29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy trip itinerary maker

Make it your trip
Fly
1
Pisa
— 1 day
Drive
2
Florence
— 4 nights
Train
3
Verona
— 4 nights
Drive
4
Venice
— 3 nights
Drive
5
Ravenna
— 1 night
Drive
6
Siena
— 5 nights
Drive
7
Assisi
— 2 nights
Drive
8
Rome
— 5 nights
Drive
9
Ravello
— 2 nights
Drive
10
Naples
— 2 nights
Fly

S M T W T F S
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19

Pisa

— 1 day
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Start off your visit on the 22nd (Sat): take in the spiritual surroundings of Duomo di Pisa, explore the different monuments and memorials at Camposanto, then examine the collection at Museo Aviotruppe Esercito Italiano, then take in panoramic vistas at Leaning Tower of Pisa, and finally contemplate in the serene atmosphere at Battistero di San Giovanni.

For where to stay, traveler tips, maps, and other tourist information, refer to the Pisa day trip planning website.

Lisbon, Portugal to Pisa is an approximately 6-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Lisbon to Pisa. In May, daytime highs in Pisa are 25°C, while nighttime lows are 13°C. Wrap up your sightseeing on the 22nd (Sat) to allow time to drive to Florence.

Things to do in Pisa

Historic Sites · Museums
Find places to stay May 22 — 23:

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.
Piazzale Michelangelo and Cathedral of Santa Maria del Fiore are good opportunities to explore the local culture. You'll explore the less-touristy side of things at Pitti Palace and Centro Storico. Dedicate the 25th (Tue) to wine at some of the top wineries in the area. Next up on the itinerary: get great views at Basilica San Miniato al Monte, take in the spiritual surroundings of The Baptistery of St. John, take in the views from Ponte Vecchio, and enjoy breathtaking views from Campanile di Giotto.

For maps, ratings, and other tourist information, read Florence trip maker app.

Drive from Pisa to Florence in 1.5 hours. Alternatively, you can take a bus; or take a train. In May in Florence, expect temperatures between 25°C during the day and 13°C at night. Cap off your sightseeing on the 26th (Wed) early enough to catch the train to Verona.

Things to do in Florence

Historic Sites · Tours · Wineries · Museums
Find places to stay May 22 — 26:

Verona

— 4 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 explore the less-touristy side of things at La Citta Alta and I Giardini di Castel Trauttmansdorff. Get some historical perspective at Borghetto sul Mincio and Museo di Castelvecchio. Get out of town with these interesting Verona side-trips: Basilica di Santa Maria Maggiore (in Bergamo) and Grotte di Catullo (in Sirmione). There's still lots to do: contemplate the long history of Verona's Cathedral (Duomo), take a stroll through Piazza delle Erbe, take in the spiritual surroundings of Basilica di San Zeno Maggiore, and see the interesting displays at Casa di Giulietta.

For traveler tips, other places to visit, and tourist information, read our Verona trip builder site.

You can take a train from Florence to Verona in 2.5 hours. Other options are to drive; or take a bus. Expect a daytime high around 27°C in May, and nighttime lows around 13°C. Cap off your sightseeing on the 30th (Sun) early enough to go by car to Venice.

Things to do in Verona

Historic Sites · Parks · Neighborhoods · Shopping

Side Trips

Find places to stay May 26 — 30:

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.
Museum-lovers will get to explore Doge's Palace and Peggy Guggenheim Collection. Explore hidden gems such as Basilica of St. Anthony and Scrovegni Chapel. Change things up with a short trip to Castello Estense in Ferrara (about 1h 25 min away). There's still lots to do: take a stroll through Cannaregio, take in the architecture and atmosphere at San Giorgio Maggiore, contemplate the waterfront views at Canal Grande, and make a trip to Basilica di San Marco.

To find where to stay, ratings, reviews, and other tourist information, use the Venice trip planner.

You can drive from Verona to Venice in 1.5 hours. Alternatively, you can take a shuttle; or take a bus. May in Venice sees daily highs of 26°C and lows of 15°C at night. Wrap up your sightseeing on the 2nd (Wed) to allow time to drive to Ravenna.

Things to do in Venice

Historic Sites · Museums · Nature · Parks

Side Trips

Find places to stay May 30 — Jun 2:

Ravenna

— 1 night

City of Mosaics

Famous for its wealth of original mosaics, Ravenna is a hub of artistic and cultural heritage.
Kick off your visit on the 3rd (Thu): make a trip to Mausoleo di Galla Placidia, take in the spiritual surroundings of Basilica San Vitale, pause for some serene contemplation at Basilica di San Francesco, then take in the spiritual surroundings of Basilica di Sant'Apollinare in Classe, then contemplate in the serene atmosphere at Basilica di Sant'Apollinare Nuovo, and finally take in the spiritual surroundings of Battistero Neoniano (Battistero degli Ortodossi).

For ratings, other places to visit, photos, and tourist information, read Ravenna trip itinerary planner.

Traveling by car from Venice to Ravenna takes 2.5 hours. Alternatively, you can take a train; or do a combination of train and bus. Expect a daytime high around 32°C in June, and nighttime lows around 19°C. Finish your sightseeing early on the 3rd (Thu) to allow enough time to drive to Siena.

