59 days in Italy Itinerary

59 days in Italy Itinerary

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Route & dates

59 days in Italy Itinerary

Start: Tampa
Fly + Drive:  19​h 30​min
1
Sorrento
— 1 night
ferry:  1​h
2
Naples
— 3 nights
train:  1​h 15​min
3
Rome
— 7 nights
Drive:  2​h 15​min
4
Porto Santo Stefano
— 2 nights
Drive:  4​h
5
Cinque Terre
— 5 nights
Drive:  2​h 30​min
6
Florence
— 5 nights
bus:  1​h 15​min
7
Siena
— 7 nights
Drive:  2​h
8
Bologna
— 6 nights
train:  1​h 15​min
9
Milan
— 3 nights
train:  1​h 15​min
10
Varenna
— 5 nights
Drive:  2​h 15​min
11
Verona
— 6 nights
Drive:  1​h 30​min
12
Bolzano
— 5 nights
Drive:  2​h 45​min
13
Venice
— 1 night
Fly:  15​h 45​min
End: Tampa


Learn more about your trip

1
night
Sorrento

Sorrento
A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
To see maps, more things to do, traveler tips, and tourist information, read Sorrento tour itinerary planner.

Tampa, USA to Sorrento is an approximately 19.5-hour combination of flight and car. The time zone difference when traveling from Tampa to Sorrento is 6 hours. Plan for slightly colder temperatures traveling from Tampa in September, with highs in Sorrento at 80°F and lows at 68°F. On the 9th (Wed), you're off toNaples.

Things to do in Sorrento

Tours Outdoors Transportation

3
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Get out of town with these interesting Naples side-trips: Villa Cimbrone Gardens (in Ravello), Duomo di Salerno (in Salerno) and Paestum Ruins (in Paestum). There's lots more to do: explore the ancient world of Pompeii Archaeological Park, get to know the fascinating history of Via Caracciolo e Lungomare di Napoli, don't miss a visit to Via San Gregorio Armeno, and steep yourself in history at Museo Cappella Sansevero.

Plan a Naples trip in moments using our itinerary builder.

Ride a ferry from Sorrento to Naples in an hour. Alternatively, you can take a subway; or drive. Expect a daytime high around 80°F in September, and nighttime lows around 64°F. Wrap up your sightseeing by early afternoon on the 12th (Sat) to allow enough time to take a train to Rome.

Things to do in Naples

Historic Sites Museums Parks

Side Trips

Duomo di Salerno, Pompeii Archaeological Park, Paestum Ruins, Villa Cimbrone Gardens, Parco Acheologico di Ercolano
Highlights from your plan
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Paestum Ruins ©
Paestum Ruins

7
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Step out of Rome to go to Tivoli and see Villa d'Este, which is approximately 48 minutes away. The adventure continues: explore the ancient world of Colosseum, steep yourself in history at Palatine Hill, admire the striking features of Pantheon, and make a trip to St. Peter's Basilica.

For where to stay, photos, and more tourist information, read Rome road trip planning tool .

You can take a train from Naples to Rome in 1.5 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 81°F in September, and nighttime lows around 60°F. Wrap up your sightseeing on the 19th (Sat) to allow time to travel to Porto Santo Stefano.

Things to do in Rome

Historic Sites Museums Tours

Side Trips

Vatican City, Villa d'Este
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

2
nights
Porto Santo Stefano

Porto Santo Stefano ©
Kick off your visit on the 20th (Sun): see the interesting displays at Forte Stella, stroll through Riva del Marchese, and then enjoy the sand and surf at Cala del Gesso. Get ready for a full day of sightseeing on the 21st (Mon): tour the pleasant surroundings at Cala Mar Morto and then discover the deep blue sea with a scuba or snorkeling tour.

To find ratings, traveler tips, where to stay, and other tourist information, use the Porto Santo Stefano road trip tool .

You can drive from Rome to Porto Santo Stefano in 2.5 hours. Expect a daytime high around 81°F in September, and nighttime lows around 61°F. Finish up your sightseeing early on the 21st (Mon) so you can travel to Cinque Terre.

Things to do in Porto Santo Stefano

Outdoors Parks Beaches

Side Trip

Porto Ercole
Highlights from your plan
Cala del Gesso ©
Cala del Gesso
Scuba & Snorkeling
Forte Stella ©
Forte Stella

5
nights
Cinque Terre

Cinque Terre ©
Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Venture out of the city with trips to Genoa (Spianata Castelletto, Cattedrale di San Lorenzo - Duomo di Genova, & more) and Portovenere (in Porto Venere). There's much more to do: take a leisurely stroll along Passeggiata Lungomare, get into the urban bustle at Vernazza, make a trip to Borgo Antico, and explore the striking landscape of Parco Nazionale Cinque Terre.

