40 days in Umbria & Tuscany Itinerary

40 days in Umbria & Tuscany Itinerary

Created using Inspirock Italy sightseeing planner

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1
Orvieto
— 1 night
Drive
2
Todi
— 2 nights
Drive
3
Assisi
— 1 night
Drive
4
Perugia
— 1 night
Drive
5
Montalcino
— 1 night
Drive
6
Siena
— 1 night
Drive
7
San Gimignano
— 1 night
Drive
8
Greve in Chianti
— 1 night
Drive
9
Florence
— 1 night
Drive
10
Lucca
— 1 night
Drive
11
Pisa
— 1 night
Drive
12
Gubbio
— 3 nights
Drive
13
Spoleto
— 3 nights
Drive
14
Trevi
— 7 nights
Drive
15
Volterra
— 2 nights
Drive
16
Castiglione del Lago
— 2 nights
Drive
17
Collodi
— 2 nights
Drive
18
Spello
— 2 nights
Drive
19
Cortona
— 2 nights
Drive
20
Pitigliano
— 3 nights
Drive

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Orvieto

— 1 night

Green Heart of Italy

The striking town of Orvieto, perched on a volcanic cliff overlooking the Umbrian countryside, is known as the Green Heart of Italy.
Kick off your visit on the 21st (Sun): do a tasting at Decugnano dei Barbi, don't miss a visit to Pozzo di San Patrizio, explore the fascinating underground world of Orvieto Underground, then admire the striking features of Duomo di Orvieto, and finally enjoy breathtaking views from Torre del Moro.

To find traveler tips, maps, ratings, and other tourist information, you can read our Orvieto trip maker site.

Plovdiv, Bulgaria to Orvieto is an approximately 10.5-hour combination of train and flight. You can also drive; or do a combination of train and bus. Due to the time zone difference, you'll gain 1 hour traveling from Plovdiv to Orvieto. In June, plan for daily highs up to 32°C, and evening lows to 17°C. Finish up your sightseeing early on the 21st (Sun) so you can go by car to Todi.

Things to do in Orvieto

Wineries · Historic Sites · Parks · Nature

Todi

— 2 nights
Todi is a town and comune (municipality) of the province of Perugia (region of Umbria) in central Italy. On the 22nd (Mon), make a trip to Piazza del Popolo, then take a stroll through Centro Storico di Todi, then pause for some serene contemplation at Tempio di Santa Maria della Consolazione, and finally take in the architecture and atmosphere at Chiesa di San Fortunato. On your second day here, pause for some serene contemplation at Chiesa della Nunziatina, learn about winemaking at Cantina Peppucci, identify plant and animal life at Leo Wild Park, then pause for some serene contemplation at Cattedrale della Santissima Annunziata, and finally pause for some photo ops at Palazzo del Capitano.

To see photos, other places to visit, more things to do, and tourist information, you can read our Todi route maker app.

You can drive from Orvieto to Todi in an hour. In June, daily temperatures in Todi can reach 32°C, while at night they dip to 18°C. Finish your sightseeing early on the 23rd (Tue) so you can drive to Assisi.

Things to do in Todi

Historic Sites · Neighborhoods · Parks · Wildlife

Assisi

— 1 night

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Start off your visit on the 24th (Wed): contemplate in the serene atmosphere at Cripta di San Francesco, pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, look for all kinds of wild species at Bosco di San Francesco, then take in the spiritual surroundings of Eremo delle Carceri, and finally step into the grandiose world of Rocca Maggiore.

To find where to stay, reviews, other places to visit, and other tourist information, read Assisi day trip tool.

Getting from Todi to Assisi by car takes about an hour. June in Assisi sees daily highs of 32°C and lows of 18°C at night. Wrap up your sightseeing on the 24th (Wed) to allow time to drive to Perugia.

