20 days in Tuscany Itinerary

20 days in Tuscany Itinerary

Created using Inspirock Tuscany route planner
Make it your trip
Fly
1
Florence
— 3 nights
Drive
2
Montalcino
— 2 nights
Drive
3
Siena
— 2 nights
Drive
4
Panzano in Chianti
— 2 nights
Drive
5
San Gimignano
— 2 nights
Drive
6
Lucca
— 2 nights
Drive
7
Pisa
— 1 night
Drive
8
Livorno
— 4 nights
Fly

S M T W T F S
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31
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5

Florence — 3 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Florence is known for sightseeing, museums, and historic sites. Your trip includes some of its best attractions: admire the masterpieces at Gallerie Degli Uffizi, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, admire the landmark architecture of The Baptistery of St. John, and take in the views from Ponte Vecchio.

To see traveler tips, more things to do, and more tourist information, read our Florence day trip planning website.

London, UK to Florence is an approximately 5.5-hour flight. You can also take a train; or do a combination of car and train. The time zone changes from Greenwich Mean Time to Central European Standard Time, which is usually a 1 hour difference. In October, Florence is a bit warmer than London - with highs of 71°F and lows of 54°F. Wrap up your sightseeing on the 21st (Fri) early enough to drive to Montalcino.
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Historic Sites · Museums · Parks
Find places to stay Oct 17 — 21:

Montalcino — 2 nights

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
On the 22nd (Sat), do a tasting at Ciacci Piccolomini d'Aragona, then pause for some serene contemplation at Abbazia di Sant'Antimo, and then appreciate the views at Val d'Orcia.

To see ratings, maps, reviews, and other tourist information, read Montalcino day trip tool.

You can drive from Florence to Montalcino in 2 hours. Other options are to take a bus; or do a combination of train and bus. In October in Montalcino, expect temperatures between 73°F during the day and 56°F at night. You will leave for Siena on the 23rd (Sun).
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Wineries · Historic Sites · Parks · Nature
Side Trip
Find places to stay Oct 21 — 23:

Siena — 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.
Step out of Siena with an excursion to Abbazia di San Galgano in Chiusdino--about 50 minutes away. And it doesn't end there: pause for some serene contemplation at Duomo di Siena, take in the spiritual surroundings of Battistero di San Giovanni, enjoy breathtaking views from Torre del Mangia, and take in the exciting artwork at Ceramiche Bianco e Nero di Staccioli.

To see where to stay, traveler tips, more things to do, and more tourist information, you can read our Siena trip builder tool.

Drive from Montalcino to Siena in an hour. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 73°F in October, and nighttime lows around 56°F. Finish your sightseeing early on the 25th (Tue) to allow enough time to drive to Panzano in Chianti.
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Historic Sites · Museums · Shopping
Side Trip
Find places to stay Oct 23 — 25:

Panzano in Chianti — 2 nights

On the 26th (Wed), indulge your taste buds at Castello di Verrazzano.

To see traveler tips, other places to visit, more things to do, and other tourist information, you can read our Panzano in Chianti driving holiday planner.

You can drive from Siena to Panzano in Chianti in an hour. In October, daily temperatures in Panzano in Chianti can reach 71°F, while at night they dip to 54°F. You will leave for San Gimignano on the 27th (Thu).
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Historic Sites · Wineries
Side Trip
Find places to stay Oct 25 — 27:
Highlights from your trip

San Gimignano — 2 nights

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.
San Gimignano is known for historic sites, wineries, and sightseeing. Your trip includes some of its best attractions: learn about winemaking at Guardastelle Vineyard, make a trip to Piazza della Cisterna, get engrossed in the history at San Gimignano 1300, and steep yourself in history at Torre Grossa.

Start your trip to San Gimignano by creating a personalized itinerary on Inspirock.

Drive from Panzano in Chianti to San Gimignano in an hour. Expect a daytime high around 71°F in October, and nighttime lows around 54°F. Finish your sightseeing early on the 29th (Sat) so you can drive to Lucca.
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Wineries · Historic Sites · Museums
Find places to stay Oct 27 — 29:

Lucca — 2 nights

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.
Start off your visit on the 30th (Sun): contemplate in the serene atmosphere at San Michele in Foro, don't miss a visit to Piazza Anfiteatro, take in panoramic vistas at Torre Guinigi, then steep yourself in history at St Martin Cathedral, and finally steep yourself in history at Le mura di Lucca.

To see where to stay, photos, traveler tips, and other tourist information, you can read our Lucca trip planner.

Traveling by car from San Gimignano to Lucca takes 2 hours. Alternatively, you can take a train; or take a bus. October in Lucca sees daily highs of 71°F and lows of 54°F at night. On the 31st (Mon), you're off to Pisa.
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Historic Sites
Find places to stay Oct 29 — 31:

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 1st (Tue): take in the spiritual surroundings of Duomo di Pisa, then don't miss a visit to Piazza dei Miracoli, then take in the spiritual surroundings of Battistero di San Giovanni, and finally take in panoramic vistas at Leaning Tower of Pisa.

To find traveler tips, photos, more things to do, and tourist information, read our Pisa day trip planner.

Pisa is very close to Lucca. In October, plan for daily highs up to 71°F, and evening lows to 54°F. Wrap up your sightseeing on the 1st (Tue) to allow time to drive to Livorno.
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Historic Sites
Find places to stay Oct 31 — Nov 1:

Livorno — 4 nights

Naples of the North

Considered one of Tuscany's newer cities, the busy port city of Livorno boasts modern charm uncharacteristic of the region.
Livorno is known for sightseeing, historic sites, and zoos & aquariums. Your trip includes some of its best attractions: don't miss a visit to Terrazza Mascagni, get up close and personal with brilliant marine life at Acquario di Livorno, stop by Papaveri, and take in the architecture and atmosphere at Santuario di Montenero.

For ratings, photos, other places to visit, and more tourist information, use the Livorno journey builder site.

Traveling by car from Pisa to Livorno takes an hour. Alternatively, you can take a train; or take a bus. November in Livorno sees daily highs of 61°F and lows of 46°F at night. On the 5th (Sat), you'll travel back home.
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Parks · Zoos & Aquariums · Historic Sites · Shopping
Find places to stay Nov 1 — 5:

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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