20 days in Italy Itinerary

20 days in Italy Itinerary

Created using Inspirock Italy Trip Planner

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Route & dates

20 days in Italy Itinerary

Start: Punta Cana, Dominican Republic
Fly:  9​h 30​min
1
Venice
— 1 day
Drive:  1​h 45​min
2
Bologna
— 3 nights
3
Florence
— 4 nights
Drive:  2​h 30​min
4
Cinque Terre
— 4 nights
train:  4​h
5
Rome
— 4 nights
train + subway:  2​h 45​min
6
Sorrento
— 2 nights
Fly:  17​h 15​min
End: Punta Cana, Dominican Republic

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.
Kick off your visit on the 20th (Fri): don't miss a visit to Dorsoduro, then snap pictures at Ponte dei Sospiri, then admire the landmark architecture of Doge's Palace, and finally get to know the fascinating history of St. Mark's Square.

For other places to visit, ratings, photos, and tourist information, use the Venice journey planner.

Punta Cana, Dominican Republic to Venice is an approximately 14.5-hour flight. You can also do a combination of flight and train; or do a combination of shuttle, flight, and train. The time zone changes from Atlantic Standard Time to Central European Time, which is usually a 5 hour difference. When traveling from Punta Cana in May, plan for slightly colder days in Venice, with highs around 26°C, while nights are colder with lows around 15°C. Finish your sightseeing early on the 20th (Fri) so you can drive to Bologna.

Things to do in Venice

Historic Sites Museums Neighborhoods
Find places to stay May 20 — 21:
Highlights from your plan
Doge's Palace ©
Doge's Palace
St. Mark's Square ©
St. Mark's Square
Ponte dei Sospiri ©
Ponte dei Sospiri

3
nights
Bologna

Bologna ©
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Satisfy your inner culture vulture at Acetaia Villa San Donnino and Basilica di San Petronio. Get some historical perspective at Basilica - Santuario di Santo Stefano and Basilica di San Domenico. Venture out of the city with trips to Vignola (Rocca di Vignola & Massaggio Californiano), Maranello (Museo Ferrari & I Love Maranello) and Modena (Piazza Grande & Acetaia di Giorgio). The adventure continues: contemplate the long history of Piazza Maggiore, don't miss a visit to Libreria Ulisse, contemplate in the serene atmosphere at Chiesa di Santa Maria della Vita, and enjoy breathtaking views from Torri degli Asinelli e Garisenda.

To find reviews, maps, and tourist information, read Bologna day trip planning site .

You can drive from Venice to Bologna in 2 hours. Other options are to take a train; or take a bus. Expect a daytime high around 27°C in May, and nighttime lows around 14°C. Finish up your sightseeing early on the 23rd (Mon) so you can catch the train to Florence.

Things to do in Bologna

Historic Sites Spas Museums

Side Trips

Modena, Vignola, Maranello
Find places to stay May 20 — 23:
Highlights from your plan
Acetaia Villa San Donnino ©
Acetaia Villa San Donnino
Basilica - Santuario di Santo Stefano ©
Basilica di San Petronio ©
Basilica di San Petronio

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Visit Cathedral of Santa Maria del Fiore and Piazza del Duomo for their historical value. Satisfy your inner culture vulture at Academy Of Florence Art Gallery and Piazzale Michelangelo. Venture out of the city with trips to Greve in Chianti (Castello di Verrazzano & Enoteca Falorni) and Castello del Trebbio (in Santa Brigida). And it doesn't end there: admire the masterpieces at Uffizi Galleries, steep yourself in history at Loggia dei Lanzi, get a sense of history and politics at Museo Nazionale del Bargello, and take in the spiritual surroundings of Santa Maria Maddalena dei Pazzi.

To see reviews, maps, more things to do, and tourist information, refer to the Florence road trip planning site .

