60 days in Italy & Greece Itinerary

60 days in Italy & Greece Itinerary

Created using Inspirock Europe tour builder

Make it your trip
Fly
1
Milan, Italy
— 4 nights
Train
2
Florence, Italy
— 5 nights
Drive
3
Siena, Italy
— 4 nights
Drive
4
Assisi, Italy
— 4 nights
Drive
5
Rome, Italy
— 6 nights
Drive
6
Positano, Italy
— 5 nights
Drive
7
Naples, Italy
— 5 nights
Fly
8
Corfu Town, Greece
— 6 nights
Fly
9
Athens, Greece
— 5 nights
Fly
10
Fira, Greece
— 5 nights
Ferry
11
Mykonos Town, Greece
— 4 nights
Fly
12
Venice, Italy
— 6 nights
Fly

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Milan, Italy

— 4 nights

Fashion Capital of World

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.
Venture out of the city with trips to Tremezzina (Villa del Balbianello & Villa Carlotta) and Como (Cathedral of Como (Duomo), Villa Olmo, &more). The adventure continues: contemplate in the serene atmosphere at Duomo di Milano, explore the world behind art at Pinacoteca di Brera, get engrossed in the history at Basilica di Sant'Ambrogio, and get the lay of the land with Walking tours.

To see photos, other places to visit, where to stay, and more tourist information, read Milan road trip planner.

Detroit, USA to Milan is an approximately 14-hour flight. The time zone difference moving from Eastern Standard Time (EST) to Central European Standard Time (CET) is 6 hours. Expect a daytime high around 73°F in May, and nighttime lows around 55°F. Finish your sightseeing early on the 6th (Thu) to allow enough time to take a train to Florence.

Things to do in Milan

Historic Sites · Museums · Tours · Parks

Side Trips

Find places to stay May 2 — 6:

Florence, Italy

— 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You'll find plenty of places to visit near Florence: Lucca (Le mura di Lucca, San Michele in Foro, &more) and Leaning Tower of Pisa (in Pisa). Next up on the itinerary: admire the masterpieces at Florence Academy of Fine Arts, get a sense of history and politics at Palazzo Vecchio, take in the spiritual surroundings of The Baptistery of St. John, and snap pictures at Ponte Vecchio.

To see where to stay, other places to visit, more things to do, and more tourist information, go to the Florence trip planner.

You can take a train from Milan to Florence in 2.5 hours. Other options are to drive; or fly. May in Florence sees daily highs of 71°F and lows of 52°F at night. Finish your sightseeing early on the 11th (Tue) to allow enough time to drive to Siena.

Things to do in Florence

Historic Sites · Museums · Wineries · Tours

Side Trips

Find places to stay May 6 — 11:

Siena, Italy

— 4 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
You'll find plenty of places to visit near Siena: Castello di Monterinaldi (in Radda in Chianti), Montalcino (Mate Winery & Castiglion del Bosco Winery) and Buccelletti - Cantina (in Castiglion Fiorentino). There's still lots to do: awaken your taste buds at some of the top wineries in the area, pause for some serene contemplation at Duomo di Siena, contemplate in the serene atmosphere at Battistero di San Giovanni, and make a trip to Complesso Museale Santa Maria della Scala.

For reviews, ratings, other places to visit, and other tourist information, read our Siena holiday builder app.

Drive from Florence to Siena in 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 74°F in May, and nighttime lows around 53°F. Wrap up your sightseeing on the 15th (Sat) to allow time to drive to Assisi.

Things to do in Siena

Wineries · Historic Sites · Tours · Museums

Side Trips

Find places to stay May 11 — 15:

Assisi, Italy

— 4 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Change things up with these side-trips from Assisi: Montioni Frantoio e Cantina (in Montefalco), Perugia (Museo-Laboratorio di Tessitura a Mano Giuditta Brozzetti & Studio Moretti Caselli) and Vineria del Carmine (in La Bruna). Next up on the itinerary: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, do a tasting at Azienda Agraria Saio, step into the grandiose world of Rocca Maggiore, and take in the spiritual surroundings of Eremo delle Carceri.

