17 days in Greece Itinerary

17 days in Greece Itinerary

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Route & dates

17 days in Greece Itinerary

Start: Winnipeg
Fly:  19​h 15​min
1
Oia
— 5 nights
Fly:  6​h 15​min
2
Chania Town
— 3 nights
Fly:  5​h 15​min
3
Naxos Town
— 2 nights
Drive:  1​h 30​min
4
Mykonos Town
— 3 nights
Fly + Subway:  2​h 30​min
5
Athens
— 2 nights
Fly:  16​h 30​min
End: Winnipeg

5
nights
Oia

Oia ©
Every day hundreds of visitors come to Oia just to experience its sunsets.
Popular historic sites such as Akrotiri and Byzantine Castle Ruins are in your itinerary. Satisfy your inner culture vulture at Wine Museum Koutsogiannopoulos and Ekklisia Panagia Platsani. Explore Oia's surroundings by going to Gavalas Winery (in Megalochori), Monastery of Profitis Ilias (in Moni Profitou Iliou) and Cultural Village (in Pyrgos). Next up on the itinerary: pause for some serene contemplation at Cathedral of Saint John the Baptist, browse the exhibits of Oria Gallery, contemplate in the serene atmosphere at Orthodox Metropolitan Cathedral, and learn about all things military at Naval Maritime Museum.

For reviews, where to stay, and tourist information, read our Oia trip itinerary planning website .

Winnipeg, Canada to Oia is an approximately 19.5-hour flight. You can also do a combination of flight, car, and ferry. You'll lose 8 hours traveling from Winnipeg to Oia due to the time zone difference. Traveling from Winnipeg in September, expect Oia to be a bit warmer, temps between 32°C and 24°C. Cap off your sightseeing on the 15th (Wed) early enough to travel to Chania Town.

Things to do in Oia

Museums Historic Sites Beaches

Side Trips

Fira, Wine Museum Koutsogiannopoulos, Cultural Village, Monastery of Profitis Ilias, Paradisos Beach
Highlights from your plan
Cathedral of Saint John the Baptist ©
Wine Museum Koutsogiannopoulos ©
Wine Museum Koutsogiannopoulos
Akrotiri ©
Akrotiri

3
nights
Chania Town

Chania Town ©
The place where Cretan and Venetian cultures merged in the 13th century, Chania Town attracts throngs of tourists with its well-preserved medieval harbor.
Step off the beaten path and head to Scuba & Snorkeling and German War Cemetery. Appreciate the collections at Greek National Football Museum and MINOAN'S WORLD. Venture out of the city with trips to Kastro Gramvoussas (in Gramvousa), To Kaniski (in Kissamos) and Rethymnon (Four Martyrs Church & Rethymnon Old Town). There's lots more to do: enjoy the sand and surf at Souda Beach, don't miss a visit to Old Venetian Harbor, and contemplate the long history of Venizelos Graves.

To see more things to do, where to stay, other places to visit, and tourist information, you can read our Chania Town road trip planner.

You can do a combination of ferry and car from Oia to Chania Town in 4 hours. Alternatively, you can fly. In September, daytime highs in Chania Town are 34°C, while nighttime lows are 23°C. Wrap up your sightseeing on the 18th (Sat) early enough to travel to Naxos Town.

Things to do in Chania Town

Outdoors Parks Tours

Side Trips

Rethymnon, Souda Beach, To Kaniski, German War Cemetery, Kastro Gramvoussas
Highlights from your plan
Greek National Football Museum ©
Greek National Football Museum
Kastro Gramvoussas ©
Kastro Gramvoussas
Scuba & Snorkeling

2
nights
Naxos Town

Naxos Town ©
Naxos Town tops the itinerary of most visitors exploring the Aegean islands, drawing their attention with taverns, shops, beaches, and ancient ruins.
On the 18th (Sat), take in the architecture and atmosphere at Church of Agios Georgios Diasoritis, then see the interesting displays at Eggares Olive Press Museum, then wander the streets of Old Town, and finally explore the ancient world of Portara. Get ready for a full day of sightseeing on the 19th (Sun): examine the collection at Distillery M. G. Vallindras Eirini Frangoudaki, then take in the exciting artwork at Fish & Olive, then kick back and relax at Agios Prokopios Beach, and finally look for gifts at Naxia Sweet Home.

To find photos, ratings, more things to do, and tourist information, use the Naxos Town route builder website .

You can fly from Chania Town to Naxos Town in 5.5 hours. Alternatively, you can do a combination of shuttle and flight; or do a combination of taxi and ferry. In September, plan for daily highs up to 32°C, and evening lows to 24°C. Finish up your sightseeing early on the 20th (Mon) so you can go by car to Mykonos Town.

Things to do in Naxos Town

Museums Historic Sites Beaches

Side Trips

Chalkio, Agios Prokopios Beach, Eggares Olive Press Museum
Highlights from your plan
Old Town ©
Old Town
Portara ©
Portara
Fish & Olive ©
Fish & Olive

3
nights
Mykonos Town

Mykonos Town ©
A holiday in Mykonos Town offers a chance to relax on picturesque beaches and explore a labyrinth of charming streets lined with traditional white houses.
Get some cultural insight at Little Venice and Monastery of Panayia Tourliani. Visit Elia Beach and Panormos Beach for some beach relaxation. And it doesn't end there: kick back and relax at Paradise Beach, pause for some serene contemplation at Church of Saint George, take in the waterfront activity at Old Port, and relax and rejuvenate at some of the top local wellness centers.

To find photos, ratings, more things to do, and other tourist information, go to the Mykonos Town day trip site .

Traveling by car from Naxos Town to Mykonos Town takes 1.5 hours. In September in Mykonos Town, expect temperatures between 30°C during the day and 24°C at night. Wrap up your sightseeing on the 23rd (Thu) early enough to travel to Athens.

Things to do in Mykonos Town

Parks Beaches Outdoors

Side Trips

Paradise Beach, Elia Beach, Panormos Beach, Monastery of Panayia Tourliani
Highlights from your plan
Little Venice ©
Little Venice
Elia Beach ©
Elia Beach
Panormos Beach ©
Panormos Beach

2
nights
Athens

Athens ©
One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
Discover out-of-the-way places like Ancient Agora of Athens and Temple of Hephaestus. Get some historical perspective at Acropolis of Athens and Philopappos Hill. Next up on the itinerary: take an in-depth tour of Acropolis Museum, don't miss a visit to Erechtheion, take in the awesome beauty at Mount Lycabettus, and take a stroll through Plaka.

For other places to visit, more things to do, and other tourist information, read our Athens day trip site .

Do a combination of flight and subway from Mykonos Town to Athens in 2.5 hours. Alternatively, you can ride a ferry; or do a combination of ferry, taxi, and flight. In September, daytime highs in Athens are 34°C, while nighttime lows are 24°C. Wrap up your sightseeing on the 25th (Sat) early enough to travel back home.

Things to do in Athens

Historic Sites Parks Neighborhoods
Highlights from your plan
Plaka ©
Plaka
Acropolis of Athens ©
Acropolis of Athens
Acropolis Museum ©
Acropolis Museum

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