27 days in Italy Itinerary

27 days in Italy Itinerary

Created using Inspirock Italy Trip Planner
Make it your trip
Fly
1
Milan
— 3 nights
Drive
2
Verona
— 2 nights
Drive
3
Venice
— 3 nights
Drive
4
Bologna
— 1 night
Train
5
Florence
— 5 nights
Drive
6
La Spezia
Drive
7
Pitigliano
— 2 nights
Drive
8
Naples
— 1 night
Drive
9
Pompeii
— 1 day
Drive
10
Positano
— 4 nights
Drive
11
Rome
— 2 nights
Fly

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Milan — 3 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.
Castello di Chignolo Po and Basilica di Sant'Andrea will appeal to history buffs. Take a break from the city and head to AC Boat and Lido di Menaggio. Change things up with these side-trips from Milan: Basilica di San Pietro in Ciel d'Oro (in Pavia), Rocca d'Olgisio (in Pianello Val Tidone) and Castello di Malpaga (in Cavernago). It doesn't end there: stop by Centro Commerciale Fiordaliso.

For maps, traveler tips, other places to visit, and tourist information, read our Milan trip website.

Sao Paulo, Brazil to Milan is an approximately 16-hour flight. The time zone difference when traveling from Sao Paulo to Milan is 4 hours. Traveling from Sao Paulo in May, expect little chillier with lows of 15°C in Milan. Cap off your sightseeing on the 8th (Tue) early enough to go by car to Verona.
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Outdoors · Historic Sites · Adventure · Tours
Side Trips
Find places to stay May 4 — 8:

Verona — 2 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.
Kick off your visit on the 8th (Tue): pause for some serene contemplation at Chiesa di San Pietro in Mavino, make a trip to Parrocchia Santa Maria Della Neve, and then enjoy the sand and surf at Spiaggia-Passeggiata delle Muse. Get ready for a full day of sightseeing on the next day: do a tasting at Villa Mosconi Bertani, then learn about winemaking at Brunelli Winery, and then take in the architecture and atmosphere at chiesa di San Lorenzo - Verona.

To see photos, ratings, reviews, and other tourist information, read Verona day trip planner.

Traveling by car from Milan to Verona takes 2 hours. Alternatively, you can take a train. In May in Verona, expect temperatures between 27°C during the day and 13°C at night. On the 10th (Thu), you'll have the morning to explore before heading off to Venice.
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Wineries · Historic Sites · Outdoors · Parks
Side Trips
Find places to stay May 8 — 10:

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.
Escape the urban bustle at Kayaking & Canoeing and Giudecca. Discover out-of-the-way places like Campo del Ghetto and Church of San Pantalon. And it doesn't end there: don't miss a visit to Chiesa di Santa Maria Assunta detta I Gesuiti, take in the spiritual surroundings of Chiesa di Santo Stefano, admire the masterpieces at Palazzo Mocenigo, and stop by Campo Santa Margherita.

To see other places to visit, reviews, where to stay, and more tourist information, go to the Venice trip itinerary app.

Getting from Verona to Venice by car takes about 1.5 hours. Other options: take a shuttle; or take a train. May in Venice sees daily highs of 26°C and lows of 15°C at night. Wrap up your sightseeing on the 13th (Sun) early enough to drive to Bologna.
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Historic Sites · Parks · Nature · Adventure
Find places to stay May 10 — 13:

Bologna — 1 night

Heart of Italian Cuisine

A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
On the 13th (Sun), contemplate the long history of Torre Prendiparte, let your taste buds guide you at a local gastronomic tour, then browse the eclectic array of goods at Mercato di Mezzo, then take in the spiritual surroundings of Chiesa di Santa Maria della Vita, and finally stop by Tamburini.

For more things to do and other tourist information, go to the Bologna trip planner.

You can drive from Venice to Bologna in 2 hours. Another option is to take a train. May in Bologna sees daily highs of 27°C and lows of 14°C at night. Cap off your sightseeing on the 14th (Mon) early enough to catch the train to Florence.
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Tours · Historic Sites · Shopping · Outdoors
Find places to stay May 13 — 14:

Florence — 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Give yourself a bit of retail therapy at Comune Di Certaldo and Chianti Cashmere Goat Farm. You'll explore the less-touristy side of things at Castello di Verrazzano and San Gimignano 1300. Get out of town with these interesting Florence side-trips: Castello di Monteriggioni (in Monteriggioni), Forte di San Leo (in San Leo) and The Mall (in Leccio). And it doesn't end there: admire the natural beauty at Castello di Brolio, browse the collection at Biblioteca Piccolomini, take in the spiritual surroundings of La Verna - Franciscan Sanctuary, and kick back and relax at Bagni Etruria.

For other places to visit, photos, traveler tips, and tourist information, refer to the Florence trip builder site.

