41 days in Italy Itinerary

41 days in Italy Itinerary

Created using Inspirock Italy holiday planner

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Route & dates

41 days in Italy Itinerary

Start: Florence
1
Florence
— 29 nights
train:  1​h
2
Pisa
— 2 nights
3
Montalcino
— 3 nights
Drive:  1​h
4
Siena
— 3 nights
5
Rome
— 3 nights
train:  1​h 45​min
End: Florence

29
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your list of things to see and do now includes M.G. Design, Tuscany Vespa Tours, Italy Segway Tours, and other attractions. Satisfy your inner culture vulture at Gallerie Degli Uffizi and Piazzale Michelangelo. Appreciate the collections at Academy Of Florence Art Gallery and Piaggio Museum. Venture out of the city with trips to Greve in Chianti (Castello di Verrazzano & Montefioralle Winery), Siena (Torre del Mangia, Centro Storico di Siena, & more) and Porto Venere (Portovenere & San Pietro Church). There's still lots to do: take in the spiritual surroundings of Eremo Le Celle, take an in-depth tour of Basilica di Santa Croce, tour the pleasant surroundings at Canyon Park, and steep yourself in history at Abbazia di Sant'Antimo.

For maps, where to stay, traveler tips, and other tourist information, use the Florence trip planner.

If you are flying in from United States, the closest major airports are Peretola Airport, Pisa International Airport and Bologna Guglielmo Marconi Airport. September in Florence sees daily highs of 78°F and lows of 59°F at night. Finish your sightseeing early on the 30th (Mon) so you can take a train to Pisa.

Things to do in Florence

Historic Sites Museums Tours

Side Trips

Siena, San Gimignano, Pisa, Chiusdino, Volterra
Find places to stay Sep 1 — 30:
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Portovenere ©
Portovenere

2
nights
Pisa

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Start off your visit on the 1st (Tue): get a new perspective on nature at Museo di Storia Naturale - Universita di Pisa, then get a new perspective on nature at Museo Nazionale della Certosa Monumentale di Calci, then see the interesting displays at Museo Aviotruppe Esercito Italiano, and finally contemplate in the serene atmosphere at Santuario Della Madonna del Ghisallo - Museo Del Ciclismo. Keep things going the next day: pause for some serene contemplation at Basilica romanica di San Piero a Grado, explore the world behind art at Museo Nazionale di Palazzo Reale, then see the interesting displays at National Museum of Saint Mathew, and finally take in the spiritual surroundings of Chiesa di Santa Caterina d'Alessandria.

For traveler tips, ratings, reviews, and other tourist information, refer to the Pisa trip maker .

Traveling by train from Florence to Pisa takes an hour. Alternatively, you can take a bus; or drive. Expect a daytime high around 78°F in September, and nighttime lows around 59°F. Wrap up your sightseeing on the 2nd (Wed) to allow time to drive to Montalcino.

Things to do in Pisa

Museums Historic Sites

Side Trips

Calci, Madonna del Ghisallo
Find places to stay Sep 30 — Oct 2:
Highlights from your plan

3
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Kick off your visit on the 3rd (Thu): learn about winemaking at Winery Solaria Patrizia Cencioni, learn about winemaking at Poggio Rubino, then do a tasting at Castello Banfi Wine Estate, and finally do a tasting at Cantina Fattoria della Talosa. Get ready for a full day of sightseeing on the 4th (Fri): learn about winemaking at Podere Le Ripi, then learn about winemaking 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.

To see other places to visit, photos, reviews, and other tourist information, read Montalcino route planner.

Traveling by car from Pisa to Montalcino takes 2.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. October in Montalcino sees daily highs of 73°F and lows of 56°F at night. On the 5th (Sat), wrap the sightseeing up by early afternoon so you can drive to Siena.

Things to do in Montalcino

Wineries Historic Sites

Side Trip

Cantina Fattoria della Talosa
Find places to stay Oct 2 — 5:
Highlights from your plan
Poggio Rubino ©
Poggio Rubino
Podere Le Ripi ©
Podere Le Ripi
Tenuta Fanti ©
Tenuta Fanti

3
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Step off the beaten path and head to Battistero di San Giovanni and Torre e Casa Campatelli. Do some cultural sightseeing at Museo dell'Opera Metropolitana and Pinacoteca Nazionale. The adventure continues: examine the collection at Museo della Tortura, take in the spiritual surroundings of San Francesco, steep yourself in history at Loggia della Mercanzia, and get engrossed in the history at Museo Archeologico di Siena.

To find where to stay, reviews, photos, and tourist information, use the Siena trip planning tool .

Traveling by car from Montalcino to Siena takes an hour. Alternatively, you can do a combination of bus and train; or take a bus. October in Siena sees daily highs of 73°F and lows of 56°F at night. Cap off your sightseeing on the 8th (Tue) early enough to go by car to Rome.

Things to do in Siena

Historic Sites Museums Shopping

Side Trip

Torre e Casa Campatelli
Find places to stay Oct 5 — 8:
Highlights from your plan
Battistero di San Giovanni ©
Battistero di San Giovanni
Museo dell'Opera Metropolitana ©
Museo dell'Opera Metropolitana
Torre e Casa Campatelli ©
Torre e Casa Campatelli

3
nights
Rome

Rome ©
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. Kick off your visit on the 9th (Wed): stop by Officine Creative Roma, appreciate the extensive heritage of Piazza Navona, look for gifts at Nuovi Quaderni di Capestrano, then hunt for treasures at Porta Portese, then take a stroll through Trastevere, and finally get a taste of local nightlife at Food Tours of Rome. On the 10th (Thu), you'll have a packed day of sightseeing: explore the ancient world of Pantheon, contemplate in the serene atmosphere at Abbey of St. Paul Outside the Walls, explore the world behind art at Palazzo Doria Pamphilj, then look for gifts at Al Sogno, and finally stop by Anglo American Book.

For photos, ratings, traveler tips, and tourist information, you can read our Rome online sightseeing planner .

Getting from Siena to Rome by car takes about 2.5 hours. Other options: 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 enough time to take a train back home.

Things to do in Rome

Tours Historic Sites Classes

Side Trip

Vatican City
Find places to stay Oct 8 — 11:
Highlights from your plan
Pantheon ©
Pantheon
Colosseum ©
Colosseum
Abbey of St. Paul Outside the Walls ©

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