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 Stroscio Gioielli and Ceramiche Dell'Artigianato Siciliano Manago. 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). And it doesn't end there: explore the ancient world of Ancient Theatre of Taormina, look for gifts at Il Laboratorio Dell'Arte, and learn and have fun at BluArte I due Giardini di Naxos.

For photos, reviews, ratings, and tourist information, read our Taormina trip itinerary planning tool.

Manila, Philippines to Taormina is an approximately 20-hour flight. Traveling from Manila to Taormina, you'll gain 7 hours due to the time zone difference. Traveling from Manila in May, things will get a bit cooler in Taormina: highs are around 28°C and lows about 19°C. Finish up your sightseeing early on the 21st (Sun) so you can travel to Capri.
Parks · Outdoors · Beaches · 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 explore the galleries 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 · 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 Galatea Pottery. Explore Oia's surroundings by going to Faros Market (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 Koukla Art.

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 · Parks · Outdoors · Beaches
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 Spinalonga (Kalydon) and Lake Voulismeni. Shop till you drop at Eklektos Bookshop and Kristina Boutique. Change things up with these side-trips from Hersonissos: Votania Herbs (in Kavousi), Maria & Vangelis - Unique Handmade Creations (in Elounda) and Nostimon (in Kritsa). 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 Bataria Beach. You'll get in some beach time at Rovinia Beach and Kanoni Beach. You'll find plenty of places to visit near Corfu Town: Elisabeth's Gift & Jewellery Shop (in Agios Stefanos), Kassiopi (Agathi's Lace Shop & Beautiful) and Marathias Beach (in Marathias). Next up on the itinerary: explore the wide array of goods at The Land Of Corfu Natural Products, stop by Corfu Sandals, examine the collection at Patounis Soap Factory, and view the masterpieces at Icon Gallery.

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 · Parks · Beaches · Shopping
Side Trips
Find places to stay May 30 — Jun 4:

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.

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.