19 days in Italy Itinerary

19 days in Italy Itinerary

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Route & dates

19 days in Italy Itinerary

Start: Boston
Fly:  11​h 45​min
1
Rome
— 2 nights
Train + Subway:  2​h 45​min
2
Sorrento
— 1 night
Drive:  4​h 45​min
3
Siena
— 3 nights
Bus:  1​h 15​min
4
Florence
— 2 nights
Train:  2​h 15​min
5
Venice
— 3 nights
Drive:  4​h 15​min
6
Cinque Terre
— 2 nights
Train:  3​h
7
Milan
— 4 nights
Fly:  13​h 45​min
End: Boston

2
nights
Rome

Rome ©
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 12th (Fri): contemplate the long history of Colosseum, steep yourself in history at Palatine Hill, get to know the fascinating history of Piazza Navona, then contemplate the long history of St. Peter's Basilica, and finally take in the architecture and atmosphere at Santa Maria in Trastevere. On the 13th (Sat), you'll have a packed day of sightseeing: explore the world behind art at Galleria Borghese, make a trip to Trevi Fountain, then explore the ancient world of Pantheon, and finally take a stroll through Trastevere.

For where to stay, other places to visit, maps, and tourist information, refer to the Rome travel itinerary planner.

Boston, USA to Rome is an approximately 12-hour flight. The time zone difference when traveling from Boston to Rome is 6 hours. Expect a bit warmer weather when traveling from Boston in June: highs in Rome hover around 84°F, while lows dip to 65°F. Wrap up your sightseeing on the 14th (Sun) early enough to travel to Sorrento.

Things to do in Rome

Historic Sites Neighborhoods Museums

Side Trip

St. Peter's Basilica
Find places to stay Jun 11 — 14:
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Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

1
night
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.
On the 14th (Sun), tour the pleasant surroundings at Villa di Pollio Felice - Bagni della Regina Giovanna and then don't miss a visit to Piazza Tasso.

To see topicsMoreInfo.option.ratings, other places to visit, where to stay, and tourist information, you can read our Sorrento vacation tool .

You can do a combination of train and subway from Rome to Sorrento in 3 hours. Alternatively, you can drive; or take a bus. In June, daily temperatures in Sorrento can reach 82°F, while at night they dip to 68°F. Finish your sightseeing early on the 15th (Mon) to allow enough time to drive to Siena.

Things to do in Sorrento

Beaches Parks Outdoors
Find places to stay Jun 14 — 15:
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3
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Piazza del Campo and Centro Storico di Siena are good opportunities to explore the local culture. There's still lots to do: take in the architecture and atmosphere at Duomo di Siena, enjoy breathtaking views from Torre del Mangia, admire the masterpieces at Museo dell'Opera Metropolitana, and take in the exciting artwork at Silvia Tanganelli.

To see topicsMoreInfo.option.ratings, photos, traveler tips, and tourist information, you can read our Siena online trip itinerary builder .

Getting from Sorrento to Siena by car takes about 5 hours. Other options: do a combination of subway and train; or do a combination of subway, train, flight, and bus. Expect slightly colder evenings in Siena when traveling from Sorrento in June, with lows around 61°F. Wrap up your sightseeing on the 18th (Thu) to allow time to take a bus to Florence.

Things to do in Siena

Historic Sites Tours Museums
Find places to stay Jun 15 — 18:
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Wine Tours & Tastings
Duomo di Siena ©
Duomo di Siena
Piazza del Campo ©
Piazza del Campo

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 18th (Thu): snap pictures at Ponte Vecchio, take in nature's colorful creations at The Boboli Gardens, make a trip to Piazzale Michelangelo, then see the interesting displays at Pitti Palace, and finally explore the world behind art at Academy Of Florence Art Gallery. Get ready for a full day of sightseeing on the 19th (Fri): ponder the world of politics at Palazzo Vecchio, take in the spiritual surroundings of The Baptistery of St. John, take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, take in panoramic vistas at Campanile di Giotto, then get engrossed in the history at Basilica di Santa Croce, and finally appreciate the history behind Loggia dei Lanzi.

To see topicsMoreInfo.option.ratings, where to stay, photos, and more tourist information, go to the Florence trip planner.

You can take a bus from Siena to Florence in 1.5 hours. Alternatively, you can drive; or take a train. In June, plan for daily highs up to 83°F, and evening lows to 65°F. Wrap up your sightseeing on the 20th (Sat) to allow time to take a train to Venice.

Things to do in Florence

Historic Sites Museums Parks
Find places to stay Jun 18 — 20:
Highlights from your plan
Piazzale Michelangelo ©
Piazzale Michelangelo
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

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.
Get a sense of the local culture at Piazza San Marco and Gallerie dell'Accademia. You'll find plenty of places to visit near Venice: Verona (Arena di Verona & Piazza delle Erbe). There's still lots to do: see the interesting displays at Doge's Palace, take in panoramic vistas at St Mark's Campanile, browse the exhibits of Peggy Guggenheim Collection, and appreciate the extensive heritage of Fondamenta Venier Savorgnan.

To find other places to visit, traveler tips, maps, and tourist information, read Venice trip itinerary maker tool .

You can take a train from Florence to Venice in 2.5 hours. Alternatively, you can drive; or take a bus. June in Venice sees daily highs of 81°F and lows of 63°F at night. Finish up your sightseeing early on the 23rd (Tue) so you can go by car to Cinque Terre.

Things to do in Venice

Historic Sites Museums Parks

Side Trip

Verona
Find places to stay Jun 20 — 23:
Highlights from your plan
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

2
nights
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 23rd (Tue): make a trip to Oratorio della Confraternita dei Neri Mortis et Orationis and then wander the streets of Portovenere. Get ready for a full day of sightseeing on the 24th (Wed): take in the spiritual surroundings of Chiesa Di San Pietro, trek along Cinque Terre Trails, explore the historical opulence of Castello Doria, then stroll through Footpath Monterosso - Vernazza, and finally take a stroll around Vernazza.

To see where to stay, topicsMoreInfo.option.ratings, maps, and other tourist information, read our Cinque Terre trip planning app .

You can drive from Venice to Cinque Terre in 4.5 hours. Other options are to take a train; or take a bus. Expect a daytime high around 81°F in June, and nighttime lows around 60°F. Wrap up your sightseeing by early afternoon on the 25th (Thu) to allow time for the train ride to Milan.

Things to do in Cinque Terre

Historic Sites Neighborhoods Parks

Side Trips

Cattedrale di San Lorenzo - Duomo di Genova, Portovenere
Find places to stay Jun 23 — 25:
Highlights from your plan
Cinque Terre Trails ©
Cinque Terre Trails
Castello Doria ©
Castello Doria
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza

4
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.
Do some cultural sightseeing at Duomo di Milano and Pinacoteca Ambrosiana. Go for a jaunt from Milan to Tremezzina to see Villa Carlotta about 1h 20 min away. There's still lots to do: explore the historical opulence of Castello Sforzesco, take an in-depth tour of Basilica di Sant'Ambrogio, take in the architecture and atmosphere at Chiesa di San Maurizio al Monastero Maggiore, and don't miss a visit to Piazza del Duomo.

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

Take a train from Cinque Terre to Milan in 3 hours. Alternatively, you can drive. Expect a daytime high around 83°F in June, and nighttime lows around 64°F. Wrap up your sightseeing by early afternoon on the 29th (Mon) to allow enough time to travel back home.

Things to do in Milan

Historic Sites Museums Parks

Side Trip

Villa Carlotta
Find places to stay Jun 25 — 29:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Villa Carlotta ©
Villa Carlotta
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

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