29 days in Tuscany Itinerary

29 days in Tuscany Itinerary

Created using Inspirock Tuscany visit planner

Make it your trip
Drive
1
Lucca
— 3 nights
Drive
2
Florence
— 6 nights
Drive
3
San Gimignano
— 5 nights
Drive
4
Arezzo
— 3 nights
Drive
5
Montalcino
— 4 nights
+2
Drive to Piombino, Ferry to Portoferraio, Drive to Capoliveri
6
Capoliveri, Elba Island
— 5 nights
+2
Drive to Portoferraio, Ferry to Piombino, Drive to Cecina
7
Cecina
— 2 nights
Drive

S M T W T F S
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16

Lucca

— 3 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.
Franklin'33 has been added to your itinerary. Explore the numerous day-trip ideas around Lucca: Bagno Maurizio (in Viareggio) and Pisa (Food Tours, Leaning Tower of Pisa, &more). Next up on the itinerary: steep yourself in history at Le mura di Lucca, admire the landmark architecture of Duomo di Pisa, indulge your taste buds at Food & Drink, and enjoy breathtaking views from Torre Guinigi.

For reviews, other places to visit, traveler tips, and other tourist information, use the Lucca driving holiday site.

Genoa to Lucca is an approximately 2-hour car ride. You can also take a train; or take a bus. Traveling from Genoa in September, plan for a bit cooler nights in Lucca, with lows around 17°C. Finish up your sightseeing early on the 19th (Sun) so you can go by car to Florence.

Things to do in Lucca

Tours · Museums · Historic Sites · Wineries

Side Trips

Find places to stay Sep 16 — 19:

Florence

— 6 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Step out of Florence to go to Santa Brigida and see Castello del Trebbio, which is approximately 36 minutes away. Dedicate the 25th (Sat) to wine at some of the top wineries in the area. The adventure continues: admire the masterpieces at Florence Academy of Fine Arts, get to know the fascinating history of Piazza del Duomo, admire the natural beauty at The Boboli Gardens, and pause for some serene contemplation at Basilica of Santa Croce.

To see other places to visit, ratings, reviews, and tourist information, read our Florence road trip tool.

You can drive from Lucca to Florence in 1.5 hours. Alternatively, you can take a bus; or take a train. In September, daytime highs in Florence are 30°C, while nighttime lows are 17°C. Wrap up your sightseeing on the 25th (Sat) early enough to drive to San Gimignano.

Things to do in Florence

Tours · Historic Sites · Wineries · Museums

Side Trips

Find places to stay Sep 19 — 25:

San Gimignano

— 5 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.
Get out of town with these interesting San Gimignano side-trips: Siena (Battistero di San Giovanni, Wine Tours & Tastings, &more) and Fattoria Casa Sola (in Barberino Val d'Elsa). There's still lots to do: learn about winemaking at Guardastelle Vineyard, take in the architecture and atmosphere at Duomo di San Gimignano, take in the spiritual surroundings of Church of Sant'Agostino, and contemplate the long history of Torre Grossa.

To find where to stay, reviews, photos, and more tourist information, read our San Gimignano road trip site.

Traveling by car from Florence to San Gimignano takes 1.5 hours. Alternatively, you can take a train; or take a bus. In September, daily temperatures in San Gimignano can reach 30°C, while at night they dip to 17°C. Finish your sightseeing early on the 30th (Thu) so you can drive to Arezzo.

Things to do in San Gimignano

Wineries · Historic Sites · Tours · Museums

Side Trips

Find places to stay Sep 25 — 30:

Arezzo

— 3 nights

Ancient City

Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Get out of town with these interesting Arezzo side-trips: Cortona (Museo Diocesano, MAEC - Museo dell'Accademia Etrusca, &more) and Buccelletti - Cantina (in Castiglion Fiorentino). Next up on the itinerary: do a tasting at Villa La Ripa, contemplate in the serene atmosphere at Santa Maria della Pieve, take in the architecture and atmosphere at San Francesco, Arezzo, and indulge your senses at some of the top wineries in the area.