Things to do in Assisi

Historic Sites · Parks · Wildlife

Perugia

— 1 night

Green Heart of Italy

Though it features Etruscan defensive walls and a medieval town center, Perugia is perhaps best known for its fine chocolate and annual chocolate festival.
Start off your visit on the 25th (Thu): learn the tricks of the trade with Casa del Cioccolato Perugina, then explore the activities along Lake Trasimeno, then take a stroll through City Centre, and finally explore the world behind art at Galleria Nazionale dell'Umbria.

For traveler tips, maps, photos, and more tourist information, refer to the Perugia trip maker site.

Perugia is very close to Assisi. In June, plan for daily highs up to 32°C, and evening lows to 18°C. Wrap up your sightseeing on the 25th (Thu) to allow time to drive to Montalcino.

Things to do in Perugia

Museums · Neighborhoods · Parks · Shopping

Montalcino

— 1 night

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Kick off your visit on the 26th (Fri): do a tasting at Mate Winery, learn about winemaking at Podere Il Cocco, then learn about winemaking at Ciacci Piccolomini d'Aragona, and finally contemplate the long history of Abbazia di Sant'Antimo.

To find photos, ratings, other places to visit, and more tourist information, use the Montalcino trip planning site.

Drive from Perugia to Montalcino in 1.5 hours. Alternatively, you can take a bus. In June, daily temperatures in Montalcino can reach 34°C, while at night they dip to 19°C. Finish up your sightseeing early on the 26th (Fri) so you can go by car to Siena.

Things to do in Montalcino

Wineries · Historic Sites

Siena

— 1 night

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 27th (Sat), get interesting insight from Tours, then take in panoramic vistas at Torre del Mangia, then pause for some serene contemplation at Duomo di Siena, and finally see the interesting displays at Museo di Storia Naturale dell'Accademia dei Fisiocritici.

To find photos, reviews, ratings, and more tourist information, you can read our Siena tour itinerary planning tool.

Traveling by car from Montalcino to Siena takes an hour. Alternatively, you can take a bus; or do a combination of bus and train. In June, daytime highs in Siena are 34°C, while nighttime lows are 19°C. Finish up your sightseeing early on the 27th (Sat) so you can go by car to San Gimignano.

Things to do in Siena

Outdoors · Tours · Wildlife · Historic Sites

San Gimignano

— 1 night

Town of Fine Towers

A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
On the 28th (Sun), contemplate the long history of Historic Centre of San Gimignano, then do a tasting at Guardastelle Vineyard, and then get engrossed in the history at Museo della Tortura di San Gimignano.

For maps, ratings, traveler tips, and tourist information, refer to the San Gimignano vacation planning website.

Drive from Siena to San Gimignano in an hour. Alternatively, you can take a bus; or take a train. In June in San Gimignano, expect temperatures between 32°C during the day and 18°C at night. Cap off your sightseeing on the 28th (Sun) early enough to go by car to Greve in Chianti.

Things to do in San Gimignano

Historic Sites · Wineries · Museums

Greve in Chianti

— 1 night
Start off your visit on the 29th (Mon): indulge your taste buds at Castello di Verrazzano, then do a tasting at Accademia del Buon Gusto, then explore the historical opulence of Castello di Monterinaldi, and finally do a tasting at Wine Gourmet La Ripa.

To find other places to visit, ratings, photos, and more tourist information, use the Greve in Chianti trip planner.

You can drive from San Gimignano to Greve in Chianti in an hour. Alternatively, you can take a bus; or do a combination of train and bus. June in Greve in Chianti sees daily highs of 32°C and lows of 18°C at night. Cap off your sightseeing on the 29th (Mon) early enough to go by car to Florence.

Things to do in Greve in Chianti

Wineries · Historic Sites

Side Trip

Florence

— 1 night

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 30th (Tue), admire the masterpieces at Florence Academy of Fine Arts, relax and float downstream with a rafting and tubing tour, don't miss a visit to Piazzale Michelangelo, get to know the fascinating history of Piazza del Duomo, then take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, and finally appreciate the history behind Loggia dei Lanzi.

To see photos, more things to do, reviews, and tourist information, use the Florence itinerary app.

