60 days in Italy Itinerary

60 days in Italy Itinerary

Created using Inspirock Italy visit planner

Make it your trip
Fly
1
Venice
— 6 nights
Drive
2
Verona
— 6 nights
Drive
3
Milan
— 5 nights
Train
4
Florence
— 6 nights
Drive
5
Siena
— 5 nights
Drive
6
Assisi
— 5 nights
Drive
7
Rome
— 7 nights
Train
8
Naples
— 6 nights
Drive
9
Positano
— 6 nights
Ferry
10
Capri, Island of Capri
— 7 nights
Ferry to Naples, Fly to Newark

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Venice

— 6 nights

City of Romance

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 (Piazza del Santo, Basilica of St. Anthony, &more). There's still lots to do: contemplate the waterfront views at Canal Grande, take in panoramic vistas at St Mark's Campanile, get to know the fascinating history of Piazza San Marco, and contemplate the long history of Ponte dei Sospiri.

For traveler tips, ratings, where to stay, and tourist information, read Venice route planning app.

New York City, USA to Venice is an approximately 12-hour flight. Due to the time zone difference, you'll lose 6 hours traveling from New York City to Venice. In May, daily temperatures in Venice can reach 72°F, while at night they dip to 55°F. Cap off your sightseeing on the 7th (Fri) early enough to go by car to Verona.

Things to do in Venice

Historic Sites · Museums · Tours · Parks

Side Trip

Find places to stay May 1 — 7:

Verona

— 6 nights

City of Romeo and Juliet

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.
Change things up with these side-trips from Verona: Villa Calicantus (in Calmasino), Adrenaline & Extreme Tours (in Maranello) and Modena (Acetaia Giuseppe Giusti, Acetaia Villa San Donnino, &more). The adventure continues: experience the emotional art of opera at Arena di Verona, contemplate in the serene atmosphere at Basilica di San Zeno Maggiore, take a stroll through Piazza delle Erbe, and take in the views from Ponte Pietra.

To find other places to visit, maps, ratings, and more tourist information, read our Verona online journey planner.

You can drive from Venice to Verona in 1.5 hours. Alternatively, you can take a shuttle; or take a bus. Expect a daytime high around 74°F in May, and nighttime lows around 53°F. Cap off your sightseeing on the 13th (Thu) early enough to go by car to Milan.

Things to do in Verona

Historic Sites · Museums · Nature · Parks

Side Trips

Find places to stay May 7 — 13:

Milan

— 5 nights

Fashion Capital of World

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.
You'll find plenty of places to visit near Milan: Tremezzina (Villa del Balbianello & Villa Carlotta), Como (Cathedral of Como (Duomo) & Tempio Voltiano) and Faro voltiano (in Brunate). There's much more to do: contemplate in the serene atmosphere at Duomo di Milano, take in the architecture and atmosphere at S. Giovanni Battista, explore the world behind art at Pinacoteca Ambrosiana, and admire the striking features of Galleria Vittorio Emanuele II.

To see traveler tips, photos, maps, and other tourist information, refer to the Milan day trip app.

Traveling by car from Verona to Milan takes 2 hours. Alternatively, you can take a train. May in Milan sees daily highs of 73°F and lows of 55°F at night. Finish your sightseeing early on the 18th (Tue) to allow enough time to take a train to Florence.

Things to do in Milan

Historic Sites · Museums · Parks · Shopping

Side Trips

Find places to stay May 13 — 18:

Florence

— 6 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Explore Florence's surroundings by going to Azienda Agricola Altiero (Winery) (in Greve in Chianti), Pisa (Piazza dei Miracoli & Leaning Tower of Pisa) and Castello del Trebbio (in Santa Brigida). There's still lots to do: admire the masterpieces at Florence Academy of Fine Arts, take in the views from Ponte Vecchio, pause for some photo ops at Campanile di Giotto, and get to know the fascinating history of Piazza del Duomo.

You can plan Florence trip in no time by asking Inspirock to help create your itinerary.

You can take a train from Milan to Florence in 2.5 hours. Alternatively, you can drive; or fly. May in Florence sees daily highs of 71°F and lows of 52°F at night. Wrap up your sightseeing on the 24th (Mon) to allow time to drive to Siena.

Things to do in Florence

Historic Sites · Museums · Wineries · Parks

Side Trips

Find places to stay May 18 — 24:

Siena

— 5 nights

Cultural Heart of Tuscany

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: Montalcino (Mate Winery, Podere Il Cocco, &more), Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate) and Azienda Agricola Sante Marie di Vignoni (in San Quirico d'Orcia). There's still lots to do: don't miss a visit to Piazza del Campo, take in the architecture and atmosphere at Duomo di Siena, admire the verdant scenery at Val d'Orcia, and explore the historical opulence of Palazzo Pubblico and Museo Civico.

To find reviews, maps, more things to do, and other tourist information, read Siena day trip planning site.

