22 days in Greece Itinerary

22 days in Greece Itinerary

Created using Inspirock Greece visit planner

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Route & dates

22 days in Greece Itinerary

Start: Boston
Fly:  11​h 45​min
1
Corfu Town, Corfu
— 3 nights
ferry + Drive:  6​h 15​min
2
Olympia
— 3 nights
Drive + ferry:  8​h
3
Paros
— 1 night
Drive:  2​h
4
Naxos
— 2 nights
Drive:  4​h 45​min
5
Pyrgos, Santorini
— 1 night
ferry:  2​h 30​min
6
Rethymnon, Crete
— 2 nights
bus:  1​h 15​min
7
Chania Town, Crete
— 2 nights
shuttle + Fly:  4​h 30​min
8
Rhodes Town, Rhodes
— 2 nights
Fly:  3​h 30​min
9
Athens
— 3 nights
Fly:  15​h
End: Boston

3
nights
Corfu Town, Corfu

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.
Let the collections at Achilleion Museum and Casa Parlante capture your imagination. Your cultural itinerary includes sights like Old Fortress Corfu and New Fortress. You'll find plenty of places to visit near Corfu Town: Agios Matheos (Gardiki Castle & Pantokrator), Canal D'Amour (in Sidari) and Porto Timoni Beach (in Afionas). The adventure continues: take a stroll through Corfu Old Town, stop by Sweet 'N Spicy Bahar Shop, step into the grandiose world of Mon Repos Palace, and stroll the grounds of British Cemetry.

For other places to visit, more things to do, and tourist information, use the Corfu Town online route planner .

Boston, USA to Corfu Town is an approximately 12-hour flight. Due to the time zone difference, you'll lose 7 hours traveling from Boston to Corfu Town. Prepare for a bit warmer weather when traveling from Boston in September: high temperatures in Corfu Town hover around 82°F and lows are around 65°F. Finish your sightseeing early on the 26th (Thu) so you can travel to Olympia.

Things to do in Corfu Town

Historic Sites Parks Outdoors

Side Trips

Agios Matheos, Achilleion Museum, Canal D'Amour, Porto Timoni Beach
Find places to stay Sep 22 — 26:
Highlights from your plan
Casa Parlante ©
Casa Parlante
Porto Timoni Beach ©
Porto Timoni Beach
Canal D'Amour ©
Canal D'Amour

3
nights
Olympia

Olympia ©
Inhabited since prehistoric times, Olympia remains best known as the site of the original Olympic Games, held there for the first time in 776 BCE.
Escape the urban bustle at Kakovatos Beach and Port of Killini. Step off the beaten path and head to Archaeological Site of Olympia and Archimedes Museum. Explore Olympia's surroundings by going to Kastro Chlemoutsi (in Kastro), Agios Andreas (in Sifnos) and Katakolo (Aristoteles Olivewood Workshop & Greek Art Gallery). There's still lots to do: get engrossed in the history at Archaeological Museum of Olympia, do a tasting at Olympia Land Winery, experience rural life at Klio's Honey Farm, and pause for some photo ops at Hermes by Praxiteles.

For where to stay, more things to do, ratings, and tourist information, read our Olympia trip itinerary planner.

You can do a combination of ferry and car from Corfu Town to Olympia in 6.5 hours. Alternatively, you can do a combination of flight and bus; or take a bus. In September in Olympia, expect temperatures between 83°F during the day and 63°F at night. Finish your sightseeing early on the 30th (Mon) to allow enough time to travel to Paros.

Things to do in Olympia

Parks Outdoors Beaches

Side Trips

Katakolo, Kakovatos Beach, Port of Killini, Glyfa Beach, Kastro Chlemoutsi
Find places to stay Sep 26 — 30:
Highlights from your plan
Archaeological Site of Olympia ©
Archaeological Site of Olympia
Archaeological Museum of Olympia ©
Archaeological Museum of Olympia
Kastro Chlemoutsi ©
Kastro Chlemoutsi

1
night
Paros

Paros ©
Long ignored by tourists because of its reputation as a plain ferry hub, Paros today serves as one of the Aegean's major holiday destinations, luring travelers with its fashionable resort towns and quaint mountain villages.
On the 1st (Tue), stop by Memories Jewellery, then head off the coast to Parikia Town, then stroll through Aliki Beach, and finally enjoy the sand and surf at Piso Aliki Beach.

