14 days in Italy Itinerary

14 days in Italy Itinerary

Created using Inspirock Italy itinerary maker

Make it your trip
Fly
1
Bologna
— 1 day
Train
2
Florence
— 1 night
Drive
3
Greve in Chianti
— 1 night
Drive
4
San Gimignano
— 1 night
Drive
5
Cinque Terre
— 1 night
Drive
6
Parma
— 1 night
Drive
7
Milan
— 1 night
Drive
8
Venice
— 1 night
Drive
9
Trieste
— 1 night
Fly
10
Naples
— 1 night
Train
11
Rome
— 3 nights
Fly

S M T W T F S
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29

Bologna

— 1 day

Heart of Italian Cuisine

A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Start off your visit on the 16th (Sun): enjoy breathtaking views from Le Due Torri Torre degli Asinell, then pause for some serene contemplation at Basilica - Santuario di Santo Stefano, and then contemplate the long history of Basilica di San Petronio.

Ask Inspirock to suggest an itinerary and make planning a trip to Bologna fast, fun, and easy.

Rio de Janeiro, Brazil to Bologna is an approximately 15-hour flight. You'll lose 4 hours traveling from Rio de Janeiro to Bologna due to the time zone difference. Expect a bit cooler temperatures when traveling from Rio de Janeiro in May; daily highs in Bologna reach 27°C and lows reach 14°C. Finish up your sightseeing early on the 16th (Sun) so you can catch the train to Florence.

Things to do in Bologna

Historic Sites
Find places to stay May 16 — 17:

Florence

— 1 night

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 17th (Mon): don't miss a visit to Ratto della Sabina, take in panoramic vistas at Campanile di Giotto, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, then appreciate the extensive heritage of Piazza del Duomo, then snap pictures at Ponte Vecchio, and finally don't miss a visit to Piazzale Michelangelo.

To see where to stay, other places to visit, maps, and more tourist information, read Florence day trip site.

Traveling by train from Bologna to Florence takes 1.5 hours. Alternatively, you can 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 17th (Mon) early enough to drive to Greve in Chianti.

Things to do in Florence

Historic Sites
Find places to stay May 16 — 17:

Greve in Chianti

— 1 night
Kick off your visit on the 18th (Tue): explore the historical opulence of Castello di Verrazzano, then do a tasting at Castello Monterinaldi, then learn about winemaking at Montefioralle Winery, and finally look for gifts at Piccole Armonie Country.

To find more things to do, where to stay, photos, and other tourist information, you can read our Greve in Chianti trip planner.

Traveling by car from Florence to Greve in Chianti takes an hour. Alternatively, you can take a bus. In May in Greve in Chianti, expect temperatures between 25°C during the day and 13°C at night. Finish up your sightseeing early on the 18th (Tue) so you can go by car to San Gimignano.

Things to do in Greve in Chianti

Wineries · Historic Sites · Tours · Shopping

Side Trip

Find places to stay May 17 — 18:
Highlights from your trip

San Gimignano

— 1 night

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.
Start off your visit on the 19th (Wed): don't miss a visit to Porta Nova, then contemplate the long history of Historic Centre of San Gimignano, then do a tasting at Azienda Agricola San Quirico, and finally make a trip to Duomo di San Gimignano.

Discover how to plan a San Gimignano trip in just a few steps with Inspirock's itinerary builder.

You can drive from Greve in Chianti to San Gimignano in an hour. Other options are to do a combination of bus and 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 19th (Wed) to allow time to drive to Cinque Terre.

Things to do in San Gimignano

Historic Sites · Wineries

Side Trip

Find places to stay May 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.
On the 20th (Thu), hike along Cinque Terre footpaths, learn about winemaking at Buranco Agriturismo, then tour the pleasant surroundings at Il Sentiero da Levanto a Monterosso, and finally trek along Footpath Monterosso - Vernazza.

To find more things to do, other places to visit, traveler tips, and more tourist information, refer to the Cinque Terre trip itinerary maker website.

Getting from San Gimignano to Cinque Terre by car takes about 2.5 hours. Other options: take a train. In May in Cinque Terre, expect temperatures between 25°C during the day and 13°C at night. Finish your sightseeing early on the 20th (Thu) so you can drive to Parma.

Things to do in Cinque Terre

Parks · Outdoors · Trails · Wineries
Find places to stay May 19 — 20:

Parma

— 1 night

Capital of Italian Food Valley

Parma is famous for its prosciutto, cheese, and architecture.
On the 21st (Fri), contemplate in the serene atmosphere at Battistero di Parma, relax in the rural setting at Caseificio San Pier Damiani, then indulge your taste buds at Food & Drink, and finally contemplate in the serene atmosphere at Cattedrale di Parma.

Plan a trip to Parma easily and quickly by telling Inspirock to suggest an itinerary.

You can drive from Cinque Terre to Parma in 2.5 hours. Another option is to take a train. In May in Parma, expect temperatures between 26°C during the day and 14°C at night. Cap off your sightseeing on the 21st (Fri) early enough to go by car to Milan.

