60 days in Italy Itinerary

Created using Inspirock Italy trip itinerary builder
Make it your trip
Drive
1
Assisi
— 5 nights
Drive
2
Siena
— 6 nights
Drive
3
Florence
— 6 nights
Drive
4
Cinque Terre
— 6 nights
Drive
5
Milan
— 5 nights
Drive
6
Verona
— 6 nights
Drive
7
Venice
— 6 nights
Fly
8
Rome
— 7 nights
Train
9
Naples
— 6 nights
Drive
10
Positano
— 6 nights
Fly

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Assisi — 5 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Explore Assisi's surroundings by going to Tenuta Cocci Grifoni (in Ripatransone), Perugia (Collegio del Cambio, Galleria Nazionale dell'Umbria, &more) and Museo Cinema a Pennello (in Montecosaro). Next up on the itinerary: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, contemplate in the serene atmosphere at Eremo delle Carceri, stroll around Mount Subasio, and examine the collection at Museo della Porziuncola.

To see where to stay, traveler tips, other places to visit, and more tourist information, refer to the Assisi trip planner.

Ancona to Assisi is an approximately 2-hour car ride. You can also take a train; or take a bus. In May, plan for daily highs up to 26°C, and evening lows to 13°C. Finish your sightseeing early on the 6th (Sat) so you can drive to Siena.
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Find places to stay May 1 — 6:

Siena — 6 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Explore Siena's surroundings by going to Guardastelle Vineyard (in San Gimignano), Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate) and Chiesa di San Michele Arcangelo (in Foiano Della Chiana). The adventure continues: indulge in some culinary diversions at a local gastronomic tour, do a tasting at Accademia del Buon Gusto, pause for some serene contemplation at Duomo di Siena, and don't miss a visit to Piazza del Campo.

To plan Siena vacation without wasting time, ask Inspirock to design an itinerary.

You can drive from Assisi to Siena in 2 hours. Alternatively, you can take a bus; or take a train. In May, daytime highs in Siena are 27°C, while nighttime lows are 13°C. Wrap up your sightseeing on the 12th (Fri) early enough to drive to Florence.
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Find places to stay May 6 — 12:

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.
Venture out of the city with trips to Leaning Tower of Pisa (in Pisa) and Castello del Trebbio (in Santa Brigida). Dedicate the 18th (Thu) to wine at some of the top wineries in the area. There's still lots to do: contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, make a trip to Piazzale Michelangelo, take in panoramic vistas at Campanile di Giotto, and admire the natural beauty at The Boboli Gardens.

For more things to do, ratings, and more tourist information, read Florence trip maker website.

Traveling by car from Siena to Florence takes 1.5 hours. Alternatively, you can take a bus; or take a train. May in Florence sees daily highs of 25°C and lows of 13°C at night. Wrap up your sightseeing on the 18th (Thu) early enough to drive to Cinque Terre.
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Find places to stay May 12 — 18:

Cinque Terre — 6 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Get out of town with these interesting Cinque Terre side-trips: Parco Naturale Regionale di Porto Venere (in La Spezia), Hike the Punta Manara (in Sestri Levante) and Genoa (Aquarium of Genoa & Cattedrale di San Lorenzo - Duomo di Genova). And it doesn't end there: see some colorful creatures with Angelo's Boat Tours - Cinque Terre Boat Tours, hike along Footpath Monterosso - Vernazza, take in the architecture and atmosphere at Convento dei Cappuccini e Chiesa di San Francesco, and get to know the fascinating history of Borgo Storico di Riomaggiore.

To find more things to do, traveler tips, reviews, and other tourist information, use the Cinque Terre day trip planning app.

You can drive from Florence to Cinque Terre in 2.5 hours. Alternatively, you can take a train. In May, plan for daily highs up to 25°C, and evening lows to 13°C. Finish up your sightseeing early on the 24th (Wed) so you can go by car to Milan.
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Find places to stay May 18 — 24:

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: Turin (Museo Egizio & Basilica di Superga), Greenway del Lago di Como (in Colonno) and Villa del Balbianello (in Tremezzina). The adventure continues: take in the spiritual surroundings of Duomo di Milano, take in the architecture and atmosphere at Chiesa di San Maurizio al Monastero Maggiore, go for a walk through Green Way dei Patriarchi, and explore the historical opulence of Castello Sforzesco.

Plan a Milan trip in moments using our itinerary builder.

