14 days in Greece & Italy Itinerary

14 days in Greece & Italy Itinerary

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Route & dates

14 days in Greece & Italy Itinerary

Start: Chicago, United States
Fly:  14​h 15​min
1
Athens, Greece
— 2 nights
Fly:  3​h 30​min
2
Fira, Greece
— 2 nights
Fly:  6​h
3
Rome, Italy
— 2 nights
train:  1​h 45​min
4
Florence, Italy
— 3 nights
train:  1​h 45​min
5
Milan, Italy
— 1 night
train:  2​h 30​min
6
Venice, Italy
— 2 nights
Fly:  12​h 30​min
End: Chicago, United States

2
nights
Athens, Greece

Athens ©
One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
Athens is known for historic sites, museums, nightlife, shopping, and fun & games. Your plan includes some of its best attractions: explore the ancient world of Acropolis of Athens, explore the world behind art at Benaki Museum, contemplate the long history of Ancient Agora of Athens, and take a stroll through Plaka.

For where to stay, more things to do, photos, and other tourist information, refer to the Athens route planner.

Chicago, USA to Athens is an approximately 14.5-hour flight. The time zone difference when traveling from Chicago to Athens is 8 hours. In December, Athens is much warmer than Chicago - with highs of 59°F and lows of 47°F. Cap off your sightseeing on the 21st (Sat) early enough to travel to Fira.

Things to do in Athens

Museums Historic Sites Neighborhoods
Find places to stay Dec 19 — 21:
Highlights from your plan
Acropolis Museum ©
Acropolis Museum
Acropolis of Athens ©
Acropolis of Athens
Plaka ©
Plaka

2
nights
Fira, Greece

Fira ©
Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
Kick off your visit on the 22nd (Sun): kick back and relax at Red Beach, then delve into the distant past at Akrotiri, then take in the architecture and atmosphere at Panagia Theoskepasti Chapel, and finally contemplate the waterfront views at Amoudi Bay. On the 23rd (Mon), you'll have a packed day of sightseeing: stroll through Kamari Beach, then take in the dramatic natural features at Skaros Rock, and then take some stellar pictures from Sunset in Oia.

To find photos, more things to do, other places to visit, and other tourist information, use the Fira trip planner .

You can fly from Athens to Fira in 3.5 hours. Alternatively, you can ride a ferry; or do a combination of flight, taxi, and ferry. In December, plan for daily highs up to 60°F, and evening lows to 52°F. Finish your sightseeing early on the 23rd (Mon) to allow enough time to travel to Rome.

Things to do in Fira

Parks Beaches Outdoors

Side Trips

Imerovigli, Akrotiri, Oia, Kamari Beach
Find places to stay Dec 21 — 23:
Highlights from your plan
Red Beach ©
Red Beach
Akrotiri ©
Akrotiri
Amoudi Bay ©
Amoudi Bay

2
nights
Rome, Italy

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 24th (Tue): steep yourself in history at St. Peter's Basilica, admire the striking features of Pantheon, then admire the local landmark of Trevi Fountain, then take in the architecture and atmosphere at Chiesa di Sant'Ignazio di Loyola, and finally explore the ancient world of Colosseum. Get ready for a full day of sightseeing on the 25th (Wed): make a trip to Vatican Museums, appreciate the extensive heritage of Piazza Navona, and then explore the ancient world of Palatine Hill.

For more things to do, reviews, photos, and other tourist information, refer to the Rome trip itinerary planning site .

Getting from Fira to Rome by flight takes about 6 hours. Other options: do a combination of ferry, bus, and flight; or do a combination of ferry and car. You'll gain 1 hour traveling from Fira to Rome due to the time zone difference. Expect a bit cooler evenings in Rome when traveling from Fira in December, with lows around 39°F. Finish your sightseeing early on the 25th (Wed) so you can take a train to Florence.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
Find places to stay Dec 23 — 25:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

3
nights
Florence, Italy

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 26th (Thu): take in the views from Ponte Vecchio, take some stellar pictures from Piazzale Michelangelo, explore the world behind art at Gallerie Degli Uffizi, then pause for some serene contemplation at Cathedral of Santa Maria del Fiore, then appreciate the extensive heritage of Piazza del Duomo, and finally admire the striking features of Loggia dei Lanzi. Keep things going the next day: see the interesting displays at Academy Of Florence Art Gallery, get engrossed in the history at Basilica di Santa Croce, examine the collection at Pitti Palace, then appreciate the extensive heritage of Piazza della Signoria, and finally enjoy breathtaking views from Campanile di Giotto.

To see where to stay, ratings, photos, and tourist information, read Florence vacation maker site .

You can take a train from Rome to Florence in 2 hours. Alternatively, you can drive; or fly. In December, daily temperatures in Florence can reach 55°F, while at night they dip to 39°F. Wrap up your sightseeing on the 28th (Sat) early enough to take a train to Milan.

Things to do in Florence

Museums Historic Sites
Find places to stay Dec 25 — 28:
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Cathedral of Santa Maria del Fiore ©

1
night
Milan, Italy

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.
On the 28th (Sat), admire the striking features of Galleria Vittorio Emanuele II, then pause for some serene contemplation at Duomo di Milano, then appreciate the extensive heritage of Piazza del Duomo, and finally step into the grandiose world of Castello Sforzesco.

Find out how to plan Milan trip without stress by asking Inspirock to help create an itinerary.

Take a train from Florence to Milan in 2 hours. Alternatively, you can drive; or fly. Plan for slightly colder temperatures traveling from Florence in December, with highs in Milan at 46°F and lows at 34°F. Wrap up your sightseeing on the 29th (Sun) early enough to take a train to Venice.

Things to do in Milan

Historic Sites Shopping
Find places to stay Dec 28 — 29:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Castello Sforzesco ©
Castello Sforzesco

2
nights
Venice, Italy

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.
Venice is known for historic sites, nature, museums, nightlife, and shopping. Your plan includes some of its best attractions: explore the activities along Canal Grande, explore the world behind art at Gallerie dell'Accademia, contemplate the long history of Peggy Guggenheim Collection, and get to know the fascinating history of Piazza San Marco.

For ratings, reviews, photos, and tourist information, read our Venice online holiday planner .

Take a train from Milan to Venice in 2.5 hours. Alternatively, you can drive; or do a combination of flight and train. In December, daily temperatures in Venice can reach 49°F, while at night they dip to 34°F. Wrap up your sightseeing on the 31st (Tue) to allow time to travel back home.

Things to do in Venice

Historic Sites Museums Parks
Find places to stay Dec 29 — 31:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace

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