Planning a trip to Italy and can’t decide between cypress-lined Tuscan hills or the rustic calm of Umbria? You’re not alone, the Tuscany vs Umbria debate has been going on for years among travelers who love wine, food, and slow-paced culture. Tuscany brings world-famous Chianti vineyards, glamorous villas, and iconic postcard views, while Umbria keeps things more intimate with medieval towns like Assisi and Orvieto, rolling green landscapes, and fewer crowds. With countless family-run wineries in Umbria, the region is also a paradise if you love wine. This guide breaks down what makes each special so you can pick your perfect match, or better yet, plan to experience both.
Tuscany vs Umbria: What are the best things to do?
Wander through Assisi and the Basilica of Saint Francis
Assisi is the soul of Umbria, a town where cobbled streets lead to one of Italy’s most celebrated basilicas. Inside, Giotto’s and Cimabue’s frescoes still glow with color, pulling you into centuries of art and devotion. Beyond the history, the town has a calm rhythm that makes it perfect for slowing down, tasting local food, and even joining one of the authentic Assisi wine tours that bring Umbrian flavors to life. With sweeping countryside views and a spirit that lingers long after you leave, Assisi deserves a spot on any itinerary.
Unlock the best Assisi things to do if you love art, food, and if you are a curious traveler!
Explore the Renaissance charms of Florence
No trip through Tuscany is complete without soaking up the beauty of Florence. From Michelangelo’s David at the Accademia to the Uffizi’s masterpieces, the city is a living gallery of the Renaissance. But it’s not just about art, evenings mean lively piazzas, elegant wine bars, and unforgettable Florence wine tours that connect you to the region’s flavors. Florence blends culture, food, and atmosphere in a way that keeps travelers coming back again and again.
Discover the top things to do in Florence for an unforgettable Tuscan city escape.
Visit the hilltop allure of Montepulciano
Montepulciano is Tuscany at its most iconic, stone streets winding uphill, piazzas framed by Renaissance palaces, and views that stretch across endless vineyards. The town is also home to celebrated Montepulciano wineries, where tastings take you underground into centuries-old cellars or out onto sunny terraces overlooking the hills. It’s a place where wine, history, and atmosphere come together effortlessly.
Catchy phrase: Explore the best things to do in Montepulciano for wine lovers, culture seekers, and anyone chasing that classic Tuscan vibe.
Explore Orvieto
Orvieto, perched dramatically on a volcanic cliff, is one of the crown jewels of Umbria. Beyond its breathtaking Duomo, the town is also celebrated for the crisp and elegant Orvieto DOC white wine, crafted from Grechetto and Trebbiano grapes. Exploring medieval streets, savoring local vintages in hidden enotecas, and taking in the views from the clifftop are among the most rewarding things to do in Orvieto, making it a perfect blend of history, flavor, and scenery.
Walk the historic streets of Siena
Close to Florence yet proudly unique, Siena charms with its striped Gothic cathedral, shell-shaped Piazza del Campo, and winding medieval lanes. Between sightseeing, settle into cozy enotecas for memorable Siena wine tours, where bold Tuscan reds meet hearty local dishes. This city blends culture and cuisine in a way that feels both timeless and inviting.
Experience the must-try things to do in Siena, Italy like a local!
Visit the vineyard trails of Montefalco
Often called the “Balcony of Umbria,” Montefalco is the birthplace of the bold red Sagrantino di Montefalco. The town is a dream for wine lovers eager to dive into an Umbrian varietal with real depth and aging potential. Beyond the glass, cobbled streets, sweeping valley views, and a laid-back pace make it easy to see why so many travelers choose to visit Montefalco Italy for an authentic taste of the region.
Explore the enchanting Spello
With its vibrant flower displays and traces of ancient Rome, Spello is one of Umbria’s prettiest small towns. It’s known for top-quality olive oil, quiet streets that burst into color during the Infiorata flower festival, and frescoes by Pietro Perugino. Scenic walks through olive groves and sweeping countryside views are just a few of the unforgettable things to do in Spello Italy, making it a must for travelers who love beauty in the details.
Relax by the tranquil shores of Lake Trasimeno
Lake Trasimeno is Umbria’s largest lake, a peaceful stretch of water framed by vineyards and villages crowned with castles. It’s perfect for a lakeside picnic, a lazy ferry ride to the islands, or an afternoon of simple food and wine tastings. Stops like this capture the heart of the Tuscany vs Umbria debate, quieter, more rustic experiences that feel worlds away from Tuscany’s busier hotspots.
Discover Pisa beyond the leaning tower
While the Leaning Tower steals the spotlight, Pisa has plenty more to offer. Wander along the Arno River promenade, step inside elegant churches, or take a break in a café buzzing with student life. Beyond the monuments, the city also surprises with wine tasting Pisa experiences, where local flavors meet Tuscan tradition. Just a short train or bus ride from Florence, it’s an easy and rewarding escape.
Enjoy our tips and your insider guide to the must-try things to do in Pisa!
Walk into the medieval magic of Gubbio
Gubbio is a medieval town frozen in time, with cobbled alleys, stone houses, and traditions that have barely changed in centuries. Hop on the open-air funicular up Mount Ingino for sweeping views, then wander back down through streets where every corner hides a story. Exploring these highlights is among the most unforgettable things to do in Gubbio Italy, especially if you love history wrapped in atmosphere.
Tour the enchanting streets of Perugia
The capital of Umbria, Perugia blends cosmopolitan energy with layers of Etruscan and Roman history. You can dive into masterpieces at the Galleria Nazionale dell’Umbria, wander ancient underground passageways, or sweeten the day with chocolate from its hometown factories. Wine lovers will also find plenty to explore thanks to nearby Perugia wineries, where Umbrian flavors take center stage.