Quickly create a custom-made itinerary for Paros using our trip planner.

Do a combination of car and ferry from Olympia to Paros in 8 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus and ferry. Expect somewhat warmer evenings in Paros when traveling from Olympia in September, with lows around 70°F. Wrap up your sightseeing on the 1st (Tue) to allow time to drive to Naxos.

Things to do in Paros

Parks Outdoors Beaches
Find places to stay Sep 30 — Oct 1:
Highlights from your plan
Parikia Town ©
Parikia Town
Aliki Beach ©
Aliki Beach
Piso Aliki Beach ©
Piso Aliki Beach

2
nights
Naxos

Naxos ©
Zeus, the master of all gods from Greek mythology, allegedly grew up in a cave on Naxos, a small but fertile island in the South Aegean Sea.
Kick off your visit on the 2nd (Wed): enjoy the sand and surf at Alyko Dimou Naxou, pause for some serene contemplation at Panagia Drossiani Church, examine the collection at Eggares Olive Press Museum, then explore the ancient world of Portara, and finally explore the ancient world of Temple of Apollo. On your second day here, take in the architecture and atmosphere at Panagia Myrtidiotissa, kick back and relax at Alyko Beach, then see the interesting displays at Distillery M. G. Vallindras Eirini Frangoudaki, then take in the exciting artwork at Fish & Olive, and finally look for gifts at Naxia Gi.

To find reviews, maps, photos, and other tourist information, go to the Naxos trip itinerary planning site .

Traveling by car from Paros to Naxos takes 2 hours. In October in Naxos, expect temperatures between 73°F during the day and 63°F at night. Cap off your sightseeing on the 3rd (Thu) early enough to go by car to Pyrgos.

Things to do in Naxos

Parks Outdoors Beaches
Find places to stay Oct 1 — 3:
Highlights from your plan
Portara ©
Portara
Fish & Olive ©
Fish & Olive
Alyko Beach ©
Alyko Beach

1
night
Pyrgos, Santorini

Pyrgos ©
Pyrgos provides one of the finest examples of Cycladic architecture in Greece, exemplified by the town's labyrinthine streets and whitewashed stone buildings.
Start off your visit on the 4th (Fri): see the interesting displays at Wine Museum Koutsogiannopoulos, take in the exciting artwork at Art Space, do a tasting at Venetsanos Winery, then see the interesting displays at Cultural Village, and finally explore the historical opulence of Castelli of Pyrgos.

For ratings, more things to do, maps, and more tourist information, read our Pyrgos trip site .

Traveling by car from Naxos to Pyrgos takes 5 hours. October in Pyrgos sees daily highs of 74°F and lows of 64°F at night. Finish up your sightseeing early on the 4th (Fri) so you can catch the ferry to Rethymnon.

Things to do in Pyrgos

Museums Wineries Shopping

Side Trips

Art Space, Wine Museum Koutsogiannopoulos, Venetsanos Winery
Find places to stay Oct 3 — 4:
Highlights from your plan
Wine Museum Koutsogiannopoulos ©
Wine Museum Koutsogiannopoulos
Venetsanos Winery ©
Venetsanos Winery
Art Space ©
Art Space

2
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.
On the 5th (Sat), learn about winemaking at Winery Dourakis, identify plant and animal life at Reptisland, experience rural life at Paraschakis Olive Oil - Crete, then explore the ancient world of Ancient Eleutherna, and finally explore the different monuments and memorials at Minoiko Nekrotafeio Armenon. On your second day here, examine the collection at Chromonastiri Military Museum, look for gifts at mariannas, see the interesting displays at Contemporary Art Museum of Crete, then take in the architecture and atmosphere at Four Martyrs Church, and finally take an in-depth tour of Historical and Folklore Museum of Rethymno.

Planning Rethymnon trip won't be overwheling when you use's Insprock itinerary maker.

You can ride a ferry from Pyrgos to Rethymnon in 2.5 hours. Another option is to do a combination of ferry and taxi. Expect a daytime high around 75°F in October, and nighttime lows around 61°F. Finish up your sightseeing early on the 6th (Sun) so you can catcht the bus to Chania Town.