Use Inspirock's suggestions to plan your Assisi trip and find the best activities and attractions for your vacation.

You can drive from Siena to Assisi in 2 hours. Other options are to take a bus; or take a train. Expect a daytime high around 72°F in May, and nighttime lows around 52°F. Wrap up your sightseeing on the 19th (Wed) early enough to drive to Rome.

Things to do in Assisi

Historic Sites · Wineries · Museums · Shopping

Side Trips

Find places to stay May 15 — 19:

Rome, Italy

— 6 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
When in Rome, make a side trip to see Villa Adriana in Tivoli, approximately Tivoli away. There's much more to do: delve into the distant past at Colosseum, ponder the design of Trevi Fountain, get to know the fascinating history of Piazza Navona, and contemplate the long history of Palatine Hill.

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

Drive from Assisi to Rome in 2.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Assisi in May, Rome is a bit warmer at night with lows of 58°F. Finish your sightseeing early on the 25th (Tue) so you can drive to Positano.

Things to do in Rome

Historic Sites · Museums · Tours · Neighborhoods

Side Trips

Find places to stay May 19 — 25:

Positano, Italy

— 5 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.
You'll find plenty of places to visit near Positano: Ravello (Duomo di Ravello, Villa Rufolo, &more), Amalfi (Duomo di Sant'Andrea, Cloister del Paradiso, &more) and Chiesa e Convento di S. Francesco (in Cetara). Next up on the itinerary: get great views at Il Sentiero Degli Dei, do a tasting at Limonoro, get outside with Amalfi Coast, and admire the natural beauty at Villa Comunale.

To find other places to visit, where to stay, ratings, and other tourist information, read our Positano holiday planning app.

You can drive from Rome to Positano in 3.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. In May, plan for daily highs up to 74°F, and evening lows to 60°F. Cap off your sightseeing on the 30th (Sun) early enough to go by car to Naples.

Things to do in Positano

Parks · Historic Sites · Outdoors · Tours

Side Trips

Find places to stay May 25 — 30:

Naples, Italy

— 5 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Get out of town with these interesting Naples side-trips: Pompeii (Odeon - Teatro Piccolo, Temple of Apollo, &more) and Bossa (in Salerno). The adventure continues: explore the ancient world of Pompeii Archaeological Park, admire the masterpieces at Museo Cappella Sansevero, explore the different monuments and memorials at Catacombe di San Gennaro, and take an in-depth tour of Museo e Real Bosco di Capodimonte.

To see other places to visit, traveler tips, and other tourist information, read Naples trip planner.

Traveling by car from Positano to Naples takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 74°F in May, and nighttime lows around 58°F. Wrap up your sightseeing on the 4th (Fri) early enough to travel to Corfu Town.

Things to do in Naples

Historic Sites · Museums · Tours · Childrens Museums

Side Trips

Find places to stay May 30 — Jun 4:

Corfu Town, Greece

— 6 nights
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.
You'll find plenty of places to visit near Corfu Town: Almyros Beach Resort & SPA (in Acharavi), St. Spyridon First Beach (in Agios Spyridonas) and Kassiopi (Church of the Panayia Kassopitra & Kassiopi Castle). There's lots more to do: explore the ancient world of Old Fortress Corfu, experience rural life at MKB Corfu Beekeeping Vasilakis, explore the historical opulence of New Fortress, and explore the striking landscape at Kaiser's Throne.

For more things to do, other places to visit, ratings, and tourist information, read Corfu Town trip itinerary app.

