Top Small Towns in Italy to Visit Famous for Wine (2024)

By | Wine & Travel Writer, Consultant & Marketer
Last Updated: November 6, 2023
Best Small Towns in Italy & Things to Do | Wine and Food in Italy

Best Picks for Small Towns in Italy to Visit Famous for Wine (Wineries & Wine Tour Options Included)

Editor’s Note: This travel guide to some of Italy’s best small towns famous for wine or close to nearby wine regions is updated frequently. If you’re looking for recommendations on where to go for a wine travel-focused vacation in Italy, be sure to bookmark this 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: The majority of towns we reference in this guide are easily accessible from Florence, Italy. Get updates on flight deals into Florence as they arise, and checkout our top picks for hotels to stay at in Florence if you’re considering using it as a base to explore the area.

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. In this guide, we’re going to cover several Italian towns in central Italy that have been integral to Italy’s wine culture for centuries, if not for thousands of years.

Small Towns in Central Italy for Wine Lovers | Central Italy Small Town and Village Travel Guide
While Florence is a delightful city to explore and use as a base to visit nearby Italian wine towns, we highly recommend extending your trip to Italy beyond the city to get a sense of flavors, scenery and hospitality you might not otherwise find. Consider spending a few days to explore Florence’s must-see attractions, and then venture out into the following towns and stay at a lovely agriturismo between the vines.

Staying in Florence? Book These Tours & Attractions Ahead of Time

Beyond Florence: Small Towns to Visit 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 (if you’re into any of these, book hop-on-hop-off bus tours), 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 Italian destinations we highly recommend.

RELATED: Siena Italy: Yes It’s Worth a Visit and Here’s Why

San Gimignano

San Gimignano: The Medieval Skyline Meets Luscious Vineyards 🍇🏰 – Discover the heart of Tuscany’s captivating charm and raise a glass to its world-renowned Vernaccia di San Gimignano wine. A must-visit destination for any true wine enthusiast.

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. We include three recommendations below, but be sure to call ahead to schedule an appointment.

RELATED: These Are the Best Wine Tours to Book in Tuscany

Wineries to Visit near San Gimignano

Fattoria Poggio Alloro

Via Sant’Andrea, 23, 53037 San Gimignano SI, Italy

+39 345 530 7767

Immerse yourself in the warm hospitality of this family-run vineyard, where generations of winemakers have passionately crafted their organic Vernaccia di San Gimignano wines. Enjoy breathtaking views of the Tuscan countryside while savoring exquisite farm-to-table cuisine.

Tenuta Torciano Winery

Via Crocetta, 18, 53037 Ulignano SI, Italy

+39 0577 950055

Established in 1720, the Giachi family’s winemaking legacy continues to thrive at Tenuta Torciano. Delight in a personalized wine tasting experience featuring their distinctive Vernaccia di San Gimignano and other Tuscan wines, paired with delicious local dishes. #CenturiesOfTradition

Montenidoli Winery

Localita’ Montenidoli, San Gimignano, Si 53037, 53037 San Gimignano SI, Italy

+39 0577 941565

At Montenidoli, the Sergiovanni family is dedicated to preserving the natural beauty and rich biodiversity of the Tuscan landscape. Savor their award-winning Vernaccia di San Gimignano wines, crafted with minimal intervention, and be captivated by the serene surroundings.

Private Wine Tours of San Gimignano

If you’re wary about exploring San Gimignano by yourself and would prefer a guided experience, we highly recommend booking a private walking tour with Tuscan Escapes by Papilio SR to explore the city itself. Then, arrange a private wine tour ahead of time with Podere la Marronaia (also very affordable) for an authentic and personal wine tasting experience in this remarkable region.


Pienza, Italy’s idyllic renaissance jewel, located on the crest of a hill overlooking the Val d’Orcia. Stroll through the charming streets of the town, an enchanting Tuscan village designed by Pope Pius II, and marvel at its harmonious blend of art, architecture, and nature. Let the captivating countryside views and gentle rolling hills transport you to a simpler, more serene time.

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!

Top Wineries to Visit near Pienza

Podere Il Casale

Via Podere Il Casale, 64, 53026 Pienza SI, Italy

+39 0578 755109

Discover the beauty of organic farming at this family-owned winery and farm, where respect for the land translates into exceptional wines and farm-to-table cuisine. Enjoy a guided tour and tasting, featuring their elegant wines, organic olive oil, and mouthwatering pecorino cheese, all produced on-site.