To see ratings, where to stay, more things to do, and more tourist information, read Cinque Terre trip maker app .

Traveling by car from Porto Santo Stefano to Cinque Terre takes 4 hours. In September, plan for daily highs up to 78°F, and evening lows to 59°F. Wrap up your sightseeing on the 26th (Sat) to allow time to drive to Florence.

Things to do in Cinque Terre

Parks Neighborhoods Trails

Side Trips

Genoa, Portovenere
Highlights from your plan
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Aquarium of Genoa ©
Aquarium of Genoa
Parco Nazionale Cinque Terre ©
Parco Nazionale Cinque Terre

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 with an excursion to Leaning Tower of Pisa in Pisa--about 1h 10 min away. There's much more to do: explore the world behind art at Gallerie Degli Uffizi, take in panoramic vistas at Campanile di Giotto, get engrossed in the history at Basilica di Santa Croce, and see the interesting displays at Pitti Palace.

To find maps, traveler tips, where to stay, and tourist information, read Florence trip itinerary maker tool .

Traveling by car from Cinque Terre to Florence takes 2.5 hours. Alternatively, you can take a train. In September in Florence, expect temperatures between 78°F during the day and 59°F at night. Cap off your sightseeing on the 1st (Thu) early enough to catcht the bus to Siena.

Things to do in Florence

Museums Historic Sites Tours

Side Trip

Leaning Tower of Pisa
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

7
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Explore the numerous day-trip ideas around Siena: Museo della Porziuncola (in Santa Maria degli Angeli), Assisi (Eremo delle Carceri, Basilica Papale e Sacro Convento di San Francesco d'Assisi, & more) and San Gimignano (Historic Centre of San Gimignano & Guardastelle Vineyard). The adventure continues: indulge your taste buds at Food & Drink, learn about winemaking at Ciacci Piccolomini d'Aragona, get a sense of history and politics at Palazzo Pubblico and Museo Civico, and pause for some serene contemplation at Duomo di Siena.

For other places to visit, photos, reviews, and other tourist information, use the Siena trip planning app .

Traveling by bus from Florence to Siena takes 1.5 hours. Alternatively, you can drive; or take a train. In October, daytime highs in Siena are 73°F, while nighttime lows are 56°F. Finish your sightseeing early on the 8th (Thu) so you can drive to Bologna.

Things to do in Siena

Historic Sites Wineries Tours

Side Trips

Assisi, San Gimignano, Abbazia di San Galgano, Ciacci Piccolomini d'Aragona, Accademia del Buon Gusto
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo

6
nights
Bologna

Bologna ©
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
You'll find plenty of places to visit near Bologna: Ravenna (Mirabilandia, Basilica San Vitale, & more), Cimitero di Guerra (in Cesena) and Italy in Miniature (in Rimini). The adventure continues: enjoy breathtaking views from Torri degli Asinelli e Garisenda, explore the world behind art at Pinacoteca Nazionale di Bologna, take in the spiritual surroundings of Basilica - Santuario di Santo Stefano, and take in the architecture and design of Academya Lingue.

For other places to visit, ratings, more things to do, and tourist information, use the Bologna online route planner .

Traveling by car from Siena to Bologna takes 2 hours. Alternatively, you can do a combination of bus and train; or take a bus. Traveling from Siena in October, you will find days in Bologna are little chillier (67°F), and nights are about the same (52°F). On the 14th (Wed), wrap the sightseeing up by early afternoon so you can take a train to Milan.

Things to do in Bologna

Historic Sites Museums Theme Parks

Side Trips

Ravenna, Italy in Miniature, Piazza Maggiore, Cattedrale di Parma, Castello Estense
Highlights from your plan
Basilica San Vitale ©
Basilica San Vitale
Le Due Torri Torre degli Asinell ©
Le Due Torri Torre degli Asinell
Academya Lingue ©
Academya Lingue

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.
Milan is known for historic sites, museums, nightlife, fun & games, and shopping. Your plan includes some of its best attractions: contemplate in the serene atmosphere at Duomo di Milano, admire the striking features of Galleria Vittorio Emanuele II, explore the different monuments and memorials at Monumental Cemetery, and step into the grandiose world of Castello Sforzesco.

To see more things to do, traveler tips, ratings, and other tourist information, you can read our Milan online trip itinerary planner .

Traveling by train from Bologna to Milan takes 1.5 hours. Alternatively, you can drive; or take a bus. In October, daily temperatures in Milan can reach 65°F, while at night they dip to 52°F. You will leave for Varenna on the 17th (Sat).

