29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

Make it your trip
Fly
1
Rome
— 4 nights
Drive
2
Siena
— 4 nights
Drive
3
Florence
— 4 nights
Drive
4
Lucca
— 1 night
Drive
5
Pisa
— 1 night
Train
6
Cinque Terre
— 1 night
Train
7
Portofino
— 3 nights
Drive
8
Milan
— 2 nights
Train
9
Bologna
— 1 night
Drive
10
Venice
— 4 nights
Fly
11
Amalfi
— 3 nights
Fly

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Rome

— 4 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: explore the ancient world of Pantheon, steep yourself in history at Palatine Hill, take in the architecture and atmosphere at St. Peter's Basilica, and make a trip to Roman Forum.

For maps, photos, other places to visit, and more tourist information, read Rome day trip website.

Tel Aviv, Israel to Rome is an approximately 7-hour flight. Traveling from Tel Aviv to Rome, you'll gain 1 hour due to the time zone difference. Prepare for slightly colder weather when traveling from Tel Aviv in October: high temperatures in Rome hover around 26°C and lows are around 15°C. Finish your sightseeing early on the 9th (Sat) so you can drive to Siena.

Things to do in Rome

Historic Sites · Museums · Tours · Neighborhoods

Side Trip

Find places to stay Oct 5 — 9:

Siena

— 4 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Venture out of the city with trips to Assisi (Basilica Papale e Sacro Convento di San Francesco d'Assisi, Rocca Maggiore, &more), Collegio del Cambio (in Perugia) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). There's lots more to do: gain insight at Scuola di Cucina di Lella, contemplate the long history of San Francesco, take in the architecture and atmosphere at Basilica Cateriniana San Domenico, and don't miss a visit to Piazza del Campo.

To see photos, ratings, reviews, and other tourist information, read Siena trip itinerary planning tool.

You can drive from Rome to Siena in 2.5 hours. Alternatively, you can take a bus; or take a train. In October, daily temperatures in Siena can reach 26°C, while at night they dip to 15°C. Wrap up your sightseeing on the 13th (Wed) to allow time to drive to Florence.

Things to do in Siena

Historic Sites · Wineries · Tours · Museums

Side Trips

Find places to stay Oct 9 — 13:

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.
Change things up with a short trip to Castello del Trebbio in Santa Brigida (about 36 minutes away). Next up on the itinerary: explore the world behind art at Florence Academy of Fine Arts, make a trip to Piazzale Michelangelo, indulge in some culinary diversions at a local gastronomic tour, and examine the collection at Pitti Palace.

Make your Florence itinerary with Inspirock to find out what to see and where to go.

Getting from Siena to Florence by car takes about 1.5 hours. Other options: take a bus; or take a train. In October, plan for daily highs up to 25°C, and evening lows to 14°C. Wrap up your sightseeing on the 17th (Sun) early enough to drive to Lucca.

Things to do in Florence

Historic Sites · Museums · Tours · Wineries

Side Trip

Find places to stay Oct 13 — 17:

Lucca

— 1 night

City of a Hundred Churches

Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Start off your visit on the 18th (Mon): enjoy breathtaking views from Torre Guinigi, contemplate in the serene atmosphere at San Michele in Foro, examine the collection at Antica Tipografia Biagini, then don't miss a visit to Le mura di Lucca, and finally admire the striking features of St Martin Cathedral.

To find where to stay, ratings, other places to visit, and more tourist information, go to the Lucca trip planner.

You can drive from Florence to Lucca in 1.5 hours. Other options are to take a bus; or take a train. In October in Lucca, expect temperatures between 25°C during the day and 14°C at night. Finish your sightseeing early on the 18th (Mon) so you can drive to Pisa.

Things to do in Lucca

Museums · Historic Sites
Find places to stay Oct 17 — 18:

Pisa

— 1 night
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Kick off your visit on the 19th (Tue): make a trip to Leaning Tower of Pisa, don't miss a visit to Piazza dei Miracoli, and then see the interesting displays at Museo Aviotruppe Esercito Italiano.

For where to stay, reviews, ratings, and tourist information, go to the Pisa driving holiday planner.

Pisa is just a short distance from Lucca. In October, daytime highs in Pisa are 25°C, while nighttime lows are 14°C. Wrap up your sightseeing on the 19th (Tue) to allow time to take a train to Cinque Terre.

Things to do in Pisa

Museums
Find places to stay Oct 18 — 19:

Cinque Terre

— 1 night

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Kick off your visit on the 20th (Wed): explore the striking landscape of Parco Nazionale Cinque Terre and then identify plant and animal life at Enjoy Cinqueterre Boat Tours.

To find photos, traveler tips, maps, and tourist information, you can read our Cinque Terre holiday app.

