58 days in Italy Itinerary

58 days in Italy Itinerary

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Route & dates

58 days in Italy Itinerary

Start: Washington DC
Fly:  14​h 45​min
1
Milan
— Few hours
train:  1​h 15​min
2
Verona
— 7 nights
bus:  1​h 15​min
3
Venice
— 6 nights
train:  2​h 15​min
4
Florence
— 6 nights
bus:  1​h
5
Siena
— 2 nights
Drive:  1​h 45​min
6
Assisi
— 6 nights
Drive:  4​h 30​min
7
Ravello
— 5 nights
Drive:  1​h
8
Capri, Island of Capri
— 4 nights
Drive:  45​min
9
Naples
— 2 nights
train:  1​h 15​min
10
Rome
— 6 nights
Fly:  4​h
11
Palermo, Sicily
— 5 nights
bus + Fly:  4​h
12
Cagliari, Sardinia
— 5 nights
Drive:  3​h
13
Alghero, Sardinia
— 1 night
Fly:  14​h 45​min
End: Washington DC

few
hours
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.
On the 1st (Tue), get to know the fascinating history of Piazza del Duomo, take a stroll through Brera District, and then take in the spiritual surroundings of Chiesa di Santa Maria presso San Satiro.

For more things to do, photos, traveler tips, and other tourist information, read our Milan trip itinerary tool .

Washington DC, USA to Milan is an approximately 15-hour flight. You can also do a combination of train and flight; or do a combination of subway, bus, and flight. You'll lose 6 hours traveling from Washington DC to Milan due to the time zone difference. When traveling from Washington DC in October, plan for a bit cooler days and about the same nights in Milan: temperatures range from 65°F by day to 52°F at night. Finish your sightseeing early on the 1st (Tue) so you can take a train to Verona.

Things to do in Milan

Shopping Neighborhoods Historic Sites
Highlights from your plan
Brera District ©
Brera District
Piazza del Duomo ©
Piazza del Duomo

7
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.
Discover out-of-the-way places like Scaliger Castle in Malcesine and Basilica di San Zeno Maggiore. Appreciate the collections at Castello del Buonconsiglio Monumenti e Collezioni Provinciali and Casa di Giulietta. Venture out of the city with trips to Piazza Duomo (in Trento), Lago di Molveno (in Molveno) and Rocca Scaligera di Sirmione (in Sirmione). Next up on the itinerary: take in a show at Arena di Verona, steep yourself in history at Museo di Castelvecchio, step into the grandiose world of Piazzale Castel San Pietro, and contemplate in the serene atmosphere at Basilica di Sant'Andrea di Mantova.

To find photos, where to stay, maps, and more tourist information, read Verona trip itinerary maker website .

Take a train from Milan to Verona in 1.5 hours. Alternatively, you can drive. In October in Verona, expect temperatures between 66°F during the day and 50°F at night. Wrap up your sightseeing on the 8th (Tue) early enough to drive to Venice.

Things to do in Verona

Historic Sites Parks Trails

Side Trips

Riva Del Garda, Trento, Lago di Molveno, Castel Thun, Castello Scaligero
Highlights from your plan
Castello Scaligero ©
Castello Scaligero
Castel Thun ©
Castel Thun
Basilica di Santa Anastasia ©
Basilica di Santa Anastasia

6
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.
Popular historic sites such as Peggy Guggenheim Collection and Doge's Palace are in your itinerary. You'll discover tucked-away gems like Basilica di Sant’Antonio and San Giorgio Maggiore. Get out of town with these interesting Venice side-trips: La Frassina (in Caorle) and Prato della Valle (in Padua). There's much more to do: make a trip to Basilica di San Marco, contemplate the waterfront views at Canal Grande, appreciate the extensive heritage of St. Mark's Square, and wander the streets of Cannaregio.

For ratings, where to stay, other places to visit, and other tourist information, read Venice trip itinerary site .

You can drive from Verona to Venice in 1.5 hours. Alternatively, you can take a bus; or take a shuttle. In October, plan for daily highs up to 66°F, and evening lows to 51°F. Wrap up your sightseeing on the 14th (Mon) early enough to take a train to Florence.

