Tuscany & Umbria: The Ultimate Art Lover’s Itineraries
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Planning to visit Tuscany and Umbria in the heart of Italy? Excellent idea! If you love incredible art, gorgeous landscapes, fabulous food, and world-class wines, then consider dedicating at least a week (preferably two) to exploring these two iconic regions of Italy.
Tuscany will dazzle you with cities such as Florence, Siena (my favorite), and lovely little San Gimignano. These destinations are world-class, and for good reason.
Umbria, Italy’s “green heart”, offers a slower pace, fewer crowds, quieter towns, and some awesome art. Combine a visit to both Tuscany and Umbria to see the best of all possible worlds.
I’ve designed this itinerary to help you take a breath and slow down. Savor museum visits, balance famous sites with lesser-known gems, enjoy local specialties, and most of all, relax and let the history seep into your bones.
Table of Contents
Explore Italy’s artistic heartland by pairing the Renaissance brilliance of Tuscany with the spiritual calm and medieval charm of Umbria. This itinerary blends world-class museums, hill towns, and vineyard landscapes with quieter, more intimate experiences perfect for travelers who want depth without rushing. From Florence’s masterpieces to Siena’s medieval back streets, Orvieto’s dazzling Duomo to Assisi’s incredible frescoes, you’ll enjoy a beautifully paced journey through two regions rich in history, art, and timeless Italian beauty.
Itineraries at a Glance
Tuscany
- 3 nights in Florence – stay at Serristori Palace Residence
- 3 nights in Siena – stay at Hotel Athena
- 1 night in San Gimignano – stay at Hotel Pescille
Umbria
- 2 nights in Perugia – stay at Hotel Fortuna
- 2 nights in Assisi – stay at Tenuta San Masseo
- 2 nights in Orvieto – stay at Agriturismo Podere Pescara
Map of Tuscany & Umbria
The map of Tuscany and Umbria includes all the destinations mentioned in this post. Click a number to read more about the location.
Suggested Itineraries for Exploring Tuscany & Umbria
Explore both Tuscany and Umbria by car or home-base in one or more of the towns and take day tours to others.
For Tuscany, one strategy is to spend three nights in Florence (see my suggestions below for enjoying this most Renaissance of cities), three nights in Siena, and one or two nights in San Gimignano. During those seven days in the Tuscan countryside, be sure to take a wine tour.
For Umbria, divide your time between the three main towns: Orvieto, Perugia, and Assisi, and reserve time for enjoying the rugged countryside.
If you want to explore Tuscany and Umbria by car, pick up your rental car at the Florence airport. Avoid picking your car up at the train station or some other area in central Florence. You don’t need the headache of navigating your way out of the city. Also, if you drive into a ZTL (Traffic Limited Zone) in Florence, you will get ticketed and fined.
After picking up your car at the Florence airport, you’ll be out on the highway within minutes.
TIP: Bear in mind that driving in Tuscany and Umbria can be slow going. If you home-base in a specific area or town, reserve a few days for just staying put and enjoying la dolce vita. Spending every day driving the twisting, narrow roads gets tiring.
After a week (or maybe two!) in Tuscany, spend another week in Umbria if time allows. Perugia or Assisi are good choices.
Here are my recommendations for top towns to visit in Tuscany and Umbria.
Tuscany
If you have only a week to see Tuscany, make time for Florence and two of the other towns, such as Siena (my favorite) and San Gimignano, with perhaps a day trip to Montalcino or Volterra.
For accommodation recommendations, see Where to Stay in Italy: My Best Picks and individual recommendations in the descriptions below.
Florence
You kinda have to visit Florence (#1 on the map) because it’s, well, Florence. A sizable percentage of Italy’s finest art is found in Florence, and you owe it to yourself to see it.
Unfortunately, half of the known universe descends on Florence every day (or at least that’s how it feels). I remember wondering if the medieval Ponte Vecchio was strong enough to bear the throngs streaming across it.
