41 days in Italy Itinerary

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 MEF-Museo Enzo Ferrari capture your imagination. Explore Florence's surroundings by going to Greve in Chianti (Castello di Verrazzano & Montefioralle Winery), Porto Venere (Portovenere & San Pietro Church) and Siena (Torre del Mangia, Centro Storico di Siena, &more). There's lots more to do: take in the spiritual surroundings of Eremo Le Celle, take in the architecture and atmosphere at Duomo di Pisa, explore the historical opulence of Castello dei Conti Guidi di Poppi, and examine the collection at Piaggio Museum.

For where to stay, more things to do, photos, and other tourist information, you can read our Florence day trip tool.

If you are flying in from United States, the closest major aiports 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. Cap off your sightseeing on the 30th (Mon) early enough to go by car to 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, thenexamine 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, thenexamine 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.

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, thenlearn 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, thenlearn 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.

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 Archivio di Stato. Battistero di San Giovanni and Sinagoga di Siena are good opportunities to explore the local culture. Change things up with a short trip to Torre e Casa Campatelli in San Gimignano (about 38 minutes away). There's lots more to do: contemplate the long history of Palazzo Chigi Saracini, take in the architecture and atmosphere at Basilica di San Clemente in Santa Maria dei Servi, appreciate the extensive heritage of Piazza Salimbeni, and take in the spiritual surroundings of Cappella di Piazza.

For traveler tips, other places to visit, ratings, and more tourist information, use the Siena trip maker app.

Traveling by car from Montalcino to Siena takes an hour. Alternatively, you can take a bus; or do a combination of bus and train. In October, daily temperatures in Siena can reach 73°F, while at night they dip to 56°F. Cap off your sightseeing on the 8th (Tue) early enough to go by car to 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. On the 9th (Wed), look for gifts at Officine Creative Roma, make a trip to Piazza Navona, stop by Nuovi Quaderni di Capestrano, thenbrowse the eclectic array of goods at Porta Portese, thentake 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, thensee 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.