39 days in Italy & Greece Itinerary

39 days in Italy & Greece Itinerary

Created using Inspirock Europe trip planner
Make it your trip
Fly
1
Venice, Italy
— 3 nights
Train
2
Bellagio, Italy
— 3 nights
Train
3
Cinque Terre, Italy
— 2 nights
Train
4
Florence, Italy
— 3 nights
Drive
5
Siena, Italy
— 2 nights
Drive
6
Cortona, Italy
— 2 nights
Drive
7
Rome, Italy
— 1 day
Fly
8
Athens, Greece
— 3 nights
Fly
9
Rhodes Town, Greece
— 3 nights
+3
Fly to Heraklion, Bus to Néa Alikarnassós, Foot to Heraklion, Ferry to Fira
10
Fira, Greece
— 2 nights
Ferry
11
Milos, Greece
— 3 nights
Drive
12
Brindisi, Italy
— 7 nights
Fly
13
Rome, Italy
— 3 nights
Fly

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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.
Explore the numerous day-trip ideas around Venice: Padua (Scrovegni Chapel, Basilica of St. Anthony, &more). And it doesn't end there: explore the activities along Canal Grande, take a stroll through Cannaregio, admire the landmark architecture of Basilica di San Marco, and don't miss a visit to St Mark's Campanile.

To find traveler tips, photos, maps, and other tourist information, refer to the Venice day trip app.

Sydney, Australia to Venice is an approximately 24.5-hour flight. The time zone difference when traveling from Sydney to Venice is minus 9 hours. Traveling from Sydney in August, expect Venice to be somewhat warmer, temps between 34°C and 22°C. Cap off your sightseeing on the 24th (Thu) early enough to go by car to Bellagio.
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Historic Sites · Museums · Nature · Parks
Side Trip
Find places to stay Aug 21 — 24:

Bellagio, Italy — 3 nights

Pearl of Lake Como

Known as the pearl of Lake Como for its luxury accommodations, high-end shops, and fine dining options, Bellagio serves as the lake's premiere resort town.
Get out of town with these interesting Bellagio side-trips: Tremezzina (Villa del Balbianello & Villa Carlotta), Varenna (S. Giovanni Battista & Villa Monastero) and Cathedral of Como (Duomo) (in Como). The adventure continues: explore the historical opulence of Castello di Vezio, add some adventure to your tour with a kayaking and canoeing tour, do a tasting at Enoteca Principessa, and walk around La Punta Spartivento.

To find traveler tips, ratings, other places to visit, and tourist information, you can read our Bellagio trip itinerary builder tool.

Getting from Venice to Bellagio by car takes about 3.5 hours. Other options: take a train; or do a combination of train and bus. In August, daytime highs in Bellagio are 33°C, while nighttime lows are 20°C. Finish your sightseeing early on the 27th (Sun) so you can drive to Cinque Terre.
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Parks · Museums · Historic Sites · Shopping
Side Trips
Find places to stay Aug 24 — 27:

Cinque Terre, Italy — 2 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Kick off your visit on the 28th (Mon): explore the wealth of natural beauty at Parco Nazionale Cinque Terre, then get great views at View Point Corniglia, and then hike along Footpath Monterosso - Vernazza. On the 29th (Tue), you'll have a packed day of sightseeing: see some colorful creatures with Enjoy Cinqueterre Boat Tours, hike along Cinque Terre Trails, and then get into the urban bustle at Vernazza.

To see traveler tips, maps, and other tourist information, read Cinque Terre day trip website.

Traveling by car from Bellagio to Cinque Terre takes 4 hours. Alternatively, you can take a train; or do a combination of bus and train. In August, daytime highs in Cinque Terre are 35°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 29th (Tue) early enough to drive to Florence.
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Parks · Nature · Outdoors · Trails
Find places to stay Aug 27 — 29:

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.
Venture out of the city with trips to Pisa (Piazza dei Miracoli, Leaning Tower of Pisa, &more). Next up on the itinerary: steep yourself in history at Cathedral of Santa Maria del Fiore, explore the world behind art at Pitti Palace, appreciate the extensive heritage of Piazza del Duomo, and contemplate in the serene atmosphere at The Baptistery of St. John.

To see photos, maps, where to stay, and more tourist information, go to the Florence road trip website.

Drive from Cinque Terre to Florence in 2.5 hours. Alternatively, you can take a train. Expect a daytime high around 35°C in August, and nighttime lows around 20°C. Wrap up your sightseeing on the 1st (Fri) to allow time to drive to Siena.
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Historic Sites · Museums · Parks
Side Trip
Find places to stay Aug 29 — Sep 1:

Siena, Italy — 2 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 2nd (Sat), explore the historical opulence of Castello di Monteriggioni, then learn about winemaking at Guardastelle Vineyard, then pause for some serene contemplation at Duomo di Siena, and finally steep yourself in history at Centro Storico di Siena. On the 3rd (Sun), you'll have a packed day of sightseeing: enjoy breathtaking views from Torre del Mangia, indulge your taste buds at Food & Drink, and then make a trip to Piazza del Campo.

