tuscany and Umbria. These shoulder-season months offer cooler temperatures, fewer crowds, and front-row access to harvest season in some of Italy’s most celebrated wine regions.

As a travel advisor specializing in custom Italy food and wine travel, I recently experienced this journey firsthand—and it’s even better than it looks on social media. From vineyard tastings to perfectly paired local cuisine, this time of year delivers both education and indulgence.

Below is a guide to the must-visit Tuscany and Umbria wine regions to help you plan an unforgettable Italian wine adventure.

Why Visit Tuscany & Umbria in September and October?

Traveling to Italy in early fall offers unique advantages for wine lovers:

• Grape harvest season brings vineyards to life

• Ideal weather for wine tastings and countryside touring

• Seasonal menus featuring truffles, cheeses, and fresh olive oil

• Fewer tourists compared to peak summer months

This is the perfect time for travelers seeking authentic Italian wine experiences.

Tuscany Wine Regions to Visit

Chianti (Florence to Siena)

Wines to Try:Chianti Classico (red), Vin Santo (dessert wine)

Why Visit in Fall:The Chianti region is at its most vibrant during harvest season. Vineyards buzz with activity, and wineries often offer special tastings and cellar visits.

Montalcino

Wine to Try:Brunello di Montalcino

Why Visit in Fall:Enjoy pre-harvest tastings and discover the richness of aged Sangiovese in one of Italy’s most prestigious wine destinations.

Montepulciano

Wine to Try:Vino Nobile di Montepulciano

Why Visit in Fall:This region shines when paired with local pecorino cheese and cured meats—an ideal stop for travelers who love food and wine pairings.

San Gimignano

Wine to Try:Vernaccia di San Gimignano (white)

Why Visit in Fall:Crisp, aromatic white wines and vineyard tours make San Gimignano a refreshing contrast to Tuscany’s bold reds.

Umbria Wine Regions to Explore

Often called Italy’s green heart, Umbria offers exceptional wines with fewer crowds and a more relaxed pace.

Montefalco

Wines to Try:Sagrantino di Montefalco, Montefalco Rosso

Why Visit in Fall:Harvest season highlights the bold, tannic structure of Sagrantino wines—perfect for serious red wine lovers.

Orvieto

Wine to Try:Orvieto Classico (white)

Why Visit in Fall:Orvieto is famous for its crisp white wines, which pair beautifully with traditional Umbrian cuisine.

Torgiano

Wine to Try:Torgiano Rosso Riserva

Why Visit in Fall:This region is ideal for travelers interested in wine and olive oil tastings, offering immersive agricultural experiences.

Insider Tips for Planning an Italian Wine Trip

• Reserve winery visits in advance, especially during harvest season

• Pair wine tastings with regional cuisine for a complete experience

• Consider a private driver or guided wine tour

• Stay at wineries offering on-site lodging to fully enjoy the countryside

Working with a travel advisor ensures access to vetted wineries and seamless logistics.

Ready to Plan Your Tuscany & Umbria Wine Vacation?

If you’re thinking about an Italy wine trip in 2026, now is the perfect time to start planning. As a travel agent specializing in custom Italy itineraries, I design personalized food and wine journeys through Tuscany, Umbria, and beyond.

Contact me today to begin planning your Italian wine adventure.