Discover Central Italy: A Wine & Food Lover’s Travel Guide

It is hard to think of a place more suited to the wine and food lover than the rolling hills and lush valleys of central Italy’s Tuscany and Umbria. Cyprus trees and ancient oaks dot the landscape, and as you wind the many white gravel roads you’ll find yourself in awe that somewhere so unspoiled extends in every direction.

Winetraveler Tip: Get updates on flight deals into Florence as they arise, and checkout our top picks for hotels to stay at in Florence.

All those pictures in the coffee table books, online travel sites, even those on your wall calendar are rolled out before you – tangible, inspiring and ready to delight every one of your senses.

Small Towns in Central Italy for Wine Lovers | Central Italy Small Town and Village Travel Guide


Beyond Florence – Small Towns in Central Italy and Things to Do

While Florence is known to food and wine lovers the world over, and is renowned for its art museums, shopping, and breathtaking sunsets atop Piazzale Michelangelo, many of the region’s treasures lie beyond the city in the small towns and villages scattered throughout Chianti, Tuscany and Umbria.

From San Gimignano and Pienza to Assisi and Cortona, Italy’s charm, warmth and authenticity will have you wishing you never had to leave. The days are dream-like as you stroll through streets and walls built hundreds of years ago sampling the local Pecorino cheese, house-made gelato or sipping one of Italy’s finest red wines; all the while you’re surrounded by colorful flowers, the clanking of dishes in the kitchen as a meal is prepared from scratch, and the quiet chatter and laughter of others simply relishing in the good life.

While you can easily find such scenes across the countryside, here are a few destinations we highly recommend:

How to Visit Central Italy | Touring San Gimignano Wine & FoodSan Gimignano

A small walled village, San Gimignano, known for its medieval architecture and the 14 towers that rise above the city is a UNESCO World Heritage Site, which will transport you back in time. Food and wine lovers will delight in the locally grown saffron and its white wine, the Vernaccia di San Gimignano. We also recommend finding a local, family vineyard for an intimate encounter with Chianti – call ahead to schedule an appointment.


Another UNESCO World Heritage Site, Pienza is a small medieval village known as the “ideal city of the Renaissance.” It was created by Enea Silvio Piccolomini, later known as Pope Pius II, who had both the means and influence to transform his birthplace village into his version of a utopian city. Located in the Val d’Orcia region of Tuscany, Pienza is known for its local sheep’s cheese, Pecorino and is the ideal place for a stroll. Make sure to sample the local gelato shop’s flavor of the day too!

Wine Tours in Montepulciano | Visiting MontepulcianoMontepulciano

Now, this is a wine lover’s dream destination. Set atop a hill with views of the surrounding Tuscan farms, Montepulciano is an easy village to burn through your camera card! Make sure to visit one of the many wine cellars which extend deep beneath the city streets – the Vino Nobile di Montepulciano is the local red wine and it shouldn’t be missed.

What to do in Montalcino Italy | Wine and Food Tours in Montalcino ItalyMontalcino

Wine lovers would be remiss to pass up this destination, another idyllic hilltop town, set within fortified walls. Montalcino is renowned for the production of Brunello red wine which you can taste at any number of wine shops scattered throughout town while taking in the view of the surrounding countryside with its picturesque olive groves, ancient trees and miles upon miles of vineyards. If you’re there for a meal, which we recommend so you can take in more wine, make sure to try the wild boar ragu.

Visiting Montefalco in Central Italy | What to do in Montefalco ItalyMontefalco

In Umbria, the charming town of Montefalco will delight you with its simplicity and welcoming hospitality. A small village in the heart of Italy, you can spend the afternoon sampling the local wines at a family-owned vineyard, taking a private cooking class in a chef’s home or dining al fresco at one of the many eateries tucked in this town’s winding streets. You’ll want to grab a bottle of Sagrantino di Montefalco for the cellar – it’s an ager!

What to do in Assisi Italy | Wine Tours in Assisi Italy | Visiting Small Towns in Central ItalyAssisi

Obviously one of the more well-known destinations of Umbria, Assisi made famous by St. Francis, is a crown jewel of the region. We recommend visiting in the evening when the crowds disperse and the city takes on a beguiling atmosphere. Tour the church near closing for a more personal and less crowded viewing, and then snag a seat for dinner on a westward facing balcony to watch the sunset over the Umbrian valley. We guarantee it will be difficult to leave this enchanting village, and while you’re there make sure to taste the Umbrian olive oil. It’s simply superior.

Believe the Hype

Italy is one of those dream destinations. We’ve all heard the stories, read the descriptions or watched the travel shows depicting a paradise for the food and wine traveler. Fortunately, for those lucky enough to visit, it does not disappoint.

The rolling hills with scattered ancient castles and old farm houses provide a picturesque backdrop, but the intimate encounters with the food, wine, landscape and above all, the Italian people are the true treasures.

ALSO READ: 10 Charming Italian Towns To Visit Across Italy

Perhaps the best word to describe central Italy is authentic. Everything from the homemade pastas, to the forest-forged truffles, or even the delicately painted ceramics exude an authenticity which both inspires and awes. And as for the Italians, try not to be engrossed by their passion, hospitality and penchant for instilling a dual sense of wonder and relaxation.

Like we said, it’s a “must-see.” As Francis Mayes said in Under the Tuscan Sun, “My idea of heaven still is to drive the gravel farm roads of Umbria and Tuscany, very pleasantly lost.”

More Ways To Explore Italy

Learn All About The Wine Region of Tuscany

Everything You Need To Know About Veneto

How To Explore Venice Italy in One Day

7 Reasons To Take a Dream Trip to Sicily

Free Wine Fountain in Italy Now Open To The Public

Pin This Article

Get Articles Like These Directly in Your Inbox!

Subscribe to Winetraveler and receive notifications when new articles are published.

Leave a Comment, Ask a Question or Share a Review

Comments ( 9 )

  1. I need another trip to Italy stat – all these places are now on my travel list. Thanks for all the info 🙂

    • Couldn’t agree with you more Casey! I’m dying to go back as well. Here’s to travel planning!

  2. We haven’t spent nearly enough time in Italy — so many wine regions so little time! Thanks for the inspiration, and particularly love the focus on small towns (prefer a more authentic local experience). Cheers!

  3. I love a good road trip and I can definitely see this itenerary done in a spunky Italian car!

    Seeing UNESCO sites is always rewarding – and we’ve got a few on this list.

    Great post!

  4. What an amazing picture you have painted of these places. Would you suggest all in one trip, or is each place worthy of it’s own week?

    • Hi Robin – Honestly it depends how much time you’ll have in the region and how much you’d like to dive in. If you have a few weeks, you could easily fill it with the itinerary outlined. It’s hard to go wrong in Central Italy!

  5. Had a fabulous time in Florence and wished I could have spent more time there this year, but the list you put together is on my next trip this fall. I did not know that Montalcino was the capital of Brunello! Definitely adding that one. Great piece and very informative. Thank you!

Send this to a friend