To see photos, ratings, reviews, and other tourist information, you can read our Siena trip itinerary maker website.

You can drive from Florence to Siena in 1.5 hours. Alternatively, you can take a bus; or take a train. In September in Siena, expect temperatures between 32°C during the day and 19°C at night. Cap off your sightseeing on the 3rd (Sun) early enough to go by car to Cortona.
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Wineries · Tours · Historic Sites
Side Trips
Find places to stay Sep 1 — 3:

Cortona, Italy — 2 nights

City of Art

The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
Start off your visit on the 4th (Mon): make a trip to Piazza della Repubblica, then indulge your senses at some of the top wineries in the area, then see the interesting displays at Museo Diocesano, and finally get engrossed in the history at MAEC - Museo dell'Accademia Etrusca.

To find more things to do, ratings, photos, and more tourist information, use the Cortona day trip planning app.

You can drive from Siena to Cortona in 1.5 hours. Alternatively, you can take a train; or do a combination of bus and train. Finish your sightseeing early on the 5th (Tue) so you can drive to Rome.
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Tours · Wineries · Museums
Find places to stay Sep 3 — 5:

Rome, Italy — 1 day

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Start off your visit on the 5th (Tue): take in the architecture and atmosphere at Church of St. Louis of the French, make a trip to Roman Forum, and then wander the streets of Trastevere.

To find maps and more tourist information, read our Rome holiday planning app.

You can drive from Cortona to Rome in 2.5 hours. Alternatively, you can take a train. Expect a daytime high around 32°C in September, and nighttime lows around 18°C. Finish your sightseeing early on the 5th (Tue) so you can fly to Athens.
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Neighborhoods · Historic Sites
Find places to stay Sep 5 — 6:

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.
Change things up with these side-trips from Athens: Mycenae (Lion Gate & Archaeological Site Mycenae) and Moni Osiou Patapiou (in Loutraki). The adventure continues: delve into the distant past at Acropolis of Athens, get engrossed in the history at Acropolis Museum, pause for some photo ops at Temple of Olympian Zeus, and take in nature's colorful creations at National Garden.

To see more things to do, ratings, reviews, and tourist information, refer to the Athens sightseeing planning website.

Traveling by flight from Rome to Athens takes 5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of train, ferry, and bus. You'll lose 1 hour traveling from Rome to Athens due to the time zone difference. Plan for somewhat warmer nights when traveling from Rome in September since evenings lows in Athens dip to 24°C. Finish your sightseeing early on the 8th (Fri) so you can fly to Rhodes Town.
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Historic Sites · Museums · Neighborhoods · Parks
Side Trips
Find places to stay Sep 5 — 8:

Rhodes Town, Greece — 3 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.
On the 9th (Sat), stop by Petra Kamara, then explore the historical opulence of Palace of the Grand Master of the Knights of Rhodes, then appreciate the extensive heritage of Medieval City, and finally cast your line with Makarounas Fishing Trip Rhodes. On the 10th (Sun), you'll have a packed day of sightseeing: contemplate the long history of Village of Lindos.

For traveler tips, other places to visit, and tourist information, refer to the Rhodes Town online trip itinerary maker.

Traveling by flight from Athens to Rhodes Town takes 2.5 hours. Alternatively, you can ride a ferry; or do a combination of car and ferry. Expect a daytime high around 33°C in September, and nighttime lows around 26°C. Wrap up your sightseeing on the 11th (Mon) early enough to travel to Fira.
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Historic Sites · Tours · Wildlife · Outdoors
Side Trip
Find places to stay Sep 8 — 11:

Fira, Greece — 2 nights

Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
Start off your visit on the 11th (Mon): enjoy the sand and surf at Perissa Black Sand Beach, then explore the ancient world of Akrotiri, then kick back and relax at Red Beach, and finally look for gifts at Oneiro Jewelry. Keep things going the next day: view the masterpieces at Eduart Gjopalaj Workshop, enjoy the sand and surf at Kamari Beach, and then indulge your taste buds at Food & Drink.

For other places to visit, traveler tips, reviews, and tourist information, read Fira trip itinerary planning tool.

Traveling by combination of flight, bus, and ferry from Rhodes Town to Fira takes 6 hours. Alternatively, you can ride a ferry. Expect a daytime high around 32°C in September, and nighttime lows around 24°C. Finish up your sightseeing early on the 13th (Wed) so you can catch the ferry to Milos.
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Beaches · Parks · Outdoors · Tours
Side Trips
Find places to stay Sep 11 — 13:

Milos, Greece — 3 nights

Island of Colors

The result of thousands of years of volcanic activity, the island of Milos features a craggy coastline interspersed by shallow beaches.
Milos is known for beaches, wildlife, and nature. Your trip includes some of its best attractions: kick back and relax at Kleftiko Beach, tour the pleasant surroundings at Tsigrado Beach, discover the deep blue sea with Oneiro Milos, and explore the historical opulence of Venetian Castle of Milos.

For ratings, traveler tips, other places to visit, and other tourist information, you can read our Milos trip maker site.

