35 days in Tuscany & Milan Itinerary

35 days in Tuscany & Milan Itinerary

Created using Inspirock Italy trip planner

Make it your trip
Fly
1
Florence
— 2 nights
Drive
2
Siena
— 11 nights
Drive
3
Montepulciano
— 3 nights
Drive
4
Siena
— 5 nights
Drive
5
San Gimignano
— 2 nights
Drive
6
Siena
— 5 nights
Train
7
Milan
— 4 nights
Fly

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Florence

— 2 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 2nd (Sat), examine the collection at Museo Opificio delle Pietre Dure, view the masterpieces at M.G. Design, then wander the streets of Piazza della Repubblica, and finally examine the collection at Museo di Palazzo Davanzati.

To find reviews, maps, ratings, and more tourist information, go to the Florence travel route site.

San Francisco, USA to Florence is an approximately 17-hour flight. The time zone difference when traveling from San Francisco to Florence is 9 hours. In October, daytime highs in Florence are 71°F, while nighttime lows are 54°F. Wrap up your sightseeing on the 3rd (Sun) early enough to drive to Siena.

Things to do in Florence

Museums · Shopping · Neighborhoods

Siena

— 11 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Your inner history buff will appreciate Banca Monte dei Paschi di Siena and Chiesa di Santa Maria in Portico a Fontegiusta. Torre del Mangia and Basilica di San Clemente in Santa Maria dei Servi are good opportunities to explore the local culture. Venture out of the city with trips to Radda in Chianti (Castello di Albola, Castello Monterinaldi, &more), Dievole (in Vagliagli) and Abbadia Isola (in Monteriggioni). On the 9th (Sat), give your taste buds a day to remember with a local gastronomic tour. There's much more to do: steep yourself in history at Cappella di Piazza, take in the architecture and atmosphere at Chiesa di Santo Spirito, gain insight at Scuola di Cucina di Lella, and contemplate in the serene atmosphere at Oratorio di San Bernardino e Museo Diocesano.

For reviews, where to stay, ratings, and tourist information, read our Siena trip planner.

Traveling by car from Florence to Siena takes 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 73°F in October, and nighttime lows around 56°F. Cap off your sightseeing on the 14th (Thu) early enough to go by car to Montepulciano.

Things to do in Siena

Historic Sites · Wineries · Tours · Museums

Side Trips

Montepulciano

— 3 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 hidden gems such as Az. Agr. Poliziano and Via di Gracciano nel Corso. Do some cultural sightseeing at Icario Winery and Boscarelli Di De Ferrari Luca E Nicolo' Soc.Semp.. Next up on the itinerary: learn about winemaking at Villa Sant'Anna, get to know the fascinating history of Centro storico, take in the spiritual surroundings of Parrocchia Santissimo Nome Di Gesu', and pause for some serene contemplation at Chiesa di Santa Maria Assunta.

To see reviews, where to stay, ratings, and more tourist information, you can read our Montepulciano visit planner.

You can drive from Siena to Montepulciano in an hour. Other options are to take a train; or take a bus. October in Montepulciano sees daily highs of 73°F and lows of 56°F at night. Finish your sightseeing early on the 17th (Sun) so you can drive to Siena.

Things to do in Montepulciano

Historic Sites · Wineries · Shopping

Side Trips

Siena

— 5 nights

Cultural Heart of Tuscany

You'll discover tucked-away gems like Cappella di Piazza and Casa di Santa Caterina. For shopping fun, head to Casa della Pelle or Piazza del Mercato. Change things up with these side-trips from Siena: Cantalici Winery (in Gaiole in Chianti) and Dievole (in Vagliagli). See some other sides of Siena: deepen your understanding at Scuola di Cucina di Lella, contemplate the long history of Palazzo Chigi Saracini, don't miss a visit to Via di Citta, and have fun and explore at Museo di Storia Naturale dell'Accademia dei Fisiocritici.

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

Getting from Montepulciano to Siena by car takes about an hour. Other options: take a train; or take a bus. Finish up your sightseeing early on the 22nd (Fri) so you can go by car to San Gimignano.

