18 days in Italy & Greece Itinerary

Created using Inspirock Europe holiday planner
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Bellagio, Italy
— 2 nights
Cinque Terre, Italy
— 2 nights
Florence, Italy
— 3 nights
Fira, Greece
— 2 nights
Athens, Greece
— 2 nights
Tsilivi (Planos), Greece
— 5 nights


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.
Get out of town with these interesting Bellagio side-trips: Varenna (S. Giovanni Battista & Villa Monastero), Tremezzina (Villa Carlotta, Chiesa di San Lorenzo a Tremezzo, &more) and Chiesa di San Giacomo (in Ossuccio). The adventure continues: explore the activities along Lago di Como, paddle through the water with a kayaking and canoeing tour, take in the architecture and atmosphere at Basilica di San Giacomo, and take in nature's colorful creations at I Giardini di Villa Melzi.

To find reviews, traveler tips, ratings, and more tourist information, go to the Bellagio trip planning website.

Toronto, Canada to Bellagio is an approximately 11.5-hour flight. The time zone difference moving from Eastern Standard Time to Central European Standard Time is 6 hours. In May, daily temperatures in Bellagio can reach 25°C, while at night they dip to 13°C. Finish your sightseeing early on the 7th (Sun) to allow enough time to drive to Cinque Terre.
Parks · Nature · Museums · Historic Sites
Side Trips
Find places to stay May 5 — 7:

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.
On the 8th (Mon), don't miss a visit to Oratorio della Confraternita dei Neri Mortis et Orationis, hike along Cinque Terre Trails, then get into the urban bustle at Vernazza, then stroll through Footpath Monterosso - Vernazza, and finally explore the historical opulence of Castello Doria. Keep things going the next day: pause for some serene contemplation at Convento dei Cappuccini e Chiesa di San Francesco and then take a tour by water with Enjoy Cinqueterre Boat Tours.

To see ratings, traveler tips, more things to do, and more tourist information, you can read our Cinque Terre trip planning tool.

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. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. On the 9th (Tue), wrap the sightseeing up by early afternoon so you can drive to Florence.
Historic Sites · Outdoors · Parks · Trails
Find places to stay May 7 — 9:

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.
Start off your visit on the 9th (Tue): admire the landmark architecture of Loggia dei Lanzi. On the next day, explore the world behind art at Florence Academy of Fine Arts, steep yourself in history at Basilica of Santa Croce, then see the interesting displays at Pitti Palace, then contemplate in the serene atmosphere at The Baptistery of St. John, and finally get to know the fascinating history of Piazza della Signoria.

To see more things to do, maps, and tourist information, you can read our Florence online holiday planner.

Drive from Cinque Terre to Florence in 2.5 hours. Alternatively, you can take a train. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. You'll set off for Fira on the 12th (Fri).
Find places to stay May 9 — 12:

Fira, Greece — 2 nights

Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
On the 13th (Sat), you'll have a packed day of sightseeing: indulge your senses at some of the top wineries in the area, then take in the spiritual surroundings of Orthodox Metropolitan Cathedral, then take a tour by water with Boat Tours & Water Sports, and finally take in the exciting artwork at Nikola's Art Gallery.

To see ratings, where to stay, reviews, and more tourist information, read Fira road trip planning app.

Traveling by flight from Florence to Fira takes 7 hours. Alternatively, you can do a combination of train and flight; or do a combination of car and ferry. You'll lose 1 hour traveling from Florence to Fira due to the time zone difference. Traveling from Florence in May, plan for a bit warmer nights in Fira, with lows around 20°C. Finish your sightseeing early on the 14th (Sun) to allow enough time to fly to Athens.
Tours · Wineries · Outdoors · Historic Sites
Side Trips
Find places to stay May 12 — 14:

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.
To see other places to visit, traveler tips, more things to do, and tourist information, read Athens sightseeing planning app.

Fly from Fira to Athens in 2.5 hours. Alternatively, you can do a combination of ferry and taxi; or ride a ferry. In May, daytime highs in Athens are 29°C, while nighttime lows are 20°C. Cap off your sightseeing on the 16th (Tue) early enough to catch the flight to Tsilivi (Planos).
Historic Sites · Museums · Neighborhoods
Find places to stay May 14 — 16:

Tsilivi (Planos), Greece — 5 nights

A growing favorite with international vacationers, Tsilivi sits on the northern coast of Zakynthos.
Explore the numerous day-trip ideas around Tsilivi (Planos): Navagio Beach (Shipwreck Beach) (in Anafonitria), Blue Caves (in Korithi) and Gerakas Beach (in Vasilikos). The adventure continues: take a memorable tour with Tours, see the interesting displays at Aristeon Ecological Olive Press, get outside with Infinity Beach Club Zante, and make a splash at Tsilivi Waterpark.

For traveler tips, reviews, photos, and tourist information, read our Tsilivi (Planos) trip itinerary builder site.

Getting from Athens to Tsilivi (Planos) by flight takes about 2.5 hours. Other options: take a bus. Traveling from Athens in May, Tsilivi (Planos) is little chillier at night with lows of 16°C. Finish your sightseeing early on the 21st (Sun) so you can fly back home.
Outdoors · Parks · Beaches · Nature
Side Trips
Find places to stay May 16 — 21:

Italy travel guide

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.

Tuscany travel guide

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.

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.

Zakynthos travel guide

Beaches · Nightlife · Nature & Wildlife Tours
Flower of the East
Located just off the west coast of mainland Greece, Zakynthos enjoys a reputation as both a party destination and a family-friendly getaway. Packed with foreign tourists along its eastern and southeastern coastline, the island also features numerous tranquil pockets in its central region of forested mountains and rolling hills. Avoid the overcrowded east by discovering the island's less-explored northern sections, which contain a series of deep caves that feature sun reflecting on seawater and white stones, creating a striking shade of azure particular to this part of the world. The northern capes of the island also offer the calmest waters, which lap a string of developed beaches with plenty of modern facilities.