33 days in Italy & Greece Itinerary

33 days in Italy & Greece Itinerary

Created using Inspirock Europe trip planner
Make it your trip
Fly
1
Venice, Italy
— 2 nights
Train
2
Bellagio, Italy
— 2 nights
Train
3
Cinque Terre, Italy
— 1 night
Drive
4
San Gimignano, Italy
— 1 night
Drive
5
Montalcino, Italy
— 1 night
Drive
6
Saturnia, Italy
— 1 night
Drive
7
Montepulciano, Italy
— 1 night
Drive
8
Florence, Italy
— 2 nights
Fly
9
Athens, Greece
— 2 nights
Fly
10
Rhodes Town, Greece
— 3 nights
+3
Fly to Heraklion, Bus to Néa Alikarnassós, Foot to Heraklion, Ferry to Fira
11
Fira, Greece
— 1 night
Ferry
12
Milos, Greece
— 1 night
Drive
13
Brindisi, Italy
— 7 nights
Fly
14
Rome, Italy
— 3 nights
Fly

S M T W T F S
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30

Venice, Italy — 2 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.
Venture out of the city with trips to Padua (Basilica of St. Anthony & Scrovegni Chapel). There's much more to do: contemplate the waterfront views at Canal Grande, see the interesting displays at Doge's Palace, snap pictures at Ponte dei Sospiri, and take in the architecture and atmosphere at San Giorgio Maggiore.

To find ratings, reviews, photos, and more tourist information, refer to the Venice online tour itinerary planner.

Sydney, Australia to Venice is an approximately 24.5-hour flight. The time zone difference moving from Australian Eastern Standard Time (AEST) to Central European Standard Time (CET) is minus 9 hours. Traveling from Sydney in August, expect Venice to be somewhat warmer, temps between 34°C and 22°C. Finish your sightseeing early on the 30th (Wed) to allow enough time to drive to Bellagio.
more
Historic Sites · Museums · Parks · Nature
Side Trip
Find places to stay Aug 28 — 30:

Bellagio, Italy — 2 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.
Start off your visit on the 31st (Thu): add some adventure to your tour with a kayaking and canoeing tour, take in the architecture and atmosphere at Basilica di San Giacomo, walk around La Punta Spartivento, stop by Profumeria Bellagio, then walk around Parco di Villa Serbelloni, and finally tour the pleasant surroundings at I Giardini di Villa Melzi.

To see photos, ratings, maps, and more tourist information, read Bellagio online trip itinerary planner.

Drive from Venice to Bellagio in 3.5 hours. Alternatively, you can take a train; or do a combination of train and bus. In August, plan for daily highs up to 33°C, and evening lows to 20°C. Cap off your sightseeing on the 1st (Fri) early enough to go by car to Cinque Terre.
more
Parks · Tours · Adventure · Outdoors
Find places to stay Aug 30 — Sep 1:

Cinque Terre, Italy — 1 night

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Start off your visit on the 1st (Fri): hike along Cinque Terre Trails, then see some colorful creatures with Enjoy Cinqueterre Boat Tours, then tour the pleasant surroundings at Footpath Monterosso - Vernazza, and finally get into the urban bustle at Vernazza.

To see more things to do, maps, where to stay, and tourist information, you can read our Cinque Terre trip planner.

You can drive from Bellagio to Cinque Terre in 4 hours. Other options are to take a train; or do a combination of bus and train. In September, daytime highs in Cinque Terre are 30°C, while nighttime lows are 17°C. Cap off your sightseeing on the 2nd (Sat) early enough to go by car to San Gimignano.
more
Outdoors · Trails · Parks · Tours
Find places to stay Sep 1 — 2:

San Gimignano, Italy — 1 night

Town of Fine Towers

A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
On the 2nd (Sat), take in the architecture and atmosphere at Duomo di San Gimignano, make a trip to Historic Centre of San Gimignano, steep yourself in history at Torre Grossa, view the masterpieces at La Bottega del Sale di Duccio Nacci photographer, then learn about winemaking at Guardastelle Vineyard, and finally make a trip to Piazza della Cisterna.

To find traveler tips, reviews, maps, and more tourist information, use the San Gimignano day trip app.