Traveling by car from Greve in Chianti to Florence takes an hour. In June, daily temperatures in Florence can reach 33°C, while at night they dip to 21°C. Wrap up your sightseeing on the 30th (Tue) to allow time to drive to Lucca.

Things to do in Florence

Outdoors · Historic Sites · Adventure · Tours

Lucca

— 1 night

City of a Hundred Churches

Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Kick off your visit on the 1st (Wed): contemplate the long history of Le mura di Lucca, take in the architecture and atmosphere at Basilica of San Frediano, admire the landmark architecture of St Martin Cathedral, then take in the spiritual surroundings of San Michele in Foro, then take in the architecture and atmosphere at Chiesa di Sant'Agostino, and finally admire the natural beauty at Palazzo Pfanner.

To find photos, more things to do, reviews, and other tourist information, go to the Lucca trip planner.

Traveling by car from Florence to Lucca takes 1.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Florence in June, Lucca is little chillier at night with lows of 18°C. Finish your sightseeing early on the 1st (Wed) to allow enough time to drive to Pisa.

Things to do in Lucca

Historic Sites · Parks

Pisa

— 1 night
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Start off your visit on the 2nd (Thu): enjoy breathtaking views from Leaning Tower of Pisa.

Ask Inspirock to suggest an itinerary and make planning a trip to Pisa fast, fun, and easy.

Pisa is just a short distance from Lucca. In July, daily temperatures in Pisa can reach 35°C, while at night they dip to 21°C. On the 2nd (Thu), wrap the sightseeing up by early afternoon so you can drive to Gubbio.
Highlights from your trip

Gubbio

— 3 nights
Gubbio is a town and comune in the far northeastern part of the Italian province of Perugia (Umbria). Step out of the city life by going to Parco del Sasso Simone e Simoncello and Passeggiata Acquedotto Medievale "Gola del Bottaccione" Gubbio. Do some cultural sightseeing at Palazzo dei Consoli and Museo Civico and Basilica of Saint Ubaldo. Explore the numerous day-trip ideas around Gubbio: Grotte di Frasassi (in Genga), Azienda Agraria Guerrieri (in Piagge) and Paper and Watermark Museum Fabriano (in Fabriano). Next up on the itinerary: take in the architecture and atmosphere at Chiesa di San Francesco, admire the landmark architecture of Cattedrale di Gubbio, don't miss a visit to Piazza Grande, and explore the ancient world of Teatro Romano.

To see maps, more things to do, ratings, and tourist information, use the Gubbio trip planner.

Drive from Pisa to Gubbio in 3 hours. Alternatively, you can do a combination of train and bus; or take a bus. In July, daily temperatures in Gubbio can reach 34°C, while at night they dip to 23°C. Wrap up your sightseeing on the 5th (Sun) to allow time to drive to Spoleto.

Things to do in Gubbio

Parks · Nature · Wildlife · Historic Sites

Side Trips

Spoleto

— 3 nights
Spoleto is an ancient city in the Italian province of Perugia in east central Umbria on a foothill of the Apennines. Start off your visit on the 6th (Mon): pause for some serene contemplation at Chiesa di Sant’Agostino, then appreciate the views at Piana di Castelluccio di Norcia, then snap pictures at Ponte delle Torri, and finally pause for some serene contemplation at Cattedrale di Santa Maria Assunta Spoleto. Get ready for a full day of sightseeing on the next day: contemplate in the serene atmosphere at Basilica di Santa Rita, identify plant and animal life at Le Fonti del Clitunno, contemplate the long history of Piazza del Duomo, then make a trip to Casa Menotti, and finally explore the historical opulence of La Rocca.

To see other places to visit, ratings, and more tourist information, refer to the Spoleto trip planner.

Traveling by car from Gubbio to Spoleto takes 1.5 hours. Alternatively, you can take a train. July in Spoleto sees daily highs of 36°C and lows of 21°C at night. Wrap up your sightseeing by early afternoon on the 8th (Wed) to allow time for the car ride to Trevi.

