15 days in Italy Itinerary

15 days in Italy Itinerary

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Route & dates

15 days in Italy Itinerary

Start: Chicago
Fly:  13​h
1
Rome
— Few hours
Train:  2​h
2
Florence
— 1 night
Train:  30​min
3
Bologna
— 1 day
Train:  30​min
4
Florence
— 1 night
Drive:  3​h
5
Cinque Terre
— 1 day
Drive:  2​h 30​min
6
Florence
— 1 night
Train:  2​h 15​min
7
Venice
— 1 day
Train:  2​h
8
Florence
— 1 night
Drive:  4​h 30​min
9
Positano
— 2 nights
Drive:  1​h 30​min
10
Capri, Island of Capri
— 3 nights
Drive:  30​min
11
Sorrento
— 2 nights
Subway + Train:  3​h
12
Rome
— 2 nights
Fly:  11​h 30​min
End: Chicago

few
hours
Rome

Rome
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
To see ratings, more things to do, other places to visit, and tourist information, go to the Rome itinerary maker tool .

Chicago, USA to Rome is an approximately 13-hour flight. You can also do a combination of flight and train. You'll lose 7 hours traveling from Chicago to Rome due to the time zone difference. Plan for a bit warmer nights when traveling from Chicago in May since evenings lows in Rome dip to 58°F. On the 3rd (Fri), you'll travel to Florence.

Things to do in Rome

Tours Historic Sites Nightlife
Find places to stay May 3 — 4:

1
night
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your day-by-day itinerary now includes Basilica di San Lorenzo, Uffizi Galleries, Cathedral of Santa Maria del Fiore, and other attractions you added. On the 3rd (Fri), explore the world behind art at Uffizi Galleries, admire the masterpieces at Basilica di San Lorenzo, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, get to know the fascinating history of Piazza del Duomo, then take in the views from Ponte Vecchio, and finally join in the after-dark buzz at Rasputin.

To find maps, ratings, reviews, and other tourist information, go to the Florence tour itinerary planner.

You can take a train from Rome to Florence in 2 hours. Alternatively, you can drive; or fly. Traveling from Rome in May, plan for little chillier nights in Florence, with lows around 52°F. You'll have a few hours on the 4th (Sat) to wrap things up before traveling to Bologna.

Things to do in Florence

Museums Historic Sites Nightlife
Find places to stay May 3 — 4:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Ponte Vecchio ©
Ponte Vecchio

1
day
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 Piazza Maggiore as well as CIBO Culinary Institute of Bologna. Kick off your visit on the 4th (Sat): expand your horizons at CIBO Culinary Institute of Bologna and then don't miss a visit to Piazza Maggiore.

To see reviews, maps, where to stay, and more tourist information, read our Bologna travel website .

Take a train from Florence to Bologna in an hour. Alternatively, you can drive; or take a bus. Expect a daytime high around 74°F in May, and nighttime lows around 54°F. Finish your sightseeing early on the 4th (Sat) so you can take a train to Florence.

Things to do in Bologna

Tours Classes Historic Sites
Find places to stay May 4 — 5:
Highlights from your plan
CIBO Culinary Institute of Bologna ©
Piazza Maggiore ©
Piazza Maggiore

1
night
Florence

Florence
To find where to stay, other places to visit, more things to do, and other tourist information, you can read our Florence itinerary builder .

Traveling by train from Bologna to Florence takes an hour. Alternatively, you can drive; or take a bus. On the 5th (Sun), you're off toCinque Terre.

Things to do in Florence

Tours Historic Sites Outdoors
Find places to stay May 4 — 5:

1
day
Cinque Terre

Cinque Terre ©
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 5th (Sun): hike along Footpath Monterosso - Vernazza, pause for some serene contemplation at Santa Margherita di Antiochia Church, then explore the historical opulence of Castello Doria, and finally appreciate the extensive heritage of Borgo Storico di Corniglia.

To find more things to do, photos, maps, and tourist information, read our Cinque Terre trip itinerary maker site .

You can drive from Florence to Cinque Terre in 2.5 hours. Another option is to take a train. In May, daily temperatures in Cinque Terre can reach 71°F, while at night they dip to 52°F. Cap off your sightseeing on the 5th (Sun) early enough to go by car to Florence.

Things to do in Cinque Terre

Outdoors Parks Trails
Find places to stay May 5 — 6:
Highlights from your plan
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Borgo Storico di Corniglia ©
Borgo Storico di Corniglia
Santa Margherita di Antiochia Church ©

1
night
Florence

Florence
To find other places to visit, traveler tips, more things to do, and other tourist information, read Florence trip itinerary planner.

Drive from Cinque Terre to Florence in 2.5 hours. Alternatively, you can take a train. On the 6th (Mon), you're off toVenice.

Things to do in Florence

Tours Historic Sites Outdoors
Find places to stay May 5 — 6:

1
day
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 day-by-day itinerary now includes Canal Grande. Kick off your visit on the 6th (Mon): don't miss a visit to St. Mark's Square, admire the striking features of Basilica di San Marco, then wander the streets of Campo del Ghetto, and finally explore the activities along Canal Grande.

To see photos, traveler tips, ratings, and other tourist information, you can read our Venice road trip site .

Traveling by train from Florence to Venice takes 2.5 hours. Alternatively, you can drive; or take a bus. In May, plan for daily highs up to 72°F, and evening lows to 55°F. Wrap up your sightseeing on the 6th (Mon) to allow time to take a train to Florence.

