16 days in Greece Itinerary

16 days in Greece Itinerary

Created using Inspirock Greece visit planner

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Route & dates

Start: Winnipeg
Fly:  17 h 30 min
1
Mykonos Town
— 3 nights
Drive:  1 h 30 min
2
Naxos Town
— 2 nights
Drive:  5 h 15 min
3
Oia
— 4 nights
Ferry + Drive:  3 h 45 min
4
Chania Town
— 3 nights
Fly:  3 h 30 min
5
Athens
— 2 nights
Subway + Fly:  16 h 30 min
End: Winnipeg

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.
Mykonos Town is known for nightlife, beaches, and historic sites. Your plan includes some of its best attractions: take a stroll through Little Venice, get engrossed in the history at Archaeological Museum of Mykonos, make a trip to The Windmills (Kato Milli), and kick back and relax at Elia Beach.

To find reviews, traveler tips, maps, and tourist information, read our Mykonos Town trip planning app.

Winnipeg, Canada to Mykonos Town is an approximately 18- hour flight. You can also do a combination of flight, bus, and ferry; or do a combination of flight and ferry. The time zone difference when traveling from Winnipeg to Mykonos Town is 8 hours. Prepare for a bit warmer weather when traveling from Winnipeg in September: high temperatures in Mykonos Town hover around 30°C and lows are around 24°C. On the 14th (Tue), wrap the sightseeing up by early afternoon so you can drive to Naxos Town.

Things to do in Mykonos Town

Beaches Parks Outdoors

Side Trips

Paradise Beach, Elia Beach, Panormos Beach, Platis Gialos Beach, Mykonos Brewing Company
Highlights from your plan
Paradise Beach ©
Paradise Beach
Little Venice ©
Little Venice
The Windmills (Kato Milli) ©
The Windmills (Kato Milli)

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 14th (Tue), view the masterpieces at Fish & Olive and then explore the ancient world of Portara.

To see photos, traveler tips, and tourist information, refer to the Naxos Town trip builder site.

Getting from Mykonos Town to Naxos Town by car takes about 1.5 hours. In September, daily temperatures in Naxos Town can reach 32°C, while at night they dip to 24°C. Finish your sightseeing early on the 16th (Thu) so you can drive to Oia.

Things to do in Naxos Town

Historic Sites Neighborhoods Beaches

Side Trips

Agios Prokopios Beach, Fish & Olive
Highlights from your plan
Portara ©
Portara
Kastro ©
Kastro
Old Town ©
Old Town

4
nights
Oia

Every day hundreds of visitors come to Oia just to experience its sunsets.
Explore Oia's surroundings by going to Akrotiri (Akrotiri & Red Beach), Perissa Black Sand Beach (in Perissa) and Kamari (Kamari Beach & Ancient Thera). Next up on the itinerary: don't miss a visit to Sunset in Oia, take in the exciting artwork at Oria Gallery, explore the galleries of Mnemossyne Gallery, and do a tasting at Santo Winery.

For other places to visit, maps, ratings, and tourist information, read Oia day trip planner.

Drive from Naxos Town to Oia in 5.5 hours. In September, daily temperatures in Oia can reach 32°C, while at night they dip to 24°C. Finish your sightseeing early on the 20th (Mon) to allow enough time to travel to Chania Town.

Things to do in Oia

Parks Beaches Outdoors

Side Trips

Fira, Akrotiri, Imerovigli, Kamari, Perissa Black Sand Beach
Highlights from your plan
Wine Tours & Tastings
Akrotiri ©
Akrotiri
Sunset in Oia ©
Sunset in Oia

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.
On the 21st (Tue), you'll have a packed day of sightseeing: explore the striking landscape of Samaria Gorge National Park, then see the interesting displays at Greek National Football Museum, then go for a stroll along the water at Old Venetian Harbor, and finally explore the different monuments and memorials at Souda Bay War Cemetery.

To find traveler tips, photos, more things to do, and tourist information, read our Chania Town journey maker site.

Do a combination of ferry and car from Oia to Chania Town in 4 hours. Alternatively, you can do a combination of bus and flight; or do a combination of ferry and bus. In September, daytime highs in Chania Town are 34°C, while nighttime lows are 23°C. You will have some time to spend on the 23rd (Thu) before leaving for Athens.

Things to do in Chania Town

Parks Nature Historic Sites

Side Trips

Rethymnon, Samaria Gorge National Park, Lake Kournas, Souda Bay War Cemetery
Highlights from your plan
Greek National Football Museum ©
Greek National Football Museum
Samaria Gorge National Park ©
Samaria Gorge National Park
Rethymnon Old Town ©
Rethymnon Old Town

2
nights
Athens

Athens ©
One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
Start off your visit on the 23rd (Thu): wander the streets of Plaka, admire the masterpieces at Benaki Museum, and then take an in-depth tour of National Archaeological Museum. On your second day here, take an in-depth tour of Acropolis Museum, appreciate the history behind Temple of Olympian Zeus, then make a trip to Plateia Syntagmatos, and finally contemplate the long history of Acropolis of Athens.

To see photos, reviews, traveler tips, and other tourist information, read our Athens driving holiday planner.

Getting from Chania Town to Athens by flight takes about 3.5 hours. Other options: do a combination of shuttle and flight; or ride a ferry. In September, plan for daily highs up to 34°C, and evening lows to 24°C. You'll have a few hours on the 25th (Sat) to wrap things up before traveling home.

Things to do in Athens

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

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