Things to do in Spoleto

Historic Sites · Parks · Nature · Wildlife

Side Trips

Trevi

— 7 nights
Visiting Lago di Pilato and Monte Vettore will get you outdoors. Borgo di Trevi and Villa Fabri are good opportunities to explore the local culture. You'll find plenty of places to visit near Trevi: Cantina Bartoloni (in Giano dell'Umbria), Museo della Vespa (in Pollenza) and Loro Piceno (Museo delle Due Guerre Mondiali & Castello Brunforte).

For other places to visit, maps, traveler tips, and other tourist information, read Trevi online itinerary planner.

Trevi is just a stone's throw from Spoleto. Expect a daytime high around 37°C in July, and nighttime lows around 20°C. Finish up your sightseeing early on the 15th (Wed) so you can travel to Volterra.

Things to do in Trevi

Historic Sites · Wineries · Parks · Museums

Side Trips

Volterra

— 2 nights
Volterra is a walled mountaintop town in the Tuscany region of Italy of which its history dates to before the 7th century BC and has substantial structures from the Etruscan, Roman, and Medieval periods.HistoryVolterra, known to the ancient Etruscans as Velathri or Vlathri and to the Romans as Volaterrae, is a town and comune in the Tuscany region of Italy. Start off your visit on the 16th (Thu): view the masterpieces at Societa Cooperativa Artieri Alabastro, step into the grandiose world of Palazzo dei Priori, take an in-depth tour of Palazzo Viti, contemplate the long history of Piazza dei Priori, then delve into the distant past at Roman Theatre, and finally steep yourself in history at Cathedral of Santa Maria Assunta. Get ready for a full day of sightseeing on the 17th (Fri): examine the collection at Museo Etrusco Guarnacci, view the masterpieces at L'Artista Gallery, then get engrossed in the history at Museo della Tortura, then delve into the distant past at Porta all'Arco, and finally do a tasting at Batzella.

For traveler tips, reviews, more things to do, and tourist information, go to the Volterra planning tool.

Drive from Trevi to Volterra in 3 hours. In July, plan for daily highs up to 35°C, and evening lows to 21°C. Finish up your sightseeing early on the 17th (Fri) so you can travel to Castiglione del Lago.

Things to do in Volterra

Historic Sites · Museums · Wineries · Shopping

Side Trip

Castiglione del Lago

— 2 nights
Castiglione del Lago is a town in the Province of Perugia of Umbria (central Italy), on the southwest corner of Lake Trasimeno. Start off your visit on the 18th (Sat): contemplate in the serene atmosphere at Tempio di San Biagio, indulge in some personalized pampering at some of the best spas, then step into the grandiose world of Palazzo della Corgna - Palazzo Ducale, and finally explore the historical opulence of Rocca del Leone. On the next day, stroll through Zocco Beach, then head off the coast to Isola Polvese, then relax in the rural setting at Suzie's Yard, and finally make a trip to Piazza Grande a Montepulciano.

To see more things to do, other places to visit, maps, and tourist information, you can read our Castiglione del Lago sightseeing planning tool.

Traveling by car from Volterra to Castiglione del Lago takes 2 hours. In July, daytime highs in Castiglione del Lago are 36°C, while nighttime lows are 21°C. Finish up your sightseeing early on the 19th (Sun) so you can travel to Collodi.

Things to do in Castiglione del Lago

Parks · Historic Sites · Outdoors · Beaches

Side Trips

Collodi

— 2 nights
Start off your visit on the 20th (Mon): identify plant and animal life at Collodi Butterfly House, then explore the engaging exhibits at Parco di Pinocchio, then learn about winemaking at TENUTA DEL BUONAMICO, and finally contemplate the long history of Villa Torrigiani. Here are some ideas for day two: snap pictures at Ponte Sospeso di San Marcello Pistoiese, admire the sheer force of Cascate del Dardagna, and then take in breathtaking views at Orrido di Botri.

For more things to do, traveler tips, maps, and other tourist information, use the Collodi day trip tool.

Drive from Castiglione del Lago to Collodi in 2.5 hours. July in Collodi sees daily highs of 35°C and lows of 21°C at night. Finish up your sightseeing early on the 21st (Tue) so you can go by car to Spello.

