53 days in Italy, Greece & Jordan Itinerary
Created using Inspirock route planner
Start: Chicago, United States
Fly
1
Venice, Italy
— 7 nights
Drive
2
Florence, Italy
— 7 nights
Train
3
Rome, Italy
— 8 nights
Train
4
Naples, Italy
— 7 nights
Fly
5
Athens, Greece
— 7 nights
Fly
6
Chania Town, Greece
— 7 nights
Fly
7
Rhodes Town, Greece
— 8 nights
Fly
8
Amman, Jordan
— 1 night
Fly
End: Chicago, United States
Fri, Aug 26 - Mon, Oct 17
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Venice, Italy — 7 nights
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City of Romance
Get some cultural insight at Piazza San Marco and Basilica di San Marco. Get some historical perspective at Doge's Palace and Centro Storico di Venezia. Explore the numerous day-trip ideas around Venice: Padua (Padua Botanical Garden - World Heritage Site, Basilica of St. Anthony, &more), Castello Estense (in Ferrara) and Verona (Piazza Bra, Basilica di San Zeno Maggiore, &more). And it doesn't end there: pause for some serene contemplation at San Giorgio Maggiore, snap pictures at Ponte dei Sospiri, admire the masterpieces at Peggy Guggenheim Collection, and visit Cannaregio.
To find reviews, traveler tips, where to stay, and other tourist information, use the Venice tour itinerary maker website.
Chicago, USA to Venice is an approximately 12-hour flight. Traveling from Chicago to Venice, you'll lose 7 hours due to the time zone difference. In August in Venice, expect temperatures between 85°F during the day and 66°F at night. Finish up your sightseeing early on the 2nd (Fri) so you can go by car to Florence.
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To find reviews, traveler tips, where to stay, and other tourist information, use the Venice tour itinerary maker website.
Chicago, USA to Venice is an approximately 12-hour flight. Traveling from Chicago to Venice, you'll lose 7 hours due to the time zone difference. In August in Venice, expect temperatures between 85°F during the day and 66°F at night. Finish up your sightseeing early on the 2nd (Fri) so you can go by car to Florence.
Side Trips
Find places to stay Aug 26 — Sep 2:
Highlights from your trip
Florence, Italy — 7 nights
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Birthplace of the Italian Renaissance
Get some historical perspective at Cathedral of Santa Maria del Fiore and Historic Centre of San Gimignano. Museum-lovers will get to explore Florence Academy of Fine Arts and Museo dell'Opera Metropolitana. You'll find plenty of places to visit near Florence: Pisa (Leaning Tower of Pisa & Duomo di Pisa) and Siena (Centro Storico di Siena & Torre del Mangia). The adventure continues: admire the masterpieces at Pitti Palace, get to know the fascinating history of Centro Storico, take in the spiritual surroundings of Basilica San Miniato al Monte, and make a trip to Piazzale Michelangelo.
To find other places to visit, traveler tips, more things to do, and tourist information, use the Florence trip planner.
Traveling by car from Venice to Florence takes 3 hours. Alternatively, you can take a train; or take a bus. In September in Florence, expect temperatures between 78°F during the day and 59°F at night. Finish your sightseeing early on the 9th (Fri) so you can take a train to Rome.
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To find other places to visit, traveler tips, more things to do, and tourist information, use the Florence trip planner.
Traveling by car from Venice to Florence takes 3 hours. Alternatively, you can take a train; or take a bus. In September in Florence, expect temperatures between 78°F during the day and 59°F at night. Finish your sightseeing early on the 9th (Fri) so you can take a train to Rome.
Side Trips
Find places to stay Sep 2 — 9:
Highlights from your trip
Rome, Italy — 8 nights
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Eternal City
Get some cultural insight at Colosseum and St. Peter's Basilica. Discover out-of-the-way places like Villa d'Este and Villa Adriana. There's still lots to do: don't miss a visit to Vatican Necropolis, take in the architecture and atmosphere at Pantheon, get engrossed in the history at Museum and Crypt of Capuchins, and delve into the distant past at Terme di Caracalla.
