21 days in Italy Itinerary

21 days in Italy Itinerary

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Route & dates

21 days in Italy Itinerary

Start: Philadelphia
Fly:  13​h 30​min
1
Bologna
— 3 nights
train:  45​min
2
Florence
— 2 nights
bus:  1​h 15​min
3
Siena
— 3 nights
train:  2​h
4
Pisa
— 1 night
5
Portofino
— 2 nights
train:  2​h 15​min
6
Milan
— 2 nights
train:  45​min
7
Como
— 2 nights
8
Verona
— 2 nights
bus:  1​h 30​min
9
Venice
— 3 nights
Fly:  11​h 30​min
End: Philadelphia


Learn more about your trip

3
nights
Bologna

Bologna ©
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Your day-by-day itinerary now includes Basilica - Santuario di Santo Stefano, Santuario di Madonna di San Luca, Portico di San Luca, and other attractions you added. Start off your visit on the 5th (Mon): get the lay of the land with Free Walking Tour Bologna, appreciate the extensive heritage of Portico di San Luca, and then take in the architecture and atmosphere at Santuario di Madonna di San Luca. On the 6th (Tue), you'll have a packed day of sightseeing: contemplate the long history of Piazza Maggiore, take in the spiritual surroundings of Basilica - Santuario di Santo Stefano, and then work some fitness into your day at Torre Prendiparte.

To see ratings, more things to do, maps, and other tourist information, read Bologna road trip site .

Philadelphia, USA to Bologna is an approximately 13.5-hour combination of flight and train. You can also fly; or do a combination of train and flight. The time zone difference when traveling from Philadelphia to Bologna is 6 hours. Expect a daytime high around 88°F in August, and nighttime lows around 66°F. Finish up your sightseeing early on the 7th (Wed) so you can catch the train to Florence.

Things to do in Bologna

Historic Sites Tours Outdoors
Find places to stay Aug 4 — 7:
Highlights from your plan
Santuario di Madonna di San Luca ©
Torre Prendiparte ©
Torre Prendiparte

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Do some cultural sightseeing at Basilica San Miniato al Monte and Cathedral of Santa Maria del Fiore. Eschew the tourist crowds and head to Centro Storico and Lido Di Camaiore. There's still lots to do: see the interesting displays at Academy Of Florence Art Gallery, appreciate the extensive heritage of Piazza del Duomo, relax and float downstream with a rafting and tubing tour, and admire the masterpieces at Gallerie Degli Uffizi.

To see maps, other places to visit, traveler tips, and more tourist information, read Florence trip planner .

You can take a train from Bologna to Florence in an hour. Other options are to take a bus; or drive. In August, daytime highs in Florence are 86°F, while nighttime lows are 64°F. Wrap up your sightseeing on the 9th (Fri) to allow time to take a bus to Siena.

Things to do in Florence

Historic Sites Outdoors Parks
Find places to stay Aug 7 — 9:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Centro Storico ©
Centro Storico
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi

3
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 10th (Sat), don't miss a visit to Centro Storico di Siena, then take in the architecture and atmosphere at Duomo di Siena, and then ponder the world of politics at Palazzo Pubblico and Museo Civico. On the next day, contemplate the long history of Palazzo Chigi Saracini, steep yourself in history at Battistero di San Giovanni, steep yourself in history at Cappella di Piazza, then contemplate in the serene atmosphere at Sinagoga di Siena, then take in the architecture and atmosphere at Basilica di San Clemente in Santa Maria dei Servi, and finally contemplate in the serene atmosphere at Santa Maria del Carmine (San Niccolo al Carmine).

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

You can take a bus from Florence to Siena in 1.5 hours. Other options are to drive; or take a train. In August in Siena, expect temperatures between 89°F during the day and 67°F at night. Wrap up your sightseeing on the 12th (Mon) to allow time to take a train to Pisa.

Things to do in Siena

Historic Sites Museums
Find places to stay Aug 9 — 12:
Highlights from your plan
Duomo di Siena ©
Duomo di Siena
Palazzo Pubblico and Museo Civico ©
Palazzo Pubblico and Museo Civico
Battistero di San Giovanni ©
Battistero di San Giovanni

1
night
Pisa

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
On the 12th (Mon), stroll through Il Paguro, look for gifts at De Bondt, then take in the architecture and atmosphere at Chiesa di Santo Stefano dei Cavalieri, and finally contemplate in the serene atmosphere at Chiesa di Santa Caterina d'Alessandria. On the 13th (Tue), you'll have a packed day of sightseeing: enjoy the sand and surf at Spiaggia Tirreno 2000, admire the landmark architecture of Palazzina Marconi, and then take in panoramic vistas at Leaning Tower of Pisa.

For where to stay, ratings, and tourist information, use the Pisa road trip planner .

Getting from Siena to Pisa by train takes about 2 hours. Other options: drive; or take a bus. In August, daytime highs in Pisa are 86°F, while nighttime lows are 64°F. Finish your sightseeing early on the 13th (Tue) to allow enough time to drive to Portofino.

Things to do in Pisa

Parks Outdoors Beaches
Find places to stay Aug 12 — 13:
Highlights from your plan
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Chiesa di Santo Stefano dei Cavalieri ©

2
nights
Portofino

Portofino ©
Portofino is an Italian fishing village and holiday resort famous for its picturesque harbour and historical association with celebrity and artistic visitors. Start off your visit on the 14th (Wed): identify plant and animal life at Area Marina Protetta Portofino, contemplate in the serene atmosphere at Church of San Giorgio, take in the exciting artwork at Galleria d'Arte Portofino, then enjoy the sea views from Faro di Portofino, then explore the historical opulence of Castello Brown, and finally explore the world behind art at Museo Del Parco. On the 15th (Thu), you'll have a packed day of sightseeing: take in the architecture and atmosphere at Parrocchia Di San Martino, then don't miss a visit to Piazza Martiri Dell'Olivetta, and then go for a stroll along the water at Marina di Portofino.

