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

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

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Route & dates

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

Start: Tel Aviv, Israel
Fly:  4 h 30 min
1
Florence, Italy
— Few hours
Drive:  1 h
2
Lucca, Italy
— 1 night
Drive:  30 min
3
Pisa, Italy
— Few hours
Drive:  1 h
4
Volterra, Italy
— 1 night
Drive:  30 min
5
San Gimignano, Italy
— Few hours
Drive:  30 min
6
Monteriggioni, Italy
— Few hours
Drive:  30 min
7
Siena, Italy
— 2 nights
Drive:  1 h
8
Montalcino, Italy
— Few hours
Drive:  30 min
9
Pienza, Italy
— 3 nights
Drive:  1 h 30 min
10
Assisi, Italy
— 1 night
Drive:  2 h 30 min
11
City of San Marino, San Marino
— 1 night
Drive:  2 h 15 min
12
Cortona, Italy
— Few hours
Drive:  30 min
13
Arezzo, Italy
— 1 night
Drive:  1 h
14
Florence, Italy
— 3 nights
Fly:  3 h 30 min
End: Tel Aviv, Israel

few
hours
Florence, Italy

Florence
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
To see reviews, other places to visit, photos, and other tourist information, you can read our Florence holiday tool .

Tel Aviv, Israel to Florence is an approximately 7-hour flight. You can also do a combination of flight and train. You'll gain 1 hour traveling from Tel Aviv to Florence due to the time zone difference. Expect little chillier temperatures when traveling from Tel Aviv in September; daily highs in Florence reach 30°C and lows reach 17°C. You'll have a few hours on the 29th (Sun) to wrap things up before traveling to Lucca.

Things to do in Florence

Tours Historic Sites Outdoors
Find places to stay Sep 29 — 30:

1
night
Lucca, Italy

Lucca ©
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
You've now added Acquedotto del Nottolini to your itinerary. On the 29th (Sun), make a trip to Piazza Anfiteatro, enjoy breathtaking views from Guinigi Tower, steep yourself in history at St Martin Cathedral, then admire the striking features of Acquedotto del Nottolini, and finally steep yourself in history at Le mura di Lucca.

To see reviews, photos, where to stay, and tourist information, go to the Lucca trip builder website .

Getting from Florence to Lucca by car takes about an hour. Other options: take a bus; or take a train. In September, daytime highs in Lucca are 30°C, while nighttime lows are 17°C. Finish your sightseeing early on the 30th (Mon) so you can drive to Pisa.

Things to do in Lucca

Historic Sites
Find places to stay Sep 29 — 30:
Highlights from your plan
St Martin Cathedral ©
St Martin Cathedral
Le mura di Lucca ©
Le mura di Lucca
Torre Guinigi ©
Torre Guinigi

few
hours
Pisa, Italy

Pisa ©
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 Pisa, then take in the architecture and atmosphere at Duomo di Pisa, and finally explore the different monuments and memorials at Camposanto.

To see where to stay, more things to do, traveler tips, and more tourist information, refer to the Pisa trip itinerary planner.

Pisa is just a stone's throw from Lucca. In September, plan for daily highs up to 30°C, and evening lows to 17°C. Wrap up your sightseeing by early afternoon on the 30th (Mon) to allow enough time to drive to Volterra.

Things to do in Pisa

Historic Sites
Find places to stay Sep 30 — Oct 1:
Highlights from your plan
Camposanto ©
Camposanto
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Duomo di Pisa ©
Duomo di Pisa

1
night
Volterra, Italy

Volterra ©
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. To see maps, other places to visit, more things to do, and tourist information, refer to the Volterra road trip planning tool .

Getting from Pisa to Volterra by car takes about 1.5 hours. Other options: do a combination of train and bus; or take a bus. In September, plan for daily highs up to 30°C, and evening lows to 17°C. Cap off your sightseeing on the 1st (Tue) early enough to go by car to San Gimignano.

Things to do in Volterra

Historic Sites Museums
Find places to stay Sep 30 — Oct 1:
Highlights from your plan
Palazzo dei Priori ©
Palazzo dei Priori
Roman Theatre ©
Roman Theatre
Museo Etrusco Guarnacci ©
Museo Etrusco Guarnacci

few
hours
San Gimignano, Italy

San Gimignano ©
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.
Kick off your visit on the 1st (Tue): browse the exhibits of San Gimignano 1300, then make a trip to Duomo di San Gimignano, and then don't miss a visit to Historic Centre of San Gimignano.