To beat the mid-day crowds, opt for lesser known but still amazing sites, such as the Masaccio frescoes in the Brancacci Chapel across the river from central Florence, the medieval Palazzo Davanzatti, and the Museo Nazionale di San Marco which houses the frescoes by Fra Angelico.
Florence Highlights
• Accademia – Home to Michelangelo’s monumental David
• Duomo & Dome Climb – Brunelleschi’s soaring dome with unforgettable city views
• Ponte Vecchio – Florence’s medieval goldsmiths’ bridge glowing at sunset
• Piazza della Signoria – An open-air gallery of sculptures in the city’s civic heart
• Palazzo Davanzati – A beautifully preserved medieval townhouse offering an intimate glimpse into medieval Florentine life
• Brancacci Chapel – Masaccio’s groundbreaking frescoes that transformed Renaissance painting
• Museo Nazionale di San Marco – Ethereal frescoes by Fra Angelico in a serene monastic setting
Staying in Florence
My favorite place to stay in Florence is Serristori Palace Residence. Although on the pricey side, the residence is excellent value because of the size of the one-bedroom apartment, its high ceilings, panoramic view of the river, and excellent location about a ten-minute walk from the action.
Tours in Florence
Here are sightseeing suggestions for Florence. Make sure you purchase tickets ahead of time for the Uffizi and the Accademia.
Siena
Spend at least two nights, preferably more, in Siena (#2). Siena is my favorite city in Tuscany, with enough great artsy sightseeing to keep you as busy as you want to be. You’ll also have time to just hang out in Siena. Walk the narrow, cobbled streets, relax in the Campo, and eat a great meal or two complemented by good Tuscan wine.
When you arrive in Siena, head first to the Campo. If the weather is dry, plop down on the 700-year-old bricks and soak up the history.
Siena Highlights
• Piccolomini Library – Brilliant Renaissance frescoes by Pinturicchio celebrating the life of Pope Pius II
• Palazzo Pubblico – Siena’s medieval town hall overlooking the Campo, home to landmark civic frescoes
• Lorenzetti’s “Good and Bad Government” Frescoes – One of the most important political fresco cycles of the Middle Ages
• Piazza del Campo – The fan-shaped heart of Siena and one of Italy’s most beautiful public squares
• Torre del Mangia – A slender 14th-century tower offering sweeping views across Siena and the Tuscan hills
• Santa Maria della Scala – A former hospital turned museum complex with frescoes, archaeological finds, and sacred art
The Campo gets very crowded during the day. Arrive later in the afternoon, enjoy a glass of wine at one of the cafés bordering the piazza, and watch the crowds disperse as the sun turns the Torre Mangia golden. Your glass of wine will be overpriced, but who cares? You’ll have a ringside seat to one of Europe’s most beautiful public piazzas.
For a breakdown of what to see and do in Siena, see my post Sensational Siena: Best Things to Do, Top Sights and How to Visit.
Wine Tour
Allocate one of your days in Tuscany to taking a wine tour of the region. Choose a tour that includes Montalcino, home of the scrumptious (and potent) Brunello di Montalcino. The tour I took included a marvelous three-course lunch and visits to three wineries that also featured tastings.
Let your guide do the driving! Here’s a good option from GetYourGuide:
Staying in Siena
I recommend the I Merli di Ada which is in a quiet area of Siena, a short walk from the Campo.
Tours in Siena
Here are more sightseeing options in Siena.
San Gimignano
Yes, it’s crowded during the day with tour busses, but once they leave, you’ll have beautiful San Gimignano (#3), medieval city of towers, all to yourself. Enjoy top-class restaurants and stroll flood-lit streets. Little has changed, apart from the souvenir shops, in 700 years.
