56 days in Italy Itinerary

56 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

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

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Venice

— 5 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.
Explore Venice's surroundings by going to Padua (Chiesa degli Eremitani, Scrovegni Chapel, &more) and Fioravanti Onesti - Vini dal 1808 (in San Biagio di Callalta). There's much more to do: explore the activities along Canal Grande, make a trip to Piazza San Marco, take in the views from Ponte dei Sospiri, and take in the architecture and atmosphere at San Giorgio Maggiore.

To find ratings, traveler tips, reviews, and more tourist information, read Venice trip itinerary tool.

Mexico City, Mexico to Venice is an approximately 17-hour flight. The time zone changes from Central Standard Time to Central European Standard Time, which is usually a 7 hour difference. When traveling from Mexico City in May, plan for a bit cooler days and about the same nights in Venice: temperatures range from 26°C by day to 15°C at night. Wrap up your sightseeing on the 14th (Fri) early enough to drive to Verona.

Things to do in Venice

Historic Sites · Tours · Museums · Neighborhoods

Side Trips

Find places to stay May 8 — 14:

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.
You'll find plenty of places to visit near Verona: Lago di Garda (in Garda), Fondazione Bisazza (in Montecchio Maggiore) and Villa Calicantus (in Calmasino). There's much more to do: experience the emotional art of opera at Arena di Verona, admire the striking features of Palazzo Bettoni, contemplate the long history of Museo di Castelvecchio, and take a stroll through Piazza delle Erbe.

For maps, traveler tips, other places to visit, and more tourist information, refer to the Verona trip itinerary maker website.

Traveling by car from Venice to Verona takes 1.5 hours. Alternatively, you can take a shuttle; or take a train. Expect a daytime high around 27°C in May, and nighttime lows around 13°C. Finish up your sightseeing early on the 20th (Thu) so you can go by car to Milan.

Things to do in Verona

Historic Sites · Parks · Shopping · Nature

Side Trips

Find places to stay May 14 — 20:

Milan

— 4 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: La Punta Spartivento (in Bellagio), Cathedral of Como (Duomo) (in Como) and Tremezzina (Villa del Balbianello & Villa Carlotta). There's much more to do: pause for some serene contemplation at Duomo di Milano, explore the different monuments and memorials at Monumental Cemetery, test your team's savvy at La Casa Maledetta, and step into the grandiose world of Castello Sforzesco.

To find where to stay, other places to visit, reviews, and other tourist information, refer to the Milan tour planning website.

Traveling by car from Verona to Milan takes 2 hours. Alternatively, you can drive; or take a train. May in Milan sees daily highs of 26°C and lows of 15°C at night. Finish up your sightseeing early on the 24th (Mon) so you can catch the train to Florence.

Things to do in Milan

Historic Sites · Museums · Parks · Shopping

Side Trips

Find places to stay May 20 — 24:

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.
When in Florence, make a side trip to see Leaning Tower of Pisa in Pisa, approximately Pisa away. Dedicate the 27th (Thu) to wine at some of the top wineries in the area. There's lots more to do: explore the world behind art at Florence Academy of Fine Arts, make a trip to Piazzale Michelangelo, see the interesting displays at Pitti Palace, and take in the views from Ponte Vecchio.

To see more things to do, maps, ratings, and other tourist information, go to the Florence trip itinerary maker website.

You can take a train from Milan to Florence in 2.5 hours. Alternatively, you can take a train; or drive; or take a bus. In May in Florence, expect temperatures between 25°C during the day and 13°C at night. Cap off your sightseeing on the 30th (Sun) early enough to go by car to Siena.

Things to do in Florence

Tours · Historic Sites · Wineries · Museums

Side Trips

Find places to stay May 24 — 30:

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.
Explore the numerous day-trip ideas around Siena: Montalcino (Poggio Rubino & Castiglion del Bosco Winery) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). Next up on the itinerary: indulge your senses at some of the top wineries in the area, contemplate the long history of Centro Storico di Siena, explore the world behind art at Museo dell'Opera Metropolitana, and take in the architecture and atmosphere at Basilica Cateriniana San Domenico.

For other places to visit, more things to do, where to stay, and other tourist information, use the Siena trip itinerary maker.

You can drive from Florence to Siena in 1.5 hours. Other options are to take a bus; or take a train. In May, daily temperatures in Siena can reach 27°C, while at night they dip to 13°C. Cap off your sightseeing on the 4th (Fri) early enough to go by car to Assisi.