To find ratings, traveler tips, where to stay, and more tourist information, you can read our San Gimignano tour itinerary maker site .

San Gimignano is very close to Volterra. October in San Gimignano sees daily highs of 25°C and lows of 14°C at night. On the 1st (Tue), wrap the sightseeing up by early afternoon so you can drive to Monteriggioni.

Things to do in San Gimignano

Historic Sites Museums
Find places to stay Oct 1 — 2:
Highlights from your plan
San Gimignano 1300 ©
San Gimignano 1300
Duomo di San Gimignano ©
Duomo di San Gimignano
Historic Centre of San Gimignano ©
Historic Centre of San Gimignano

few
hours
Monteriggioni, Italy

Monteriggioni ©
Monteriggioni is a comune in the province of Siena in the Italian region Tuscany. Your day-by-day itinerary now includes Centro storico di Monteriggioni, Castello di Monteriggioni and Walls of Monteriggioni.

To find reviews, other places to visit, traveler tips, and other tourist information, go to the Monteriggioni trip planner .

Traveling by car from San Gimignano to Monteriggioni takes an hour. Alternatively, you can take a bus. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Wrap up your sightseeing on the 1st (Tue) early enough to drive to Siena.

Things to do in Monteriggioni

Historic Sites
Find places to stay Oct 1 — 2:
Highlights from your plan
Castello di Monteriggioni ©
Castello di Monteriggioni

2
nights
Siena, Italy

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Your day-by-day itinerary now includes Facciatone. Kick off your visit on the 2nd (Wed): steep yourself in history at Centro Storico di Siena, take in the architecture and atmosphere at Siena Cathedral, explore the galleries of Palazzo Pubblico and Museo Civico, then take in panoramic vistas at Torre del Mangia, then don't miss a visit to Piazza del Campo, and finally don't miss a visit to Facciatone.

To find traveler tips, where to stay, reviews, and tourist information, read our Siena trip builder .

Siena is just a short distance from Monteriggioni. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Finish your sightseeing early on the 3rd (Thu) to allow enough time to drive to Montalcino.

Things to do in Siena

Historic Sites Museums
Find places to stay Oct 1 — 3:
Highlights from your plan
Duomo di Siena ©
Duomo di Siena
Piazza del Campo ©
Piazza del Campo
Palazzo Pubblico and Museo Civico ©
Palazzo Pubblico and Museo Civico

few
hours
Montalcino, Italy

Montalcino ©
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. On the 3rd (Thu), enjoy breathtaking views from Fortezza di Montalcino, contemplate the long history of Abbazia di Sant'Antimo, and then learn about winemaking at Podere Il Cocco.

For other places to visit, reviews, and more tourist information, use the Montalcino trip app .

You can drive from Siena to Montalcino in an hour. Alternatively, you can do a combination of train and bus; or take a 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.

Things to do in Montalcino

Historic Sites Wineries
Find places to stay Oct 3 — 4:
Highlights from your plan
Podere Il Cocco ©
Podere Il Cocco
Abbazia di Sant'Antimo ©
Abbazia di Sant'Antimo
Fortezza di Montalcino ©
Fortezza di Montalcino

3
nights
Pienza, Italy

Pienza ©
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. Your day-by-day itinerary now includes Pitigliano Centro Storico, Civita di Bagnoregio, Val d'Orcia, and other attractions you added. Kick off your visit on the 3rd (Thu): get a sense of history and politics at Palazzo Comunale di Pienza, make a trip to Corso il Rossellino, steep yourself in history at Palazzo Piccolomini, then pause for some serene contemplation at Church of San Francesco, then pause for some photo ops at Pozzo dei Cani, and finally take in the architecture and atmosphere at 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 contemplate the long history of Historic Centre of the City of Pienza.

For other places to visit, traveler tips, where to stay, and other tourist information, read Pienza trip planner .

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. Wrap up your sightseeing on the 6th (Sun) to allow time to drive to Assisi.