Traveling by flight from Naples to Corfu Town takes 4.5 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of train and ferry. The time zone difference moving from Central European Standard Time (CET) to Eastern European Standard Time (EET) is 1 hour. In June, plan for daily highs up to 85°F, and evening lows to 66°F. Finish up your sightseeing early on the 10th (Thu) so you can travel to Athens.

Things to do in Corfu Town

Historic Sites · Parks · Outdoors · Museums

Side Trips

Find places to stay Jun 4 — 10:

Athens, Greece

— 5 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 nightlife. Your plan includes some of its best attractions: explore the ancient world of Acropolis of Athens, get engrossed in the history at Acropolis Museum, explore the world behind art at Benaki Museum, and pause for some photo ops at Temple of Olympian Zeus.

To see maps, ratings, photos, and tourist information, refer to the Athens day trip planner.

You can fly from Corfu Town to Athens in 3 hours. Alternatively, you can do a combination of ferry and car; or take a bus. Expect a daytime high around 86°F in June, and nighttime lows around 70°F. Wrap up your sightseeing on the 15th (Tue) early enough to travel to Fira.

Things to do in Athens

Historic Sites · Museums · Tours · Neighborhoods
Find places to stay Jun 10 — 15:

Fira, Greece

— 5 nights
Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
Fira is known for wineries, nightlife, and museums. Your plan includes some of its best attractions: delve into the distant past at Akrotiri, awaken your taste buds at some of the top wineries in the area, explore the striking landscape at Skaros Rock, and contemplate the waterfront views at Amoudi Bay.

Inspirock's itinerary builder makes planning a Fira trip simple and quick.

Traveling by flight from Athens to Fira takes 3.5 hours. Alternatively, you can do a combination of taxi and ferry; or ride a ferry. In June, daytime highs in Fira are 82°F, while nighttime lows are 70°F. Cap off your sightseeing on the 20th (Sun) early enough to catch the ferry to Mykonos Town.

Things to do in Fira

Outdoors · Parks · Tours · Beaches

Side Trips

Find places to stay Jun 15 — 20:

Mykonos Town, Greece

— 4 nights

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.
You'll find plenty of places to visit near Mykonos Town: Delos (Mount Kynthos, Archaeological Site of Delos, &more). And it doesn't end there: stop by Little Venice, kick back and relax at Ornos Beach, experience rural life at Mykonos Vioma Organic Farm, and tour the pleasant surroundings at Panormos Beach.

To see ratings, other places to visit, more things to do, and tourist information, refer to the Mykonos Town sightseeing planner.

You can ride a ferry from Fira to Mykonos Town in 2.5 hours. Another option is to fly. In June, plan for daily highs up to 80°F, and evening lows to 69°F. Finish your sightseeing early on the 24th (Thu) so you can travel to Venice.

Things to do in Mykonos Town

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Find places to stay Jun 20 — 24:

Venice, Italy

— 6 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.
You'll find plenty of places to visit near Venice: Fondazione Bisazza (in Montecchio Maggiore), Verona (Museo di Castelvecchio & Arena di Verona) and Padua (Prato della Valle, Scrovegni Chapel, &more). There's still lots to do: contemplate the waterfront views at Canal Grande, examine the collection at Doge's Palace, admire the masterpieces at Gallerie dell'Accademia, and snap pictures at Ponte di Rialto.

To see where to stay, more things to do, other places to visit, and tourist information, refer to the Venice trip itinerary planner.

You can fly from Mykonos Town to Venice in 5 hours. Other options are to do a combination of ferry and car; or do a combination of ferry and bus. The time zone difference when traveling from Mykonos Town to Venice is minus 1 hour. Traveling from Mykonos Town in June, Venice is slightly colder at night with lows of 63°F. Wrap up your sightseeing by early afternoon on the 30th (Wed) to allow time for travel back home.

Things to do in Venice

Historic Sites · Museums · Tours · Nature

Side Trips

Find places to stay Jun 24 — 30:

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.

Greece travel guide

4.2
Beaches · Ruins · History Museums
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.