Things to do in Collodi

Parks · Nature · Childrens Museums · Museums

Side Trips

Spello

— 2 nights
Spello is an ancient town and comune of Italy, in the province of Perugia in east central Umbria, on the lower southern flank of Mt. Start off your visit on the 22nd (Wed): take in the architecture and atmosphere at Chiesa di Santa Maria Maggiore, get to know the fascinating history of Centro Storico, then indulge your thirst for a good beer at MicroBirrificio DieciNove, then stop by La Bottega Di Teresa, and finally take in the spiritual surroundings of Cappella Baglioni. Keep things going the next day: learn about winemaking at Cantina Sportoletti, contemplate the long history of Borgo Antico di Colle Pino, then take in the architecture and atmosphere at Saint Andrea, and finally make a trip to Torri di Properzio e Porta Venere.

To see where to stay, other places to visit, maps, and more tourist information, go to the Spello trip planning site.

You can drive from Collodi to Spello in 3 hours. Other options are to take a train; or take a bus. July in Spello sees daily highs of 37°C and lows of 20°C at night. Finish your sightseeing early on the 23rd (Thu) so you can drive to Cortona.

Things to do in Spello

Historic Sites · Breweries & Distilleries · Wineries · Shopping

Cortona

— 2 nights

City of Art

The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
On the 24th (Fri), take in the architecture and atmosphere at Duomo di Cortona, contemplate in the serene atmosphere at Eremo Le Celle, then pause for some serene contemplation at Santa Margherita, Cortona, then do a tasting at Buccelletti - Cantina, and finally look for gifts at DelBrenna Jewelry. Here are some ideas for day two: do a tasting at Azienda Agricola Leuta, make a trip to Piazza della Repubblica, then examine the collection at Museo Diocesano, then get engrossed in the history at MAEC - Museo dell'Accademia Etrusca, and finally Head underground at Belvedere di Cortona.

For traveler tips, more things to do, other places to visit, and other tourist information, read Cortona holiday planner.

Traveling by car from Spello to Cortona takes an hour. Finish your sightseeing early on the 25th (Sat) so you can drive to Pitigliano.

Things to do in Cortona

Historic Sites · Wineries · Parks · Museums

Side Trip

Pitigliano

— 3 nights
Pitigliano is a town in the province of Grosseto, located about 80km south-east of the city of Grosseto, in Italy. On the 26th (Sun), take in the spiritual surroundings of Antico Ghetto e Sinagoga Pitigliano, then appreciate the extensive heritage of Pitigliano Centro Storico, then step into the grandiose world of Piazza del Castello di Montemerano, and finally witness a stunning natural landmark at Cascate del Mulino. Here are some ideas for day two: take in the architecture and atmosphere at Chiesa di San Pietro, then pause for some serene contemplation at Chiesa di Santa Maria e San Rocco, and then indulge in some personalized pampering at Terme di Saturnia - Parco Termale.

To see photos, ratings, other places to visit, and tourist information, refer to the Pitigliano online route planner.

Traveling by car from Cortona to Pitigliano takes 2 hours. July in Pitigliano sees daily highs of 36°C and lows of 21°C at night. Wrap up your sightseeing by early afternoon on the 28th (Tue) to allow enough time to travel back home.

Things to do in Pitigliano

Parks · Historic Sites · Nature · Spas

Side Trips

Umbria travel guide

4.4
Churches · Sacred & Religious Sites · Landmarks
Characterized by a landscape of green hills, attractive towns, and World Heritage-listed monuments, Umbria is the only region in the country with neither a coastline nor an international border. Umbria is home to the town of Assisi, a World Heritage Site and a major religious center that houses a number of attractions. Its Franciscan church has one of the world's finest medieval collections of frescos, a must-see on any itinerary here. Umbria is one of Italy's smaller regions, yet what it lacks in size, it more than makes up in the natural beauty of its agricultural lands and quaint villages.

Tuscany travel guide

4.4
Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.