44 days in Italy Itinerary

44 days in Italy Itinerary

Created using Inspirock Italy attractions planner

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Route & dates

44 days in Italy Itinerary

Start: Newark
Fly:  11 h
1
Venice
— 4 nights
Bus:  1 h 30 min
2
Verona
— 4 nights
Train:  1 h 15 min
3
Milan
— 3 nights
Train:  1 h 45 min
4
Florence
— 5 nights
Bus:  1 h 15 min
5
Siena
— 5 nights
Drive:  1 h 45 min
6
Assisi
— 5 nights
Drive:  2 h 15 min
7
Rome
— 5 nights
Train:  1 h 45 min
8
Salerno
— 5 nights
Ferry:  1 h 30 min
9
Positano
— 6 nights
Drive + Fly:  15 h
End: Newark

4
nights
Venice

Venice ©
Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
You'll find plenty of places to visit near Venice: Padua (Basilica di Sant’Antonio, Scrovegni Chapel, &more). The adventure continues: contemplate the waterfront views at Canal Grande, take in the views from Ponte di Rialto, appreciate the extensive heritage of Piazza San Marco, and enjoy breathtaking views from St Mark's Campanile.

For where to stay, ratings, and tourist information, read Venice vacation planning app.

Newark, USA to Venice is an approximately 11-hour flight. You can also do a combination of train and flight; or do a combination of flight and train. Traveling from Newark to Venice, you'll lose 6 hours due to the time zone difference. Expect a daytime high around 77°F in September, and nighttime lows around 59°F. Finish your sightseeing early on the 30th (Wed) so you can take a bus to Verona.

Things to do in Venice

Historic Sites Museums Parks

Side Trip

Padua
Find places to stay Sep 25 — 30:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Piazza San Marco ©
Piazza San Marco

4
nights
Verona

Verona ©
The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.
Verona is known for nightlife, historic sites, and museums. Your plan includes some of its best attractions: experience the emotional art of opera at Arena di Verona, don't miss a visit to Piazza Bra, take a stroll through Piazza delle Erbe, and visit Quinzano.

Ask Inspirock to suggest an itinerary and make planning a trip to Verona fast, fun, and easy.

You can take a bus from Venice to Verona in 1.5 hours. Other options are to drive; or take a shuttle. Expect a daytime high around 78°F in September, and nighttime lows around 58°F. Wrap up your sightseeing on the 4th (Sun) early enough to take a train to Milan.

Things to do in Verona

Historic Sites Outdoors Neighborhoods
Find places to stay Sep 30 — Oct 4:
Highlights from your plan
Arena di Verona ©
Arena di Verona
Piazza delle Erbe ©
Piazza delle Erbe
Basilica di San Zeno Maggiore ©
Basilica di San Zeno Maggiore

3
nights
Milan

Milan ©
In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.
Get out of town with these interesting Milan side-trips: Santuario Del Ghisallo (in Magreglio) and Anything But Work (in Mandello del Lario). Next up on the itinerary: take in the spiritual surroundings of Duomo di Milano, step into the grandiose world of Castello Sforzesco, admire the striking features of Galleria Vittorio Emanuele II, and explore the different monuments and memorials at Monumental Cemetery.

To see reviews, ratings, photos, and other tourist information, read Milan route planning site.

Traveling by train from Verona to Milan takes 1.5 hours. Alternatively, you can drive. Expect a daytime high around 65°F in October, and nighttime lows around 52°F. Cap off your sightseeing on the 7th (Wed) early enough to catch the train to Florence.

Things to do in Milan

Historic Sites Parks Outdoors

Side Trips

Anything But Work, Santuario Del Ghisallo
Find places to stay Oct 4 — 7:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

5
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Step out of Florence to go to Pisa and see Leaning Tower of Pisa, which is approximately 1h 10 min away. There's lots more to do: explore the world behind art at Academy Of Florence Art Gallery, see the interesting displays at Pitti Palace, contemplate the long history of Basilica of Santa Croce, and contemplate in the serene atmosphere at The Baptistery of St. John.

For ratings, where to stay, photos, and other tourist information, you can read our Florence vacation planner.

You can take a train from Milan to Florence in 2 hours. Other options are to drive; or fly. Expect somewhat warmer weather when traveling from Milan in October: highs in Florence hover around 71°F, while lows dip to 54°F. Wrap up your sightseeing on the 12th (Mon) early enough to take a bus to Siena.

Things to do in Florence

Historic Sites Museums Tours

Side Trip

Leaning Tower of Pisa
Find places to stay Oct 7 — 12:
Highlights from your plan
Art Gallery Studio Iguarnieri ©
Art Gallery Studio Iguarnieri
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

5
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Get out of town with these interesting Siena side-trips: San Gimignano (Guardastelle Vineyard & Podere La Marronaia- Sosta Alle Colonne), Castiglion del Bosco (in Montalcino) and Museo Diocesano (in Cortona). The adventure continues: indulge your senses at some of the top wineries in the area, ponder the world of politics at Palazzo Pubblico and Museo Civico, learn about winemaking at Fattoria di Montemaggio, and deepen your understanding at Scuola di Cucina di Lella.