You can ride a ferry from Fira to Milos in 3 hours. Another option is to fly. In September in Milos, expect temperatures between 32°C during the day and 24°C at night. On the 16th (Sat), you'll have the morning to explore before heading off to Brindisi.
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Outdoors · Beaches · Parks · Tours
Find places to stay Sep 13 — 16:

Brindisi, Italy — 7 nights

Brindisi is a city in the region of Apulia in southern Italy, the capital of the province of Brindisi, on the coast of the Adriatic Sea. Explore Brindisi's surroundings by going to Libreria Agora (in Manduria), San Donaci (Cantine Paololeo & Cantina San Donaci) and Castello Monaci (in San Pancrazio Salentino). There's lots more to do: head outdoors with New Basket Brindisi, relax in the rural setting at Masseria Arciprete, take in the pleasant sights at Lungomare Regina Margherita, and look for all kinds of wild species at Punta del Serrone.

To see where to stay, traveler tips, reviews, and other tourist information, read our Brindisi trip itinerary planner.

Getting from Milos to Brindisi by car takes about 20 hours. Other options: drive. The time zone changes from Eastern European Standard Time to Central European Standard Time, which is usually a -1 hour difference. In September in Brindisi, expect temperatures between 30°C during the day and 22°C at night. Finish your sightseeing early on the 23rd (Sat) so you can fly to Rome.
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Historic Sites · Wineries · Tours · Wildlife
Side Trips
Find places to stay Sep 16 — 23:

Rome, Italy — 3 nights

Eternal City

Explore Rome further: steep yourself in history at St. Peter's Basilica, admire the masterpieces at Vatican Museums, browse the exhibits of Museo Nazionale di Castel Sant'Angelo, and appreciate the extensive heritage of Piazza Navona.

To see traveler tips, other places to visit, maps, and tourist information, go to the Rome road trip planner.

Traveling by flight from Brindisi to Rome takes 3 hours. Alternatively, you can drive; or take a train. Traveling from Brindisi in September, plan for little chillier nights in Rome, with lows around 18°C. Wrap up your sightseeing on the 26th (Tue) early enough to fly back home.
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Historic Sites · Museums
Side Trip
Find places to stay Sep 23 — 26:

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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Lake Como travel guide

4.2
Gardens · Architectural Buildings · Churches
A favorite vacation spot for more than a century, Lake Como was once an exclusive retreat for local aristocrats and wealthy people. It is not only one of Europe's most beautiful lakes, but also one of the deepest at more than 400 m (1,300 ft). Surrounded by elegant villas, the lake has become a popular holiday destination for tourists because of its range of attractions, from landscapes, wildlife, and spas, to activities like sailing, windsurfing, and kite-surfing. The area has been an inspiration for artists since Roman times. English poet Percy Bysshe Shelley wrote, "This lake exceeds anything I ever beheld in beauty…It is long and narrow and has the appearance of a mighty river winding among the mountains and the forests."
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Tuscany travel guide

4.4
Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.
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Greece travel guide

4.3
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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Rhodes travel guide

4.2
Beaches · Ruins · Nightlife
Island of the Knights
An island of green hills, fertile valleys, and golden beaches, Rhodes blends cosmopolitan and traditional cultures, exemplified by its traditional taverns, upscale hotels, and archaeological sites. Nicknamed the "Island of Roses," this island offers visitors a chance to discover lively tourist resorts in the north and tranquil rural areas in the south. The island's slow pace seems utterly unaffected by the challenges of mass tourism, its permanent residents stubbornly clinging to their age-old traditions and relaxed lifestyle. As you explore the areas farther away from the busy coastline, take time to meet the garrulous locals in their natural environment, the village tavern.
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Santorini travel guide

4.1
Beaches · Landmarks · Ruins
Wine Island
Known for dramatic views and romantic sunsets, the island of Santorini draws visitors with its long string of black, white, and red beaches. The largest and most significant of a small group of volcanic islands located just 200 km (120 mi) southeast of Greece's mainland, Santorini boasts just over 15,000 permanent residents. Created by a massive volcanic eruption that likely destroyed a single large island, the archipelago still features an active volcano, which saw its last eruption in the 1950s. The easiest way to explore Santorini's craggy coastline is on foot. Start by visiting the archaeological sites on the island's southwestern side, which offer a chance to discover the area's ancient past with unobstructed views of the famed volcano.
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Puglia travel guide

4.1
Beaches · Landmarks · Churches
Situated at the southeastern tip of the country, Puglia forms the heel on the "boot" of Italy. First colonized by Mycenaean Greeks, the region flourished during Roman times as a major producer of grain and oil. Today, Puglia remains a predominantly agricultural part of the country, though its warm and sunny coastal weather makes it a favorite holiday destination with an ever-increasing number of tourists. The long coastline features attractions like sun-kissed beaches and lively resorts, many of which are overlooked by limestone cliffs. Deeper inland, Puglia is largely flat, a land of charming villages and world-class cuisine. Here, you'll find olive oil, grapes, tomatoes, peppers, mushrooms, and fresh seafood to give you sustenance as you continue sightseeing. Despite its reputation as a producer of some Italy's best food and wines, Puglia still has numerous rural corners that most tourists have yet to explore.
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