Traveling by car from Cinque Terre to San Gimignano takes 2.5 hours. Alternatively, you can take a train. September in San Gimignano sees daily highs of 30°C and lows of 17°C at night. Finish up your sightseeing early on the 3rd (Sun) so you can go by car to Montalcino.
more
Wineries · Historic Sites · Shopping · Museums
Find places to stay Sep 2 — 3:

Montalcino, Italy — 1 night

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
On the 3rd (Sun), take in panoramic vistas at Fortezza di Montalcino, do a tasting at Winery Solaria Patrizia Cencioni, then don't miss a visit to Terme Bagno Vignoni, then get into the urban bustle at San Quirico d'Orcia, and finally take in the architecture and atmosphere at Chiesa di Santa Maria Assunta.

For more things to do, ratings, photos, and more tourist information, go to the Montalcino trip website.

Getting from San Gimignano to Montalcino by car takes about 1.5 hours. Other options: do a combination of train and bus; or take a bus. September in Montalcino sees daily highs of 32°C and lows of 19°C at night. Finish your sightseeing early on the 4th (Mon) to allow enough time to drive to Saturnia.
more
Historic Sites · Shopping · Wineries
Side Trips
Find places to stay Sep 2 — 4:

Saturnia, Italy — 1 night

On the 4th (Mon), witness a stunning natural landmark at Terme di Saturnia - Parco Termale, then take in the natural beauty of Cascate del Mulino, then step into the grandiose world of Piazza del Castello di Montemerano, and finally explore the fascinating underground world of Via Cava.

To see where to stay, ratings, other places to visit, and other tourist information, you can read our Saturnia itinerary builder site.

Traveling by car from Montalcino to Saturnia takes 1.5 hours. Alternatively, you can do a combination of bus and train. In September, daily temperatures in Saturnia can reach 32°C, while at night they dip to 19°C. Finish up your sightseeing early on the 5th (Tue) so you can go by car to Montepulciano.
more
Parks · Nature · Historic Sites · Spas
Side Trips
Find places to stay Sep 4 — 5:

Montepulciano, Italy — 1 night

Pearl of the 16th Century

Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Start off your visit on the 5th (Tue): don't miss a visit to Terrazza Del Palazzo Comunale, don't miss a visit to Piazza Grande a Montepulciano, learn about winemaking at Icario Winery, do a tasting at Az. Agr. Poliziano, then do a tasting at Avignonesi, and finally do a tasting at Tenuta Valdipiatta. On the next day, contemplate the long history of Historic Centre of the City of Pienza, then make a trip to Piazza Pio II, then take in the spiritual surroundings of Tempio di San Biagio, and finally indulge in some personalized pampering at some of the best spas.

For photos, reviews, ratings, and tourist information, refer to the Montepulciano trip site.

You can drive from Saturnia to Montepulciano in 2 hours. Alternatively, you can do a combination of taxi and bus. In September, daily temperatures in Montepulciano can reach 32°C, while at night they dip to 19°C. Finish up your sightseeing early on the 6th (Wed) so you can go by car to Florence.
more
Wineries · Historic Sites · Spas
Side Trips
Find places to stay Sep 5 — 6:

Florence, Italy — 2 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Here are some ideas for day two: contemplate the long history of Basilica of Santa Croce, admire the masterpieces at Florence Academy of Fine Arts, then admire the natural beauty at The Boboli Gardens, then explore the world behind art at Pitti Palace, and finally appreciate the extensive heritage of Piazza della Signoria.

For photos, ratings, other places to visit, and more tourist information, use the Florence road trip website.

You can drive from Montepulciano to Florence in 2 hours. Alternatively, you can take a train; or take a bus. In September, daily temperatures in Florence can reach 30°C, while at night they dip to 17°C. Cap off your sightseeing on the 8th (Fri) early enough to catch the flight to Athens.
more
Historic Sites · Museums · Parks
Find places to stay Sep 6 — 8:

Athens, Greece — 2 nights

The Birthplace of Democracy

One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
You'll find plenty of places to visit near Athens: Mycenae (Citadel and Treasury of Atreus & Archaeological Site Mycenae). There's lots more to do: steep yourself in history at Acropolis of Athens, don't miss a visit to Ancient Agora of Athens, admire the masterpieces at National Archaeological Museum, and take in nature's colorful creations at National Garden.

For maps, traveler tips, where to stay, and tourist information, read Athens travel itinerary planner.