Things to do in Siena

Historic Sites · Museums · Wineries · Tours

Side Trips

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.
Start off your visit on the 22nd (Fri): pause for some serene contemplation at Chiesa di San Pietro in Forliano and then take in the exciting artwork at Oibo Re-Design. Get ready for a full day of sightseeing on the 23rd (Sat): take in the exciting artwork at Art Gallery in Tuscany, Gordon's Studio, stop by (MR) Marri e Rossi, take in the exciting artwork at Balducci Ceramica, then pause for some serene contemplation at Chiesa di San Bartolo, and finally view the masterpieces at Vitalita Cultural Association.

For where to stay, ratings, maps, and tourist information, you can read our San Gimignano journey planner.

You can drive from Siena to San Gimignano in an hour. Other options are to take a train; or take a bus. In October in San Gimignano, expect temperatures between 71°F during the day and 54°F at night. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to Siena.

Things to do in San Gimignano

Shopping · Museums · Historic Sites · Wineries

Siena

— 5 nights

Cultural Heart of Tuscany

Your cultural itinerary includes sights like Basilica Cateriniana San Domenico and Loggia della Mercanzia. Cappella di Piazza and Chiesa di Sant'Andrea will appeal to history buffs. Go for a jaunt from Siena to Monteriggioni to see Abbadia Isola about 32 minutes away. Enjoy Siena some more: gain insight at Scuola di Cucina di Lella, take an in-depth tour of Archivio di Stato, browse the eclectic array of goods at Piazza del Mercato, and appreciate the extensive heritage of Centro storico di Monteriggioni.

For where to stay, more things to do, ratings, and more tourist information, refer to the Siena trip maker.

Traveling by car from San Gimignano to Siena takes an hour. Alternatively, you can take a train; or take a bus. Cap off your sightseeing on the 29th (Fri) early enough to go by car to Milan.

Things to do in Siena

Historic Sites · Museums · Shopping · Childrens Museums

Side Trip

Milan

— 4 nights

Fashion Capital of World

In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.
Visit Vicolo Privato Lavandai and Abbazia di Chiaravalle for their historical value. Discover out-of-the-way places like Basilica di Sant'Eustorgio and Basilica di San Babila. Change things up with these side-trips from Milan: Contadi Castaldi (in Adro) and Rocca Sforzesca (in Soncino). There's much more to do: pause for some serene contemplation at Chiesa di Sant'Alessandro in Zebedia, admire the landmark architecture of Casa di Riposo per Musicisti Giuseppe Verdi, take in the spiritual surroundings of Civico Tempio di San Sebastiano, and contemplate the long history of Palazzo Clerici.

To find where to stay, reviews, ratings, and more tourist information, read our Milan road trip planner.

Getting from Siena to Milan by train takes about 4 hours. Other options: drive; or take a train; or do a combination of bus and train. When traveling from Siena in October, plan for little chillier days in Milan, with highs around 65°F, while nights are about the same with lows around 52°F. Wrap up your sightseeing on the 2nd (Tue) early enough to fly back home.

Things to do in Milan

Historic Sites · Wineries · Museums · Parks

Side Trips

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.

Province of Siena travel guide

4.4
Landmarks · Wineries & Vineyards · Churches
Siena is a city in Tuscany, Italy. It is the capital of the province of Siena.The historic centre of Siena has been declared by UNESCO a World Heritage Site. It is one of the nation's most visited tourist attractions, with over 163,000 international arrivals in 2008. Siena is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year.HistorySiena, like other Tuscan hill towns, was first settled in the time of the Etruscans (c. 900–400 BC) when it was inhabited by a tribe called the Saina. The Etruscans were a tribe of advanced people who changed the face of central Italy through their use of irrigation to reclaim previously unfarmable land, and their custom of building their settlements in well-defended hill forts. A Roman town called Saena Julia was founded at the site in the time of the Emperor Augustus. Some archaeologists assert that Siena was controlled for a period by a Gaulish tribe called the Senones.According to local legend, Siena was founded by Senius and Aschius, two sons of Remus and thus nephews of Romulus, after whom Rome was named. Supposedly after their father's murder by Romulus, they fled Rome, taking with them the statue of the she-wolf suckling the infants (Capitoline Wolf), thus appropriating that symbol for the town. Additionally they rode white and black horses, giving rise to the Balzana, or coat of arms of Siena with a white band atop a dark band. Some claim the name Siena derives from Senius. Other etymologies derive the name from the Etruscan family name Saina, the Roman family name Saenii, or the Latin word senex "old" or its derived form seneo "to be old".

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