15 days in Tuscany, Assisi & City of San Marino Itinerary

Created using Inspirock Europe holiday planner
Make it your trip
Fly
1
Florence, Italy
Drive
2
Lucca, Italy
— 1 night
Drive
3
Pisa, Italy
Drive
4
Volterra, Italy
— 1 night
Drive
5
San Gimignano, Italy
Drive
6
Monteriggioni, Italy
Drive
7
Siena, Italy
— 2 nights
Drive
8
Montalcino, Italy
Drive
9
Pienza, Italy
— 3 nights
Drive
10
Assisi, Italy
— 1 night
Drive
11
City of San Marino, San Marino
— 1 night
Drive
12
Cortona, Italy
Drive
13
Arezzo, Italy
— 1 night
Drive
14
Florence, Italy
— 3 nights
Fly

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Florence, Italy

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
To find traveler tips, where to stay, reviews, and other tourist information, use the Florence vacation builder.

Tel Aviv, Israel to Florence is an approximately 7-hour flight. The time zone difference moving from Israel Standard Time to Central European Standard Time is minus 1 hour. Expect little chillier temperatures when traveling from Tel Aviv in September; daily highs in Florence reach 30°C and lows reach 17°C. You will have some time to spend on the 29th (Sun) before leaving for Lucca.
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Tours · Historic Sites · Shopping · Wineries
Find places to stay Sep 29 — 30:

Lucca, Italy — 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.
Your day by day itinerary now includes Acquedotto del Nottolini. Start off your visit on the 29th (Sun): don't miss a visit to Piazza Anfiteatro, enjoy breathtaking views from Torre Guinigi, admire the landmark architecture of St Martin Cathedral, then contemplate the long history of Acquedotto del Nottolini, and finally make a trip to Le mura di Lucca.

To find more things to do and more tourist information, you can read our Lucca trip planner.

Getting from Florence to Lucca by car takes about an hour. Other options: drive; or take a bus; or take a train. September in Lucca sees daily highs of 30°C and lows of 17°C at night. Cap off your sightseeing on the 30th (Mon) early enough to go by car to Pisa.
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Historic Sites
Find places to stay Sep 29 — 30:

Pisa, Italy

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
On the 30th (Mon), don't miss a visit to Piazza dei Miracoli, take in panoramic vistas at Leaning Tower of Pisa, then take in the spiritual surroundings of Duomo di Pisa, and finally contemplate the long history of Camposanto.

For photos, maps, reviews, and tourist information, read Pisa trip maker website.

Pisa is just a short distance from Lucca. September in Pisa sees daily highs of 30°C and lows of 17°C at night. Wrap up your sightseeing by early afternoon on the 30th (Mon) to allow enough time to drive to Volterra.
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Historic Sites
Find places to stay Sep 30 — Oct 1:

Volterra, Italy — 1 night

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. On the 30th (Mon), see the interesting displays at Museo Etrusco Guarnacci, then step into the grandiose world of Palazzo dei Priori, and then explore the ancient world of Roman Theatre.

To find ratings, other places to visit, where to stay, and other tourist information, read Volterra itinerary planning app.

Drive from Pisa to Volterra in 1.5 hours. Alternatively, you can drive; or take a bus. In September, daily temperatures in Volterra can reach 30°C, while at night they dip to 17°C. Finish your sightseeing early on the 1st (Tue) so you can drive to San Gimignano.
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Historic Sites · Museums
Find places to stay Sep 30 — Oct 1:

San Gimignano, Italy

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.
Start off your visit on the 1st (Tue): take an in-depth tour of San Gimignano 1300, then don't miss a visit to Duomo di San Gimignano, and then don't miss a visit to Historic Centre of San Gimignano.

Plan my day in San Gimignano using traveler tips and tourist information provided by Inspirock.

San Gimignano is very close to Volterra. In October, daily temperatures in San Gimignano can reach 25°C, while at night they dip to 14°C. On the 1st (Tue), wrap the sightseeing up by early afternoon so you can drive to Monteriggioni.
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Historic Sites · Museums
Find places to stay Oct 1 — 2:

Monteriggioni, Italy

Your day by day itinerary now includes Centro storico di Monteriggioni, Castello di Monteriggioni and Walls of Monteriggioni. On the 1st (Tue), admire the striking features of Walls of Monteriggioni, then explore the historical opulence of Castello di Monteriggioni, and then don't miss a visit to Centro storico di Monteriggioni.