San Gimignano Highlights
• Chapel of Santa Fina – Ghirlandaio’s luminous frescoes honoring San Gimignano’s beloved saint
• Sant’Agostino – Benozzo Gozzoli’s elegant frescoes illustrating the Life of St. Augustine
• Historic Towers – Fourteen surviving medieval towers that shape the town’s dramatic skyline
• Piazza della Cisterna – A picturesque triangular square framed by stone palaces and towers
• Palazzo del Popolo & Civic Museum – Medieval art, local history, and access to the Torre Grossa for sweeping views
• Torre Grossa – The tallest tower in town, offering panoramic vistas across Tuscan vineyards and rolling hills
• San Gimignano 1300 – A detailed ceramic reconstruction of the town as it appeared in the year 1300, offering a fascinating window into its medieval past
For an in-depth look at San Gimignano and why it deserves top billing on your itinerary, read San Gimignano: Top Things to See in Tuscany’s Tower Town.
And if you’re looking for something to read while staying in San Gimignano, consider downloading The Towers of Tuscany, my award-winning novel about a female artist in San Gimignano and Siena in the 1300s.
Staying in San Gimignano
Stay overnight in San Gimignano so you can enjoy this magical city without the crowds. If you’re driving, good options are the Hotel Pescille and the Cappuccina Country Resort, both located outside the city.
Tours to San Gimignano
If you don’t have a car and/or time to stay overnight in San Gimignano, consider taking a day tour from Florence or Siena. Here are some options, some of which include other towns in the area.
Volterra
Fans of the Medici series on Netflix will recognize the town hall in Volterra (#4) as the stand-in for Florence’s Palazzo Vecchio.
Volterra, known as the City of Alabaster, is considerably less crowded than its neighbor, San Gimignano, and has just as much (maybe more) to offer the artsy traveler.
Volterra Highlights
• Guarnacci Etruscan Museum – One of Italy’s oldest museums, with extraordinary Etruscan urns, bronzes, and funerary sculptures
• Palazzo dei Priori – Tuscany’s oldest town hall, with medieval frescoes and a tower offering views over the rooftops
• Volterra Cathedral & Baptistery – A serene Romanesque interior with Renaissance additions and a striking octagonal baptistery
• Etruscan Gate (Porta all’Arco) – A monumental 4th-century BCE gateway still bearing its original stone heads
• Alabaster Workshops – Traditional craft studios where artisans carve Volterra’s famous translucent alabaster
• Medici Fortress – A dramatic hilltop stronghold dominating the skyline (viewable from outside only)
If you’re interested in the Etruscans, then Volterra is a must-see.
Staying in Volterra
Settle into a country place near Volterra and take a break from sightseeing. Agriturismo properties such as Agriturismo Pampilla are perfect places to while away a hot summer afternoon in Tuscany.
Tours in Volterra
You can find tours that take you around local wineries or teach you Tuscan cooking techniques. How about truffle hunting? That sounds very cool!
Lucca
The walled city of Lucca (#5) is a charming place to spend half a day. Walk along the top of the walls, visit Lucca Cathedral (Lucca is known as the city of a hundred churches so there’s more than enough to choose from), and breathe in the medieval atmosphere.
Lucca Highlights
• Duomo di San Martino – A graceful Romanesque cathedral with the exquisite Tomb of Ilaria del Carretto by Jacopo della Quercia
• San Michele in Foro – A dazzling marble façade rising above the site of Lucca’s ancient Roman forum
• Guinigi Tower – A medieval tower crowned with oak trees and sweeping views over Lucca’s red rooftops
• Piazza dell’Anfiteatro – An oval piazza built atop the remains of the Roman amphitheater, now ringed with cafés and shops
• Torre delle Ore – The city’s tallest tower, offering a classic climb and historic clock mechanism.
• Puccini Sites – Birthplace of composer Giacomo Puccini, with a dedicated museum celebrating his life and work
On one visit to Lucca, I saw a group of young people dressed in medieval garb presenting a flag-waving demonstration to the accompaniment of some serious medieval drumming. I was entranced.
Staying in Lucca
Lucca is a magical place to stay overnight. The virtually traffic-free streets have emptied of tourists, and you can stroll around the ramparts for a floodlit view. I stayed at Hotel Alla Corte degli Angeli which was inside the town walls. It was delightful!
Tours in Lucca
Here’s an interesting tour option for opera lovers visiting Lucca during the Puccini Festival:
Pisa
I’ve visited Pisa (#6) once, and that’s enough for me, although perhaps I’m being unfair. The area around the famous Leaning Tower teems with tacky souvenir stalls. I like a good tacky souvenir as much as the next gal, but even I reached my limit in Pisa.
