20 days in Greek Isles Itinerary

20 days in Greek Isles Itinerary

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Route & dates

20 days in Greek Isles Itinerary

Start: Vancouver
Fly:  18​h
1
Oia, Santorini
— 4 nights
ferry + Drive:  3​h 45​min
2
Chania Town, Crete
— 3 nights
bus:  1​h 15​min
3
Rethymnon, Crete
— 3 nights
shuttle + Fly:  3​h 45​min
4
Rhodes Town, Rhodes
— 3 nights
Fly:  5​h 15​min
5
Mykonos Town, Mykonos
— 5 nights
Fly:  17​h 30​min
End: Vancouver

4
nights
Oia, Santorini

Oia ©
Every day hundreds of visitors come to Oia just to experience its sunsets.
Escape the urban bustle at Kamari Beach and Red Beach. Visit Perissa Black Sand Beach and Caldera Beach for some beach relaxation. Explore the numerous day-trip ideas around Oia: Artemis Karamolegos Winery (in Exo Gonia), Akrotiri (Akrotiri & Santo Horse Riding) and Perivolos (in Perivolos). Next up on the itinerary: take in the architecture and atmosphere at Ekklisia Panagia Platsani, hike along Ekklisia Theoskepasti hiking trail, get great views at Sunset in Oia, and get a taste of the local shopping with Mnemossyne Gallery.

Plan trip to Oia with our itinerary maker to find out where to go and what to do.

Vancouver, Canada to Oia 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. You'll lose 10 hours traveling from Vancouver to Oia due to the time zone difference. Plan for somewhat warmer temperatures traveling from Vancouver in September, with highs in Oia at 32°C and lows at 24°C. Finish your sightseeing early on the 27th (Fri) so you can travel to Chania Town.

Things to do in Oia

Outdoors Parks Beaches

Side Trips

Akrotiri, Imerovigli, Artemis Karamolegos Winery, Perissa Black Sand Beach, Ekklisia Theoskepasti hiking trail
Highlights from your plan
Akrotiri ©
Akrotiri
Kamari Beach ©
Kamari Beach
Red Beach ©
Red Beach

3
nights
Chania Town, Crete

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.
You'll get in some beach time at Balos Lagoon and Falassarna Beach. Popular historic sites such as Souda Bay War Cemetery and Kastro Gramvoussas are in your itinerary. There's much more to do: take in breathtaking views at Samaria Gorge National Park, do a tasting at Manousakis Winery, stroll the grounds of German War Cemetery, and see the interesting displays at MINOAN'S WORLD.

Plan a Chania Town trip in moments using our itinerary builder.

Traveling by combination of ferry and car from Oia to Chania Town takes 4 hours. Alternatively, you can fly. In September, daytime highs in Chania Town are 34°C, while nighttime lows are 23°C. Finish your sightseeing early on the 30th (Mon) so you can take a bus to Rethymnon.

Things to do in Chania Town

Parks Outdoors Beaches

Side Trips

German War Cemetery, Samaria Gorge National Park, Kastro Gramvoussas, Souda Bay War Cemetery, Balos Lagoon
Highlights from your plan
Balos Lagoon ©
Balos Lagoon
Samaria Gorge National Park ©
Samaria Gorge National Park
Falassarna Beach ©
Falassarna Beach

3
nights
Rethymnon, Crete

Rethymnon ©
Rethymnon combines the old-fashioned charm of a small town with proximity to long sandy beaches with all the modern conveniences usually found in big tourist resorts.
Deepen your sense of the past at sights like The Palace of Knossos and Monastery of Arkadi. Take a break from the city and head to Reptisland and The Natural History Museum of Crete. Venture out of the city with trips to Heraklion (Church of Saint Titus & Heraklion Archaeological Museum) and Monastery Savvathiana (in Rodia). There's lots more to do: wander the streets of Rethymnon Old Town, contemplate the long history of The Venetian Fortezza, relax in the rural setting at Paraschakis Olive Oil - Crete, and contemplate in the serene atmosphere at Monastery of Panagia Chalevi.

To see where to stay, maps, more things to do, and more tourist information, you can read our Rethymnon tour itinerary planner.

Take a bus from Chania Town to Rethymnon in 1.5 hours. Alternatively, you can drive. September in Rethymnon sees daily highs of 34°C and lows of 23°C at night. Wrap up your sightseeing on the 3rd (Thu) to allow time to travel to Rhodes Town.

Things to do in Rethymnon

Historic Sites Museums Wildlife

Side Trips

Heraklion, Reptisland, Monastery Savvathiana, The Palace of Knossos
Highlights from your plan
Rethymnon Old Town ©
Rethymnon Old Town
The Palace of Knossos ©
The Palace of Knossos
Monastery of Arkadi ©
Monastery of Arkadi

3
nights
Rhodes Town, Rhodes

Rhodes Town ©
A conglomeration of many distinct architectural styles, Rhodes Town is the biggest urban center of the eponymous Greek island known for its golden beaches and relaxed way of life.
Get some historical perspective at Village of Lindos and Palace of the Grand Master of the Knights of Rhodes. Escape the urban bustle at Faliraki Beach and Lindos Beach. Venture out of the city with trips to Acropolis of Lindos (in Lindos) and Agathi Beach (in Haraki). Next up on the itinerary: stroll through Cave Archangel Michael Panormitis and explore the engaging exhibits at Rodos Nature - Folklore Museum.

For photos, ratings, maps, and other tourist information, read Rhodes Town online day trip planner .

Traveling by combination of shuttle and flight from Rethymnon to Rhodes Town takes 4 hours. Alternatively, you can do a combination of car and ferry. In October, plan for daily highs up to 28°C, and evening lows to 22°C. Cap off your sightseeing on the 6th (Sun) early enough to travel to Mykonos Town.

Things to do in Rhodes Town

Parks Outdoors Beaches

Side Trips

Lindos, Faliraki Beach, Rodos Nature - Folklore Museum, Agathi Beach
Highlights from your plan
Village of Lindos ©
Village of Lindos
Faliraki Beach ©
Faliraki Beach
Acropolis of Lindos ©
Acropolis of Lindos

5
nights
Mykonos Town, Mykonos

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.
Your itinerary includes some good beach time at Panormos Beach and Platis Gialos Beach. Take a break from the city and head to Paradise Beach and Super Paradise Beach. There's still lots to do: take a stroll through Little Venice, kick back and relax at Kapari Beach, don't miss a visit to The Windmills (Kato Milli), and visit a coastal fixture at Armenistis Lighthouse.

For photos, maps, and tourist information, read our Mykonos Town trip planner .

Getting from Rhodes Town to Mykonos Town by flight takes about 5.5 hours. Other options: do a combination of flight, taxi, and ferry; or ride a ferry. When traveling from Rhodes Town in October, plan for slightly colder days in Mykonos Town, with highs around 25°C, while nights are about the same with lows around 20°C. Cap off your sightseeing on the 11th (Fri) early enough to travel back home.

Things to do in Mykonos Town

Outdoors Parks Beaches

Side Trips

Mykonos, Paradise Beach, Armenistis Lighthouse, Elia Beach, Agios Sostis Beach
Highlights from your plan
Little Venice ©
Little Venice
Panormos Beach ©
Panormos Beach
Paradise Beach ©
Paradise Beach

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