25 days in Italy Itinerary

25 days in Italy Itinerary

Created using Inspirock Italy trip planner
Make it your trip
Fly
1
Milan
— 4 nights
Drive
2
Santa Margherita Ligure
— 1 night
Drive
3
Florence
— 2 nights
Drive
4
San Gimignano
— 3 nights
Drive
5
Montepulciano
— 1 night
Drive
6
Rome
— 3 nights
Train
7
Naples
— 1 night
Drive
8
Sorrento
— 2 nights
Drive
9
Lecce
— 2 nights
Fly
10
Verona
— 1 night
Drive
11
Venice
— 3 nights
Fly

S M T W T F S
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28
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31
1

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.
Explore hidden gems such as Monumental Cemetery and Chiesa di Santa Maria presso San Satiro. Satisfy your inner culture vulture at Duomo di Milano and Tenuta Quvestra. Explore Milan's surroundings by going to Cantina Sociale di Castagnole Monferrato (in Castagnole Monferrato), Borgo di Pagliari (in Carona) and Borgo Moncalvo (in Loazzolo). There's lots more to do: take a stroll through Brera District, shop like a local with Galleria Vittorio Emanuele II, learn about winemaking at Goggiano Winery, and explore the historical opulence of Castello Sforzesco.

For reviews, other places to visit, more things to do, and tourist information, you can read our Milan day trip website.

Toronto, Canada to Milan is an approximately 11.5-hour flight. The time zone difference when traveling from Toronto to Milan is 6 hours. Expect a bit warmer weather when traveling from Toronto in May: highs in Milan hover around 26°C, while lows dip to 15°C. Wrap up your sightseeing on the 10th (Fri) to allow time to drive to Santa Margherita Ligure.
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Historic Sites · Wineries · Neighborhoods · Shopping
Side Trips
Find places to stay May 6 — 10:

Santa Margherita Ligure — 1 night

Santa Margherita Ligure is a comune (municipality) in the Metropolitan City of Genoa in the Italian region Liguria, located about 35km southeast of Genoa, in the Tigullio traditional area.Santa Margherita Ligure borders the following municipalities: Camogli, Portofino, Rapallo.It has a port, used for both tourism and fishing activities. To find ratings, more things to do, reviews, and other tourist information, read Santa Margherita Ligure journey planner.

You can drive from Milan to Santa Margherita Ligure in 2.5 hours. Alternatively, you can take a train. In May, daily temperatures in Santa Margherita Ligure can reach 24°C, while at night they dip to 17°C. On the 11th (Sat), you'll travel to Florence.
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Outdoors · Historic Sites · Parks · Tours
Find places to stay May 10 — 11:

Florence — 2 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get some historical perspective at Cathedral of Santa Maria del Fiore and Basilica San Miniato al Monte. Satisfy your inner culture vulture at Centro Storico and Castello di Verrazzano. Change things up with these side-trips from Florence: San Casciano in Val di Pesa (Terre di Perseto & Podere San Pierino). There's much more to do: explore the world behind art at Gallerie Degli Uffizi, make a trip to Mercato Centrale, get to know the fascinating history of Piazza del Duomo, and look for gifts at Officina Profumo-Farmaceutica di Santa Maria Novella.

To find reviews, ratings, more things to do, and tourist information, refer to the Florence road trip planning site.

You can drive from Santa Margherita Ligure to Florence in 2.5 hours. Other options are to take a train; or do a combination of train and bus. Expect slightly colder evenings in Florence when traveling from Santa Margherita Ligure in May, with lows around 13°C. Wrap up your sightseeing on the 13th (Mon) to allow time to drive to San Gimignano.
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Historic Sites · Wineries · Museums · Shopping
Side Trips
Find places to stay May 11 — 13:

San Gimignano — 3 nights

Town of Fine Towers

A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
Get some cultural insight at Historic Centre of San Gimignano and Duomo di Siena. Discover out-of-the-way places like Abbazia di San Galgano and Accademia del Buon Gusto. You'll find plenty of places to visit near San Gimignano: Siena (Santuario di Santa Caterina & Piazza del Campo), Castello Monterinaldi (in Radda in Chianti) and Cathedral of Santa Maria Assunta (in Volterra). There's lots more to do: contemplate the long history of Torre Grossa, take in the spiritual surroundings of Chiesa di Santa Caterina, take in the exciting artwork at La Bottega del Sale di Duccio Nacci photographer, and do a tasting at Podere La Marronaia- Sosta Alle Colonne.