Things to do in Venice

Historic Sites Parks Nature
Find places to stay May 6 — 7:
Highlights from your plan
Piazza San Marco ©
Piazza San Marco
Basilica di San Marco
Basilica di San Marco
Canal Grande ©
Canal Grande

1
night
Florence

Florence
To find where to stay, other places to visit, more things to do, and more tourist information, use the Florence road trip site .

Getting from Venice to Florence by train takes about 2.5 hours. Other options: drive; or take a bus. You'll set off for Positano on the 7th (Tue).

Things to do in Florence

Tours Historic Sites Outdoors
Find places to stay May 6 — 7:

2
nights
Positano

Positano ©
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.
Kick off your visit on the 7th (Tue): take in the spiritual surroundings of Duomo di Ravello, then take in the exciting artwork at Ceramiche d'Arte Carmela, then see the interesting displays at Museo della Carta, and finally contemplate in the serene atmosphere at Duomo di Sant'Andrea. Get ready for a full day of sightseeing on the 8th (Wed): contemplate the long history of Villa Rufolo, then pause for some serene contemplation at Cappella Sant'Angelo all'Ospedale, and then go for a walk through Sentiero degli dei (Path of the Gods).

To see more things to do, reviews, where to stay, and other tourist information, read our Positano online trip planner .

Traveling by car from Florence to Positano takes 5.5 hours. Alternatively, you can do a combination of train and subway; or do a combination of flight, train, and subway. Traveling from Florence in May, you can expect nighttime temperatures to be a bit warmer in Positano, with lows of 60°F. You will have some time to spend on the 9th (Thu) before leaving for Capri.

Things to do in Positano

Historic Sites Museums Shopping

Side Trips

Ravello, Amalfi
Find places to stay May 7 — 9:
Highlights from your plan
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Duomo di Ravello ©
Duomo di Ravello
Duomo di Sant'Andrea ©
Duomo di Sant'Andrea

3
nights
Capri, Island of Capri

Capri ©
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Eschew the tourist crowds and head to Villa San Michele and Santa Maria a Cetrella. Step out of the city life by going to Fortini Coastal Walk and Capri Rent Boats. There's still lots to do: get interesting insight from Capri Blue Boats, tour the pleasant surroundings at Marina Grande Public Beach, enjoy the sand and surf at Marina Piccola, and enjoy the sea views from Punta Carena Lighthouse.

To see traveler tips, photos, other places to visit, and tourist information, read our Capri tour itinerary planning app .

Capri is just a stone's throw from Positano. In May, daytime highs in Capri are 74°F, while nighttime lows are 60°F. You'll have a few hours on the 12th (Sun) to wrap things up before traveling to Sorrento.

Things to do in Capri

Outdoors Tours Transportation

Side Trips

Anacapri, Capri Blue Boats
Find places to stay May 9 — 12:
Highlights from your plan
Villa San Michele ©
Villa San Michele
Fortini Coastal Walk ©
Fortini Coastal Walk
Marina Grande Public Beach ©
Marina Grande Public Beach

2
nights
Sorrento

Sorrento ©
A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
Start off your visit on the 12th (Sun): contemplate in the serene atmosphere at St Francis Church and Convent, explore the world behind art at Correale di Terranova Museum, then pause for some serene contemplation at Cattedrale di Sorrento, then admire the natural beauty at I Giardini di Cataldo, and finally don't miss a visit to Piazza Tasso. On the 13th (Mon), you'll have a packed day of sightseeing: take in the spiritual surroundings of Basilica di Sant'Antonino, then admire all the interesting features of La Masseria Farm, then take in the waterfront at Marina Grande - Antico Borgo Marinaro, and finally admire the masterpieces at Museobottega della Tarsialignea.

For traveler tips, reviews, maps, and more tourist information, read our Sorrento trip planner .

Sorrento is just a stone's throw from Capri. In May, daytime highs in Sorrento are 74°F, while nighttime lows are 60°F. You will have some time to spend on the 14th (Tue) before leaving for Rome.

Things to do in Sorrento

Museums Historic Sites Parks

Side Trip

La Masseria Farm Experience
Find places to stay May 12 — 14:
Highlights from your plan
Correale di Terranova Museum ©
Correale di Terranova Museum
St Francis Church and Convent ©
St Francis Church and Convent
Marina Grande - Antico Borgo Marinaro ©

2
nights
Rome

Rome ©
Your day-by-day itinerary now includes Museo Nazionale di Castel Sant'Angelo as well as Trevi Fountain. On the 14th (Tue), admire the masterpieces at Sistine Chapel, take in the architecture and atmosphere at St. Peter's Basilica, then admire the masterpieces at Vatican Museums, then admire the striking features of Pantheon, and finally get to know the fascinating history of Piazza Navona. Here are some ideas for day two: enjoy breathtaking views from Museo Nazionale di Castel Sant'Angelo, don't miss a visit to Trevi Fountain, pause for some serene contemplation at St. Clement Basilica, then steep yourself in history at Palatine Hill, then delve into the distant past at Colosseum, and finally steep yourself in history at Roman Forum.

To see more things to do, other places to visit, traveler tips, and tourist information, read Rome tour itinerary maker .

Do a combination of subway and train from Sorrento to Rome in 3 hours. Alternatively, you can drive; or take a bus. You will have some time to spend on the 16th (Thu) before leaving for home.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
Find places to stay May 14 — 16:
Highlights from your plan
St. Peter's Basilica ©
St. Peter's Basilica
Vatican Museums
Vatican Museums
Pantheon ©
Pantheon

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