That said, there are some interesting artsy sites to enjoy in Pisa. Your best bet is to go in the late afternoon and stay overnight. That way, you may be able to enjoy the tower and the cathedral without crowds.
Pisa Highlights
• Pisa Cathedral (Duomo) – A stunning Romanesque basilica with striped marble, glittering mosaics, and an elegant nave
• Baptistery – The largest in Italy, known for its perfect acoustics and remarkable blend of Romanesque and Gothic styles
• Camposanto Monumentale – A serene cemetery cloistered around medieval frescoes and ancient sarcophagi
• Museo dell’Opera del Duomo – Sculptures, treasures, and architectural fragments from the cathedral complex
• Piazza dei Miracoli – The “Square of Miracles,” a UNESCO masterpiece where all the major monuments unite in dazzling harmony
• Arno Riverside Walks – Charming riverside promenades lined with pastel façades and university energy
The cathedral is definitely worth visiting, and you must get someone to take the obligatory shot of you holding up the tower.
Staying in Pisa
For a place with a view of the leaning tower, check out the Grand Hotel Duomo.
Tours in Pisa
Here’s a guided tour of the baptistery, cathedral, and leaning tower that would be a good bet if you didn’t purchase tickets in advance:
Other Towns in Tuscany
Tuscany is one of the largest provinces in Italy, with many worthwhile hill towns to visit, including Montalcino, Montepulciano, Monteriggioni, Cortono, and Pienza.
Check out my post about a country resort I stayed at in Montepulciano: Stay at Sant’Antonio Country Resort near Spectacular Montepulciano in Tuscany. It was awesome!
All these small towns in Tuscany are best visited by car. Driving in Tuscany is relatively easy but not speedy. The roads are narrow and twisting. Slow down, relax, and enjoy the journey.
TIP: Never (and I mean never!) attempt to drive into a Tuscan hill town. First, you risk getting a stiff fine (being a tourist is no excuse), second, you risk ripping one or both of your side mirrors off your rental car, and third, you risk never again speaking to your partner.
Find the parking lot outside the city walls and walk into the town. Yes, you’ll likely be walking uphill (that’s why they are called hill towns), but some towns, such as San Gimignano, thoughtfully provide an elevator to take you from the car park to the town.
Others don’t, but if you’re going to travel in Tuscany, you need to be up for some good, stiff walking.
Umbria
Umbria (#7) has much to offer the artsy traveler. The landscape is just as stunning as the landscape in Tuscany, with even more rugged mountains, and the hill towns are just as interesting and historic.
Highlights include Perugia, Assisi, Gubbio, and Orvieto.
Perugia
Perugia (#8) is the capital of Umbria and one of its largest towns. Enjoy strolling around the central piazza and ducking into the cathedral. Perugia is laid-back and not overly crowded.
Perugia Highlights
• Piazza IV Novembre – The city’s grand central square, anchored by the elegant Fontana Maggiore and the cathedral façade
• Fontana Maggiore – A 13th-century marble fountain adorned with scenes of daily life, zodiac signs, and biblical storie.
• Palazzo dei Priori – A monumental Gothic palace housing important civic halls and the National Gallery
• Perugia Cathedral (San Lorenzo) – A striking interior with notable artworks, including the Baroque sacristy and relics of local saints
• Rocca Paolina – An incredible underground fortress and “hidden city” of vaulted corridors built by the papacy
• Corso Vannucci – The lively main street lined with shops, cafés, and the perfect atmosphere for an evening stroll
The highlight of my visit to Perugia was discovering the Civic Museum at the Palazzo della Penna. There, I viewed the work of Gerardo Dottori, the leader of the Umbrian Futurists and one of the founders of Aeropainting.
The Palazzo della Penna is one of Perugia’s little-known museums and worth seeking out. It’s constructed on the ruins of a Roman amphitheater and an ancient Roman road.