Fly from Florence to Athens in 5.5 hours. Alternatively, you can drive; or do a combination of train and bus. The time zone difference moving from Central European Standard Time to Eastern European Standard Time is 1 hour. Plan for a bit warmer temperatures traveling from Florence in September, with highs in Athens at 34°C and lows at 24°C. Wrap up your sightseeing on the 11th (Mon) to allow time to fly to Rhodes Town.
more
Historic Sites · Museums · Neighborhoods · Parks
Side Trip
Find places to stay Sep 8 — 11:

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.
Start off your visit on the 12th (Tue): cast your line with Makarounas Fishing Trip Rhodes, then step into the grandiose world of Palace of the Grand Master of the Knights of Rhodes, then appreciate the extensive heritage of Medieval City, and finally stop by Savvas Samourakis Handmade Jewellery. Get ready for a full day of sightseeing on the next day: contemplate the long history of Village of Lindos.

To find ratings, reviews, more things to do, and more tourist information, you can read our Rhodes Town online journey planner.

Getting from Athens to Rhodes Town by flight takes about 2.5 hours. Other options: ride a ferry; or do a combination of car and ferry. In September, daily temperatures in Rhodes Town can reach 33°C, while at night they dip to 26°C. You'll set off for Fira on the 14th (Thu).
more
Historic Sites · Tours · Outdoors · Wildlife
Side Trip
Find places to stay Sep 11 — 14:

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 14th (Thu): delve into the distant past at Akrotiri, enjoy the sand and surf at Red Beach, then pause for some serene contemplation at Orthodox Metropolitan Cathedral, and finally view the masterpieces at Nikola's Art Gallery.

To see photos, traveler tips, where to stay, and more tourist information, read our Fira tour itinerary maker site.

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. Cap off your sightseeing on the 15th (Fri) early enough to catch the ferry to Milos.
more
Historic Sites · Beaches · Parks · Outdoors
Side Trip
Find places to stay Sep 14 — 15:

Milos, Greece — 1 night

Island of Colors

The result of thousands of years of volcanic activity, the island of Milos features a craggy coastline interspersed by shallow beaches.
Start off your visit on the 15th (Fri): kick back and relax at Sarakiniko Beach, then step into the grandiose world of Venetian Castle of Milos, and then see some colorful creatures with Oneiro Milos.

To find other places to visit, reviews, and more tourist information, refer to the Milos online trip planner.

Ride a ferry from Fira to Milos in 3 hours. Alternatively, you can fly. In September, daily temperatures in Milos can reach 32°C, while at night they dip to 24°C. On the 16th (Sat), you'll have the morning to explore before heading off to Brindisi.
more
Outdoors · Tours · Wildlife · Beaches
Find places to stay Sep 14 — 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. Get out of town with these interesting Brindisi side-trips: Zoosafari (in Fasano), Ostuni (Masseria Brancati, Centro Storico, &more) and Taranto (Mostra Storico-Artigiana dell’Arsenale Militare Marittimo & Castello Aragonese). The adventure continues: admire the landmark architecture of I Trulli di Alberobello - World Heritage Site, awaken your taste buds at I Pastini, make a trip to Portico dei Cavalieri Templari, and take in the pleasant sights at Lungomare Regina Margherita.

To see other places to visit, reviews, where to stay, and other tourist information, read Brindisi driving holiday site.

Traveling by car from Milos to Brindisi takes 20 hours. Alternatively, you can drive. Due to the time zone difference, you'll gain 1 hour traveling from Milos to Brindisi. September in Brindisi sees daily highs of 30°C and lows of 22°C at night. Finish your sightseeing early on the 23rd (Sat) so you can fly to Rome.
more
Historic Sites · Museums · Tours · Outdoors
Side Trips
Find places to stay Sep 16 — 23:

Rome, Italy — 3 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: contemplate the long history of St. Peter's Basilica, explore the world behind art at Vatican Museums, explore the ancient world of Pantheon, and admire the local landmark of Trevi Fountain.

To see maps, other places to visit, and other tourist information, use the Rome journey planner.

Traveling by flight from Brindisi to Rome takes 3 hours. Alternatively, you can drive; or take a train. Traveling from Brindisi in September, you can expect nighttime temperatures to be slightly colder in Rome, with lows of 18°C. Finish your sightseeing early on the 26th (Tue) to allow enough time to fly back home.
more
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.
more

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."
more

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.
more

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.
more

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.
more

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.
more

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.
more