8 days in Tuscany Itinerary

8 days in Tuscany Itinerary

Created using Inspirock Tuscany trip builder

Make it your trip
Train
1
Siena
— 2 nights
Train
2
San Gimignano
— 3 nights
Train
3
Monteriggioni
— 2 nights
Train

S M T W T F S
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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.
Kick off your visit on the 8th (Sat): take in the architecture and atmosphere at Duomo di Siena, enjoy breathtaking views from Torre del Mangia, then take in the architecture and atmosphere at Basilica di San Clemente in Santa Maria dei Servi, then don't miss a visit to Piazza del Campo, and finally contemplate the long history of Palazzo Chigi Saracini. On the 9th (Sun), you'll have a packed day of sightseeing: contemplate the long history of Centro Storico di Siena, then gain insight at Scuola di Cucina di Lella, and then get outside with Truffle Hunting in Tuscany.

To see more things to do, maps, traveler tips, and other tourist information, read Siena day trip tool.

Milan to Siena is an approximately 4-hour train ride. You can also drive; or take a train; or do a combination of train and bus. In August, plan for daily highs up to 37°C, and evening lows to 22°C. Wrap up your sightseeing on the 10th (Mon) early enough to drive to San Gimignano.

Things to do in Siena

Historic Sites · Outdoors

Side Trip

San Gimignano

— 3 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.
Eschew the tourist crowds and head to San Gimignano 1300 and Guardastelle Vineyard. There's lots more to do: learn about winemaking at Podere La Marronaia- Sosta Alle Colonne, appreciate the extensive heritage of Piazza del Duomo, contemplate the long history of Torre Grossa, and pause for some serene contemplation at Church of Sant'Agostino.

For ratings, maps, other places to visit, and more tourist information, go to the San Gimignano trip itinerary planning app.

Getting from Siena to San Gimignano by train takes about 2.5 hours. Other options: drive; or take a train; or take a bus. In August in San Gimignano, expect temperatures between 35°C during the day and 20°C at night. Wrap up your sightseeing on the 13th (Thu) to allow time to drive to Monteriggioni.

Things to do in San Gimignano

Historic Sites · Wineries · Museums · Shopping

Monteriggioni

— 2 nights
Kick off your visit on the 13th (Thu): step into the grandiose world of Castello di Monteriggioni, steep yourself in history at Walls of Monteriggioni, then steep yourself in history at Porta Franca, then don't miss a visit to Abbazia dei Santi Salvatore e Cirino, and finally get to know the fascinating history of Abbadia Isola. Get ready for a full day of sightseeing on the 14th (Fri): do a tasting at Poggio al Bosco, learn about winemaking at L'Orcio a Ca di Pesa srl, then learn about winemaking at La Cantina di Casalvento, and finally experience rural life at Mulino di Quercegrossa.

For maps, more things to do, where to stay, and other tourist information, use the Monteriggioni day trip tool.

Getting from San Gimignano to Monteriggioni by car takes about an hour. Other options: take a train; or take a bus. In August, daytime highs in Monteriggioni are 37°C, while nighttime lows are 22°C. You'll have a few hours on the 15th (Sat) to wrap things up before traveling home.

Things to do in Monteriggioni

Historic Sites · Wineries · Museums · Shopping

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.