20 days in Italy & Greece Itinerary

20 days in Italy & Greece Itinerary

Created using Inspirock Europe Trip Planner
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Taormina, Italy
— 3 nights
Fly to Naples, Ferry to Capri
Capri, Italy
— 2 nights
Ferry to Naples, Fly to Santorini, Bus to Oia
Oia, Greece
— 4 nights
Drive to Santorini, Ferry to Heraklion, Drive to Hersonissos
Hersonissos, Greece
— 3 nights
Corfu Town, Greece
— 5 nights
Drive to Ioannis Kapodistrias International Airport, Fly to Manila


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 Ceramiche Dell'Artigianato Siciliano Manago and BluArte I due Giardini di Naxos. Get in touch with nature at Spiaggia libera - Santa Teresa di Riva and Lido La Dolce Vita. Change things up with these side-trips from Taormina: Bronte (Il Pistacchio di Corica Alfio & Pastificio Il Mattarello) and Libreria Incantastorie (in Milazzo). There's still lots to do: delve into the distant past at Ancient Theatre of Taormina and look for gifts at Stroscio Gioielli.

For reviews, other places to visit, more things to do, and other tourist information, you can read our Taormina trip itinerary builder site.

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.
Beaches · Outdoors · Parks · 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.
Shopping · Parks · Historic Sites · Nature
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 Faros Market. Shop till you drop at Aquamarine Jewelry and Oneiro Jewelry. Explore Oia's surroundings by going to Galatea Pottery (in Akrotiri) and Perissa Black Sand Beach (in Perissa). There's more to do: pause for some serene contemplation at Ekklisia Panagia Platsani and stop by Epilekton.

To see other places to visit, maps, more things to do, and more tourist information, read Oia online visit planner.

You can do a combination of ferry, flight, and bus from Capri to Oia in 7.5 hours. Other options are to do a combination of ferry, bus, and taxi; or do a combination of ferry, bus, and taxi. The time zone difference when traveling from Capri to Oia is 1 hour. In May, daily temperatures in Oia can reach 28°C, while at night they dip to 20°C. Finish up your sightseeing early on the 27th (Sat) so you can travel to Hersonissos.
Shopping · Beaches · Outdoors · Parks
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 out of the city life by going to Fortress Spinalonga and Lake Voulismeni. Shop till you drop at Eklektos Bookshop and Kristina Boutique. Change things up with these side-trips from Hersonissos: Nostimon (in Kritsa), Maria & Vangelis - Unique Handmade Creations (in Elounda) and Votania Herbs (in Kavousi). There's more to do: look for gifts at Luxurious Furs and learn something new at The Bronze - Kelesis Yannis.

For maps, photos, traveler tips, and other tourist information, read our Hersonissos journey planner.

Traveling by combination of car and ferry from Oia to Hersonissos takes 3.5 hours. Alternatively, you can do a combination of taxi, ferry, and bus. Traveling from Oia in May, Hersonissos is little chillier at night with lows of 15°C. Wrap up your sightseeing on the 30th (Tue) to allow time to fly to Corfu Town.
Shopping · Nature · Parks · 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 Rovinia Beach. You'll get in some beach time at Bataria Beach and Marathias Beach. You'll find plenty of places to visit near Corfu Town: Gardenos Beach (in Gardenos), Kassiopi (Agathi's Lace Shop, Beautiful, &more) and Elisabeth's Gift & Jewellery Shop (in Agios Stefanos). Next up on the itinerary: look for gifts at Corfu Sandals, examine the collection at Patounis Soap Factory, browse for treasures at Icon Gallery, and pick up some local products at The Land Of Corfu Natural Products.

To find photos, traveler tips, where to stay, and other tourist information, refer to the Corfu Town trip itinerary planning website.

You can fly from Hersonissos to Corfu Town in 4.5 hours. Other options are to do a combination of bus and ferry; or do a combination of bus, ferry, and train. In May in Corfu Town, expect temperatures between 28°C during the day and 17°C at night. Cap off your sightseeing on the 4th (Sun) early enough to travel back home.
Outdoors · Beaches · Parks · Shopping
Side Trips
Find places to stay May 30 — Jun 4:

Italy travel guide

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

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.