Take a train from Pisa to Cinque Terre in 2 hours. Alternatively, you can drive. In October in Cinque Terre, expect temperatures between 25°C during the day and 14°C at night. Cap off your sightseeing on the 20th (Wed) early enough to catch the train to Portofino.

Things to do in Cinque Terre

Parks · Nature · Tours · Wildlife
Find places to stay Oct 19 — 20:

Portofino

— 3 nights
Portofino is an Italian fishing village and holiday resort famous for its picturesque harbour and historical association with celebrity and artistic visitors. Portofino is known for historic sites, parks, and adventure. Your trip includes some of its best attractions: stroll through Area Marina Protetta Portofino, explore the historical opulence of Castello Brown, admire the striking features of Oratorio di Nostra Signora Assunta, and pause for some serene contemplation at Parrocchia Di San Martino.

To see ratings, maps, more things to do, and tourist information, you can read our Portofino day trip planning app.

Traveling by train from Cinque Terre to Portofino takes 1.5 hours. Alternatively, you can drive. In October, plan for daily highs up to 24°C, and evening lows to 17°C. Finish your sightseeing early on the 23rd (Sat) to allow enough time to drive to Milan.

Things to do in Portofino

Historic Sites · Parks · Wildlife · Tours
Find places to stay Oct 20 — 23:

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.
On the 24th (Sun), explore the historical opulence of Castello Sforzesco, then explore the different monuments and memorials at Monumental Cemetery, and then browse the collection at Pinacoteca Ambrosiana. On the 25th (Mon), you'll have a packed day of sightseeing: admire the landmark architecture of Galleria Vittorio Emanuele II, then awaken your taste buds at Milan Walking Tours, then take in the spiritual surroundings of Duomo di Milano, and finally get engrossed in the history at Basilica di Sant'Ambrogio.

To see reviews, other places to visit, more things to do, and tourist information, use the Milan day trip app.

Getting from Portofino to Milan by car takes about 2 hours. Other options: take a train. Traveling from Portofino in October, you can expect nighttime temperatures to be little chillier in Milan, with lows of 13°C. Finish your sightseeing early on the 25th (Mon) to allow enough time to take a train to Bologna.

Things to do in Milan

Historic Sites · Museums · Tours · Wineries
Find places to stay Oct 23 — 25:

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.
Kick off your visit on the 26th (Tue): admire the masterpieces at Pinacoteca Nazionale di Bologna, pause for some serene contemplation at Basilica - Santuario di Santo Stefano, then get engrossed in the history at Museo Civico Medievale, then make a trip to Le Due Torri Torre degli Asinell, and finally ponder the world of politics at Palazzo Comunale.

For more things to do, other places to visit, where to stay, and tourist information, refer to the Bologna trip site.

You can take a train from Milan to Bologna in 2 hours. Alternatively, you can drive; or take a bus. In October, daytime highs in Bologna are 22°C, while nighttime lows are 13°C. Wrap up your sightseeing on the 26th (Tue) to allow time to drive to Venice.

Things to do in Bologna

Museums · Historic Sites
Find places to stay Oct 25 — 26:

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 Doge's Palace, get to know the fascinating history of Piazza San Marco, and take in the architecture and atmosphere at Basilica di San Marco.

To see other places to visit, reviews, traveler tips, and more tourist information, refer to the Venice day trip planning app.

Traveling by car from Bologna to Venice takes 2 hours. Alternatively, you can take a train. In October, daytime highs in Venice are 22°C, while nighttime lows are 12°C. Finish up your sightseeing early on the 30th (Sat) so you can catch the flight to Amalfi.

Things to do in Venice

Historic Sites · Museums · Tours · Neighborhoods
Find places to stay Oct 26 — 30:

Amalfi

— 3 nights

Painted Town

Known for its impressive hillside cascade of colorful stone buildings down to the Mediterranean shore, Amalfi is the cultural and commercial heart of southern Italy's Amalfi Coast.
Change things up with a short trip to Walk of the Gods in Positano (about 32 minutes away). The adventure continues: awaken your taste buds at Amalfi Coast Drive, admire the landmark architecture of Villa Rufolo, steep yourself in history at Duomo di Ravello, and take in the spiritual surroundings of Duomo di Sant'Andrea.

For reviews, other places to visit, more things to do, and other tourist information, read Amalfi route builder website.

You can fly from Venice to Amalfi in 3 hours. Other options are to do a combination of train and taxi; or drive. Plan for a bit warmer temperatures traveling from Venice in October, with highs in Amalfi at 26°C and lows at 20°C. Finish your sightseeing early on the 2nd (Tue) to allow enough time to fly back home.

Things to do in Amalfi

Historic Sites · Outdoors · Museums · Scenic Drive

Side Trips

Find places to stay Oct 30 — Nov 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.

Tuscany travel guide

4.4
Landmarks · Art Museums · Historic Walking Areas
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.