To find reviews, where to stay, and more tourist information, go to the Arezzo trip maker app.

Traveling by car from San Gimignano to Arezzo takes 2 hours. Alternatively, you can take a bus; or take a train. Finish your sightseeing early on the 3rd (Sun) so you can drive to Montalcino.

Things to do in Arezzo

Wineries · Historic Sites · Museums · Tours

Side Trips

Find places to stay Sep 30 — Oct 3:

Montalcino

— 4 nights

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Explore the numerous day-trip ideas around Montalcino: Crete Senesi (in Asciano) and Montepulciano (Tempio di San Biagio, Piazza Grande a Montepulciano, &more). There's still lots to do: learn about winemaking at Winery Solaria Patrizia Cencioni, make a trip to Piazza Pio II, steep yourself in history at Abbazia di Sant'Antimo, and stroll through Val d'Orcia.

To find where to stay, photos, ratings, and other tourist information, read our Montalcino tour planning site.

You can drive from Arezzo to Montalcino in 1.5 hours. Other options are to take a bus; or do a combination of train and bus. October in Montalcino sees daily highs of 26°C and lows of 15°C at night. Wrap up your sightseeing on the 7th (Thu) to allow time to travel to Capoliveri.

Things to do in Montalcino

Wineries · Parks · Historic Sites · Nature

Side Trips

Find places to stay Oct 3 — 7:

Capoliveri, Elba Island

— 5 nights
Capoliveri is a comune (municipality) on the island of Elba in Italy. Change things up with these side-trips from Capoliveri: Spiaggia La Sorgente (in Portoferraio) and Spiaggia di Cavoli (in Seccheto). There's lots more to do: head outdoors with Aloha Center, kick back and relax at Spiaggia Di Buzzancone o Cera, stroll through Acqua marina, and look for all kinds of wild species at Rio Diving Center.

To see reviews, maps, and more tourist information, you can read our Capoliveri driving holiday planning app.

Do a combination of car and ferry from Montalcino to Capoliveri in 3.5 hours. Alternatively, you can do a combination of bus, train, and ferry. Traveling from Montalcino in October, expect nights in Capoliveri to be about the same, around 17°C, while days are little chillier, around 22°C. Finish up your sightseeing early on the 12th (Tue) so you can travel to Cecina.

Things to do in Capoliveri

Outdoors · Parks · Beaches · Tours

Side Trips

Find places to stay Oct 7 — 12:

Cecina

— 2 nights
Cecina is a comune (municipality) of 28,322 inhabitants in the Province of Livorno in the Italian region Tuscany, located about 80km southwest of Florence and about 30km southeast of Livorno.The territory of Cecina borders the following municipalities: Bibbona, Casale Marittimo, Castellina Marittima, Guardistallo, Montescudaio, Riparbella, Rosignano Marittimo.An archaeological park close to the town houses the remains of a Roman villa from the 1st century BC.HistoryA settlement was founded here by the Roman consul Albinus Caecina, who was a descendant of an ancient Etruscan family. Start off your visit on the 13th (Wed): indulge your senses at Italy Shore Drivers and then tour the pleasant surroundings at Bagni Etruria. Get ready for a full day of sightseeing on the 14th (Thu): learn about winemaking at Terre del Marchesato and then learn about winemaking at Batzella.

To see traveler tips, where to stay, more things to do, and tourist information, use the Cecina online tour itinerary planner.

Traveling by combination of car and ferry from Capoliveri to Cecina takes 3 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of bus, ferry, and train. In October, plan for daily highs up to 25°C, and evening lows to 14°C. Cap off your sightseeing on the 14th (Thu) early enough to go by car back home.

Things to do in Cecina

Wineries · Tours · Outdoors · Parks

Side Trips

Find places to stay Oct 12 — 14:

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.