Things to do in Milan

Historic Sites Museums Fun & Games
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Castello Sforzesco ©
Castello Sforzesco

5
nights
Varenna

Varenna ©
Varenna is a comune (municipality) on Lake Como in the Province of Lecco in the Italian region Lombardy, located about 60km north of Milan and about 20km northwest of Lecco.Varenna was founded by local fishermen in 769, and was later allied of the commune of Milan. Venture out of the city with trips to i Giardini di Villa Melzi (in Bellagio), Tremezzina (Villa del Balbianello & Villa Carlotta) and Stand-Up Paddleboarding (in Dervio). And it doesn't end there: enjoy the sand and surf at Riva Bianca Beach, admire the landmark architecture of Villa Monastero, admire the natural beauty at Il Giardino Botanico - Hotel Villa Cipressi, and get a taste of the local shopping with Il Tornio.

To find other places to visit, more things to do, photos, and other tourist information, read our Varenna trip itinerary maker website .

You can take a train from Milan to Varenna in 1.5 hours. Alternatively, you can drive. In October, daytime highs in Varenna are 64°F, while nighttime lows are 49°F. You will have some time to spend on the 22nd (Thu) before leaving for Verona.

Things to do in Varenna

Parks Outdoors Museums

Side Trips

Tremezzina, Bellano, Castello di Vezio, Riva Bianca Beach, i Giardini di Villa Melzi
Highlights from your plan
Villa Carlotta ©
Villa Carlotta
Villa del Balbianello ©
Villa del Balbianello
Riva Bianca Beach ©
Riva Bianca Beach

6
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.
Venture out of the city with trips to Lago di Garda (in Garda) and Gardaland Park (in Castelnuovo del Garda). There's still lots to do: 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 get outside with King Rock arrampicata.

For more things to do, traveler tips, other places to visit, and other tourist information, use the Verona tour itinerary tool .

Traveling by car from Varenna to Verona takes 2.5 hours. Alternatively, you can take a train; or do a combination of train and shuttle. October in Verona sees daily highs of 66°F and lows of 50°F at night. Finish your sightseeing early on the 28th (Wed) to allow enough time to drive to Bolzano.

Things to do in Verona

Historic Sites Parks Nature

Side Trips

Gardaland Park, Lago di Garda
Highlights from your plan
Arena di Verona ©
Arena di Verona
Basilica di San Zeno Maggiore ©
Basilica di San Zeno Maggiore
Piazza delle Erbe ©
Piazza delle Erbe

5
nights
Bolzano

Bolzano ©
South Tyrol's capital, Bolzano, has been named the Italian city with the highest quality of life.
Get out of town with these interesting Bolzano side-trips: Lago di Braies (in Braies), I Giardini di Castel Trauttmansdorff (in Merano) and Lago di Molveno (in Molveno). The adventure continues: stroll around Puez-Geisler Nature Park, get engrossed in the history at South Tyrol Museum of Archaeology, take in the architecture and atmosphere at Chiesa San Pietro sul Colle, and see the interesting displays at Messner Mountain Museum MMM Firmian.

To find reviews, maps, and more tourist information, use the Bolzano trip planner.

You can drive from Verona to Bolzano in 1.5 hours. Other options are to take a bus; or take a train. In October, daytime highs in Bolzano are 66°F, while nighttime lows are 47°F. Wrap up your sightseeing on the 2nd (Mon) to allow time to drive to Venice.

Things to do in Bolzano

Parks Nature Historic Sites

Side Trips

I Giardini di Castel Trauttmansdorff, Lago di Molveno, Lago di Braies, Chiesa San Pietro sul Colle
Highlights from your plan
Puez-Geisler Nature Park ©
Puez-Geisler Nature Park
I Giardini di Castel Trauttmansdorff ©
Lago di Braies ©
Lago di Braies

1
night
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.
Kick off your visit on the 3rd (Tue): contemplate the waterfront views at Canal Grande, admire the striking features of Basilica di San Marco, then contemplate the long history of Ponte dei Sospiri, and finally browse the exhibits of Doge's Palace.

For where to stay, photos, traveler tips, and more tourist information, read our Venice journey maker website .

Traveling by car from Bolzano to Venice takes 3 hours. Alternatively, you can take a train; or take a bus. Traveling from Bolzano in November, you can expect nighttime temperatures to be somewhat warmer in Venice, with lows of 43°F. Wrap up your sightseeing on the 3rd (Tue) to allow time to travel back home.

Things to do in Venice

Historic Sites Parks Nature
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace

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