20 days in Italy & Greece Itinerary

20 days in Italy & Greece Itinerary

Created using Inspirock Europe Trip Planner

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Make it your trip
Fly
1
Taormina, Italy
— 3 nights
Fly to Naples, Ferry to Capri
2
Capri, Italy
— 2 nights
Ferry to Naples, Fly to Oia
3
Oia, Greece
— 4 nights
Ferry to Heraklion, Drive to Hersonissos
4
Hersonissos, Greece
— 3 nights
Fly
5
Corfu Town, Greece
— 5 nights
Fly

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Taormina, Italy

— 3 nights
With its warm island weather and cliffside location overlooking the Ionion Sea, Taormina has been one of Sicily's most popular getaway destinations since the early 19th century.
You'll discover tucked-away gems like Stroscio Gioielli and Spiaggia libera - Santa Teresa di Riva. Give yourself a bit of retail therapy at Ceramiche Dell'Artigianato Siciliano Manago and Pastificio Il Mattarello. Change things up with these side-trips from Taormina: Il Pistacchio di Corica Alfio (in Bronte) and Libreria Incantastorie (in Milazzo). There's much more to do: explore the ancient world of Ancient Theatre of Taormina, look for gifts at Il Laboratorio Dell'Arte, enjoy the sand and surf at Lido La Dolce Vita, and learn something new at BluArte I due Giardini di Naxos.

For more things to do, traveler tips, other places to visit, and other tourist information, use the Taormina travel route builder website.

Manila, Philippines to Taormina is an approximately 20-hour flight. The time zone changes from Philippine Standard Time (PST) to Central European Standard Time (CET), which is usually a -7 hour difference. Traveling from Manila in May, expect Taormina to be little chillier, temps between 28°C and 19°C. Finish your sightseeing early on the 21st (Sun) to allow enough time to travel to Capri.

Things to do in Taormina

Parks · Beaches · Outdoors · Shopping

Side Trips

Find places to stay May 17 — 21:

Capri, Italy

— 2 nights
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Start off your visit on the 21st (Sun): don't miss a visit to Belvedere Cannone, enjoy the sand and surf at Marina Piccola, and then contemplate the long history of Villa San Michele. Keep things going the next day: take your sightseeing to a higher altitude at Monte Solaro, stop by Limoncello di Capri, look for gifts at Eco Capri, look for gifts at The Sea Gull, then admire the natural beauty at Giardini di Augusto, and finally take in the dramatic natural features at I Faraglioni.

To find photos, where to stay, traveler tips, and tourist information, read Capri tour planning tool.

You can do a combination of flight and ferry from Taormina to Capri in 4.5 hours. Alternatively, you can do a combination of train and ferry; or do a combination of bus and ferry. In May, daytime highs in Capri are 27°C, while nighttime lows are 18°C. On the 23rd (Tue), wrap the sightseeing up by early afternoon so you can travel to Oia.

Things to do in Capri

Shopping · Parks · Nature · Historic Sites

Side Trip

Find places to stay May 21 — 23:

Oia, Greece

— 4 nights
Every day hundreds of visitors come to Oia just to experience its sunsets.
You'll discover tucked-away gems like Atlantis Books E.E. and Stardust. Shop till you drop at Aquamarine Jewelry and Oneiro Jewelry. Explore Oia's surroundings by going to Akrotiri (Galatea Pottery & Faros Market) and Perissa Black Sand Beach (in Perissa). There's more to do: pause for some serene contemplation at Ekklisia Panagia Platsani and look for gifts at Eponymo.

To find more things to do, ratings, reviews, and tourist information, read our Oia online travel planner.

Do a combination of ferry and flight from Capri to Oia in 6.5 hours. Alternatively, you can do a combination of ferry and bus; or do a combination of ferry and bus. Due to the time zone difference, you'll lose 1 hour traveling from Capri to Oia. May in Oia sees daily highs of 28°C and lows of 20°C at night. Wrap up your sightseeing on the 27th (Sat) early enough to travel to Hersonissos.

Things to do in Oia

Shopping · Parks · Beaches · Outdoors

Side Trips

Find places to stay May 23 — 27:

Hersonissos, Greece

— 3 nights
Wholeheartedly dedicated to tourism, Hersonissos remains best known for its vibrant nightlife, its bars and clubs attracting partygoers from around the world.
Step off the beaten path and head to Lake Voulismeni and Eklektos Bookshop. For shopping fun, head to Luxurious Furs or Kristina Boutique. Get out of town with these interesting Hersonissos side-trips: Votania Herbs (in Kavousi), Nostimon (in Kritsa) and Elounda (Maria & Vangelis - Unique Handmade Creations & Fortress Spinalonga). There's still lots to do: look for gifts at Hantra.

To see reviews, ratings, where to stay, and tourist information, go to the Hersonissos travel itinerary planner.

Traveling by combination of ferry and car from Oia to Hersonissos takes 3 hours. Alternatively, you can do a combination of ferry and bus. Traveling from Oia in May, you can expect nighttime temperatures to be little chillier in Hersonissos, with lows of 15°C. Wrap up your sightseeing on the 30th (Tue) early enough to fly to Corfu Town.

Things to do in Hersonissos

Shopping · Parks · Nature · Historic Sites

Side Trips

Find places to stay May 27 — 30:

Corfu Town, Greece

— 5 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.
Get outdoors at Porto Timoni Beach and Bataria Beach. You'll get in some beach time at Marathias Beach and Kanoni Beach. You'll find plenty of places to visit near Corfu Town: Kassiopi (Agathi's Lace Shop & Beautiful), Elisabeth's Gift & Jewellery Shop (in Agios Stefanos) and Gardenos Beach (in Gardenos). Next up on the itinerary: enjoy the sand and surf at Rovinia Beach, browse for treasures at Icon Gallery, look for gifts at Corfu Sandals, and browse the fresh offerings at The Land Of Corfu Natural Products.

To see where to stay, more things to do, maps, and other tourist information, refer to the Corfu Town journey maker website.

Getting from Hersonissos to Corfu Town by flight takes about 4.5 hours. Other options: do a combination of bus and ferry; or do a combination of bus, ferry, and train. In May, daytime highs in Corfu Town are 28°C, while nighttime lows are 17°C. Finish your sightseeing early on the 4th (Sun) so you can travel back home.

Things to do in Corfu Town

Outdoors · Parks · Beaches · Shopping

Side Trips

Find places to stay May 30 — Jun 4:

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.