Plan a Rome trip in moments using our itinerary builder.
Take a train from Florence to Rome in 2.5 hours. Alternatively, you can fly; or drive. In September, daytime highs in Rome are 81°F, while nighttime lows are 60°F. Wrap up your sightseeing on the 17th (Sat) to allow time to take a train to Naples.
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Plan a Rome trip in moments using our itinerary builder.
Take a train from Florence to Rome in 2.5 hours. Alternatively, you can fly; or drive. In September, daytime highs in Rome are 81°F, while nighttime lows are 60°F. Wrap up your sightseeing on the 17th (Sat) to allow time to take a train to Naples.
Side Trips
Find places to stay Sep 9 — 17:
Highlights from your trip
Naples, Italy — 7 nights
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Relax by the water at Fornillo and Spiaggia di castiglione. Deepen your sense of the past at sights like Pompeii Archaeological Park and Catacombe di San Gennaro. Get out of town with these interesting Naples side-trips: Ravello (Villa Cimbrone Gardens & Duomo di Ravello), Duomo di Sant'Andrea (in Amalfi) and Vesuvio National Park (in Ottaviano).
To find photos, where to stay, maps, and other tourist information, use the Naples holiday maker app.
You can take a train from Rome to Naples in 2 hours. Alternatively, you can drive; or fly. September in Naples sees daily highs of 80°F and lows of 64°F at night. Finish your sightseeing early on the 24th (Sat) to allow enough time to fly to Athens.
more
To find photos, where to stay, maps, and other tourist information, use the Naples holiday maker app.
You can take a train from Rome to Naples in 2 hours. Alternatively, you can drive; or fly. September in Naples sees daily highs of 80°F and lows of 64°F at night. Finish your sightseeing early on the 24th (Sat) to allow enough time to fly to Athens.
Side Trips
Find places to stay Sep 17 — 24:
Highlights from your trip
Athens, Greece — 7 nights
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The Birthplace of Democracy
Acropolis of Athens and Fortress Palamidi will appeal to history buffs. Bring the kids along to Acropolis Museum and Ancient Agora of Athens. You'll find plenty of places to visit near Athens: Archaeological Site Mycenae (in Mycenae), Bourtzi (in Nafplio) and Corinth (Akrokorinthos & Archea Korinthos). And it doesn't end there: explore the world behind art at National Archaeological Museum, admire the natural beauty at National Garden, wander the streets of Plaka, and pause for some photo ops at Temple of Olympian Zeus.
To see where to stay, traveler tips, more things to do, and other tourist information, go to the Athens holiday planning app.
You can fly from Naples to Athens in 5 hours. Other options are to do a combination of car and ferry; or do a combination of bus 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. Expect a daytime high around 84°F in September, and nighttime lows around 69°F. Finish up your sightseeing early on the 1st (Sat) so you can catch the flight to Chania Town.
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To see where to stay, traveler tips, more things to do, and other tourist information, go to the Athens holiday planning app.
You can fly from Naples to Athens in 5 hours. Other options are to do a combination of car and ferry; or do a combination of bus 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. Expect a daytime high around 84°F in September, and nighttime lows around 69°F. Finish up your sightseeing early on the 1st (Sat) so you can catch the flight to Chania Town.
Side Trips
Find places to stay Sep 24 — Oct 1:
Chania Town, Greece — 7 nights
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Explore hidden gems such as Samaria Gorge National Park and Lake Kournas. You'll explore and learn at Greek National Football Museum and Maritime Museum of Crete. Explore Chania Town's surroundings by going to Falassarna Beach (in Falassarna), Seitan Limania Beach (in Akrotiri) and St. Nicholas Church (in Georgioupolis). And it doesn't end there: don't miss a visit to Monastery of Arkadi, explore the different monuments and memorials at German Military Cemetery, see some colorful creatures with a scuba or snorkeling tour, and take an in-depth tour of Archaeological Museum of Chania.
