53 days in Italy, Greece & Jordan Itinerary

53 days in Italy, Greece & Jordan Itinerary

Created using Inspirock route planner
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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

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Venice, Italy — 7 nights

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.
Get some cultural insight at Piazza San Marco and Centro Storico di Venezia. Get some historical perspective at Doge's Palace and Scrovegni Chapel. Explore the numerous day-trip ideas around Venice: Padua (Padua Botanical Garden - World Heritage Site & Basilica of St. Anthony), Castello Estense (in Ferrara) and Verona (Piazza Bra, Basilica di San Zeno Maggiore, &more). Next up on the itinerary: take in the spiritual surroundings of Basilica di Santa Maria Gloriosa dei Frari, explore the activities along Canal Grande, take in panoramic vistas at St Mark's Campanile, and pause for some serene contemplation at San Giorgio Maggiore.

To see other places to visit, where to stay, maps, and other tourist information, refer to the Venice trip builder site.

Chicago, USA to Venice is an approximately 12-hour flight. The time zone difference moving from Central Standard Time (CST) to Central European Standard Time (CET) is 7 hours. In August, daily temperatures in Venice can reach 85°F, while at night they dip to 66°F. Finish your sightseeing early on the 2nd (Fri) so you can drive to Florence.
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Historic Sites · Museums · Parks · Nature
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Find places to stay Aug 26 — Sep 2:

Florence, Italy — 7 nights

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get some historical perspective at Cathedral of Santa Maria del Fiore and Basilica San Miniato al Monte. 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), Siena (Centro Storico di Siena & Torre del Mangia) and Historic Centre of San Gimignano (in San Gimignano). There's much more to do: appreciate the extensive heritage of Centro Storico, steep yourself in history at Palazzo Vecchio, don't miss a visit to Piazzale Michelangelo, and snap pictures at Ponte Vecchio.

To see maps, other places to visit, traveler tips, and other tourist information, read our Florence planning app.

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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Find places to stay Sep 2 — 9:

Rome, Italy — 8 nights

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Get some cultural insight at Colosseum and St. Peter's Basilica. Discover out-of-the-way places like Villa d'Este and Villa Borghese. Go for a jaunt from Rome to Tivoli to see Villa Adriana about 36 minutes away. There's still lots to do: pause for some serene contemplation at Arcibasilica di San Giovanni in Laterano, explore the world behind art at Vatican Museums, take an in-depth tour of Museum and Crypt of Capuchins, and appreciate the extensive heritage of Piazza Navona.

To find ratings, traveler tips, other places to visit, and other tourist information, read our Rome day trip planner.

You can take a train from Florence to Rome in 2.5 hours. Other options are to 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) early enough to take a train to Naples.
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Find places to stay Sep 9 — 17:

Naples, Italy — 7 nights

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Relax by the water at Fornillo and Spiaggia di castiglione. Deepen your sense of the past at sights like Pompeii Archaeological Park and Villa Cimbrone Gardens. Get out of town with these interesting Naples side-trips: Pompeii (Forum, Lupanar, &more), Vesuvio National Park (in Ottaviano) and Duomo di Ravello (in Ravello). The adventure continues: don't miss a visit to I Faraglioni, take an in-depth tour of Villa San Michele, delve into the distant past at Teatro Grande, and steep yourself in history at Parco Acheologico di Ercolano.

For reviews, other places to visit, more things to do, and tourist information, you can read our Naples route maker tool.

You can take a train from Rome to Naples in 2 hours. Other options are to drive; or fly. In September, daytime highs in Naples are 80°F, while nighttime lows are 64°F. Wrap up your sightseeing on the 24th (Sat) early enough to fly to Athens.
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Find places to stay Sep 17 — 24:

Athens, Greece — 7 nights

One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
Acropolis of Athens and Archea Korinthos will appeal to history buffs. Bring the kids along to Acropolis Museum and Fortress Palamidi. You'll find plenty of places to visit near Athens: Bourtzi (in Nafplio), Akrokorinthos (in Corinth) and Archaeological Site Mycenae (in Mycenae). There's lots more to do: explore the world behind art at National Archaeological Museum, stop by Plaka, take in nature's colorful creations at National Garden, and contemplate the long history of Ancient Agora of Athens.

To see reviews, photos, and more tourist information, you can read our Athens tour itinerary builder site.

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. Traveling from Naples to Athens, you'll lose 1 hour due to the time zone difference. In September in Athens, expect temperatures between 84°F during the day and 69°F at night. Finish your sightseeing early on the 1st (Sat) to allow enough time to fly to Chania Town.
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Find places to stay Sep 24 — Oct 1:

Chania Town, Greece — 7 nights

The place where Cretan and Venetian cultures merged in the 13th century, Chania Town attracts throngs of tourists with its well-preserved medieval harbor.
Explore hidden gems such as Samaria Gorge National Park and Seitan Limania Beach. You'll explore and learn at Greek National Football Museum and Archaeological Museum of Chania. Explore Chania Town's surroundings by going to Falassarna Beach (in Falassarna), St. Nicholas Church (in Georgioupolis) and Lake Kournas (in Kournas). And it doesn't end there: explore the ancient world of Archaeological Site of Ancient Aptera, kick back and relax at Agia Marina Beach, stroll through Old Venetian Harbor, and explore the different monuments and memorials at Souda Bay War Cemetery.

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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Parks · Outdoors · Historic Sites · Beaches
Side Trips
Find places to stay Oct 1 — 8:

Rhodes Town, Greece — 8 nights

A conglomeration of many distinct architectural styles, Rhodes Town is the biggest urban center of the eponymous Greek island known for its golden beaches and relaxed way of life.
You'll get in some beach time at Anthony Quinn Bay and Faliraki Beach. Get outdoors at Agios Pavlos Beach and Pefkos Beach. Venture out of the city with trips to Lindos Beach (in Lindos), Monastery Tsambika (in Kolimbia) and Agathi Beach (in Haraki). There's lots more to do: stroll through Tsambika Beach, kick back and relax at Stegna Beach, appreciate the extensive heritage of Medieval City, and make a trip to Palace of the Grand Master of the Knights of Rhodes.

To find reviews, more things to do, and tourist information, use the Rhodes Town online trip maker.

Getting from Chania Town to Rhodes Town by flight takes about 2.5 hours. Other options: do a combination of car and ferry; or do a combination of bus and ferry. October in Rhodes Town sees daily highs of 76°F and lows of 66°F at night. Finish up your sightseeing early on the 16th (Sun) so you can catch the flight to Amman.
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Outdoors · Beaches · Parks · Historic Sites
Side Trips
Find places to stay Oct 8 — 16:

Amman, Jordan — 1 night

Jordan's capital city, Amman spreads across 19 hills and includes many distinct districts, each with their own historical and cultural marvels.
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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Historic Sites
Find places to stay Oct 16 — 17:
Highlights from your trip

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
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

4.2
Beaches · Ruins · Nightlife
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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Jordan travel guide

4.3
Historic Sites · Ruins · Deserts
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.
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