18 days in Italy & Greece Itinerary

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Fly
1
Rome, Italy
— 2 nights
Drive
2
Positano, Italy
— 2 nights
Fly
3
Corfu Town, Greece
— 1 night
Fly
4
Athens, Greece
— 3 nights
Fly
5
Fira, Greece
— 1 night
Ferry
6
Mykonos Town, Greece
— 1 night
Fly
7
Florence, Italy
— 3 nights
Drive
8
Venice, Italy
— 3 nights
Fly

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Rome, Italy — 2 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Rome is known for historic sites, sightseeing, and nightlife. Your trip includes some of its best attractions: steep yourself in history at St. Peter's Basilica, get to know the fascinating history of Piazza Navona, admire the masterpieces at Vatican Museums, and don't miss a visit to Roman Forum.

To find where to stay, maps, more things to do, and more tourist information, go to the Rome trip planner.

Charleston, USA to Rome is an approximately 19-hour flight. You'll lose 6 hours traveling from Charleston to Rome due to the time zone difference. In May, daytime highs in Rome are 75°F, while nighttime lows are 58°F. Finish up your sightseeing early on the 15th (Mon) so you can go by car to Positano.
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Side Trip
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Positano, Italy — 2 nights

Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
On the 16th (Tue), take in the spiritual surroundings of Duomo di Ravello, admire the striking features of Villa Rufolo, admire the natural beauty at Villa Cimbrone Gardens, then examine the collection at Museo della Carta, then contemplate in the serene atmosphere at Duomo di Sant'Andrea, and finally contemplate in the serene atmosphere at Cloister del Paradiso. Keep things going the next day: head outdoors with Outdoor Activities and then get great views at Il Sentiero Degli Dei.

To see photos, where to stay, other places to visit, and other tourist information, read our Positano online trip maker.

You can drive from Rome to Positano in 3.5 hours. Other options are to do a combination of train and bus; or take a bus. Expect a daytime high around 74°F in May, and nighttime lows around 60°F. Cap off your sightseeing on the 17th (Wed) early enough to catch the flight to Corfu Town.
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Historic Sites · Tours · Outdoors · Parks
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Corfu Town, Greece — 1 night

Often called "Kastropolis" because of its majestic Venetian castle, Corfu Town once featured such extensive fortifications that a force of over 20,000 soldiers defended them.
Kick off your visit on the 18th (Thu): admire the striking features of Corfu Museum of Asian Art, delve into the distant past at Old Fortress Corfu, then appreciate the history behind Schulenburg Statue, and finally take a tour by water with Madalena Boat Trips.

To see ratings, maps, other places to visit, and more tourist information, read Corfu Town day trip planner.

Getting from Positano to Corfu Town by flight takes about 5 hours. Other options: do a combination of bus, train, and ferry; or do a combination of car and ferry. The time zone changes from Central European Standard Time (CET) to Eastern European Standard Time (EET), which is usually a 1 hour difference. In May, plan for daily highs up to 76°F, and evening lows to 58°F. Wrap up your sightseeing on the 18th (Thu) to allow time to fly to Athens.
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Historic Sites · Wildlife · Tours · Outdoors
Side Trip
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Athens, Greece — 3 nights

The Birthplace of Democracy

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 sightseeing. Your trip includes some of its best attractions: contemplate the long history of Acropolis of Athens, get engrossed in the history at Acropolis Museum, delve into the distant past at Ancient Agora of Athens, and tour the pleasant surroundings at Mount Lycabettus.

To find other places to visit, more things to do, reviews, and more tourist information, refer to the Athens trip app.

Traveling by flight from Corfu Town to Athens takes 2.5 hours. Alternatively, you can take a bus; or do a combination of ferry and car. Traveling from Corfu Town in May, you can expect nighttime temperatures to be a bit warmer in Athens, with lows of 64°F. Wrap up your sightseeing on the 21st (Sun) early enough to fly to Fira.
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Museums · Historic Sites · Neighborhoods · Parks
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Fira, Greece — 1 night

Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
Start off your visit on the 22nd (Mon): explore the ancient world of Akrotiri and then awaken your taste buds at some of the top wineries in the area.

