14 days in Greece & Italy Itinerary

14 days in Greece & Italy Itinerary

Created using Inspirock Europe journey planner

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Route & dates

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, and nightlife. Your plan includes some of its best attractions: get engrossed in the history at Acropolis Museum, don't miss a visit to Ancient Agora of Athens, explore the world behind art at National Archaeological Museum, and take your sightseeing to a higher altitude at Mount Lycabettus.

To find traveler tips, where to stay, more things to do, and tourist information, refer to the Athens trip planner.

Chicago, USA to Athens is an approximately 14.5- hour flight. You can also do a combination of train and flight; or do a combination of train, bus, and flight. Traveling from Chicago to Athens, you'll lose 8 hours due to the time zone difference. Traveling from Chicago in December, things will get much hotter in Athens: highs are around 59°F and lows about 47°F. Finish your sightseeing early on the 21st (Sat) to allow enough time 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
National Archaeological Museum ©
National Archaeological Museum

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): enjoy the sand and surf at Red Beach, then explore the ancient world of Akrotiri, then take in the architecture and atmosphere at Panagia Theoskepasti Chapel, and finally explore the activities along Amoudi Bay. Get ready for a full day of sightseeing on the 23rd (Mon): enjoy the sand and surf at Kamari Beach, then explore the striking landscape at Skaros Rock, and then don't miss a visit to Sunset in Oia.

To find photos, more things to do, maps, and tourist information, read Fira road trip planner.

Traveling by flight from Athens to Fira takes 3.5 hours. Alternatively, you can ride a ferry; or do a combination of flight, taxi, and ferry. December in Fira sees daily highs of 60°F and lows of 52°F at night. Wrap up your sightseeing on the 23rd (Mon) early enough to travel to Rome.

Things to do in Fira

Parks Outdoors Beaches

Side Trips

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

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.
On the 24th (Tue), steep yourself in history at St. Peter's Basilica, delve into the distant past at Pantheon, make a trip to Trevi Fountain, then take in the architecture and atmosphere at Chiesa di Sant'Ignazio di Loyola, and finally delve into the distant past at Colosseum. On your second day here, admire the masterpieces at Vatican Museums, appreciate the extensive heritage of Piazza Navona, and then delve into the distant past at Palatine Hill.

Plan trip to Rome with our itinerary maker to find out where to go and what to do.

Traveling by flight from Fira to Rome takes 6 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. Traveling from Fira to Rome, you'll gain 1 hour due to the time zone difference. Traveling from Fira in December, you can expect nighttime temperatures to be slightly colder in Rome, with lows of 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
St. Peter's Basilica ©
St. Peter's Basilica

3
nights
Florence, Italy

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Kick off your visit on the 26th (Thu): take in the views from Ponte Vecchio, don't miss a visit to Piazzale Michelangelo, explore the world behind art at Gallerie Degli Uffizi, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, then appreciate the extensive heritage of Piazza del Duomo, and finally appreciate the history behind Loggia dei Lanzi. Get ready for a full day of sightseeing on the 27th (Fri): explore the world behind art at Florence Academy of Fine Arts, steep yourself in history at Basilica of Santa Croce, examine the collection at Pitti Palace, then appreciate the extensive heritage of Piazza della Signoria, and finally admire the landmark architecture of Campanile di Giotto.

To find reviews, more things to do, other places to visit, and tourist information, read Florence tour itinerary builder tool.

Take a train from Rome to Florence in 2 hours. Alternatively, you can drive; or fly. In December, plan for daily highs up to 55°F, and evening lows to 39°F. Cap off your sightseeing on the 28th (Sat) early enough to catch the 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
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts

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 take in the spiritual surroundings of Duomo di Milano, then make a trip to Piazza del Duomo, and finally contemplate the long history of Castello Sforzesco.

To see more things to do, traveler tips, other places to visit, and more tourist information, you can read our Milan trip itinerary builder tool.

Getting from Florence to Milan by train takes about 2 hours. Other options: drive; or fly. Prepare for little chillier weather when traveling from Florence in December: high temperatures in Milan hover around 46°F and lows are around 34°F. Finish your sightseeing early on the 29th (Sun) so you can 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, museums, and nature. Your plan includes some of its best attractions: explore the activities along Canal Grande, explore the world behind art at Peggy Guggenheim Collection, get to know the fascinating history of Piazza San Marco, and enjoy breathtaking views from St Mark's Campanile.

For reviews, where to stay, photos, and tourist information, read our Venice online holiday planner.

Traveling by train from Milan to Venice takes 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 Nature
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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