41 days in Italy Itinerary

41 days in Italy Itinerary

Created using Inspirock Italy holiday planner

Plan created by another user. Make it yours
1
Florence
— 29 nights
Drive
2
Pisa
— 2 nights
Drive
3
Montalcino
— 3 nights
Drive
4
Siena
— 3 nights
Drive
5
Rome
— 3 nights
Train

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29
nights
Florence

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You've added M.G. Design, Tuscany Vespa Tours, Fat Tire Tours - Florence, and other attractions to your itinerary. Get a sense of the local culture at Cathedral of Santa Maria del Fiore and Florence Academy of Fine Arts. Let the collections at Museo Ferrari and Gallerie Degli Uffizi capture your imagination. Explore Florence's surroundings by going to Siena (Torre del Mangia, Centro Storico di Siena, &more), Greve in Chianti (Castello di Verrazzano & Montefioralle Winery) and Porto Venere (Portovenere & San Pietro Church). Next up on the itinerary: contemplate in the serene atmosphere at Eremo Le Celle, examine the collection at Piaggio Museum, contemplate the long history of Abbazia di Sant'Antimo, and take in the architecture and atmosphere at Abbazia di San Galgano.

To find where to stay, other places to visit, traveler tips, and more tourist information, use the Florence trip itinerary app.

If you are flying in from United States, the closest major aiports are Peretola Airport, Pisa International Airport and Bologna Guglielmo Marconi Airport. In September in Florence, expect temperatures between 78°F during the day and 59°F at night. Finish up your sightseeing early on the 30th (Mon) so you can go by car to Pisa.

Things to do in Florence

Historic Sites · Museums · Wineries · Tours

Side Trips

Find places to stay Sep 1 — 30:
Highlights from your trip
Florence Academy of Fine Arts ©
Must see
Florence Academy of Fine Arts
4.4
Gallerie Degli Uffizi ©
World heritage site
Gallerie Degli Uffizi
4.5
Anghiari ©
Must see
Anghiari
4.9

2
nights
Pisa

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
On the 1st (Tue), get a new perspective on nature at Museo di Storia Naturale - Universita di Pisa, learn more about the world around you at Museo Nazionale della Certosa Monumentale di Calci, then examine the collection at Museo Aviotruppe Esercito Italiano, and finally see the interesting displays at Madonna del Ghisallo. Get ready for a full day of sightseeing on the 2nd (Wed): take in the architecture and atmosphere at Basilica romanica di San Piero a Grado, admire the masterpieces at Museo Nazionale di Palazzo Reale, then examine the collection at National Museum of Saint Mathew, and finally take in the architecture and atmosphere at Chiesa di Santa Caterina d'Alessandria.

To find out how to plan a trip to Pisa, use our trip itinerary maker.

Drive from Florence to Pisa in 1.5 hours. Alternatively, you can take a train; or take a bus. In September, daily temperatures in Pisa can reach 78°F, while at night they dip to 59°F. Finish your sightseeing early on the 2nd (Wed) to allow enough time to drive to Montalcino.

Things to do in Pisa

Side Trips

Find places to stay Sep 30 — Oct 2:
Highlights from your trip

3
nights
Montalcino

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
On the 3rd (Thu), do a tasting at Winery Solaria Patrizia Cencioni, do a tasting at Poggio Rubino, then learn about winemaking at Castello Banfi Wine Estate, and finally learn about winemaking at Cantina Fattoria della Talosa. Get ready for a full day of sightseeing on the 4th (Fri): learn about winemaking at Podere Le Ripi, do a tasting at Casanova di Neri, then learn about winemaking at Enoteca di Piazza Wine Room, and finally take in the architecture and atmosphere at Parrocchia Di S. Egidio Abate.

For reviews, photos, maps, and tourist information, refer to the Montalcino tour planner.

Drive from Pisa to Montalcino in 2.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. In October, daily temperatures in Montalcino can reach 73°F, while at night they dip to 56°F. Wrap up your sightseeing by early afternoon on the 5th (Sat) to allow time for the car ride to Siena.

Things to do in Montalcino

Wineries · Historic Sites

Side Trip

Find places to stay Oct 2 — 5:
Highlights from your trip
Poggio Rubino ©
Winery / Vineyard
Poggio Rubino
4.7
Podere Le Ripi ©
Winery / Vineyard
Podere Le Ripi
4.6

3
nights
Siena

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Appreciate the collections at Museo della Tortura and Museo Archeologico di Siena. Battistero di San Giovanni and Archivio di Stato are good opportunities to explore the local culture. Change things up with a short trip to Torre e Casa Campatelli in San Gimignano (about 50 minutes away). There's still lots to do: steep yourself in history at Palazzo Chigi Saracini, pause for some serene contemplation at Basilica di San Clemente in Santa Maria dei Servi, appreciate the extensive heritage of Piazza Salimbeni, and admire the masterpieces at Pinacoteca Nazionale.

To find where to stay, maps, ratings, and other tourist information, you can read our Siena driving holiday planning website.

Getting from Montalcino to Siena by car takes about an hour. Other options: take a bus; or do a combination of bus and train. In October, plan for daily highs up to 73°F, and evening lows to 56°F. Cap off your sightseeing on the 8th (Tue) early enough to go by car to Rome.

Things to do in Siena

Side Trip

Find places to stay Oct 5 — 8:
Highlights from your trip
Battistero di San Giovanni ©
Religious Site
Battistero di San Giovanni
4.5
Torre e Casa Campatelli ©
History Museum
Torre e Casa Campatelli
4.8
Archivio di Stato ©
History Museum
Archivio di Stato
4.4

3
nights
Rome

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Your day by day itinerary now includes Nuovi Quaderni di Capestrano, Officine Creative Roma, Anglo American Book, and other attractions you added. On the 9th (Wed), look for gifts at Officine Creative Roma, make a trip to Piazza Navona, stop by Nuovi Quaderni di Capestrano, then browse the eclectic array of goods at Porta Portese, then take a stroll through Trastevere, and finally get a taste of local nightlife at Food Tours of Rome. Get ready for a full day of sightseeing on the next day: delve into the distant past at Pantheon, contemplate in the serene atmosphere at Abbey of St. Paul Outside the Walls, admire the striking features of Palazzo Doria Pamphilj, then see the interesting displays at Al Sogno, and finally look for gifts at Anglo American Book.

For more things to do, ratings, traveler tips, and other tourist information, use the Rome driving holiday planning website.

Drive from Siena to Rome in 2.5 hours. Alternatively, you can take a bus; or take a train. October in Rome sees daily highs of 73°F and lows of 55°F at night. Wrap up your sightseeing by early afternoon on the 11th (Fri) to allow time for the train ride back home.

Things to do in Rome

Tours · Historic Sites · Classes · Nightlife

Side Trip

Find places to stay Oct 8 — 11:
Highlights from your trip
Pantheon ©
Must see
Pantheon
4.8
Colosseum ©
Must see
Colosseum
4.7

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