One of the highlights of artsy traveling is looking for these lesser known but amazing small museums (of which Italy has many). They are almost always deserted, and most contain marvelous collections.
Assisi
Assisi is delightful. It does get crowded because of the famous Giotto frescoes, but not as crowded as Florence. Definitely stop in and even stay the night if you can. The frescoes are worth the journey, and the town itself is a great place to wander.
Assisi Highlights
• Giotto’s Life of St. Francis – Revolutionary narrative frescoes that mark a turning point in Western art
• Basilica of Santa Chiara – A serene Gothic church housing the relics of St. Clare and early Franciscan artworks
• Piazza del Comune – The ancient Roman forum turned central square, framed by medieval palaces and the Temple of Minerva
• Temple of Minerva – A remarkably preserved Roman temple with a striking Corinthian façade
• Eremo delle Carceri – A peaceful hermitage in the Monte Subasio woods where St. Francis retreated to pray
• Rocca Maggiore – A dramatic hilltop fortress offering sweeping panoramas over Assisi and the Umbrian valley
One of the hippest things I saw during our visit to Assisi (#9) wasn’t even on the tourist radar. I spied a small sign in a side street advertising a special exhibition of medieval costumes. As an historical novelist with a yen for all things medieval and Italian, I’d found my bliss.
Here are a few of the costumes on display in the exhibition.
When traveling to small towns in Tuscany and Umbria, check at the tourist office for local exhibitions and events and keep an eye out for posters. You never know what gems you’ll find.
Also taking place while we were in Assisi was an annual festival where all the locals dressed in medieval garb and paraded through the streets. Many other events were included in the festival, but we had neglected to get tickets.
More reason to do your research before you go!
The big draw to Assisi is, of course, the Basilica of Saint Francis of Assisi, with its marvelous frescoes by Giotto. Start your visit to Assisi here, then walk up into the medieval town, and from there continue up to the fortezza for some stunning views.
Where to Stay in Assisi
The highly rated Hotel Umbra is right in the centre of Assisi.
Tours in Assisi
Here’s a guided tour of the Basilica of Saint Francis of Assisi that would help you interpret Giotto’s famous frescoes:
Gubbio
What a delightful town! Nicknamed the City of Fools, Gubbio (#10) is unpretentious and relaxed. We spent a pleasant day wandering its cobbled streets, enjoying lunch in the panoramic Piazza Grande, and visiting the municipal museum.
Gubbio Highlights
• Piazza Grande – A dramatic terrace-like square suspended above the city with sweeping views of rooftops and hills
• Roman Theater – One of Italy’s best-preserved ancient theaters, set just outside the medieval walls
• Gubbio Cathedral – A serene Gothic interior with a graceful rose window and notable Renaissance paintings
• Basilica of Sant’Ubaldo – Reached by funicular, home to the patron saint’s relics and magnificent views over the Umbrian valley
• Funivia Colle Eletto – A charming open-air cable car offering a scenic ride up to Monte Ingino
• Historic Ceramics & Craft Shops – Traditional artisans producing Gubbio’s famous maiolica and ceramics
One of the fun attractions of Gubbio is the Big Barrel, otherwise known as La Botte dei Canonici. The barrel is reputed to be the world’s largest and oldest. It’s worth a photo op, and there’s a gift shop. Entrance is free, so if you pass it during your wanderings around Gubbio, pop in and find out more.
We also checked out the Roman Theatre outside the walls of Gubbio near where we parked.
Remember: always park outside the city walls!
Orvieto
The stunning cathedral is the draw to Orvieto (#11), a beautiful Umbrian town perched atop a volcanic plug and worth an overnight stay.