For reviews, other places to visit, more things to do, and other tourist information, use the Siena trip itinerary planner.

You can take a bus from Florence to Siena in 1.5 hours. Other options are to drive; or take a train. October in Siena sees daily highs of 73°F and lows of 56°F at night. Finish your sightseeing early on the 17th (Sat) so you can drive to Assisi.

Things to do in Siena

Wineries Tours Museums

Side Trips

San Gimignano, Castiglion del Bosco, Museo Diocesano, Accademia del Buon Gusto, Fattoria Casa Sola
Find places to stay Oct 12 — 17:
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Guardastelle Vineyard ©
Guardastelle Vineyard

5
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Explore Assisi's surroundings by going to Vineria del Carmine (in La Bruna), Lago di Pilato (in Montemonaco) and Montioni Frantoio e Cantina (in Montefalco). There's still lots to do: take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, explore the historical opulence of Rocca Maggiore, contemplate in the serene atmosphere at Eremo delle Carceri, and do a tasting at Azienda Agraria Saio.

To find where to stay, traveler tips, other places to visit, and other tourist information, read our Assisi trip builder website.

You can drive from Siena to Assisi in 2 hours. Alternatively, you can take a bus; or take a train. Traveling from Siena in October, Assisi is slightly colder at night with lows of 51°F. Finish up your sightseeing early on the 22nd (Thu) so you can go by car to Rome.

Things to do in Assisi

Historic Sites Wineries Parks

Side Trips

Perugia, Lago di Pilato, Piana di Castelluccio di Norcia, Montioni Frantoio e Cantina
Find places to stay Oct 17 — 22:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Eremo delle Carceri ©
Eremo delle Carceri

5
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Rome is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: explore the ancient world of Colosseum, ponder the design of Trevi Fountain, admire the masterpieces at Vatican Museums, and steep yourself in history at Palatine Hill.

For where to stay, maps, ratings, and tourist information, read our Rome holiday planner.

Traveling by car from Assisi to Rome takes 2.5 hours. Alternatively, you can take a train; or take a bus. In October in Rome, expect temperatures between 73°F during the day and 55°F at night. Finish up your sightseeing early on the 27th (Tue) so you can catch the train to Salerno.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Find places to stay Oct 22 — 27:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

5
nights
Salerno

Salerno ©
While often overshadowed by the Amalfi Coast's array of quaint villages, Salerno has become one of the region's main areas for culture and entertainment, while remaining relatively unmarked by tourism.
Explore the numerous day-trip ideas around Salerno: Spiaggia Lannio (in Cetara), Ravello (Ceramiche Cosmolena di Margherita di Palma & Cappella Sant'Angelo all'Ospedale) and Spiaggia di castiglione (in Castiglione). The adventure continues: explore the ancient world of Pompeii Archaeological Park, race across the water with a speed boat tour, enjoy the sand and surf at Spiaggia di Marina d'Albori, and step into the grandiose world of Castello di San Nicola de Thoro-Plano.

For other places to visit, reviews, photos, and other tourist information, use the Salerno trip planner.

Take a train from Rome to Salerno in 2 hours. Alternatively, you can drive; or take a bus. Traveling from Rome in October, Salerno is somewhat warmer at night with lows of 63°F. Finish up your sightseeing early on the 1st (Sun) so you can catch the ferry to Positano.

Things to do in Salerno

Outdoors Parks Beaches

Side Trips

Ravello, Maiori, Vietri sul Mare, Pompeii Archaeological Park, Monte Finestra
Find places to stay Oct 27 — Nov 1:
Highlights from your plan
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Spiaggia di castiglione ©
Spiaggia di castiglione

6
nights
Positano

Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
Get out of town with these interesting Positano side-trips: Vivaio Ruoppo (in Sorrento), Ravello (San Giovanni del Toro, Villa Rufolo, &more) and Lido di Ravello (in Castiglione). And it doesn't end there: cool off at Fornillo, enjoy the sand and surf at Bagni d'Arienzo Beach Club, Positano, go for a walk through Positano, and take a memorable tour with Tours.

To see other places to visit, ratings, more things to do, and tourist information, read Positano tour planner.

Getting from Salerno to Positano by ferry takes about 1.5 hours. Other options: do a combination of train and taxi; or drive. In November, plan for daily highs up to 64°F, and evening lows to 56°F. On the 7th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Positano

Outdoors Parks Beaches

Side Trips

Ravello, Amalfi, Sorrento, Praiano, Spiaggia di Atrani
Find places to stay Nov 1 — 7:
Highlights from your plan
Food Tours
Fornillo ©
Fornillo
Boat Tours & Water Sports

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