Things to do in Venice

Historic Sites Museums Neighborhoods

Side Trips

Padua, Tre Ponti, La Frassina
Highlights from your plan
Doge's Palace ©
Doge's Palace
Piazza San Marco ©
Piazza San Marco
Basilica di San Marco
Basilica di San Marco

6
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Satisfy your inner culture vulture at Pitti Palace and Academy Of Florence Art Gallery. You'll discover tucked-away gems like Centro Storico and Basilica San Miniato al Monte. Venture out of the city with trips to Castello di Verrazzano (in Greve in Chianti), Botanical Garden Maria Ansaldi Pania di Corfino (in Villa Collemandina) and Sentiero n. 7b - Via delle Ginestre (in Massarosa). There's much more to do: take in the architecture and atmosphere at Cathedral of Santa Maria del Fiore, contemplate in the serene atmosphere at The Baptistery of St. John, ponder the world of politics at Museo Nazionale del Bargello, and take in the views from Ponte Vecchio.

For reviews, other places to visit, and tourist information, refer to the Florence trip itinerary maker site .

Getting from Venice to Florence by train takes about 2.5 hours. Other options: drive; or take a bus. In October, plan for daily highs up to 71°F, and evening lows to 54°F. Finish your sightseeing early on the 20th (Sun) so you can drive to Siena.

Things to do in Florence

Historic Sites Museums Parks

Side Trips

Pisa, Greve in Chianti, Sentiero n. 7b - Via delle Ginestre, Botanical Garden Maria Ansaldi Pania di Corfino, Agriturismo Diacceroni
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

2
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Kick off your visit on the 21st (Mon): step into the grandiose world of Castello di Monterinaldi, pause for some serene contemplation at Siena Cathedral, and then make a trip to Piazza del Campo. On the 22nd (Tue), you'll have a packed day of sightseeing: do a tasting at Podere La Marronaia- Sosta Alle Colonne, then steep yourself in history at Torre Grossa, then take in the exciting artwork at La Bottega del Sale di Duccio Nacci photographer, and finally steep yourself in history at Historic Centre of San Gimignano.

For traveler tips, reviews, maps, and tourist information, read our Siena trip itinerary planner.

You can drive from Florence to Siena in an hour. Alternatively, you can take a bus; or take a 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 22nd (Tue) early enough to go by car to Assisi.

Things to do in Siena

Historic Sites Wineries Shopping

Side Trips

San Gimignano, Castello di Monterinaldi
Highlights from your plan
Historic Centre of San Gimignano ©
Historic Centre of San Gimignano
Duomo di Siena ©
Duomo di Siena
Castello di Monterinaldi ©
Castello di Monterinaldi

6
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
You'll discover tucked-away gems like Basilica di Santa Maria degli Angeli - Porziuncola and Montioni Frantoio e Cantina. Deepen your sense of the past at sights like Basilica inferiore di San Francesco d'Assisi and Rocca Maggiore. Venture out of the city with trips to Gubbio (Palazzo dei Consoli and Museo Civico & Basilica of Saint Ubaldo), Piazza del Duomo (in Spoleto) and Fabriano (Paper and Watermark Museum Fabriano & Oratorio della Carita). Next up on the itinerary: see the interesting displays at Museo della Porziuncola, do a tasting at Tili Vini Societa Agricola, gain insight at Grotte di Camerano - Citta Sotterranea di Camerano, and contemplate in the serene atmosphere at Eremo delle Carceri.

To see traveler tips, maps, more things to do, and tourist information, you can read our Assisi route planning app .

Drive from Siena to Assisi in 2 hours. Alternatively, you can take a bus; or take a train. Traveling from Siena in October, you can expect nighttime temperatures to be slightly colder in Assisi, with lows of 51°F. Wrap up your sightseeing on the 28th (Mon) early enough to drive to Ravello.

Things to do in Assisi

Historic Sites Museums Wineries

Side Trips

Gubbio, Fabriano, Perugia, Cattedrale San Ciriaco, Museo Civico e Diocesano La Castellina
Highlights from your plan
Basilica of Saint Ubaldo ©
Basilica of Saint Ubaldo
Museo della Porziuncola ©
Museo della Porziuncola

5
nights
Ravello

Ravello ©
Museum-lovers will appreciate Ceramiche D'Arte Pascal and Museo della Carta. Your inner history buff will appreciate Duomo di Ravello and Villa Cimbrone Gardens. Explore the numerous day-trip ideas around Ravello: Positano (Wine Tours & Tastings & Fornillo). And it doesn't end there: don't miss a visit to Villa Rufolo, get to know the fascinating history of Centro Storico Ravello, go for a walk through Sentiero degli dei (Path of the Gods), and take in the spiritual surroundings of Duomo di Sant'Andrea.