Things to do in Pienza

Historic Sites Parks Nature

Side Trips

Tuscany, Piazza Grande a Montepulciano, Civita di Bagnoregio, Pitigliano Centro Storico
Find places to stay Oct 3 — 6:
Highlights from your plan
Val d'Orcia ©
Val d'Orcia
Pitigliano Centro Storico ©
Pitigliano Centro Storico
Civita di Bagnoregio ©
Civita di Bagnoregio

1
night
Assisi, Italy

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Your day-by-day itinerary now includes Piana di Castelluccio di Norcia. Start off your visit on the 6th (Sun): pause for some serene contemplation at Basilica inferiore di San Francesco d'Assisi, contemplate in the serene atmosphere at San Damiano, then step into the grandiose world of Rocca Maggiore, and finally appreciate the views at Piana di Castelluccio di Norcia.

To find where to stay, more things to do, reviews, and other tourist information, use the Assisi trip planner .

You can drive from Pienza to Assisi in 1.5 hours. Alternatively, you can do a combination of taxi and train. Traveling from Pienza in October, expect a bit cooler with lows of 12°C in Assisi. Finish up your sightseeing early on the 7th (Mon) so you can go by car to City of San Marino.

Things to do in Assisi

Parks Nature Historic Sites

Side Trip

Piana di Castelluccio di Norcia
Find places to stay Oct 6 — 7:
Highlights from your plan
Rocca Maggiore ©
Rocca Maggiore
San Damiano ©
San Damiano

1
night
City of San Marino, San Marino

City of San Marino ©
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 your sightseeing to a higher altitude at Mount Titan, contemplate the long history of Cesta Tower, examine the collection at Museum of Torture, ponder the world of politics at Palazzo Pubblico, then pause for some serene contemplation at Basilica del Santo Marino, and finally contemplate the long history of Piazza della Liberta.

To see where to stay, photos, and other tourist information, refer to the City of San Marino trip maker site .

Getting from Assisi to City of San Marino by car takes about 2.5 hours. Other options: do a combination of train and bus; or take a bus. Traveling from Assisi in October, expect nights in City of San Marino to be about the same, around 13°C, while days are little chillier, around 19°C. Cap off your sightseeing on the 8th (Tue) early enough to go by car to Cortona.

Things to do in City of San Marino

Historic Sites Parks Nature
Find places to stay Oct 7 — 8:
Highlights from your plan
Guaita ©
Guaita
Mount Titan ©
Mount Titan
Basilica del Santo Marino ©
Basilica del Santo Marino

few
hours
Cortona, Italy

Cortona ©
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.

To see traveler tips, maps, reviews, and tourist information, read Cortona online route planner .

You can drive from Assisi to Cortona in 1.5 hours. Another option is to take a train. Wrap up your sightseeing by early afternoon on the 7th (Mon) to allow enough time to take a train to Arezzo.

Things to do in Cortona

Historic Sites
Find places to stay Oct 8 — 9:
Highlights from your plan
Duomo di Cortona ©
Duomo di Cortona

1
night
Arezzo, Italy

Arezzo ©
Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
On the 8th (Tue), don't miss a visit to Piazza Grande, then take in the spiritual surroundings of Basilica di San Francesco, and then admire the masterpieces at Galleria Ivan Bruschi.

To find reviews and other tourist information, read our Arezzo route planner .

Arezzo is very close to Cortona. Finish your sightseeing early on the 9th (Wed) so you can take a train to Florence.

Things to do in Arezzo

Museums Historic Sites
Find places to stay Oct 8 — 9:
Highlights from your plan
Galleria Ivan Bruschi ©
Galleria Ivan Bruschi
San Francesco, Arezzo ©
San Francesco, Arezzo

3
nights
Florence, Italy

Florence ©
Your list of things to see and do now includes Monumento a Dante Alighieri, Arco di Trionfo, Basilica di San Lorenzo, and other attractions. Visiting Easy Living - Spiaggia sull'Arno and Giardino di Villa Strozzi will get you outdoors. Get some cultural insight at Galleria dell'Accademia and Ponte Vecchio. Explore Florence further: take in the architecture and atmosphere at Cathedral of Santa Maria del Fiore, get engrossed in the history at Basilica di Santa Croce, make a trip to The Baptistery of St. John, and enjoy breathtaking views from Campanile di Giotto.

For reviews, photos, other places to visit, and tourist information, read our Florence trip itinerary maker app .

Traveling by train from Arezzo to Florence takes an hour. Alternatively, you can drive; or take a bus. Wrap up your sightseeing on the 12th (Sat) to allow time to travel back home.

Things to do in Florence

Historic Sites Museums Parks
Find places to stay Oct 9 — 12:
Highlights from your plan
Ponte Vecchio ©
Ponte Vecchio
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi

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