11 days in Rome & Tuscany Itinerary

11 days in Rome & Tuscany Itinerary

Created using Inspirock Italy journey builder

Make it your trip
Fly
1
Rome
— 3 nights
Drive
2
San Gimignano
— 1 night
Drive
3
Monteriggioni
— 1 night
Drive
4
Siena
Drive
5
Montalcino
Drive
6
Pienza
Drive
7
Montepulciano
— 4 nights
Drive
8
Rome
Fly

S M T W T F S
19
20
21
22
23
24
25
26
27
28
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30
1
2

Rome

— 3 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Rome is known for historic sites, nightlife, and museums. Your trip includes some of its best attractions: take in the spiritual surroundings of Vatican Museums, explore the world behind art at Galleria Borghese, pause for some serene contemplation at Church of St. Louis of the French, and stop by Trastevere.

To find maps, photos, ratings, and more tourist information, refer to the Rome vacation maker.

Montreal, Canada to Rome is an approximately 12-hour flight. The time zone difference moving from Eastern Standard Time to Central European Standard Time is 6 hours. When traveling from Montreal in September, plan for somewhat warmer days in Rome, with highs around 81°F, while nights are about the same with lows around 60°F. Cap off your sightseeing on the 25th (Sat) early enough to go by car to San Gimignano.

Things to do in Rome

Historic Sites · Museums · Neighborhoods

Side Trip

Find places to stay Sep 22 — 25:

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.
To find photos, ratings, reviews, and other tourist information, use the San Gimignano online trip builder.

Traveling by car from Rome to San Gimignano takes 3 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 78°F in September, and nighttime lows around 59°F. On the 26th (Sun), you're off to Monteriggioni.

Things to do in San Gimignano

Historic Sites · Wineries · Tours · Outdoors
Find places to stay Sep 25 — 26:

Monteriggioni

— 1 night
Kick off your visit on the 26th (Sun): contemplate the long history of Walls of Monteriggioni, then make a trip to Centro storico di Monteriggioni, and then step into the grandiose world of Castello di Monteriggioni.

To see reviews, ratings, traveler tips, and other tourist information, you can read our Monteriggioni vacation planner.

Traveling by car from San Gimignano to Monteriggioni takes an hour. Alternatively, you can take a train; or take a bus. Expect a daytime high around 81°F in September, and nighttime lows around 61°F. Finish your sightseeing early on the 27th (Mon) so you can drive to Siena.

Things to do in Monteriggioni

Historic Sites
Find places to stay Sep 26 — 27:

Siena

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
For more things to do, other places to visit, and more tourist information, you can read our Siena vacation maker website.

Siena is just a stone's throw from Monteriggioni. Expect a daytime high around 81°F in September, and nighttime lows around 61°F. You will leave for Montalcino on the 27th (Mon).

Things to do in Siena

Historic Sites · Wineries · Shopping · Museums
Find places to stay Sep 26 — 27:

Montalcino

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
To see ratings, maps, reviews, and more tourist information, read our Montalcino trip builder site.

Getting from Siena to Montalcino by car takes about an hour. Other options: take a bus; or do a combination of train and bus. In September in Montalcino, expect temperatures between 81°F during the day and 61°F at night. On the 27th (Mon), you're off to Pienza.

Things to do in Montalcino

Historic Sites · Wineries · Shopping · Tours
Find places to stay Sep 27 — 28:

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. For maps, ratings, other places to visit, and other tourist information, refer to the Pienza vacation planner.

Pienza is just a short distance from Montalcino. September in Pienza sees daily highs of 81°F and lows of 61°F at night. On the 27th (Mon), you're off to Montepulciano.

Things to do in Pienza

Historic Sites · Wineries · Tours · Museums
Find places to stay Sep 27 — 28:

Montepulciano

— 4 nights

Pearl of the 16th Century

Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Explore the numerous day-trip ideas around Montepulciano: Cortona (Museo Diocesano, Eremo Le Celle, &more) and Orvieto (Duomo di Orvieto & Pozzo di San Patrizio). And it doesn't end there: learn about winemaking at Tenuta Valdipiatta, take in the spiritual surroundings of Dome of Montepulciano, don't miss a visit to Piazza Grande a Montepulciano, and indulge in some personalized pampering at some of the best spas.

To find ratings, where to stay, more things to do, and other tourist information, read our Montepulciano holiday planning website.

Montepulciano is just a stone's throw from Pienza. September in Montepulciano sees daily highs of 81°F and lows of 61°F at night. Wrap up your sightseeing on the 1st (Fri) early enough to drive to Rome.

Things to do in Montepulciano

Historic Sites · Wineries · Spas · Museums

Side Trips

Find places to stay Sep 27 — Oct 1:

Rome

Eternal City

On the 1st (Fri), delve into the distant past at Colosseum, then delve into the distant past at Pantheon, and then contemplate the long history of St. Peter's Basilica.

To find maps, other places to visit, ratings, and other tourist information, read Rome visit planning app.

You can drive from Montepulciano to Rome in 2 hours. Other options are to take a train; or take a bus. Cap off your sightseeing on the 1st (Fri) early enough to catch the flight back home.

Things to do in Rome

Historic Sites

Side Trip

Find places to stay Oct 1 — 2:

Tuscany travel guide

4.4
Landmarks · Art Museums · Historic Walking Areas
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.