To find maps, photos, reviews, and more tourist information, you can read our Ravello day trip planning app .

Drive from Assisi to Ravello in 4.5 hours. Alternatively, you can take a train; or do a combination of train and bus. Traveling from Assisi in October, you can expect nighttime temperatures to be a bit warmer in Ravello, with lows of 63°F. Finish your sightseeing early on the 2nd (Sat) to allow enough time to ride a ferry to Capri.

Things to do in Ravello

Historic Sites Parks Outdoors

Side Trips

Amalfi, Positano, Villa Romana e Antiquarium
Highlights from your plan
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Duomo di Ravello ©
Duomo di Ravello
Duomo di Sant'Andrea ©
Duomo di Sant'Andrea

4
nights
Capri, Island of Capri

Capri
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Get some historical perspective at Villa San Michele and Punta Carena Lighthouse. Your cultural itinerary includes sights like Chiesa San Michele and Santa Maria a Cetrella. On the 5th (Tue), spend a fun day on foot with Walking tours. There's much more to do: explore the striking landscape at I Faraglioni, take in nature's colorful creations at Giardini di Augusto, steep yourself in history at Villa Jovis, and take in panoramic vistas at Belvedere di Tragara.

To find where to stay, reviews, and more tourist information, use the Capri road trip planning tool .

Traveling by ferry from Ravello to Capri takes an hour. Alternatively, you can do a combination of taxi and ferry; or do a combination of bus and ferry. Expect a daytime high around 64°F in November, and nighttime lows around 56°F. Finish your sightseeing early on the 6th (Wed) so you can ride a ferry to Naples.

Things to do in Capri

Parks Historic Sites Outdoors

Side Trip

Anacapri
Highlights from your plan
I Faraglioni
I Faraglioni
Villa San Michele ©
Villa San Michele
Giardini di Augusto ©
Giardini di Augusto

2
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Kick off your visit on the 7th (Thu): don't miss a visit to Scavi Archeologici di Ercolano, get impressive views of Vesuvio, and then delve into the distant past at Pompeii Archaeological Park. On the next day, see the interesting displays at National Archaeological Museum of Naples, admire the masterpieces at Museo Cappella Sansevero, and then delve into the distant past at Ruins of Herculaneum.

To find more things to do, ratings, traveler tips, and more tourist information, use the Naples trip itinerary site .

You can ride a ferry from Capri to Naples in an hour. Another option is to do a combination of ferry and subway. Traveling from Capri in November, plan for slightly colder nights in Naples, with lows around 50°F. Finish your sightseeing early on the 8th (Fri) so you can take a train to Rome.

Things to do in Naples

Historic Sites Museums Nature

Side Trips

Parco Acheologico di Ercolano, Vesuvio National Park, Pompeii Archaeological Park
Highlights from your plan
Vesuvio National Park ©
Vesuvio National Park
Parco Acheologico di Ercolano ©
Parco Acheologico di Ercolano
Pompeii Archaeological Park ©
Pompeii Archaeological Park

6
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Visit Palatine Hill and Colosseum for their historical value. Step off the beaten path and head to Parco Archeologico di Ostia Antica and Centro Storico Associazione Centro Storico. Step out of Rome to go to Tivoli and see Villa d'Este, which is approximately 48 minutes away. And it doesn't end there: take in the architecture and atmosphere at St. Peter's Basilica, admire the striking features of Pantheon, don't miss a visit to Trevi Fountain, and appreciate the extensive heritage of Piazza Navona.

To see photos, ratings, more things to do, and tourist information, refer to the Rome trip itinerary maker site .

You can take a train from Naples to Rome in 1.5 hours. Alternatively, you can drive; or take a bus. In November, plan for daily highs up to 63°F, and evening lows to 47°F. Cap off your sightseeing on the 14th (Thu) early enough to travel to Palermo.

