22 days in Greece Itinerary

22 days in Greece Itinerary

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Route & dates

22 days in Greece Itinerary

Start: Toronto
Fly:  14 h 15 min
1
Milos
— 2 nights
Drive:  2 h 15 min
2
Oia
— 5 nights
Drive:  1 h 15 min
3
Vlychada
— 2 nights
Drive + Fly:  4 h 15 min
4
Athens
— 5 nights
Subway + Fly:  2 h 45 min
5
Skiathos
— 2 nights
Ferry + Taxi:  3 h 45 min
6
Kalambaka
— 4 nights
Train + Fly:  17 h
End: Toronto

2
nights
Milos

Milos ©
The result of thousands of years of volcanic activity, the island of Milos features a craggy coastline interspersed by shallow beaches.
On the 13th (Fri), enjoy a perfect day by the water at Pollonia Beach. And it doesn't end there: stroll through Kleftiko Beach, enjoy the sand and surf at Sikia Beach, and make a trip to Adamas World War Two Bomb Shelter.

To find ratings, more things to do, maps, and tourist information, refer to the Milos trip planner .

Toronto, Canada to Milos is an approximately 14.5-hour flight. You can also do a combination of flight, taxi, and ferry; or do a combination of flight, bus, and ferry. The time zone changes from Eastern Standard Time to Eastern European Time, which is usually a 7 hour difference. In September, Milos is somewhat warmer than Toronto - with highs of 32°C and lows of 24°C. Wrap up your sightseeing on the 14th (Sat) to allow time to travel to Oia.

Things to do in Milos

Outdoors Parks Beaches
Find places to stay Sep 12 — 14:
Highlights from your plan
Kleftiko Beach ©
Kleftiko Beach
Sarakiniko Beach ©
Sarakiniko Beach
Sikia Beach ©
Sikia Beach

5
nights
Oia

Every day hundreds of visitors come to Oia just to experience its sunsets.
Explore the numerous day-trip ideas around Oia: Kamari (Ancient Thera & KAMARA BEACH) and Akrotiri (Caldera Beach, Akrotiri, & more). There's still lots to do: savor the flavors at Food & Drink, stop by Sand Lily Boutique, contemplate the waterfront views at Amoudi Bay, and take in the architecture and atmosphere at Panagia Theoskepasti Chapel.

To find where to stay, reviews, maps, and more tourist information, read our Oia vacation planner .

Ride a ferry from Milos to Oia in 2.5 hours. In September, daytime highs in Oia are 32°C, while nighttime lows are 24°C. Finish your sightseeing early on the 19th (Thu) to allow enough time to travel to Vlychada.

Things to do in Oia

Parks Outdoors Beaches

Side Trips

Akrotiri, Imerovigli, Santorini, Kamari, Fira
Find places to stay Sep 14 — 19:
Highlights from your plan
Wine Tours & Tastings
Akrotiri ©
Akrotiri
Amoudi Bay ©
Amoudi Bay

2
nights
Vlychada

Kick off your visit on the 20th (Fri): explore the historical opulence of Castelli of Emporio, then examine the collection at Monastery of Profitis Ilias, then kick back and relax at Vlychada Beach, and finally don't miss a visit to Santorini Arts Factory. Get ready for a full day of sightseeing on the 21st (Sat): stroll through Vlichada Beach and then get a new perspective on things with Boat Tours & Water Sports.

To find where to stay, more things to do, photos, and more tourist information, use the Vlychada road trip website .

You can drive from Oia to Vlychada in an hour. Expect a daytime high around 32°C in September, and nighttime lows around 24°C. Cap off your sightseeing on the 21st (Sat) early enough to travel to Athens.

