29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy attractions planner

Make it your trip
Fly
1
Florence
— 4 nights
Drive
2
Siena
— 3 nights
Drive
3
Assisi
— 2 nights
Drive
4
Rome
— 5 nights
Fly
5
Cinque Terre
— 3 nights
Drive
6
Milan
— 2 nights
Drive
7
Verona
— 1 night
Drive
8
Venice
— 4 nights
Fly
9
Positano
— 4 nights
Fly

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Florence

— 4 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Step out of Florence to go to Pisa and see Leaning Tower of Pisa, which is approximately 1h 20 min away. Dedicate the 7th (Tue) to wine at some of the top wineries in the area. There's still lots to do: explore the world behind art at Florence Academy of Fine Arts, take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, see the interesting displays at Pitti Palace, and steep yourself in history at Basilica of Santa Croce.

To find maps, other places to visit, more things to do, and tourist information, refer to the Florence sightseeing planning website.

Casablanca, Morocco to Florence is an approximately 5-hour flight. You can also do a combination of train and bus; or take a bus. The time zone difference when traveling from Casablanca to Florence is 1 hour. Expect somewhat warmer weather when traveling from Casablanca in June: highs in Florence hover around 33°C, while lows dip to 21°C. Wrap up your sightseeing on the 8th (Wed) to allow time to drive to Siena.

Things to do in Florence

Historic Sites · Tours · Wineries · Museums

Side Trip

Find places to stay Jun 4 — 8:
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Siena

— 3 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: Podere La Marronaia- Sosta Alle Colonne (in San Gimignano), Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate) and Podere Il Cocco (in Montalcino). There's lots more to do: savor the flavors at Food & Drink, contemplate the long history of San Francesco, ponder the world of politics at Palazzo Pubblico and Museo Civico, and don't miss a visit to Piazza del Campo.

To see more things to do, maps, photos, and tourist information, you can read our Siena trip planner.

Traveling by car from Florence to Siena takes 1.5 hours. Alternatively, you can take a bus; or take a train. In June, plan for daily highs up to 34°C, and evening lows to 19°C. Wrap up your sightseeing on the 11th (Sat) early enough to drive to Assisi.

Things to do in Siena

Wineries · Historic Sites · Tours · Museums

Side Trips

Find places to stay Jun 8 — 11:
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Assisi

— 2 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Kick off your visit on the 12th (Sun): pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, explore the historical opulence of Rocca Maggiore, then contemplate in the serene atmosphere at Eremo delle Carceri, and finally learn about winemaking at Montioni Frantoio e Cantina. Here are some ideas for day two: do a tasting at Tili Vini Societa Agricola, then admire the masterpieces at Galleria Nazionale dell'Umbria, and then surround yourself with nature on Wild Foods Italy.

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

You can drive from Siena to Assisi in 2 hours. Alternatively, you can take a bus; or take a train. In June, plan for daily highs up to 32°C, and evening lows to 18°C. Finish your sightseeing early on the 13th (Mon) so you can drive to Rome.

Things to do in Assisi

Wineries · Historic Sites · Outdoors · Wildlife

Side Trips

Find places to stay Jun 11 — 13:
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Rome

— 5 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 trip includes some of its best attractions: pause for some serene contemplation at St. Peter's Basilica, steep yourself in history at Roman Forum, admire the masterpieces at Vatican Museums, and get to know the fascinating history of Piazza Navona.

To find photos, other places to visit, and other tourist information, you can read our Rome trip itinerary maker website.

You can drive from Assisi to Rome in 2.5 hours. Alternatively, you can take a train; or take a bus. In June in Rome, expect temperatures between 34°C during the day and 21°C at night. Finish your sightseeing early on the 18th (Sat) to allow enough time to fly to Cinque Terre.