Getting from Bologna to Florence by train takes about an hour. Other options: drive; or take a bus. In May, daily temperatures in Florence can reach 25°C, while at night they dip to 13°C. Wrap up your sightseeing on the 27th (Fri) to allow time to drive to Cinque Terre.

Things to do in Florence

Historic Sites Wineries Museums

Side Trips

Greve in Chianti, Castello del Trebbio
Find places to stay May 23 — 27:
Highlights from your plan
Uffizi Galleries ©
Uffizi Galleries
Cathedral of Santa Maria del Fiore ©
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

4
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.
Satisfy your inner culture vulture at Terra di Bargon and Passeggiata Anita Garibaldi a Nervi. Get some historical perspective at Cinque Terre Trails and Chiesa del Gesu e dei Santi Ambrogio e Andrea. Get out of town with these interesting Cinque Terre side-trips: Baia del Silenzio (in Sestri Levante) and Genoa (Piazza Raffaele De Ferrari & Via Garibaldi). Spend the 30th (Mon) exploring nature at Parco Nazionale Cinque Terre. There's still lots to do: trek along Footpath Monterosso - Vernazza.

To find ratings, traveler tips, where to stay, and other tourist information, read our Cinque Terre road trip planner .

Drive from Florence to Cinque Terre in 2.5 hours. Alternatively, you can take a train. In May, plan for daily highs up to 25°C, and evening lows to 13°C. Finish your sightseeing early on the 31st (Tue) to allow enough time to take a train to Rome.

Things to do in Cinque Terre

Parks Outdoors Nature

Side Trips

Genoa, Baia del Silenzio
Find places to stay May 27 — 31:
Highlights from your plan
Baia del Silenzio ©
Baia del Silenzio
Terra di Bargon ©
Terra di Bargon
Cinque Terre Trails ©
Cinque Terre Trails

4
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Do some cultural sightseeing at Palatine Hill and Piazza Navona. Get some historical perspective at Colosseum and Santa Maria della Vittoria. There's lots more to do: make a trip to Pantheon, kick back and relax at V Lounge Beach Club, appreciate the extensive heritage of Rione Ponte, and admire the local landmark of Trevi Fountain.

For photos, more things to do, reviews, and more tourist information, read Rome trip itinerary planner .

You can take a train from Cinque Terre to Rome in 4 hours. Other options are to do a combination of train and flight; or drive. Traveling from Cinque Terre in May, you can expect nighttime temperatures to be a bit warmer in Rome, with lows of 17°C. Finish your sightseeing early on the 4th (Sat) to allow enough time to travel to Sorrento.

Things to do in Rome

Historic Sites Neighborhoods Outdoors
Find places to stay May 31 — Jun 4:
Highlights from your plan
Palatine Hill ©
Palatine Hill
Colosseum ©
Colosseum
Piazza Navona ©
Piazza Navona

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 5th (Sun): kick back and relax at Fornillo, explore the ancient world of Gli Scavi Archeologici di Pompei, and then don't miss a visit to Piazza Tasso. Get ready for a full day of sightseeing on the 6th (Mon): enjoy the sand and surf at Villa di Pollio Felice - Bagni della Regina Giovanna and then delve into the distant past at Ruins of Herculaneum.

To find maps, reviews, more things to do, and tourist information, use the Sorrento vacation planner.

You can do a combination of train and subway from Rome to Sorrento in 3 hours. Other options are to drive; or take a bus. In June, daytime highs in Sorrento are 32°C, while nighttime lows are 23°C. Finish your sightseeing early on the 6th (Mon) to allow enough time to travel back home.

Things to do in Sorrento

Historic Sites Outdoors Beaches

Side Trips

Gli Scavi Archeologici di Pompei, Ruins of Herculaneum, Fornillo
Find places to stay Jun 4 — 6:
Highlights from your plan
Fornillo ©
Fornillo
Gli Scavi Archeologici di Pompei ©
Ruins of Herculaneum ©
Ruins of Herculaneum

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