For other places to visit, where to stay, and more tourist information, use the San Gimignano tour itinerary maker tool.

Traveling by car from Florence to San Gimignano takes 1.5 hours. Alternatively, you can take a train; or take a bus. In May, daytime highs in San Gimignano are 25°C, while nighttime lows are 13°C. Wrap up your sightseeing on the 16th (Thu) early enough to drive to Montepulciano.
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Side Trips
Find places to stay May 13 — 16:

Montepulciano — 1 night

Pearl of the 16th Century

Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Kick off your visit on the 17th (Fri): do a tasting at Icario Winery, get to know the fascinating history of Via di Gracciano nel Corso, take in the exciting artwork at Art Studio di Adelina Quadri, then learn about winemaking at Gattavecchi Winery, then learn about winemaking at De' Ricci, and finally stop by Bottega del Rame.

For where to stay, reviews, ratings, and more tourist information, you can read our Montepulciano trip planner.

Traveling by car from San Gimignano to Montepulciano takes 1.5 hours. Alternatively, you can take a train; or take a bus. May in Montepulciano sees daily highs of 27°C and lows of 13°C at night. Cap off your sightseeing on the 17th (Fri) early enough to go by car to Rome.
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Wineries · Shopping · Museums · Historic Sites
Side Trip
Find places to stay May 16 — 17:

Rome — 3 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
You'll explore the less-touristy side of things at I Colori di Dentro di Maria Grazia Luffarelli and NamasTey. Do some cultural sightseeing at Colosseum and St. Peter's Basilica. And it doesn't end there: admire the landmark architecture of Pantheon, get to know the fascinating history of Piazza Navona, view the masterpieces at Trevimage, and take a stroll through Trastevere.

To find ratings, maps, other places to visit, and tourist information, read our Rome route planner.

Drive from Montepulciano to Rome in 2 hours. Alternatively, you can take a train; or take a bus. In May, daytime highs in Rome are 28°C, while nighttime lows are 17°C. Wrap up your sightseeing on the 20th (Mon) early enough to take a train to Naples.
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Historic Sites · Museums · Shopping · Neighborhoods
Side Trip
Find places to stay May 17 — 20:

Naples — 1 night

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 21st (Tue): explore the ancient world of Pompeii Archaeological Park, take in the architecture and atmosphere at Duomo di Napoli, then don't miss a visit to Decumani di Napoli, and finally get a taste of the local shopping with Via Toledo.

To find where to stay, reviews, ratings, and tourist information, go to the Naples trip planning app.

Getting from Rome to Naples by train takes about 2 hours. Other options: drive; or fly. In May, daily temperatures in Naples can reach 27°C, while at night they dip to 17°C. Finish up your sightseeing early on the 21st (Tue) so you can go by car to Sorrento.
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Historic Sites · Neighborhoods · Shopping
Side Trip
Find places to stay May 20 — 21:

Sorrento — 2 nights

Land of the Sirens

A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
Kick off your visit on the 22nd (Wed): take in the spiritual surroundings of Monastero di San Paolo, take in the spiritual surroundings of Basilica di Sant'Antonino, pause for some serene contemplation at Cattedrale di Sorrento, then learn about winemaking at I Giardini di Cataldo, then don't miss a visit to Piazza Tasso, and finally contemplate in the serene atmosphere at St Francis Church and Convent.

For maps, more things to do, other places to visit, and more tourist information, go to the Sorrento attractions planner.

Traveling by car from Naples to Sorrento takes 1.5 hours. Alternatively, you can ride a ferry; or take a train. In May, plan for daily highs up to 27°C, and evening lows to 18°C. Cap off your sightseeing on the 23rd (Thu) early enough to go by car to Lecce.
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Historic Sites · Wineries · Parks
Side Trip
Find places to stay May 21 — 23:

Lecce — 2 nights

Florence of the South

Known as the Florence of the South, Lecce is distinguished for its elaborate Baroque monuments.
Start off your visit on the 23rd (Thu): appreciate the extensive heritage of Centro Storico Medievale di Specchia, take in the architecture and atmosphere at Basilica di Santa Caterina d'Alessandria, then get into the urban bustle at Nardo, and finally take an in-depth tour of Museo Faggiano. On the 24th (Fri), you'll have a packed day of sightseeing: join in the after-dark buzz at Origano Cibo e Vino, then get to know the fascinating history of Centro Storico Otranto, and then take an in-depth tour of Jewish Museum Lecce.

To see photos, where to stay, reviews, and other tourist information, use the Lecce trip planner.