Traveling by car from Florence to Siena takes 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 74°F in May, and nighttime lows around 53°F. Wrap up your sightseeing on the 29th (Sat) to allow time to drive to Assisi.

Things to do in Siena

Historic Sites · Wineries · Museums · Nature

Side Trips

Find places to stay May 24 — 29:

Assisi

— 5 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Venture out of the city with trips to Montefalco (Wild Foods Italy, Cantine Il Gheppio Winery, &more), Perugia (Museo-Laboratorio di Tessitura a Mano Giuditta Brozzetti, Studio Moretti Caselli, &more) and Vineria del Carmine (in La Bruna). The adventure continues: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, explore the historical opulence of Rocca Maggiore, make a trip to Scoglio della Preghiera, and learn about winemaking at Cantina Dionigi.

To see ratings, photos, reviews, and more tourist information, you can read our Assisi online day trip planner.

Getting from Siena to Assisi by car takes about 2 hours. Other options: take a bus; or take a train. Expect a daytime high around 72°F in May, and nighttime lows around 52°F. Finish your sightseeing early on the 3rd (Thu) to allow enough time to drive to Rome.

Things to do in Assisi

Wineries · Historic Sites · Museums · Wildlife

Side Trips

Find places to stay May 29 — Jun 3:

Rome

— 7 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
When in Rome, make a side trip to see Villa d'Este in Tivoli, approximately Tivoli away. And it doesn't end there: contemplate the long history of Colosseum, explore the ancient world of Palatine Hill, visit Trastevere, and pause for some serene contemplation at St. Peter's Basilica.

To find other places to visit, traveler tips, more things to do, and other tourist information, read our Rome vacation planner.

You can drive from Assisi to Rome in 2.5 hours. Other options are to take a train; or take a bus. In June, plan for daily highs up to 84°F, and evening lows to 65°F. Finish up your sightseeing early on the 10th (Thu) so you can catch the train to Naples.

Things to do in Rome

Historic Sites · Museums · Parks · Neighborhoods

Side Trips

Find places to stay Jun 3 — 10:

Naples

— 6 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Venture out of the city with trips to Pompeii (Casa del Poeta Tragico, Terme del Foro, &more), Sorrento (Villa Comunale, Food Tours, &more) and Salerno (Giardino della Minerva & Duomo di Salerno). The adventure continues: explore the ancient world of Pompeii Archaeological Park, admire the masterpieces at Chiesa dei Santi Filippo e Giacomo - Complesso Museale dell'Arte della Seta, contemplate the long history of Catacombe di San Gennaro, and get curious at MUSA - Museo Universitario delle Scienze e delle Arti.

Planning Naples trip won't be overwhelming when you use Inspirock's itinerary maker.

You can take a train from Rome to Naples in 2 hours. Alternatively, you can drive; or fly. June in Naples sees daily highs of 82°F and lows of 66°F at night. Wrap up your sightseeing on the 16th (Wed) early enough to drive to Positano.

Things to do in Naples

Historic Sites · Tours · Wineries · Museums

Side Trips

Find places to stay Jun 10 — 16:

Positano

— 6 nights
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.
Change things up with these side-trips from Positano: Ravello (Ceramiche Cosmolena di Margherita di Palma, Duomo di Ravello, &more), Amalfi (Duomo di Sant'Andrea, Cloister del Paradiso, &more) and Basilica of Saint Trofimena (in Minori). There's still lots to do: take a memorable drive along Amalfi Coast, get great views at Il Sentiero Degli Dei, explore the fascinating underground world of Cave of Smeraldo, and take in the architecture and atmosphere at Collegiate Santa Maria Maddalena.

To find reviews, maps, ratings, and tourist information, use the Positano online travel route builder.

Getting from Naples to Positano by car takes about 1.5 hours. Other options: take a bus. In June, plan for daily highs up to 82°F, and evening lows to 68°F. Wrap up your sightseeing on the 22nd (Tue) to allow time to ride a ferry to Capri.

Things to do in Positano

Parks · Nature · Outdoors · Historic Sites

Side Trips

Find places to stay Jun 16 — 22:

Capri, Island of Capri

— 7 nights
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
On the 24th (Thu), spend a thrilling day on the water with a speed boat tour. And it doesn't end there: explore the striking landscape at I Faraglioni, Head underground at White Grotta, look for gifts at Eco Capri, and pause for some photo ops at Natural Arch.

To find where to stay, other places to visit, more things to do, and more tourist information, go to the Capri trip planner.

You can ride a ferry from Positano to Capri in 1.5 hours. Alternatively, you can do a combination of taxi and ferry; or do a combination of bus and ferry. In June, daytime highs in Capri are 82°F, while nighttime lows are 68°F. Cap off your sightseeing on the 29th (Tue) early enough to travel back home.

Things to do in Capri

Outdoors · Tours · Parks · Nature

Side Trip

Find places to stay Jun 22 — 29:

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.