For ratings, where to stay, more things to do, and more tourist information, use the Monteriggioni sightseeing planner.

Traveling by car from San Gimignano to Monteriggioni takes an hour. Alternatively, you can drive; or take a bus. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Finish your sightseeing early on the 1st (Tue) to allow enough time to drive to Siena.
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Historic Sites
Find places to stay Oct 1 — 2:

Siena, Italy — 2 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
You've now added Facciatone to your itinerary. Start off your visit on the 2nd (Wed): contemplate the long history of Centro Storico di Siena, pause for some serene contemplation at Duomo di Siena, get a sense of history and politics at Palazzo Pubblico and Museo Civico, take in panoramic vistas at Torre del Mangia, then don't miss a visit to Piazza del Campo, and finally make a trip to Facciatone.

For maps, reviews, ratings, and more tourist information, read Siena trip itinerary builder.

Siena is just a short distance from Monteriggioni. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Wrap up your sightseeing on the 3rd (Thu) to allow time to drive to Montalcino.
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Historic Sites · Museums
Find places to stay Oct 1 — 3:

Montalcino, Italy

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Your day by day itinerary now includes Abbazia di Sant'Antimo as well as Fortezza di Montalcino. Start off your visit on the 3rd (Thu): explore the historical opulence of Fortezza di Montalcino, steep yourself in history at Abbazia di Sant'Antimo, and then learn about winemaking at il Cocco.

To see photos, ratings, and tourist information, refer to the Montalcino road trip planning app.

You can drive from Siena to Montalcino in an hour. Alternatively, you can drive; or take a bus; or do a combination of train and bus. In October, daytime highs in Montalcino are 26°C, while nighttime lows are 15°C. Wrap up your sightseeing by early afternoon on the 3rd (Thu) to allow time for the car ride to Pienza.
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Historic Sites · Wineries
Find places to stay Oct 3 — 4:

Pienza, Italy — 3 nights

Pienza, a town and comune in the province of Siena, in the Val d'Orcia in Tuscany (central Italy), between the towns of Montepulciano and Montalcino, is the "touchstone of Renaissance urbanism."In 1996, UNESCO declared the town a World Heritage Site, and in 2004 the entire valley, the Val d'Orcia, was included on the list of UNESCO's World Cultural Landscapes.HistoryBefore the village was renamed to Pienza its name was Corsignano. You've added Pitigliano Centro Storico, Civita di Bagnoregio, Val d'Orcia, and other attractions to your itinerary. Kick off your visit on the 3rd (Thu): get a sense of history and politics at Palazzo Comunale di Pienza, steep yourself in history at Corso il Rossellino, examine the collection at Palazzo Piccolomini, pause for some serene contemplation at Church of San Francesco, then appreciate the history behind Pozzo dei Cani, and finally take in the spiritual surroundings of Cathedral. Get ready for a full day of sightseeing on the 4th (Fri): don't miss a visit to Piazza Grande a Montepulciano, appreciate the views at Val d'Orcia, and then steep yourself in history at Historic Centre of the City of Pienza.

To see traveler tips, where to stay, maps, and other tourist information, you can read our Pienza trip itinerary builder.

Pienza is just a stone's throw from Montalcino. In October in Pienza, expect temperatures between 26°C during the day and 15°C at night. Finish your sightseeing early on the 6th (Sun) to allow enough time to drive to Assisi.
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Historic Sites · Nature · Parks · Museums
Side Trips
Find places to stay Oct 3 — 6:

Assisi, Italy — 1 night

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Piana di Castelluccio di Norcia has been added to your itinerary. On the 6th (Sun), pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, then take in the architecture and atmosphere at San Damiano, then explore the historical opulence of Rocca Maggiore, and finally admire the verdant scenery at Piana di Castelluccio di Norcia.

To see maps, photos, traveler tips, and other tourist information, go to the Assisi journey maker app.