You can drive from Cinque Terre to Milan in 3 hours. Alternatively, you can take a train. In May in Milan, expect temperatures between 26°C during the day and 15°C at night. Wrap up your sightseeing on the 29th (Mon) to allow time to drive to Verona.
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Side Trips
Find places to stay May 24 — 29:

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: Piazza Garibaldi e Monumento ai Caduti (in Lonigo), Mantua (Palazzo Ducale di Mantova, Skyline di Mantova, &more) and Fondazione Bisazza (in Montecchio Maggiore). And it doesn't end there: see a show at Arena di Verona, get in on the family fun at Gardaland Park, don't miss a visit to Piazza Bra, and examine the collection at Casa di Giulietta.

To see where to stay, traveler tips, maps, and more tourist information, read Verona trip planner.

Getting from Milan to Verona by car takes about 2 hours. Other options: take a train. In May, daily temperatures in Verona can reach 27°C, while at night they dip to 13°C. Finish up your sightseeing early on the 4th (Sun) so you can go by car to Venice.
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Find places to stay May 29 — Jun 4:

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.
Venture out of the city with trips to Padua (Padua Botanical Garden - World Heritage Site, Basilica of St. Anthony, &more). There's much more to do: contemplate the waterfront views at Canal Grande, contemplate the long history of Peggy Guggenheim Collection, snap pictures at Ponte di Rialto, and admire the masterpieces at Gallerie dell'Accademia.

To find other places to visit, photos, ratings, and more tourist information, go to the Venice itinerary planning website.

Getting from Verona to Venice by car takes about 1.5 hours. Other options: take a shuttle; or take a train. In June, daily temperatures in Venice can reach 32°C, while at night they dip to 20°C. Wrap up your sightseeing on the 10th (Sat) to allow time to fly to Rome.
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Find places to stay Jun 4 — 10:

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.
Explore the numerous day-trip ideas around Rome: Tivoli (Villa d'Este & Villa Adriana). And it doesn't end there: pause for some serene contemplation at St. Peter's Basilica, get to know the fascinating history of Piazza Navona, delve into the distant past at Palatine Hill, and admire the striking features of Pantheon.

To find traveler tips, where to stay, maps, and other tourist information, you can read our Rome trip planner.

You can fly from Venice to Rome in 3 hours. Alternatively, you can take a train; or drive. In June, daytime highs in Rome are 34°C, while nighttime lows are 21°C. Finish up your sightseeing early on the 17th (Sat) so you can catch the train to Naples.
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Find places to stay Jun 10 — 17:

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 (Odeon - Teatro Piccolo & Villa dei Misteri), Castello di Arechi (in Salerno) and Archaeological Park of Paestum (in Paestum). And it doesn't end there: explore the ancient world of Pompeii Archaeological Park, pause for some serene contemplation at Cloister of Santa Chiara, make a trip to Miglio Sacro, and view the masterpieces at Sol’Art Ceramiche.

For ratings, maps, where to stay, and other tourist information, refer to the Naples road trip planning tool.

Traveling by train from Rome to Naples takes 2 hours. Alternatively, you can drive; or fly. In June, plan for daily highs up to 32°C, and evening lows to 22°C. Finish up your sightseeing early on the 23rd (Fri) so you can go by car to Positano.
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Find places to stay Jun 17 — 23:

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.
Venture out of the city with trips to Ravello (Duomo di Ravello, Villa Rufolo, &more), Amalfi (Museo della Carta, Fontana sant'Andrea, &more) and Sorrento (Piazza Tasso, St Francis Church and Convent, &more). On the 26th (Mon), give your taste buds a day to remember with a local gastronomic tour. There's much more to do: get great views at Il Sentiero Degli Dei, get a new perspective on things with Boat Tours & Water Sports, brush up on your knowledge of spirits at Liquorificio Mansi Carlo, and get engrossed in the history at MAR - Museo Archeologico Romano Positano.

To see where to stay, other places to visit, more things to do, and more tourist information, read our Positano planner.

Drive from Naples to Positano in 1.5 hours. Alternatively, you can take a bus. In June, daily temperatures in Positano can reach 32°C, while at night they dip to 23°C. Finish your sightseeing early on the 29th (Thu) to allow enough time to fly back home.
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Side Trips
Find places to stay Jun 23 — 29:

Italy travel guide

4.6
Landmarks · Ruins · Beaches
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.
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