Things to do in Siena

Wineries · Historic Sites · Tours · Museums

Side Trip

Find places to stay May 30 — Jun 4:

Assisi

— 5 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Get out of town with these interesting Assisi side-trips: Montefalco (The Chiacchiarini Farm, Montioni Frantoio e Cantina, &more), Vineria del Carmine (in La Bruna) and Perugia (Museo-Laboratorio di Tessitura a Mano Giuditta Brozzetti & Studio Moretti Caselli). There's lots more to do: take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, make a trip to Eremo delle Carceri, step into the grandiose world of Rocca Maggiore, and examine the collection at Museo della Porziuncola.

For more things to do, reviews, traveler tips, and more tourist information, read Assisi attractions planner.

Getting from Siena to Assisi by car takes about 2 hours. Other options: take a bus; or take a train. In June, daily temperatures in Assisi can reach 32°C, while at night they dip to 18°C. Wrap up your sightseeing on the 9th (Wed) early enough to drive to Positano.

Things to do in Assisi

Historic Sites · Wineries · Museums · Wildlife

Side Trips

Find places to stay Jun 4 — 9:

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 Cattedrale di San Lorenzo (in Scala), Ravello (Villa Cimbrone Gardens, Ceramiche Cosmolena di Margherita di Palma, &more) and Collegiate Santa Maria Maddalena (in Atrani). There's still lots to do: see the interesting displays at Museo della Carta, get outside with Outdoor Activities, explore the fascinating underground world of Grotte di Suppraiano, and take some stellar pictures from Il Sentiero Degli Dei.

For photos, traveler tips, reviews, and tourist information, read Positano tour builder app.

You can drive from Assisi to Positano in 5 hours. Alternatively, you can do a combination of train and bus; or take a bus. Traveling from Assisi in June, you can expect nighttime temperatures to be somewhat warmer in Positano, with lows of 23°C. You will leave for Capri on the 15th (Tue).

Things to do in Positano

Outdoors · Historic Sites · Parks · Tours

Side Trips

Find places to stay Jun 9 — 15:

Capri, Island of Capri

— 5 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 17th (Thu), spend a thrilling day on the water with a speed boat tour. The adventure continues: explore the striking landscape at I Faraglioni, get great views at Belvedere Cannone, stroll through Fortini Coastal Walk, and look for gifts at Eco Capri.

To see ratings, other places to visit, and more tourist information, go to the Capri trip planner.

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 in Capri, expect temperatures between 32°C during the day and 23°C at night. Cap off your sightseeing on the 20th (Sun) early enough to catch the ferry to Naples.

Things to do in Capri

Outdoors · Tours · Parks · Nature

Side Trip

Find places to stay Jun 15 — 20:

Naples

— 5 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Change things up with these side-trips from Naples: Pompeii (Odeon - Teatro Piccolo, Tempio di Giove Capitolino, &more). There's much more to do: explore the ancient world of Pompeii Archaeological Park, stroll the grounds of Catacombe di San Gennaro, take in the spiritual surroundings of Museo Cappella Sansevero, and pause for some serene contemplation at Duomo di Napoli.

To see other places to visit, where to stay, ratings, and more tourist information, read our Naples online trip itinerary maker.

Getting from Capri to Naples by ferry takes about 1.5 hours. Expect a daytime high around 32°C in June, and nighttime lows around 22°C. Wrap up your sightseeing on the 25th (Fri) early enough to take a train to Rome.

Things to do in Naples

Historic Sites · Museums · Tours · Childrens Museums

Side Trips

Find places to stay Jun 20 — 25:

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.
Rome is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: explore the ancient world of Colosseum, contemplate the long history of Palatine Hill, explore the world behind art at Vatican Museums, and ponder the design of Trevi Fountain.

For traveler tips, reviews, ratings, and other tourist information, use the Rome online vacation maker.

Getting from Naples to Rome by train takes about 2 hours. Other options: drive; or fly. In June in Rome, expect temperatures between 34°C during the day and 21°C at night. Finish your sightseeing early on the 2nd (Fri) to allow enough time to fly back home.

Things to do in Rome

Historic Sites · Museums · Tours · Neighborhoods

Side Trip

Find places to stay Jun 25 — Jul 2:

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.