14 days in Tuscany Itinerary

14 days in Tuscany Itinerary

Created using Inspirock Tuscany trip planner
Make it your trip
Fly
1
Pisa
— 3 nights
Drive
2
Florence
— 3 nights
Drive
3
Siena
— 3 nights
Drive
4
Pienza
— 2 nights
Drive to Piombino, Ferry to Portoferraio
5
Portoferraio, Elba Island
— 2 nights
Ferry to Porto Biglietterie Sud, Fly to London

S M T W T F S
11
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1

Pisa — 3 nights

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Satisfy your inner culture vulture at Basilica of San Frediano and Palazzo Pfanner. Chiesa di Santa Maria della Spina and Chiesa di Santa Caterina d'Alessandria will appeal to history buffs. There's lots more to do: admire the striking features of Leaning Tower of Pisa, pause for some serene contemplation at San Piero a Grado, and steep yourself in history at St Martin Cathedral.

For ratings, other places to visit, traveler tips, and tourist information, go to the Pisa tour itinerary tool.

London, UK to Pisa is an approximately 5.5-hour flight. You can also take a train; or do a combination of car and train. Traveling from London to Pisa, you'll lose 1 hour due to the time zone difference. Traveling from London in September, things will get somewhat warmer in Pisa: highs are around 30°C and lows about 17°C. Cap off your sightseeing on the 15th (Thu) early enough to go by car to Florence.
Historic Sites · Parks
Side Trip
Find places to stay Sep 12 — 15:

Florence — 3 nights

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You'll discover tucked-away gems like Centro Storico and Museo Nazionale del Bargello. Take a break from the city and head to Horseback Riding Tours and Parco Chico Mendes. There's still lots to do: take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, admire the landmark architecture of Cappelle Medicee, steep yourself in history at The Baptistery of St. John, and get to know the fascinating history of Piazza della Signoria.

For traveler tips, where to stay, reviews, and tourist information, use the Florence tour itinerary website.

You can drive from Pisa to Florence in 1.5 hours. Alternatively, you can take a bus; or take a train. In September, daily temperatures in Florence can reach 30°C, while at night they dip to 17°C. Wrap up your sightseeing on the 18th (Sun) to allow time to drive to Siena.
Historic Sites · Outdoors · Tours · Parks
Side Trip
Find places to stay Sep 15 — 18:

Siena — 3 nights

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Get some historical perspective at Centro Storico di Siena and Historic Centre of San Gimignano. Torre del Mangia and Basilica di San Clemente in Santa Maria dei Servi are good opportunities to explore the local culture. Explore Siena's surroundings by going to San Gimignano (Church of Sant'Agostino, Torre Grossa, &more). Next up on the itinerary: pause for some serene contemplation at Duomo di Siena, contemplate in the serene atmosphere at Cappella di Piazza, make a trip to Piazza del Campo, and steep yourself in history at San Francesco.

To see where to stay, more things to do, traveler tips, and tourist information, read Siena trip maker website.

Drive from Florence to Siena in 1.5 hours. Alternatively, you can take a bus; or take a train. In September, plan for daily highs up to 32°C, and evening lows to 19°C. Finish your sightseeing early on the 21st (Wed) so you can drive to Pienza.
Historic Sites
Side Trip
Find places to stay Sep 18 — 21:

Pienza — 2 nights

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. Kick off your visit on the 22nd (Thu): contemplate in the serene atmosphere at Collegiata di San Quirico, then steep yourself in history at Corso il Rossellino, and then learn about winemaking at Enoteca Di Ghino. Here are some ideas for day two: take a stroll through Monticchiello, then browse the exhibits of Art Studio di Adelina Quadri, and then take in the spiritual surroundings of Pieve dei Santi Leonardo e Cristoforo.

For ratings, photos, and more tourist information, you can read our Pienza trip itinerary maker tool.

Getting from Siena to Pienza by car takes about 1.5 hours. Other options: take a bus; or do a combination of train and bus. Expect a daytime high around 32°C in September, and nighttime lows around 19°C. Cap off your sightseeing on the 23rd (Fri) early enough to travel to Portoferraio.
Historic Sites · Museums · Shopping · Neighborhoods
Side Trip
Find places to stay Sep 21 — 23:

Portoferraio, Elba Island — 2 nights

Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Start off your visit on the 24th (Sat): tour the pleasant surroundings at Spiaggia Di Sottobomba, then enjoy the sand and surf at Spiaggia di Seccione, and then enjoy the sand and surf at Spiaggia di Enfola. Here are some ideas for day two: get engrossed in the history at Napoleonic Mills House and then kick back and relax at Spiaggia di Capo Bianco.

To see photos, more things to do, where to stay, and other tourist information, use the Portoferraio route planning website.

Traveling by combination of car and ferry from Pienza to Portoferraio takes 4 hours. Alternatively, you can do a combination of bus, train, and ferry. When traveling from Pienza in September, plan for slightly colder days in Portoferraio, with highs around 28°C, while nights are about the same with lows around 19°C. Wrap up your sightseeing by early afternoon on the 25th (Sun) to allow enough time to travel back home.
Beaches · Parks · Outdoors · Museums
Find places to stay Sep 23 — 25:

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.