Orvieto Highlights
• Signorelli’s Last Judgment Frescoes – A dramatic, visionary cycle in the San Brizio Chapel that influenced Michelangelo
• Pozzo di San Patrizio (St. Patrick’s Well) – A remarkable double-helix well designed for mules to descend and ascend without crossing paths
• Orvieto Underground – A network of ancient tunnels, caves, and Etruscan passageways carved beneath the city
• Torre del Moro – A medieval clock tower offering panoramic views of Orvieto and the surrounding countryside
• Etruscan Museum (Museo Archeologico Nazionale) – Outstanding artifacts, urns, and bronzes revealing Orvieto’s ancient past
• Piazza della Repubblica & Historic Streets – Atmospheric lanes lined with stone buildings, cafés, and artisan shops
Unlike its better-known Tuscan counterparts, Orvieto is relaxed and approachable. Park in the large lot at the bottom of the hill and take the elevator or escalator to the medieval upper town.
The façade of the cathedral is unusual in its inclusion of golden mosaics, sculpture, and stained glass.
For more information about what to see in Orvieto, check out this article by Rick Steves, my fave travel writer.
Where to Stay in Orvieto
Orvieto makes a good homebase for touring Umbria. Borgo La Chiaracia Resort & Spa is a posh option outside the town that features a spa. Treat yourself!
Tours in Orvieto
Here are some options, including a tour from Rome that takes you to Orvieto and Assisi, a good choice if your time is limited.
Tuscany & Umbria FAQs
I’ve traveled a lot in Tuscany and Umbria. Here are the questions I get asked most often:
A week to ten days is ideal for exploring both regions without rushing. This gives you time to spend at least two nights each in Florence and Siena in Tuscany, and then to explore Orvieto, Assisi, and Perugia in Umbria. With fewer days, focus on just one region; with more time, you can add visits to towns such as San Gimignano, Volterra, Montalcino, and Montepulciano.
Yes. Tuscany attracts far more international visitors, especially Florence, which can be painfully overcrowded. Umbria feels quieter and more authentic, with smaller crowds even in major towns such as Assisi and Orvieto. Umbria is an optimal choice if you’re looking to savor Italy’s medieval charm without tour groups.
If you want to explore the countryside, stay in rural hotels, and visit smaller towns then yes, a car is recommended. Rent one from the airport in Florence after you’ve toured the city (don’t drive into Florence!). If you prefer public transit, you can reach Siena and Orvieto by train from Florence, and other towns by bus, although schedules can be limited. Another option is to home base in Siena or Florence and take small group or private tours around the region.
Florence is best for art lovers and museum visits, while Siena works well if you prefer a quieter, more medieval atmosphere and easier access to the countryside. For wine and hill towns, consider basing in the Val d’Orcia near Pienza or Montepulciano, or stay near San Gimignano and visit Volterra and Cortona.
Orvieto and Assisi both make excellent bases. Orvieto offers dramatic views, a spectacular cathedral, and good train connections. Assisi has a peaceful atmosphere and some of Italy’s most important fresco cycles. Perugia works well if you prefer a lively university city with excellent museums.
Partially. Major cities such as Florence, Siena (via bus), Arezzo, Orvieto, Perugia, and Assisi are connected by train. However, public transportation rarely reaches the hill towns, vineyards, or smaller villages. If you don’t want to drive, choose your bases carefully and rely on guided day tours for harder-to-reach places.
Tuscany is known for its Renaissance art, wine towns, and famous cities like Florence and Siena. Umbria is quieter, greener, and more spiritual, with medieval hill towns, important fresco cycles such as those by Giotto in Assisi, and far fewer crowds. Visiting both gives you a rich contrast between Italy’s artistic heart and its peaceful countryside soul.
Keep Exploring Italy with Artsy Traveler
Here are more posts to give you a taste of Italy. Check Visiting Italy to see the full list of posts about Italy.
- Ten Must-See Art Masterpieces in Tuscany
- Beyond Romeo and Juliet: What to See in Verona, Italy
- Exploring Tuscany, Umbria and La Dolce Vita
- 3 Days in Venice: Best Itinerary for First-Time Visitors
- Rome in 3 Days: Best Itinerary for First-Time Visitors
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Love your descriptions! If you were going to pick a home base in each area (Umbria and Tuscany) which would allow you to explore the nearby towns, which two cities would you pick?
I’d pick Siena in Tuscany and Perugia or Orvieto in Umbria! You can’t really go wrong. So much to see!
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