Tenuta di Trinoro

Via Val d’Orcia, 15, 53047 Sarteano SI, Italy

+39 0578 267110

Explore the passion for winemaking that drives the Franchetti family at their secluded estate in the heart of Val d’Orcia. Revel in the extraordinary complexity and character of their wines, including the celebrated Bordeaux-style blend, as you take in the breathtaking views of the surrounding countryside.

Capitoni Winery

Podere Sedime, 63, 53026 Pienza SI, Italy

+39 338 898 1597

Immerse yourself in the welcoming atmosphere of this family-run winery, where traditional winemaking techniques meet modern innovation. Delight in the range of wines produced from their vineyards, which boast an array of terroirs, and savor the essence of Tuscany with every glass.

Wine Tours of Pienza from Rome

RECOMMENDED: Take Our Most Higly-Rated Tour Through Pienza and More Departing from Rome


Montepulciano: A Panoramic Masterpiece – From the top, take in the awe-inspiring sights of this hilltop town, nestled amidst verdant vineyards and rolling Tuscan hills. The harmonious blend of medieval architecture and lush landscapes creates an unforgettable vista that beckons travelers to explore further.

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.

Wineries to Visit near Montepulciano

Avignonesi Winery

Via Colonica, 1, 53045 Montepulciano SI, Italy

+39 0577 941565

Journey through the art of winemaking at this historic estate, owned by the Virginie Saverys family since 2009. Delight in the winery’s commitment to biodynamic agriculture while sampling their renowned Vino Nobile di Montepulciano and other exquisite wines that express the essence of the terroir.

De’ Ricci Winery

Via Ricci, 11, 53045 Montepulciano SI, Italy

+39 0578 757166

Step into the rich heritage of Montepulciano wine production at De’ Ricci, a family-owned winery with roots dating back to the 14th century. Taste the passion and tradition in every sip of their Vino Nobile di Montepulciano, crafted using time-honored methods in the winery’s historic cellars.

Poliziano Winery

Via Fontago, 1, 53045 Montepulciano SI, Italy

+39 0578 738171

Named after the famous poet Angelo Ambrogini, aka “Poliziano,” this family-run winery has been crafting exceptional wines since 1961. Indulge in a guided tour and tasting, where you’ll experience the depth and elegance of their Vino Nobile di Montepulciano, Rosso di Montepulciano, and other prized wines that reflect the soul of the region.

Guided Wine Tours in Montepulciano

Montalcino, Orcia Valley, Pienza, and Montepulciano: Wine and Cheese Guided Tour from Florence

If you’re staying in Florence, Ciao Florence Tours & Travels Srl offers an unbeatable day trip from the city. It includes stops in most of the cities referenced in this travel guide.

Embark on a memorable Tuscany day trip from Florence by coach and explore the region’s charming historical hill towns: Pienza, Montalcino, and Montepulciano. Immerse yourself in the picturesque, vineyard-draped landscape of the Orcia Valley (Val d’Orcia) and indulge in delightful cheese and wine tastings at local wineries and venues. Experience an unforgettable day in the enchanting Italian countryside.

Delight in the beauty of hill towns Montalcino, Montepulciano, and UNESCO-listed Pienza. Take in the breathtaking views as you drive through the rolling vineyard hills of Val d’Orcia. Savor the flavors of regional wines, including Brunello and Vino Nobile, along with a taste of local cheese. Enjoy the convenience of round-trip transportation for a seamless and stress-free journey.

If you’d rather not travel by coach and are willing to shell out a little extra, book a private tour of Montepulciano that can be customizable with Chiara Fanti.


Behold the majestic beauty of Montalcino, a region of paramount importance in the world of wine, where the esteemed Brunello di Montalcino originates. This elevated perspective captures the essence of the vine-covered hills and the time-honored winemaking traditions that define this iconic Tuscan landscape.

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.

Top Wineries to Visit near Montalcino

Cantine Neri

Località Bardano, 28, 05018 Orvieto TR, Italy

+39 0763 316196

Experience the devotion to quality and tradition at this family-run estate, founded in 1971 by Giovanni Neri. Today, his son Giacomo continues the family’s commitment to crafting exceptional Brunello di Montalcino wines that express the unique terroir of the region. Join a guided tour and tasting to explore their range of critically acclaimed wines.

Poggio Antico

Loc. Poggio Antico, 53024 Montalcino SI, Italy

+39 0577 848044

Nestled amidst the picturesque hills of Montalcino, Poggio Antico is a family-owned winery that has been producing exceptional Brunello di Montalcino wines since 1984. Indulge in a tasting experience that showcases the winery’s dedication to elegance, balance, and complexity while taking in the panoramic views of the stunning Tuscan landscape.