Things to do in Parma

Tours · Historic Sites
Find places to stay May 20 — 21:

Milan

— 1 night

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 22nd (Sat), admire the landmark architecture of Galleria Vittorio Emanuele II, take in the spiritual surroundings of Duomo di Milano, make a trip to Piazza del Duomo, then explore the different monuments and memorials at Monumental Cemetery, and finally browse the collection at Pinacoteca Ambrosiana.

To find where to stay, reviews, ratings, and more tourist information, read our Milan trip itinerary builder website.

You can drive from Parma to Milan in 1.5 hours. Alternatively, you can take a train. Expect a daytime high around 26°C in May, and nighttime lows around 15°C. Finish your sightseeing early on the 22nd (Sat) so you can drive to Venice.

Things to do in Milan

Historic Sites · Museums · Shopping
Find places to stay May 21 — 22:

Venice

— 1 night

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.
Start off your visit on the 23rd (Sun): don't miss a visit to Piazza San Marco, admire the landmark architecture of Doge's Palace, then admire the landmark architecture of Basilica di San Marco, and finally contemplate the waterfront views at Canal Grande.

To find other places to visit, photos, ratings, and tourist information, you can read our Venice trip builder site.

Getting from Milan to Venice by car takes about 3 hours. Other options: take a train; or take a bus. In May in Venice, expect temperatures between 26°C during the day and 15°C at night. Finish your sightseeing early on the 23rd (Sun) so you can drive to Trieste.

Things to do in Venice

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

Trieste

— 1 night

Pearl of the Adriatic

Trieste is a charming old town with a quiet atmosphere often compared to eastern European cities.
Kick off your visit on the 24th (Mon): get a sense of history and politics at Palazzo del Municipio, make a trip to Piazza dell'Unita d'Italia, then admire the striking features of Magazzino 26, then explore the historical opulence of Castello di Miramare - Museo Storico, and finally indulge in some personalized pampering at some of the best spas.

For traveler tips, photos, more things to do, and more tourist information, read Trieste vacation planning site.

Traveling by car from Venice to Trieste takes 2 hours. Alternatively, you can take a shuttle; or take a train. Expect a daytime high around 25°C in May, and nighttime lows around 16°C. Cap off your sightseeing on the 24th (Mon) early enough to catch the flight to Naples.

Things to do in Trieste

Spas · Historic Sites · Museums
Find places to stay May 23 — 24:

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 25th (Tue): pause for some serene contemplation at Duomo di Napoli, get curious at MUSA - Museo Universitario delle Scienze e delle Arti, then see the interesting displays at Museo Archeologico Nazionale di Napoli, and finally contemplate the long history of Pompeii Archaeological Park.

To find traveler tips, where to stay, and more tourist information, refer to the Naples road trip planner.

Getting from Trieste to Naples by flight takes about 3 hours. Other options: take a train; or drive. In May, daytime highs in Naples are 27°C, while nighttime lows are 17°C. Wrap up your sightseeing on the 25th (Tue) early enough to take a train to Rome.

Things to do in Naples

Historic Sites · Museums · Childrens Museums

Side Trip

Find places to stay May 24 — 25:

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.
Kick off your visit on the 26th (Wed): take in the spiritual surroundings of Chiesa di Sant'Ignazio di Loyola, get lost in a book at Biblioteca Casanatense, ponder the design of Trevi Fountain, then explore the ancient world of Pantheon, then get to know the fascinating history of Piazza Navona, and finally delve into the distant past at Palatine Hill. Keep things going the next day: appreciate the history behind La Pieta, pause for some serene contemplation at St. Peter's Basilica, then explore the world behind art at Vatican Museums, and finally take in the architecture and atmosphere at Church of St. Louis of the French.

For more things to do, photos, traveler tips, and tourist information, go to the Rome route planner.

Getting from Naples to Rome by train takes about 2 hours. Other options: drive; or fly. In May, daytime highs in Rome are 28°C, while nighttime lows are 17°C. On the 28th (Fri), wrap the sightseeing up by early afternoon so you can fly back home.

Things to do in Rome

Historic Sites · Museums

Side Trip

Find places to stay May 25 — 28:

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.

Friuli Venezia Giulia travel guide

4.2
Landmarks · Castles · Sacred & Religious Sites
One of five autonomous regions of Italy, Friuli Venezia Giulia is one of the country's easiest areas to tour, as it is on most of the major routes between the east and west sections of southern Europe. This region has its own distinct history, traditions, identity, and language. The majority of the inhabitants speak Friulian, as well as fluent Italian. Friuli Venezia Giulia overlooks the Adriatic Sea and is bordered by high mountains and dotted with lakes, valleys, and natural preserves, making it an ideal vacation spot for outdoor lovers. Explore the long coastline's secluded lagoons, sandy beaches, and seaside resorts on your trip.