You can drive from Pienza to Assisi in 1.5 hours. Alternatively, you can drive; or do a combination of taxi and train. Expect a bit cooler evenings in Assisi when traveling from Pienza in October, with lows around 12°C. Finish up your sightseeing early on the 7th (Mon) so you can go by car to City of San Marino.
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Nature · Parks · Historic Sites
Side Trip
Find places to stay Oct 6 — 7:

City of San Marino, San Marino — 1 night

The capital of one of the world's smallest and oldest republics, the hillside city of San Marino boasts a World Heritage-listed old town that's known for its winding cobblestone streets and sweeping views of the surrounding countryside.
Your day by day itinerary now includes Cesta Tower as well as Mount Titan. Kick off your visit on the 7th (Mon): take in the awesome beauty at Mount Titan, contemplate the long history of Cesta Tower, see the interesting displays at Museo Della Totura, then get a sense of history and politics at Palazzo Pubblico, then pause for some serene contemplation at Basilica del Santo Marino, and finally steep yourself in history at Piazza della Liberta.

To see other places to visit, ratings, and more tourist information, go to the City of San Marino trip maker app.

Traveling by car from Assisi to City of San Marino takes 2.5 hours. Alternatively, you can drive; or do a combination of train and bus; or take a bus. Traveling from Assisi in October, you will find days in City of San Marino are a bit cooler (19°C), and nights are about the same (13°C). Finish up your sightseeing early on the 8th (Tue) so you can go by car to Cortona.
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Historic Sites · Nature · Parks · Museums
Find places to stay Oct 7 — 8:

Cortona, Italy

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.
Your day by day itinerary now includes Duomo di Cortona as well as Piazza della Repubblica. Kick off your visit on the 8th (Tue): make a trip to Piazza della Repubblica and then take in the spiritual surroundings of Duomo di Cortona.

For where to stay, ratings, maps, and other tourist information, read Cortona online itinerary planner.

Traveling by car from City of San Marino to Cortona takes 2.5 hours. Alternatively, you can drive; or do a combination of bus and train; or take a bus. Wrap up your sightseeing by early afternoon on the 8th (Tue) to allow time for the car ride to Arezzo.
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Historic Sites
Find places to stay Oct 8 — 9:
Highlights from your trip

Arezzo, Italy — 1 night

Ancient City

Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
On the 8th (Tue), make a trip to Piazza Grande, then take in the spiritual surroundings of San Francesco, Arezzo, and then explore the world behind art at Galleria Ivan Bruschi.

To find maps, other places to visit, traveler tips, and tourist information, you can read our Arezzo trip planner.

You can drive from Cortona to Arezzo in an hour. Other options are to drive; or take a train; or take a bus. Finish your sightseeing early on the 9th (Wed) to allow enough time to drive to Florence.
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Historic Sites · Museums
Find places to stay Oct 8 — 9:

Florence, Italy — 3 nights

Birthplace of the Italian Renaissance

You've added Monumento a Dante Alighieri, Arco di Trionfo, Basilica di San Lorenzo, and other attractions to your itinerary. Satisfy your inner culture vulture at Piazzale Michelangelo and Cathedral of Santa Maria del Fiore. Your inner history buff will appreciate Basilica of Santa Croce and The Baptistery of St. John. Enjoy Florence some more: explore the world behind art at Gallerie Degli Uffizi, enjoy breathtaking views from Campanile di Giotto, see the interesting displays at Pitti Palace, and appreciate the extensive heritage of Piazza del Duomo.

To see where to stay, maps, more things to do, and more tourist information, use the Florence trip itinerary maker tool.

You can drive from Arezzo to Florence in an hour. Other options are to drive; or take a train. Finish your sightseeing early on the 12th (Sat) to allow enough time to fly back home.
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Historic Sites · Museums · Parks · Nature
Find places to stay Oct 9 — 12:

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.
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San Marino travel guide

3.2
Historic Sites · Specialty Museums · Castles
San Marino is a country characterized by its architecture--namely, the three towers that adorn the country's flag and coat of arms. As a result, most of the tourist attractions here center around the structures protruding from the hill of the country. The third-smallest nation in Europe, it is surprising that San Marino managed to gain independence from robust Italy. This status has created great pride among the Sanmarinese, although Italian culture is still quite influential as the country is completely surrounded by Italy. And while its size has obvious disadvantages, the advantages for tourism strongly outweigh them. Visitors don't need to travel to get a sense of the country (there isn't far to go!), and this generates an intimacy and friendliness among locals that is lost in most larger countries.
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