You can take a train from Bologna to Florence in 1.5 hours. Other options are to drive; or take a bus. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. Wrap up your sightseeing on the 19th (Sat) to allow time to drive to La Spezia.
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Historic Sites · Shopping · Parks · Wineries
Side Trips
Find places to stay May 14 — 19:

La Spezia

La Spezia, at the head of the Gulf of La Spezia in the Liguria region of Northern Italy, is the capital city of the province of La Spezia.In terms of population, La Spezia is the second city in the Liguria region, preceded just by Genoa. On the 19th (Sat), look for gifts at Stoppani & Peer - Drogheria Storica La Spezia.

Inspirock's itinerary builder makes planning a La Spezia trip simple and quick.

You can drive from Florence to La Spezia in 2 hours. Alternatively, you can drive; or take a train. May in La Spezia sees daily highs of 25°C and lows of 13°C at night. You will have some time to spend on the 19th (Sat) before leaving for Pitigliano.
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Shopping
Find places to stay May 19 — 20:

Pitigliano — 2 nights

Pitigliano is a town in the province of Grosseto, located about 80km south-east of the city of Grosseto, in Italy. Kick off your visit on the 19th (Sat): explore the fascinating underground world of Insediamento rupestre di Vitozza.

To see maps, ratings, and tourist information, you can read our Pitigliano trip planner.

Drive from La Spezia to Pitigliano in 3.5 hours. Alternatively, you can drive; or do a combination of train and taxi. In May, daytime highs in Pitigliano are 25°C, while nighttime lows are 12°C. Finish your sightseeing early on the 21st (Mon) to allow enough time to drive to Naples.
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Shopping · Historic Sites · Nature · Parks
Side Trips
Find places to stay May 19 — 21:

Naples — 1 night

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Start off your visit on the 21st (Mon): explore the galleries of Monumental Complex Donnaregina - Diocesan Museum of Naples, admire the striking features of Chiesa di San Gregorio Armeno, and then get engrossed in the history at Museo delle Torture.

For where to stay, reviews, more things to do, and more tourist information, you can read our Naples travel planner.

Traveling by car from Pitigliano to Naples takes 4 hours. Alternatively, you can do a combination of taxi and train; or do a combination of bus and train. Traveling from Pitigliano in May, expect a bit warmer with lows of 17°C in Naples. On the 22nd (Tue), you'll have the morning to explore before heading off to Pompeii.
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Museums · Historic Sites · Neighborhoods · Shopping
Find places to stay May 21 — 22:

Pompeii — 1 day

Underground City

Pompeii has been a tourist destination for more than 250 years.
On the 22nd (Tue), delve into the distant past at Casa di Ottavio Quartione, explore the ancient world of Termopolio di Vetuzio Placido, and then delve into the distant past at House of Paquius Proculus.

To see more things to do, photos, maps, and tourist information, use the Pompeii planning site.

Pompeii is just a short distance from Naples. In May, daily temperatures in Pompeii can reach 27°C, while at night they dip to 17°C. Wrap up your sightseeing on the 22nd (Tue) early enough to drive to Positano.
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Historic Sites
Find places to stay May 22 — 23:

Positano — 4 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.
You'll explore the less-touristy side of things at Baia di Ieranto and L'Uomo e il Mare. Get outdoors at Monte Faito e Panorama and Arienzo Beach Club, Positano. Get out of town with these interesting Positano side-trips: Ceramiche Cosmolena di Margherita di Palma (in Ravello), Sorrento (Marina di Puolo, Basilica di Sant'Antonino, &more) and Piccadilly Ceramics (in Conca dei Marini). It doesn't end there: look for gifts at Ceramiche Casola.

For ratings, other places to visit, where to stay, and more tourist information, refer to the Positano vacation planner.

Drive from Pompeii to Positano in 1.5 hours. Alternatively, you can take a bus. May in Positano sees daily highs of 27°C and lows of 18°C at night. Wrap up your sightseeing on the 26th (Sat) early enough to drive to Rome.
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Outdoors · Parks · Beaches · Shopping
Side Trips
Find places to stay May 22 — 26:

Rome — 2 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
We've included these beaches for you: Bau Beach and El Pareo. Escape the urban bustle at Colle Aventino and Paradise Beach. You'll find plenty of places to visit near Rome: Necropoli della Banditaccia (in Cerveteri) and Mediterraneo Beach (in Fiumicino). Next up on the itinerary: explore the different monuments and memorials at Vatican Necropolis, admire the striking features of Villa Borghese, contemplate the long history of Villa Farnesina, and look for gifts at Bartolucci.

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

Drive from Positano to Rome in 3.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In May in Rome, expect temperatures between 28°C during the day and 17°C at night. Finish your sightseeing early on the 28th (Mon) to allow enough time to fly back home.
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Parks · Outdoors · Beaches · Historic Sites
Side Trips
Find places to stay May 26 — 28:

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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