To find reviews, photos, maps, and tourist information, you can read our Portofino tour itinerary planning app .

Getting from Pisa to Portofino by car takes about 2 hours. Other options: take a train; or take a bus. Plan for somewhat warmer nights when traveling from Pisa in August since evenings lows in Portofino dip to 71°F. Finish your sightseeing early on the 15th (Thu) so you can take a train to Milan.

Things to do in Portofino

Parks Historic Sites Wildlife
Find places to stay Aug 13 — 15:
Highlights from your plan
Area Marina Protetta Portofino ©
Area Marina Protetta Portofino
Faro di Portofino ©
Faro di Portofino
Parrocchia Di San Martino ©
Parrocchia Di San Martino

2
nights
Milan

Milan ©
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.
Get ready for a full day of sightseeing on the 16th (Fri): take a stroll through Brera District, then take in the spiritual surroundings of Duomo di Milano, then get to know the fascinating history of Piazza del Duomo, and finally take in the architecture and atmosphere at Chiesa di Santa Maria presso San Satiro.

To see more things to do, other places to visit, ratings, and other tourist information, you can read our Milan trip planner.

Take a train from Portofino to Milan in 2.5 hours. Alternatively, you can drive. Traveling from Portofino in August, plan for little chillier nights in Milan, with lows around 66°F. Wrap up your sightseeing on the 17th (Sat) early enough to take a train to Como.

Things to do in Milan

Historic Sites Shopping Neighborhoods
Find places to stay Aug 15 — 17:
Highlights from your plan
Brera District ©
Brera District
Duomo di Milano ©
Duomo di Milano

2
nights
Como

Como ©
Known for its idyllic location on the shores of Lake Como and at the foot of the Alps, Como is one of northern Italy's most popular tourist destinations.
On the 17th (Sat), take in the architecture and atmosphere at Basilica di San Fedele. Get ready for a full day of sightseeing on the 18th (Sun): kick back and relax at Lido Villa Olmo, contemplate in the serene atmosphere at Tempio Voltiano, then pause for some serene contemplation at Cathedral of Como (Duomo), then pause for some serene contemplation at Basilica di Sant'Abbondio, and finally look for gifts at Le Mille e Una Mella Caramelleria.

For reviews, photos, traveler tips, and more tourist information, refer to the Como online route planner .

Getting from Milan to Como by train takes about an hour. Other options: drive. In August, plan for daily highs up to 83°F, and evening lows to 64°F. On the 19th (Mon), wrap the sightseeing up by early afternoon so you can drive to Verona.

Things to do in Como

Parks Outdoors Historic Sites
Find places to stay Aug 17 — 19:
Highlights from your plan
Lido Villa Olmo ©
Lido Villa Olmo
Cathedral of Como (Duomo) ©
Cathedral of Como (Duomo)
Basilica di Sant'Abbondio ©
Basilica di Sant'Abbondio

2
nights
Verona

Verona ©
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 19th (Mon): enjoy breathtaking views from Torre dei Lamberti, then don't miss a visit to Piazza delle Erbe, and then see the grandeur of opera at Arena di Verona. Here are some ideas for day two: admire the masterpieces at AMO - Arena Museo Opera, take in the spiritual surroundings of Basilica di San Zeno Maggiore, then explore the historical opulence of Museo di Castelvecchio, then pause for some serene contemplation at chiesa di San Lorenzo - Verona, and finally pause for some serene contemplation at Chiesa dei Santi Apostoli.

To see other places to visit, where to stay, ratings, and more tourist information, you can read our Verona trip builder website .

Traveling by car from Como to Verona takes 2 hours. Alternatively, you can take a train; or take a bus. In August, plan for daily highs up to 86°F, and evening lows to 64°F. Wrap up your sightseeing by early afternoon on the 21st (Wed) to allow enough time to take a bus to Venice.

Things to do in Verona

Historic Sites Museums Shopping
Find places to stay Aug 19 — 21:
Highlights from your plan
Arena di Verona ©
Arena di Verona
Basilica di San Zeno Maggiore ©
Basilica di San Zeno Maggiore
Museo di Castelvecchio ©
Museo di Castelvecchio

3
nights
Venice

Venice ©
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.
Your cultural itinerary includes sights like Dorsoduro and Basilica di Santa Maria Gloriosa dei Frari. Scuola Grande di San Rocco and San Giorgio Maggiore will appeal to history buffs. Next up on the itinerary: browse the exhibits of Doge's Palace, get to know the fascinating history of Piazza San Marco, take in the spiritual surroundings of Santa Maria dei Miracoli, and take a stroll through Cannaregio.

To see where to stay, reviews, other places to visit, and tourist information, you can read our Venice online attractions planner .

Take a bus from Verona to Venice in 1.5 hours. Alternatively, you can drive; or take a shuttle. In August, daytime highs in Venice are 85°F, while nighttime lows are 66°F. Wrap up your sightseeing on the 24th (Sat) to allow time to travel back home.

Things to do in Venice

Historic Sites Neighborhoods Parks
Find places to stay Aug 21 — 24:
Highlights from your plan
San Giorgio Maggiore ©
San Giorgio Maggiore
Piazza San Marco ©
Piazza San Marco

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