You can drive from Sorrento to Lecce in 5 hours. Alternatively, you can do a combination of train and flight; or take a train. Traveling from Sorrento in May, you can expect nighttime temperatures to be little chillier in Lecce, with lows of 15°C. Finish your sightseeing early on the 25th (Sat) so you can fly to Verona.
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Historic Sites · Museums · Nightlife · Shopping
Side Trips
Find places to stay May 23 — 25:

Verona — 1 night

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.
On the 25th (Sat), steep yourself in history at Museo di Castelvecchio, take in the spiritual surroundings of Basilica di San Zeno Maggiore, take in the architecture and atmosphere at Basilica di Santa Anastasia, then wander the streets of Piazza delle Erbe, and finally see a show at Arena di Verona.

To see photos, maps, traveler tips, and tourist information, refer to the Verona trip planner.

Traveling by flight from Lecce to Verona takes 3 hours. Alternatively, you can drive; or take a train. In May, plan for daily highs up to 27°C, and evening lows to 13°C. Wrap up your sightseeing on the 26th (Sun) to allow time to drive to Venice.
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Historic Sites · Neighborhoods · Shopping · Nightlife
Find places to stay May 25 — 26:

Venice — 3 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.
Shop till you drop at Palazzo dei Diamanti and Mercati di Rialto. Get some historical perspective at Piazza San Marco and Basilica di San Marco. Step out of Venice with an excursion to Castello Estense in Ferrara--about 1h 25 min away. The adventure continues: contemplate in the serene atmosphere at Basilica di Santa Maria Gloriosa dei Frari, take a stroll through Cannaregio, take in the views from Ponte di Rialto, and pause for some serene contemplation at Basilica di Santa Maria della Salute.

For reviews, traveler tips, and other tourist information, use the Venice online sightseeing planner.

You can drive from Verona to Venice in 1.5 hours. Alternatively, you can take a shuttle; or take a train. In May, daytime highs in Venice are 26°C, while nighttime lows are 15°C. Wrap up your sightseeing by early afternoon on the 29th (Wed) to allow time for the flight back home.
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Historic Sites · Museums · Shopping · Neighborhoods
Side Trip
Find places to stay May 26 — 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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Province of Siena travel guide

4.3
Landmarks · Wineries & Vineyards · Churches
Siena is a city in Tuscany, Italy. It is the capital of the province of Siena.The historic centre of Siena has been declared by UNESCO a World Heritage Site. It is one of the nation's most visited tourist attractions, with over 163,000 international arrivals in 2008. Siena is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year.HistorySiena, like other Tuscan hill towns, was first settled in the time of the Etruscans (c. 900–400 BC) when it was inhabited by a tribe called the Saina. The Etruscans were a tribe of advanced people who changed the face of central Italy through their use of irrigation to reclaim previously unfarmable land, and their custom of building their settlements in well-defended hill forts. A Roman town called Saena Julia was founded at the site in the time of the Emperor Augustus. Some archaeologists assert that Siena was controlled for a period by a Gaulish tribe called the Senones.According to local legend, Siena was founded by Senius and Aschius, two sons of Remus and thus nephews of Romulus, after whom Rome was named. Supposedly after their father's murder by Romulus, they fled Rome, taking with them the statue of the she-wolf suckling the infants (Capitoline Wolf), thus appropriating that symbol for the town. Additionally they rode white and black horses, giving rise to the Balzana, or coat of arms of Siena with a white band atop a dark band. Some claim the name Siena derives from Senius. Other etymologies derive the name from the Etruscan family name Saina, the Roman family name Saenii, or the Latin word senex "old" or its derived form seneo "to be old".

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Puglia travel guide

4.1
Beaches · Landmarks · Churches
Situated at the southeastern tip of the country, Puglia forms the heel on the "boot" of Italy. First colonized by Mycenaean Greeks, the region flourished during Roman times as a major producer of grain and oil. Today, Puglia remains a predominantly agricultural part of the country, though its warm and sunny coastal weather makes it a favorite holiday destination with an ever-increasing number of tourists. The long coastline features attractions like sun-kissed beaches and lively resorts, many of which are overlooked by limestone cliffs. Deeper inland, Puglia is largely flat, a land of charming villages and world-class cuisine. Here, you'll find olive oil, grapes, tomatoes, peppers, mushrooms, and fresh seafood to give you sustenance as you continue sightseeing. Despite its reputation as a producer of some Italy's best food and wines, Puglia still has numerous rural corners that most tourists have yet to explore.
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