Things to do in Rethymnon

Museums Historic Sites Shopping

Side Trips

Minoiko Nekrotafeio Armenon, Reptisland, Winery Dourakis, Chromonastiri Military Museum
Find places to stay Oct 4 — 6:
Highlights from your plan
Reptisland ©
Reptisland
Chromonastiri Military Museum ©
Chromonastiri Military Museum
Minoiko Nekrotafeio Armenon ©
Minoiko Nekrotafeio Armenon

2
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.
On the 7th (Mon), see the interesting displays at Greek National Football Museum, take in the architecture and atmosphere at Cathedral of Eisodion tis Theotokou, then tour the pleasant surroundings at Agii Apostoli Beach, then examine the collection at Ancient Olive Tree, and finally explore the different monuments and memorials at German War Cemetery. Get ready for a full day of sightseeing on the next day: take in the architecture and atmosphere at Cathedral of Assumption, explore the different monuments and memorials at Souda Bay War Cemetery, pause for some serene contemplation at Holy Trinity Monastery (Agia Triada), steep yourself in history at The Venizelos Tombs, then examine the collection at Museum-Residence of Eleftherios Venizelos, and finally stop by Alexia Handmade Jewelry.

To find traveler tips, more things to do, reviews, and more tourist information, use the Chania Town trip site .

You can take a bus from Rethymnon to Chania Town in 1.5 hours. Another option is to drive. Expect a daytime high around 75°F in October, and nighttime lows around 61°F. Finish up your sightseeing early on the 8th (Tue) so you can travel to Rhodes Town.

Things to do in Chania Town

Historic Sites Parks Outdoors

Side Trips

Holy Trinity Monastery (Agia Triada), Ancient Olive Tree, German War Cemetery, Souda Bay War Cemetery
Find places to stay Oct 6 — 8:
Highlights from your plan
Greek National Football Museum ©
Greek National Football Museum
Agii Apostoli Beach ©
Agii Apostoli Beach
German War Cemetery ©
German War Cemetery

2
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.
Start off your visit on the 9th (Wed): explore the ancient world of Ancient Kamiros, look for gifts at Natura Rodos, pause for some serene contemplation at Filerimos Monastery, then make a trip to Mandraki Harbour, and finally explore the ancient world of The Acropolis of Rhodes. Get ready for a full day of sightseeing on the 10th (Thu): pause for some serene contemplation at Our Lady of the Castle, then contemplate the long history of Street of the Knights, then examine the collection at Bee Museum, and finally pause for some serene contemplation at Church of Our Lady of Filerimos.

Ask Inspirock to suggest an itinerary and make planning a trip to Rhodes Town fast, fun, and easy.

You can do a combination of shuttle and flight from Chania Town to Rhodes Town in 4.5 hours. Other options are to fly; or do a combination of car and ferry. In October, plan for daily highs up to 76°F, and evening lows to 66°F. Wrap up your sightseeing on the 10th (Thu) to allow time to travel to Athens.

Things to do in Rhodes Town

Historic Sites Shopping Museums

Side Trips

Filerimos, Ancient Kamiros, Bee Museum, Natura Rodos
Find places to stay Oct 8 — 10:
Highlights from your plan
Ancient Kamiros
Ancient Kamiros
Church of Our Lady of Filerimos ©
Church of Our Lady of Filerimos
Street of the Knights ©
Street of the Knights

3
nights
Athens

Athens ©
One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
On the 11th (Fri), take a stroll through Plaka, then take an in-depth tour of Acropolis Museum, and then explore the ancient world of Acropolis of Athens. On the next day, admire the masterpieces at National Archaeological Museum, take in the architecture and atmosphere at Church of Kapnikarea, explore the ancient world of Temple of Hephaestus, then make a trip to Erechtheion, and finally pause for some photo ops at Temple of Athena Nike.

To see maps, reviews, and other tourist information, read Athens vacation planner .

Getting from Rhodes Town to Athens by flight takes about 3.5 hours. Other options: ride a ferry; or do a combination of ferry and car. Plan for slightly colder nights when traveling from Rhodes Town in October since evenings lows in Athens dip to 60°F. Wrap up your sightseeing by early afternoon on the 13th (Sun) to allow enough time to travel back home.

Things to do in Athens

Historic Sites Museums Neighborhoods

Side Trip

Citadel and Treasury of Atreus
Find places to stay Oct 10 — 13:
Highlights from your plan
Plaka ©
Plaka
Acropolis of Athens ©
Acropolis of Athens
Acropolis Museum ©
Acropolis Museum

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