To see ratings, maps, and more tourist information, use the Fira online trip itinerary maker.

Traveling by flight from Athens to Fira takes 2.5 hours. Alternatively, you can do a combination of taxi and ferry; or ride a ferry. In May, daily temperatures in Fira can reach 75°F, while at night they dip to 63°F. Finish your sightseeing early on the 22nd (Mon) so you can ride a ferry to Mykonos Town.
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Tours · Wineries · Historic Sites
Side Trip
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Mykonos Town, Greece — 1 night

Chora Mykonos

A holiday in Mykonos Town offers a chance to relax on picturesque beaches and explore a labyrinth of charming streets lined with traditional white houses.
Kick off your visit on the 23rd (Tue): don't miss a visit to Rarity Gallery, take a stroll through Little Venice, then don't miss a visit to The Windmills (Kato Milli), and finally relax and rejuvenate at Beautyworld Spa.

For ratings, more things to do, other places to visit, and other tourist information, read our Mykonos Town road trip planning tool.

You can ride a ferry from Fira to Mykonos Town in 2.5 hours. Another option is to fly. In May, daytime highs in Mykonos Town are 73°F, while nighttime lows are 63°F. Finish your sightseeing early on the 23rd (Tue) to allow enough time to fly to Florence.
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Neighborhoods · Spas
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Florence, Italy — 3 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Florence is known for sightseeing, museums, and historic sites. Your trip includes some of its best attractions: admire the masterpieces at Florence Academy of Fine Arts, get to know the fascinating history of Piazza del Duomo, take in the architecture and atmosphere at Basilica of Santa Croce, and examine the collection at Pitti Palace.

To see other places to visit, photos, where to stay, and tourist information, you can read our Florence trip itinerary website.

Getting from Mykonos Town to Florence by flight takes about 5.5 hours. Other options: do a combination of ferry and car; or do a combination of ferry, bus, and train. Due to the time zone difference, you'll gain 1 hour traveling from Mykonos Town to Florence. Traveling from Mykonos Town in May, expect a bit cooler with lows of 52°F in Florence. Finish your sightseeing early on the 26th (Fri) so you can drive to Venice.
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Venice, Italy — 3 nights

City of Romance

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.
Start off your visit on the 27th (Sat): steep yourself in history at Doge's Palace, appreciate the extensive heritage of Piazza San Marco, then make a trip to Basilica di San Marco, and finally pause for some serene contemplation at San Giorgio Maggiore. Get ready for a full day of sightseeing on the next day: contemplate the waterfront views at Canal Grande, snap pictures at Ponte di Rialto, then explore the world behind art at Peggy Guggenheim Collection, then steep yourself in history at Ponte dei Sospiri, and finally enjoy breathtaking views from St Mark's Campanile.

To see ratings and more tourist information, go to the Venice online trip itinerary builder.

Getting from Florence to Venice by car takes about 3 hours. Other options: take a train; or take a bus. In May, daytime highs in Venice are 72°F, while nighttime lows are 55°F. Finish your sightseeing early on the 29th (Mon) so you can travel back home.
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Historic Sites · Museums · Nature · Parks
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Italy travel guide

4.6
Landmarks · Ruins · Beaches
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.
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Greece travel guide

4.3
Few places manage to capture the world's imagination quite like Greece, a land of sun-kissed coastlines, tranquil whitewashed villages, lively seaside towns, and well-preserved ancient sites. One of the world's top tourist destinations since ancient times, the country draws nearly 20 million visitors each year. Athens, the birthplace of Western civilization, continues to attract the biggest crowds and serves as a base for exploring the country and its 227 inhabited islands. Away from its cities, Greece features a picturesque countryside of olive groves, vineyards, and tiny settlements nestled against rolling hills and rugged mountain ranges. Explore the old mainland on foot and discover the islands on a guided boat or ferry tour.
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