To find where to stay, other places to visit, photos, and tourist information, you can read our Chania Town day trip planning app.
Fly from Athens to Chania Town in 2.5 hours. Alternatively, you can do a combination of ferry and bus; or do a combination of ferry and bus. October in Chania Town sees daily highs of 75°F and lows of 61°F at night. Finish up your sightseeing early on the 8th (Sat) so you can catch the flight to Rhodes Town.
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To find where to stay, other places to visit, photos, and tourist information, you can read our Chania Town day trip planning app.
Fly from Athens to Chania Town in 2.5 hours. Alternatively, you can do a combination of ferry and bus; or do a combination of ferry and bus. October in Chania Town sees daily highs of 75°F and lows of 61°F at night. Finish up your sightseeing early on the 8th (Sat) so you can catch the flight to Rhodes Town.
Side Trips
Find places to stay Oct 1 — 8:
Highlights from your trip
Rhodes Town, Greece — 8 nights
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You'll get in some beach time at Anthony Quinn Bay and Tsambika Beach. Get outdoors at Agios Pavlos Beach and Agathi Beach. Venture out of the city with trips to Lindos Beach (in Lindos), Stegna Beach (in Archangelos) and Monastery Tsambika (in Kolimbia). On the 16th (Sun), enjoy a perfect day by the water at Faliraki Beach. The adventure continues: contemplate the long history of Street of the Knights, delve into the distant past at Ancient Kamiros, explore the historical opulence of Palace of the Grand Master of the Knights of Rhodes, and appreciate the extensive heritage of Medieval City.
To find ratings, more things to do, other places to visit, and tourist information, refer to the Rhodes Town travel route planning app.
Traveling by flight from Chania Town to Rhodes Town takes 2.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. In October, plan for daily highs up to 76°F, and evening lows to 66°F. Finish up your sightseeing early on the 16th (Sun) so you can catch the flight to Amman.
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To find ratings, more things to do, other places to visit, and tourist information, refer to the Rhodes Town travel route planning app.
Traveling by flight from Chania Town to Rhodes Town takes 2.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. In October, plan for daily highs up to 76°F, and evening lows to 66°F. Finish up your sightseeing early on the 16th (Sun) so you can catch the flight to Amman.
Side Trips
Find places to stay Oct 8 — 16:
Highlights from your trip
Amman, Jordan — 1 night
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White City
Start off your visit on the 17th (Mon): steep yourself in history at The Citadel.
To find reviews, ratings, maps, and other tourist information, read our Amman tour planning website.
You can fly from Rhodes Town to Amman in 8 hours. Alternatively, you can do a combination of ferry and car. Traveling from Rhodes Town in October, Amman is little chillier at night with lows of 60°F. Wrap up your sightseeing by early afternoon on the 17th (Mon) to allow time for the flight back home.
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To find reviews, ratings, maps, and other tourist information, read our Amman tour planning website.
You can fly from Rhodes Town to Amman in 8 hours. Alternatively, you can do a combination of ferry and car. Traveling from Rhodes Town in October, Amman is little chillier at night with lows of 60°F. Wrap up your sightseeing by early afternoon on the 17th (Mon) to allow time for the flight back home.
Find places to stay Oct 16 — 17:
Highlights from your trip
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Italy travel guide
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.
Greece travel guide
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.
Jordan travel guide
For such a small country, Jordan boasts a surprising variety of natural landscapes and urban attractions. A trip to Jordan takes visitors on a journey back to biblical times, when sites like the Dead Sea and the ancient yet astonishingly well-preserved city of Petra seemed to be at the heart of world events. Although covered in rocky deserts, Jordan boasts a good network of roads, which makes sightseeing by car an easy way to discover many of the country's top highlights. Begin your tour of Jordan in Amman, the largest urban center and a major political, cultural, and economic hub of this Middle Eastern kingdom.