Things to do in Vlychada

Outdoors Wildlife Tours

Side Trips

Monastery of Profitis Ilias, Castelli of Emporio, Santorini Arts Factory
Find places to stay Sep 19 — 21:
Highlights from your plan
Nature & Wildlife Tours
Vlychada Beach ©
Vlychada Beach
Castelli of Emporio ©
Castelli of Emporio

5
nights
Athens

Athens ©
One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
Athens is known for historic sites, museums, nightlife, shopping, and fun & games. Your plan includes some of its best attractions: contemplate the long history of Acropolis of Athens, pause for some photo ops at Temple of Olympian Zeus, make a trip to Plateia Syntagmatos, and savor the flavors at Food & Drink.

To see ratings, traveler tips, more things to do, and more tourist information, use the Athens online trip itinerary maker .

The Route module can help you plan travel from Vlychada to Athens. In September, plan for daily highs up to 34°C, and evening lows to 24°C. Cap off your sightseeing on the 26th (Thu) early enough to travel to Skiathos.

Things to do in Athens

Museums Historic Sites Neighborhoods
Find places to stay Sep 21 — 26:
Highlights from your plan
Acropolis of Athens ©
Acropolis of Athens
Acropolis Museum ©
Acropolis Museum
Plaka ©
Plaka

2
nights
Skiathos

Skiathos ©
Boasting some of Greece's finest beaches, Skiathos swells with vacationers from colder European countries at the height of the tourist season.
Kick off your visit on the 27th (Fri): delve into the distant past at Kastro Ke Medieval Ekklisia, then don't miss a visit to monastero di Panagia Evangelistria, and then stroll through Lalaria Beach. On the 28th (Sat), you'll have a packed day of sightseeing: tour the pleasant surroundings at Elia Beach and then look for all kinds of wild species at Wildlife Areas.

To find maps, reviews, other places to visit, and tourist information, go to the Skiathos trip itinerary tool .

Getting from Athens to Skiathos by combination of subway and flight takes about 3 hours. Other options: do a combination of car and ferry; or do a combination of bus and ferry. Expect little chillier weather when traveling from Athens in September: highs in Skiathos hover around 30°C, while lows dip to 24°C. Wrap up your sightseeing on the 28th (Sat) early enough to travel to Kalambaka.

Things to do in Skiathos

Outdoors Parks Beaches
Find places to stay Sep 26 — 28:
Highlights from your plan
Lalaria Beach ©
Lalaria Beach
Kastro Ke Medieval Ekklisia ©
Kastro Ke Medieval Ekklisia
monastero di Panagia Evangelistria ©
monastero di Panagia Evangelistria

4
nights
Kalambaka

Kalambaka ©
The gateway to one of the largest monastery complexes in Greece, the small town of Kalambaka nestles against a landscape of imposing rock formations rising 400 m (1,300 ft) into the air. Nearly leveled during World War II, the town rebuilt and reinvented itself in the post-war period, quickly becoming one of the region's major travel destinations.
Change things up with these side-trips from Kalambaka: Metsovo (Folk Art Museum Tossizza Mansion & Averofeios Garden). There's much more to do: take in the spiritual surroundings of Meteora, contemplate the long history of Holy Trinity Monastery (Agia Triada), see the interesting displays at Digital Projection Centre of Meteora’s History and Culture, and look for gifts at Ekfrasi - Meteora.

For other places to visit, photos, ratings, and other tourist information, refer to the Kalambaka online sightseeing planner .

Getting from Skiathos to Kalambaka by combination of ferry and car takes about 4 hours. Other options: do a combination of ferry and bus; or do a combination of ferry and train. Traveling from Skiathos in September, expect a bit cooler with lows of 15°C in Kalambaka. Wrap up your sightseeing by early afternoon on the 2nd (Wed) to allow time for travel back home.

Things to do in Kalambaka

Historic Sites Parks Museums

Side Trips

Metsovo, Spileo Theopetras- Kentro Tekmiriosis & Ekpedevsis
Find places to stay Sep 28 — Oct 2:
Highlights from your plan
Meteora ©
Meteora
Monastery of the Great Meteoron ©
Monastery of the Great Meteoron
Holy Trinity Monastery (Agia Triada) ©

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