20 days in Italy & Greece Itinerary

20 days in Italy & Greece Itinerary

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Route & dates

20 days in Italy & Greece Itinerary

Start: Manila, Philippines
Fly:  31​h
1
Taormina, Italy
— 3 nights
+3
Drive + ferry + Drive + ferry:  5​h 30​min
2
Capri, Italy
— 2 nights
+3
ferry + shuttle + Fly + bus:  6​h
3
Oia, Greece
— 4 nights
+2
Drive + ferry + Drive:  3​h 30​min
4
Hersonissos, Greece
— 3 nights
shuttle + Fly:  5​h 30​min
5
Corfu Town, Greece
— 5 nights
Fly:  27​h
End: Manila, Philippines

3
nights
Taormina, Italy

Taormina ©
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.
Get outdoors at Spiaggia libera - Santa Teresa di Riva and Lido La Dolce Vita. Head to Pastificio Il Mattarello and Il Pistacchiofor plenty of shopping. When in Taormina, make a side trip to see Libreria Incantastorie in Milazzo, approximately 1 hour away. Next up on the itinerary: delve into the distant past at Greek Theatre, look for gifts at Sicilian Food Lucia, and shop like a local with Ceramiche Dell'Artigianato Siciliano Manago.

To find more things to do, reviews, traveler tips, and tourist information, read our Taormina itinerary maker.

Manila, Philippines to Taormina is an approximately 31-hour combination of car and flight. You'll gain 7 hours traveling from Manila to Taormina due to the time zone difference. In May, Taormina is a bit cooler than Manila - with highs of 28°C and lows of 19°C. Wrap up your sightseeing on the 21st (Sun) to allow time to travel to Capri.

Things to do in Taormina

Outdoors Beaches Parks

Side Trips

Bronte, BluArte I due Giardini di Naxos, Libreria Incantastorie, Spiaggia libera - Santa Teresa di Riva
Find places to stay May 17 — 21:
Highlights from your plan
Lido La Dolce Vita ©
Lido La Dolce Vita
Ancient Theatre of Taormina ©
Ancient Theatre of Taormina
Pastificio Il Mattarello ©
Pastificio Il Mattarello

2
nights
Capri, Italy

Capri ©
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
On the 21st (Sun), take some stellar pictures from Belvedere Cannone, explore the activities along Marina Piccola, and then take an in-depth tour of Villa San Michele. On the 22nd (Mon), you'll have a packed day of sightseeing: take in the awesome beauty at Monte Solaro, stop by Limoncello Di Capri, look for gifts at Eco Capri, stop by Sea Gull, then take in nature's colorful creations at Gardens of Augustus, and finally make a trip to I Faraglioni.

To find traveler tips, more things to do, reviews, and tourist information, refer to the Capri trip itinerary planner.

Traveling by combination of train, bus, flight, shuttle, and ferry from Taormina to Capri takes 5.5 hours. Alternatively, you can do a combination of train, ferry, and shuttle. May in Capri sees daily highs of 28°C and lows of 19°C at night. 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

Side Trip

Anacapri
Find places to stay May 21 — 23:
Highlights from your plan
Villa San Michele ©
Villa San Michele
Chiesa San Michele ©
Chiesa San Michele
Monte Solaro ©
Monte Solaro

4
nights
Oia, Greece

Oia ©
Every day hundreds of visitors come to Oia just to experience its sunsets.
Head to Aquamarine Jewelry and Epilektonfor some retail therapy. You'll discover tucked-away gems like Perissa Black Sand Beach and The Good Heart. Change things up with these side-trips from Oia: Akrotiri (Galatea Pottery & Faros Market) and Oneiro Jewelry (in Fira). Next up on the itinerary: stop by Stardust and pause for some serene contemplation at Ekklisia Panagia Platsani.

To see photos, ratings, maps, and more tourist information, you can read our Oia itinerary maker.

Traveling by combination of ferry, shuttle, flight, and taxi from Capri to Oia takes 6 hours. Alternatively, you can do a combination of ferry, bus, and taxi. The time zone difference moving from Central European Time to Eastern European Time is 1 hour. In May, plan for daily highs up to 27°C, and evening lows to 20°C. Finish your sightseeing early on the 27th (Sat) to allow enough time to travel to Hersonissos.

Things to do in Oia

Shopping Outdoors Beaches

Side Trips

Fira, Akrotiri, Perissa Black Sand Beach
Find places to stay May 23 — 27:
Highlights from your plan
Perissa Black Sand Beach ©
Perissa Black Sand Beach
Atlantis Books ©
Atlantis Books
Ekklisia Panagia Platsani ©
Ekklisia Panagia Platsani

3
nights
Hersonissos, Greece

Hersonissos ©
Wholeheartedly dedicated to tourism, Hersonissos remains best known for its vibrant nightlife, its bars and clubs attracting partygoers from around the world.
Get in touch with nature at Votania Pure Herbs of Crete and Spinalonga (Kalydon). You'll explore the less-touristy side of things at Eklektos Bookshop and Maria & Vangelis - Unique Handmade Creations. You'll find plenty of places to visit near Hersonissos: Nostimon (in Kritsa) and Lake Voulismeni (in Agios Nikolaos). There's more to do: stop by Hantra.

To find reviews, more things to do, other places to visit, and more tourist information, go to the Hersonissos travel itinerary planner.

You can do a combination of taxi, ferry, and bus from Oia to Hersonissos in 3.5 hours. In May, daily temperatures in Hersonissos can reach 27°C, while at night they dip to 18°C. Finish up your sightseeing early on the 30th (Tue) so you can travel to Corfu Town.

Things to do in Hersonissos

Shopping Nature Parks

Side Trips

Elounda, Agios Nikolaos, Nostimon
Find places to stay May 27 — 30:
Highlights from your plan
Lake Voulismeni ©
Lake Voulismeni
Fortress Spinalonga ©
Fortress Spinalonga
Eklektos Bookshop ©
Eklektos Bookshop

5
nights
Corfu Town, Greece

Corfu Town ©
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.
Step off the beaten path and head to Gardenos Beach and Elisabeth's Gift & Jewellery Shop. Head to Beautiful and Sweet 'N Spicy Bahar Shopfor some retail therapy. You'll find plenty of places to visit near Corfu Town: Marathias Beach (in Marathias), Kassiopi (Agathi's Lace Shop, Bataria Beach, & more), Rovinia Beach (in Paleokastritsa) and Porto Timoni (in Afionas). Next up on the itinerary: relax in the rural setting at Theotoky Estate, stop by Patounis Soap Factory, and view the masterpieces at Icon Gallery.

To find where to stay, reviews, other places to visit, and more tourist information, go to the Corfu Town holiday planner.

Do a combination of bus and flight from Hersonissos to Corfu Town in 5.5 hours. Alternatively, you can do a combination of bus, ferry, and train; or do a combination of bus and ferry. May in Corfu Town sees daily highs of 28°C and lows of 17°C at night. Wrap up your sightseeing on the 4th (Sun) early enough to travel back home.

Things to do in Corfu Town

Outdoors Beaches Parks

Side Trips

Kassiopi, Corfu, Marathias Beach, Gardenos Beach, Rovinia Beach
Find places to stay May 30 — Jun 4:
Highlights from your plan
Porto Timoni Beach ©
Porto Timoni Beach
Bataria Beach ©
Bataria Beach
Theotoky Estate ©
Theotoky Estate

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