16 days in Italy & Fira Itinerary

16 days in Italy & Fira Itinerary

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Route & dates

16 days in Italy & Fira Itinerary

Start: Pittsburgh, United States
Fly:  12​h 30​min
1
Rome, Italy
— 3 nights
train + bus:  2​h
2
Montepulciano, Italy
— Few hours
bus + train:  2​h
3
Florence, Italy
— 3 nights
train:  2​h 30​min
4
Venice, Italy
— 3 nights
Drive:  30​min
5
Tessera, Italy
— 1 night
+2
Drive + Fly + Drive:  2​h 30​min
6
Fira, Greece
— 4 nights
Fly:  3​h
7
Rome, Italy
— Few hours
Fly:  14​h 15​min
End: Pittsburgh, United States


Learn more about your trip

3
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.
You've added Trevi Fountain, Roman Forum, Rooftop American Bar by OTIVM Hotel, and other attractions to your itinerary. Popular historic sites such as Pantheon and Palatine Hill are in your itinerary. There's more to do: appreciate the extensive heritage of Piazza del Campidoglio and explore the ancient world of Foro di Cesare.

For other places to visit, more things to do, reviews, and tourist information, use the Rome tour itinerary planning site .

Pittsburgh, USA to Rome is an approximately 14.5-hour flight. You can also do a combination of flight and train. The time zone changes from Eastern Standard Time (EST) to Central European Time (CET), which is usually a 6 hour difference. In September, daytime highs in Rome are 81°F, while nighttime lows are 60°F. On the 16th (Mon), you'll have the morning to explore before heading off to Montepulciano.

Things to do in Rome

Historic Sites Nightlife
Highlights from your plan
Pantheon ©
Pantheon
Palatine Hill ©
Palatine Hill
Piazza Navona ©
Piazza Navona

few
hours
Montepulciano, Italy

Montepulciano ©
Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Your day-by-day itinerary now includes Cantina Fattoria della Talosa, Bottega del Rame and Piazza Grande a Montepulciano. Start off your visit on the 16th (Mon): do a tasting at Cantina Fattoria della Talosa, then stop by Bottega del Rame, then don't miss a visit to Piazza Grande a Montepulciano, and finally make a trip to Terrazza Del Palazzo Comunale.

To see reviews, where to stay, ratings, and tourist information, read our Montepulciano day trip website .

Getting from Rome to Montepulciano by car takes about 2 hours. Other options: do a combination of train and bus; or take a bus. September in Montepulciano sees daily highs of 81°F and lows of 61°F at night. Wrap up your sightseeing on the 16th (Mon) early enough to drive to Florence.

Things to do in Montepulciano

Shopping Wineries
Highlights from your plan
Bottega del Rame ©
Bottega del Rame
Cantina Fattoria della Talosa ©
Cantina Fattoria della Talosa

3
nights
Florence, Italy

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your list of things to see and do now includes Loggia dei Lanzi, Tuscany Vespa Tours, Titty Twister Club, and other attractions. Start off your visit on the 16th (Mon): admire the striking features of Loggia dei Lanzi. On your second day here, get interesting insight from Tuscany Vespa Tours, snap pictures at Ponte Vecchio, and then pause for some photo ops at Perseus Statue.

For ratings, maps, photos, and tourist information, refer to the Florence road trip planning app .

Drive from Montepulciano to Florence in 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. In September, daily temperatures in Florence can reach 78°F, while at night they dip to 59°F. On the 19th (Thu), you'll have the morning to explore before heading off to Venice.

Things to do in Florence

Outdoors Tours Nightlife
Highlights from your plan
Tuscany Vespa Tours ©
Tuscany Vespa Tours
Ponte Vecchio ©
Ponte Vecchio
Loggia dei Lanzi ©
Loggia dei Lanzi

3
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.
Your list of things to see and do now includes Doge's Palace, Canal Grande, Venice Art Mask, and other attractions. Visit Centro Storico Sirmione and Arena di Verona for their historical value. You'll explore the less-touristy side of things at Verona's Cathedral (Duomo) and Chiesa di San Pietro in Mavino. The adventure continues: admire the landmark architecture of Venetian Arsenal, take in the waterfront activity at Riva degli Schiavoni, take in the architecture and atmosphere at Basilica di Santa Maria della Salute, and steep yourself in history at Squero di San Trovaso.

For photos, maps, reviews, and other tourist information, refer to the Venice online trip planner .

Getting from Florence to Venice by train takes about 2.5 hours. Other options: drive; or take a bus. In September, daytime highs in Venice are 77°F, while nighttime lows are 59°F. Finish your sightseeing early on the 22nd (Sun) to allow enough time to drive to Tessera.

Things to do in Venice

Historic Sites Museums Parks

Side Trips

Verona, Sirmione
Highlights from your plan
Doge's Palace ©
Doge's Palace
Canal Grande ©
Canal Grande
Verona's Cathedral (Duomo) ©
Verona's Cathedral (Duomo)

1
night
Tessera, Italy

Tessera
For more things to do, ratings, traveler tips, and more tourist information, use the Tessera trip itinerary site .

Tessera is just a short distance from Venice. In September in Tessera, expect temperatures between 77°F during the day and 59°F at night. On the 23rd (Mon), you'll have the morning to explore before heading off to Fira.

Things to do in Tessera

Shopping Outdoors Tours

4
nights
Fira, Greece

Fira ©
Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
Kamari Beach Watersports has been added to your itinerary. Give yourself a bit of retail therapy at MATI Art Gallery and Asimis Kolaitou Art Gallery Santorini. You'll discover tucked-away gems like Ancient Thera and Red Beach. Step out of Fira to go to Perivolos and see Waterskiing & Jetskiing, which is approximately 32 minutes away. Next up on the itinerary: examine the collection at Museum of Prehistoric Thira, learn about winemaking at Artemis Karamolegos Winery, take a tour by water with Boat Tours & Water Sports, and make a trip to Megalochori - Traditional Village.

For more things to do, ratings, photos, and other tourist information, read our Fira trip planning app .

Use the Route module to find suitable travel options from Tessera to Fira. The time zone difference when traveling from Tessera to Fira is 1 hour. Traveling from Tessera in September, Fira is a bit warmer at night with lows of 70°F. On the 27th (Fri), you'll have the morning to explore before heading off to Rome.

Things to do in Fira

Outdoors Museums Tours

Side Trips

Oia, Kamari, Tomato Industrial Museum, Red Beach, Megalochori - Traditional Village
Highlights from your plan
Ancient Thera ©
Ancient Thera
Museum of Prehistoric Thira ©
Museum of Prehistoric Thira
Red Beach ©
Red Beach

few
hours
Rome, Italy

Rome
For maps, traveler tips, more things to do, and other tourist information, refer to the Rome attractions planner.

You can fly from Fira to Rome in 6 hours. Other options are to do a combination of ferry, bus, and flight; or do a combination of ferry and car. The time zone difference moving from Eastern European Time to Central European Time is minus 1 hour. Traveling from Fira in September, plan for a bit cooler nights in Rome, with lows around 60°F. You'll set off for home on the 27th (Fri).

Things to do in Rome

Tours Nightlife Historic Sites

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