Things to do in Rome

Side Trip

Find places to stay Jun 13 — 18:
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Cinque Terre

— 3 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Change things up with these side-trips from Cinque Terre: Bagno Maurizio (in Viareggio) and Aquarium of Genoa (in Genoa). There's still lots to do: get up close to creatures of the deep with 5 Terre Pelagos Boat Tours, pause for some serene contemplation at Convento dei Cappuccini e Chiesa di San Francesco, explore the wealth of natural beauty at Parco Nazionale Cinque Terre, and trek along Footpath Monterosso - Vernazza.

For traveler tips, reviews, ratings, and tourist information, read our Cinque Terre travel route tool.

Traveling by flight from Rome to Cinque Terre takes 3 hours. Alternatively, you can take a train; or drive. Traveling from Rome in June, Cinque Terre is a bit cooler at night with lows of 18°C. Finish your sightseeing early on the 21st (Tue) so you can drive to Milan.

Things to do in Cinque Terre

Parks · Outdoors · Nature · Trails

Side Trips

Find places to stay Jun 18 — 21:
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Milan

— 2 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.
Kick off your visit on the 22nd (Wed): step into the grandiose world of Castello Sforzesco, then take in the spiritual surroundings of Duomo di Milano, then pause for some serene contemplation at Basilica San Lorenzo Maggiore, and finally admire the landmark architecture of Galleria Vittorio Emanuele II. Get ready for a full day of sightseeing on the 23rd (Thu): see La Casa Maledetta, then stroll the grounds of Monumental Cemetery, and then take an in-depth tour of Pinacoteca Ambrosiana.

To find maps, reviews, more things to do, and more tourist information, read our Milan day trip planner.

You can drive from Cinque Terre to Milan in 3 hours. Alternatively, you can take a train. In June in Milan, expect temperatures between 33°C during the day and 20°C at night. Cap off your sightseeing on the 23rd (Thu) early enough to go by car to Verona.

Things to do in Milan

Find places to stay Jun 21 — 23:
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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 24th (Fri), contemplate in the serene atmosphere at Basilica di San Zeno Maggiore, steep yourself in history at Museo di Castelvecchio, see the grandeur of opera at Arena di Verona, then make a trip to Torre dei Lamberti, then make a trip to Piazza delle Erbe, and finally make a trip to Piazza Bra.

To see more things to do, photos, other places to visit, and tourist information, read our Verona tour planning website.

Traveling by car from Milan to Verona takes 2 hours. Alternatively, you can take a train. In June, daytime highs in Verona are 34°C, while nighttime lows are 20°C. Finish your sightseeing early on the 24th (Fri) to allow enough time to drive to Venice.

Things to do in Verona

Historic Sites · Neighborhoods · Shopping · Nightlife
Find places to stay Jun 23 — 24:
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Venice

— 4 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.
Venice is known for historic sites, nature, and museums. Your trip includes some of its best attractions: explore the activities along Canal Grande, admire the striking features of Basilica di San Marco, explore the world behind art at Peggy Guggenheim Collection, and see the interesting displays at Doge's Palace.

For maps, other places to visit, where to stay, and more tourist information, go to the Venice online trip planner.

Getting from Verona to Venice by car takes about 1.5 hours. Other options: take a shuttle; or take a train. June in Venice sees daily highs of 32°C and lows of 20°C at night. Wrap up your sightseeing on the 28th (Tue) early enough to fly to Positano.

Things to do in Venice

Find places to stay Jun 24 — 28:
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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 find plenty of places to visit near Positano: Ravello (Duomo di Ravello, Villa Rufolo, &more) and Amalfi (Museo della Carta, Amalfi Coast Drive, &more). There's much more to do: enjoy the sand and surf at Fornillo, stroll through Spiaggia Grande, take a tour by water with Boat Tours & Water Sports, and take a memorable drive along Amalfi Coast.

To find ratings, traveler tips, photos, and other tourist information, you can read our Positano route builder tool.

Traveling by flight from Venice to Positano takes 3 hours. Alternatively, you can drive; or do a combination of train and 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 2nd (Sat) to allow enough time to fly back home.

Things to do in Positano

Outdoors · Parks · Beaches · Historic Sites

Side Trips

Find places to stay Jun 28 — Jul 2:
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Italy travel guide

4.6
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.