Things to do in Ravenna

Historic Sites

Side Trip

Find places to stay Jun 2 — 3:

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.
Get a sense of the local culture at Historic Centre of San Gimignano and Abbazia di Sant'Antimo. You'll discover tucked-away gems like Centro Storico di Siena and San Gimignano Bell Tower. Change things up with these side-trips from Siena: Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate), Poggio Amorelli (in Castellina In Chianti) and Castiglion del Bosco Winery (in Montalcino). The adventure continues: ponder the world of politics at Palazzo Pubblico and Museo Civico, explore the historical opulence of Castello di Monteriggioni, surround yourself with nature on a nature and wildlife tour, and enjoy breathtaking views from Torre del Mangia.

For more things to do, maps, and more tourist information, read Siena journey planner.

You can drive from Ravenna to Siena in 3 hours. Other options are to take a train; or do a combination of train and bus. Expect a daytime high around 34°C in June, and nighttime lows around 19°C. Finish your sightseeing early on the 8th (Tue) to allow enough time to drive to Assisi.

Things to do in Siena

Historic Sites · Wineries · Tours · Wildlife

Side Trips

Find places to stay Jun 3 — 8:

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 9th (Wed): admire the landmark architecture of Basilica di Santa Chiara, take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, then take in the architecture and atmosphere at San Damiano, and finally do a tasting at Tili Vini Societa Agricola. Keep things going the next day: pause for some serene contemplation at Cattedrale di Santa Maria Assunta Spoleto, step into the grandiose world of Rocca Maggiore, don't miss a visit to Eremo delle Carceri, then examine the collection at Museo della Porziuncola, and finally take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola.

To find photos, ratings, other places to visit, and other tourist information, read our Assisi holiday planner.

Traveling by car from Siena to Assisi takes 2 hours. Alternatively, you can take a bus; or take a train. In June, daytime highs in Assisi are 32°C, while nighttime lows are 18°C. Finish your sightseeing early on the 10th (Thu) so you can drive to Rome.

Things to do in Assisi

Historic Sites · Wineries · Museums

Side Trip

Find places to stay Jun 8 — 10:

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.
Eschew the tourist crowds and head to Arcibasilica di San Giovanni in Laterano and Villa Adriana. Deepen your sense of the past at sights like Colosseum and Pantheon. When in Rome, make a side trip to see Parco Archeologico di Ostia Antica in Ostia Antica, approximately Ostia Antica away. And it doesn't end there: delve into the distant past at Palatine Hill, admire the masterpieces at Galleria Borghese, pause for some serene contemplation at Church of St. Louis of the French, and make a trip to St. Peter's Basilica.

Find out how to plan Rome trip without stress by asking Inspirock to help create an itinerary.

Drive from Assisi to Rome in 2.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 34°C in June, and nighttime lows around 21°C. Wrap up your sightseeing on the 15th (Tue) to allow time to drive to Ravello.

Things to do in Rome

Historic Sites · Museums · Neighborhoods

Side Trips

Find places to stay Jun 10 — 15:

Ravello

— 2 nights
Best known for its celebrated terraced gardens, Ravello is a hidden gem of Italy's Amalfi Coast.
Kick off your visit on the 16th (Wed): take in the spiritual surroundings of Duomo di Ravello, then admire the striking features of Villa Rufolo, then contemplate the long history of Villa Cimbrone Gardens, and finally look for all kinds of wild species at Valle delle Ferriere. Get ready for a full day of sightseeing on the 17th (Thu): see the interesting displays at Museo della Carta, pause for some serene contemplation at Duomo di Sant'Andrea, then take in the spiritual surroundings of Cloister del Paradiso, then tour the pleasant surroundings at Fornillo, and finally take a memorable tour with Tours.

To see more things to do, reviews, other places to visit, and tourist information, go to the Ravello trip planner.

Traveling by car from Rome to Ravello takes 3.5 hours. Alternatively, you can do a combination of train and taxi; or take a bus. Traveling from Rome in June, expect nights in Ravello to be somewhat warmer, around 26°C, while days are slightly colder, around 30°C. Wrap up your sightseeing on the 17th (Thu) early enough to drive to Naples.

Things to do in Ravello

Parks · Historic Sites · Wildlife · Nature

Side Trips

Find places to stay Jun 15 — 17:

Naples

— 2 nights
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 18th (Fri): brush up on your military savvy at Galleria Borbonica, delve into the distant past at Parco Acheologico di Ercolano, and then explore the ancient world of Pompeii Archaeological Park. Get ready for a full day of sightseeing on the next day: stroll the grounds of Catacombe di San Gennaro, then admire the masterpieces at Museo e Real Bosco di Capodimonte, then examine the collection at Museo Archeologico Nazionale di Napoli, and finally admire the masterpieces at Museo Cappella Sansevero.

To see maps, traveler tips, more things to do, and tourist information, read Naples trip itinerary planning website.

You can drive from Ravello to Naples in 1.5 hours. Alternatively, you can take a bus. Expect little chillier evenings in Naples when traveling from Ravello in June, with lows around 22°C. Wrap up your sightseeing on the 19th (Sat) to allow time to travel back home.

Things to do in Naples

Historic Sites · Museums

Side Trips

Find places to stay Jun 17 — 19:

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
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.