Altesino Winery

Podere Capanna, 102, 53024 Montalcino SI, Italy

+39 347 328 4155

Step into the world of traditional Tuscan winemaking at Altesino, a family-owned winery renowned for its elegant and refined Brunello di Montalcino. Enjoy a guided tour of the estate, where you’ll learn about their innovative winemaking techniques and savor their exquisite wines that capture the essence of the Montalcino terroir.


Montefalco: A Tapestry of Vines and Olive Groves – Behold the captivating landscape of Montefalco, where vibrant vineyards and ancient olive trees weave a stunning patchwork across the idyllic Umbrian countryside. Wander through this scenic paradise and let the essence of Italy’s green heart charm your senses.

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!

Arnaldo Caprai Winery

Località Torre, 1, 06036 Montefalco PG, Italy

+39 0742 378802

Experience the passion for winemaking that has driven the Caprai family since 1971. Renowned for their dedication to Montefalco’s native Sagrantino grape, this winery offers a unique opportunity to taste world-class Sagrantino di Montefalco wines while learning about their innovative viticultural practices.

Antonelli San Marco Winery

Località S. Marco, 60, 06036 Montefalco PG, Italy

+39 0742 379158

Immerse yourself in the rich history and traditions of the Antonelli family’s winemaking, which dates back to 1881. Explore their sprawling estate and indulge in tastings of their Montefalco Sagrantino and Montefalco Rosso wines, crafted with dedication to the terroir and a commitment to sustainability.

Tenuta Bellafonte

Via Colle Nottolo, 2, 06031 Bevagna PG, Italy

+39 0742 710019

Discover the harmonious fusion of tradition and innovation at this family-owned winery. Nestled in the heart of Umbria, Tenuta Bellafonte produces exceptional Montefalco Sagrantino and Montefalco Rosso wines, focusing on minimal intervention to preserve the integrity of the grapes and showcase the region’s unique character.

Private Winery Tour in Montefalco

If you’d like to arrange an intimate tasting and tour of a family-operated winery in Montefalco ahead of time, look no further than Bocale Vini. The estate is stunning and vast, the wines are exceptional expressions of the local terroir, and the tour is operated by a family member. We have not yet heard one negative review.


Assisi at Twilight: A Symphony of Colors – As the sun dips below the horizon, the ancient town of Assisi is bathed in a breathtaking palette of fiery hues, casting a magical glow on the timeless stone facades. Embrace the serene beauty of this spiritual sanctuary as day turns to night.

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.

Antonelli San Marco Winery

Località S. Marco, 60, 06036 Montefalco PG, Italy

+39 0742 379158

Immerse yourself in the rich history and traditions of the Antonelli family’s winemaking, which dates back to 1881. Explore their sprawling estate and indulge in tastings of their Montefalco Sagrantino and Montefalco Rosso wines, crafted with dedication to the terroir and a commitment to sustainability.

Tenuta Bellafonte

Via Colle Nottolo, 2, 06031 Bevagna PG, Italy

+39 0742 710019

Discover the harmonious fusion of tradition and innovation at this family-owned winery. Nestled in the heart of Umbria, Tenuta Bellafonte produces exceptional Montefalco Sagrantino and Montefalco Rosso wines, focusing on minimal intervention to preserve the integrity of the grapes and showcase the region’s unique character.

Private Wine Tours in Assisi

Leave the bustling streets of Assisi behind book a tour wine a member of a local winemaking family. Venture to the picturesque hillsides for a wine tasting with breathtaking views of the Umbria Valley. Connect with a local winemaking family, and leisurely explore the estate’s vineyards and olive groves, taking in the stunning scenery. Unwind with an al fresco wine tasting, featuring four distinct organic wines, accompanied by an array of bruschette, extra-virgin olive oil, local cheeses, and cold cuts.

  • Experience local organic wines at a family-operated estate nestled in the hills near Assisi
  • Wander through the vineyard and olive grove at your leisure, admiring the picturesque views
  • Savor a variety of Umbrian specialties, from olive oil to organic jams
  • Select an afternoon time slot for your tasting to accommodate your schedule

Believe the Hype About Small Towns in Italy

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.”

Frequently Asked Questions about Italian Wine Towns

More Guides to Exploring Italy

Learn All About The Wine Region of Tuscany

Everything You Need To Know About Veneto

How To Explore Venice Italy in One Day

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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!

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