Things to do in Rome

Historic Sites Museums Tours

Side Trips

Vatican City, Villa d'Este, Parco Archeologico di Ostia Antica
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Vatican Museums
Vatican Museums

5
nights
Palermo, Sicily

Palermo ©
The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Appreciate the collections at Salina Calcara and Museo Motorismo Siciliano E Della Targa Florio. Step off the beaten path and head to Duomo di Monreale and Church of Jesus. Venture out of the city with trips to Drago Artecontemporanea (in Bagheria), Caccamo (Parrocchia Ss. Annunziata & Castello di Caccamo) and Museo Civico (in Termini Imerese). There's much more to do: make a trip to Norman Palace and Palatine Chapel, examine the collection at Museo dell'Acciuga, step into the grandiose world of Baia Santa Margherita, Castelluzzo di S.Vito Lo Capo, and contemplate in the serene atmosphere at San Giuseppe dei Teatini.

Plan a Palermo trip in moments using our itinerary builder.

Getting from Rome to Palermo by flight takes about 4 hours. Other options: do a combination of flight and bus; or do a combination of car and ferry. Wrap up your sightseeing on the 19th (Tue) to allow time to travel to Cagliari.

Things to do in Palermo

Historic Sites Museums Wildlife

Side Trips

Termini Imerese, Caccamo, Drago Artecontemporanea, Scuba & Snorkeling, Teatro Greco di Segesta
Highlights from your plan
Castello di Caccamo ©
Castello di Caccamo
Duomo di Monreale ©
Duomo di Monreale
Scuba & Snorkeling

5
nights
Cagliari, Sardinia

The capital of Sardinia, Cagliari is spread out over seven hills and still bears the marks of its past conquerors, including the Phoenicians, Carthaginians, and Romans.
Visiting Spiaggia di Solanas and Giara di Gesturi - Escursioni a Cavallo will get you outdoors. Nuraghe Arrubiu and Chiesa di San Michele are good opportunities to explore the local culture. You'll find plenty of places to visit near Cagliari: Iglesias (Isolotto Faraglione del Pan di Zucchero & Il Belvedere di Nebida), Castello di Acquafredda (in Siliqua) and Le Dune Beach (in Porto Pino). There's much more to do: take a memorable tour with Tours, head outdoors with Sella del Diavolo, surround yourself with nature on a nature and wildlife tour, and take an in-depth tour of Casa Zapata Museum.

To see ratings, photos, maps, and tourist information, read our Cagliari travel route planner.

Getting from Palermo to Cagliari by combination of bus and flight takes about 4 hours. Other options: fly; or ride a ferry. In November, plan for daily highs up to 67°F, and evening lows to 50°F. Finish up your sightseeing early on the 24th (Sun) so you can go by car to Alghero.

Things to do in Cagliari

Outdoors Parks Wildlife

Side Trips

Iglesias, Le Dune Beach, Giara di Gesturi - Escursioni a Cavallo, Castello di Acquafredda, Casa Zapata Museum
Highlights from your plan
Nature & Wildlife Tours
Nuraghe Arrubiu ©
Nuraghe Arrubiu
Le Dune Beach ©
Le Dune Beach

1
night
Alghero, Sardinia

Alghero ©
Built surrounding a 16th-century fortified port, Alghero remains one of Sardinia's most visited sites, rich in cultural and historical heritage.
Kick off your visit on the 25th (Mon): pause for some serene contemplation at Chiesa di San Francesco, pause for some serene contemplation at Cattedrale di Santa Maria, then kick back and relax at Spiaggia di Maria Pia, and finally do a tasting at Azienda Agricola Leda' d'Ittiri.

To see reviews, where to stay, traveler tips, and tourist information, read Alghero sightseeing planning tool .

Getting from Cagliari to Alghero by car takes about 3 hours. Other options: take a train; or do a combination of train and bus. In November, plan for daily highs up to 66°F, and evening lows to 48°F. Finish up your sightseeing early on the 25th (Mon) so you can travel back home.

Things to do in Alghero

Beaches Parks Outdoors
Highlights from your plan
Spiaggia di Maria Pia ©
Spiaggia di Maria Pia
Azienda Agricola Leda' d'Ittiri ©
Azienda Agricola Leda' d'Ittiri
Chiesa di San Francesco ©
Chiesa di San Francesco

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