Taste, explore, and wander through the top things to do in Perugia!
Visit Todi for classic Umbrian grace
Todi is a small yet elegant town with winding alleys, terracotta rooftops, and sweeping views that stretch for miles. It’s one of those off-the-beaten-path gems that makes Umbria feel like an explorer’s dream. Add a visit Todi Italy stop to your itinerary and you’ll discover a town that mixes charm, history, and tranquility in every corner.
Sip the world’s icons with Tuscany wine
From Chianti to Brunello di Montalcino and Vino Nobile di Montepulciano, Tuscany wine is the definition of Italian prestige. Here, vineyards roll across golden hillsides, historic estates open their doors for tastings, and every glass tells a story rooted in centuries of tradition. You’re swirling a bold Super Tuscan or sipping a lighter Vernaccia in San Gimignano, tasting wine in Tuscany means indulging in labels that have shaped Italy’s global reputation.
Taste rustic elegance with Umbria wine
Less famous but equally captivating, Umbria wine offers authenticity with every pour. Picture a glass of Sagrantino di Montefalco with its bold tannins, an elegant Montefalco Rosso, or a crisp Orvieto white, wines that taste rooted in the land itself. Here, tastings often happen in family-run cellars or small enotecas where tradition is part of the experience. Exploring these vineyards gives a whole new perspective on Tuscany vs Umbria, showing how Umbria holds its own with soulful wines and an intimacy that Tuscany’s bigger names can’t always match.
Tuscany vs Umbria: Good to know
Is Umbria or Tuscany better?
It depends on the type of experience you’re looking for. Tuscany is more famous and often more crowded, with iconic cities like Florence and Siena, rolling vineyards in Chianti, and world-class art. Umbria, on the other hand, offers a quieter, more tranquil vibe with medieval hill towns, lush countryside, and fewer tourists. If you’re after a more off-the-beaten-path experience, Umbria may be your choice. But for iconic Italian scenery and Renaissance history, Tuscany remains unbeatable.
What is the prettiest town in Umbria?
The town of Spello is often considered one of the prettiest in Umbria. Perched on the slopes of Mount Subasio, it charms visitors with flower-filled balconies, well-preserved Roman gates, cobbled streets, and quaint stone houses. Other beautiful contenders include Assisi, known for its spiritual atmosphere and architecture, and Orvieto, with its dramatic location on a volcanic plateau and its stunning Gothic cathedral.
What is the prettiest town in Tuscany to visit?
Pienza is widely regarded as one of the most picturesque towns in Tuscany. Located in the heart of the Val d’Orcia, it’s a UNESCO World Heritage Site known for its harmonious Renaissance architecture and panoramic countryside views. Other favorites include San Gimignano, famous for its medieval towers, and Montepulciano, beloved for wine and scenic vistas.
Is Umbria the new Tuscany?
Umbria is often dubbed “the new Tuscany” because it offers similar landscapes, rich history, and culinary traditions, yet remains less commercialized and more affordable. While it may not have the same global recognition, Umbria has increasingly become a destination for travelers seeking authentic Italian culture without the crowds. However, rather than replacing Tuscany, Umbria complements it as a more intimate and undiscovered experience.
What are the best hotels to stay?
In Tuscany:
- Castello di Casole – A Belmond Hotel offering a luxurious countryside escape near Siena
- Borgo Santo Pietro – A five-star estate in Chiusdino blending elegance and serenity
- Hotel Lungarno – Overlooking the Arno River in Florence, perfect for a city stay.
In Umbria:
- Relais Todini – Located in the heart of Umbria, on top of hill surrounded by vineyards, this historic property offers stunning views of the area
- La Locanda del Capitano – A charming boutique inn in Montone, offering local delights
- Palazzo Seneca – A refined Relais & Chateaux property in Norcia, ideal for food lovers
What are the best restaurants?
In Tuscany:
- Osteria le Logge (Siena) – A top choice for classic Tuscan cuisine with a gourmet twist.
- Trattoria Da Burde (Florence) – A longstanding favorite for hearty Florentine fare.
- La Porta (Monticchiello) – Small village charm with spectacular views and cuisine.
In Umbria:
- La Bastiglia (Spello) – Known for refined Umbrian cuisine and scenic dining.
- Enoteca Pinchiorri (Assisi) – A mix of traditional and innovative dishes with a great wine list.
- Trattoria del Moro Aronne (Orvieto) – Family-run spot serving local pasta and truffles.
Which region is better for wine lovers: Tuscany or Umbria?
Tuscany is world-renowned for classics like Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano, making it a dream for wine lovers. However, Umbria’s wine scene is rising, offering hidden gems like Sagrantino di Montefalco and crisp Orvieto whites. While Tuscany has the prestige, Umbria provides a more intimate and less commercial tasting experience.
What is the best time of year to visit Tuscany and Umbria?
Spring (April to June) and fall (September to October) are the best times to visit both Tuscany and Umbria. These months offer pleasant weather, fewer tourists, and vibrant natural landscapes, wildflowers in spring and grape/olive harvests in fall. Summer can be hot and crowded, especially in Tuscany, while winter is quieter and suitable for food and wine retreats.
Can you explore both regions in one trip?
Absolutely. Tuscany and Umbria are neighboring regions, and it’s quite feasible to explore both in one trip. Cities like Cortona (Tuscany) and Perugia (Umbria) are only 1–2 hours apart by car. Renting a car is highly recommended to fully enjoy the scenic drives and small towns. A 10- to 14-day itinerary would allow you to experience a satisfying blend of both regions’ highlights.
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