15 days in Greece Itinerary
Created using Inspirock Greece trip planner
Start: Portland
Bus to Boston, Fly to Fira
1
Fira, Santorini
— 5 nights
Ferry
2
Mykonos Town, Mykonos
— 3 nights
Ferry
3
Naxos Town, Naxos
— 2 nights
Fly
4
Rethymnon, Crete
— 3 nights
Drive to Chania International Airport, Fly to Portland
End: Portland
Fri, Sep 23 - Fri, Oct 7
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Fira, Santorini — 5 nights

Discover out-of-the-way places like Skaros Rock and Wine Museum Koutsogiannopoulos. Visiting Kamari Beach and Red Beach will get you outdoors. The adventure continues: relax and rejuvenate at some of the best spas, examine the collection at Museum of Prehistoric Thira, take in the architecture and atmosphere at Ekklisia Panagia Platsani, and take an unforgettable tour with a helicopter tour.
To find more things to do, photos, reviews, and tourist information, refer to the Fira trip planner.
Portland, USA to Fira is an approximately 18.5-hour combination of bus and flight. You can also fly. The time zone difference moving from Eastern Standard Time (EST) to Eastern European Standard Time (EET) is 7 hours. In September, Fira is somewhat warmer than Portland - with highs of 82°F and lows of 70°F. Wrap up your sightseeing on the 29th (Thu) to allow time to ride a ferry to Mykonos Town.
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To find more things to do, photos, reviews, and tourist information, refer to the Fira trip planner.
Portland, USA to Fira is an approximately 18.5-hour combination of bus and flight. You can also fly. The time zone difference moving from Eastern Standard Time (EST) to Eastern European Standard Time (EET) is 7 hours. In September, Fira is somewhat warmer than Portland - with highs of 82°F and lows of 70°F. Wrap up your sightseeing on the 29th (Thu) to allow time to ride a ferry to Mykonos Town.
Side Trips
Find places to stay Sep 23 — 29:
Highlights from your trip
Mykonos Town, Mykonos — 3 nights

Chora Mykonos
Escape the urban bustle at Agios Stefanos Beach and Elia Beach. Satisfy your inner culture vulture at Little Venice and Aegean Maritime Museum. The adventure continues: make a trip to Matoyianni Street and enjoy the sand and surf at Kalo Livadi Beach.
For photos, other places to visit, ratings, and more tourist information, refer to the Mykonos Town online journey maker.
You can ride a ferry from Fira to Mykonos Town in 2.5 hours. Another option is to fly. In September, plan for daily highs up to 79°F, and evening lows to 69°F. Finish your sightseeing early on the 2nd (Sun) so you can ride a ferry to Naxos Town.
more
For photos, other places to visit, ratings, and more tourist information, refer to the Mykonos Town online journey maker.
You can ride a ferry from Fira to Mykonos Town in 2.5 hours. Another option is to fly. In September, plan for daily highs up to 79°F, and evening lows to 69°F. Finish your sightseeing early on the 2nd (Sun) so you can ride a ferry to Naxos Town.
Side Trips
Find places to stay Sep 29 — Oct 2:
Highlights from your trip
Naxos Town, Naxos — 2 nights

On the 3rd (Mon), explore the ancient world of The Temple of Apollo – Portara, then wander the streets of Old Town, and then wander the streets of Kastro. Get ready for a full day of sightseeing on the next day: stroll through Plaka Beach and then enjoy the sand and surf at Agios Prokopios Beach.
To see photos, ratings, maps, and other tourist information, refer to the Naxos Town day trip site.
Getting from Mykonos Town to Naxos Town by ferry takes about 1.5 hours. Other options: fly. October in Naxos Town sees daily highs of 73°F and lows of 63°F at night. Wrap up your sightseeing on the 4th (Tue) to allow time to fly to Rethymnon.
more
To see photos, ratings, maps, and other tourist information, refer to the Naxos Town day trip site.
Getting from Mykonos Town to Naxos Town by ferry takes about 1.5 hours. Other options: fly. October in Naxos Town sees daily highs of 73°F and lows of 63°F at night. Wrap up your sightseeing on the 4th (Tue) to allow time to fly to Rethymnon.
Side Trips
Find places to stay Oct 2 — 4:
Highlights from your trip
Rethymnon, Crete — 3 nights
Start off your visit on the 5th (Wed): take a memorable tour with Tours and then stroll through Rethymno Beach. On the next day, take in the architecture and atmosphere at St. Nicholas Church, then contemplate the waterfront views at Lake Kournas, and then take a stroll through Rethymnon Old Town.
To find reviews and other tourist information, use the Rethymnon trip planner.
Traveling by flight from Naxos Town to Rethymnon takes 4 hours. Alternatively, you can do a combination of ferry and taxi; or do a combination of ferry and bus. In October, daytime highs in Rethymnon are 75°F, while nighttime lows are 61°F. Finish your sightseeing early on the 7th (Fri) to allow enough time to travel back home.
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To find reviews and other tourist information, use the Rethymnon trip planner.
Traveling by flight from Naxos Town to Rethymnon takes 4 hours. Alternatively, you can do a combination of ferry and taxi; or do a combination of ferry and bus. In October, daytime highs in Rethymnon are 75°F, while nighttime lows are 61°F. Finish your sightseeing early on the 7th (Fri) to allow enough time to travel back home.
Side Trips
Find places to stay Oct 4 — 7:
Highlights from your trip
Greece travel guide
Few places manage to capture the world's imagination quite like Greece, a land of sun-kissed coastlines, tranquil whitewashed villages, lively seaside towns, and well-preserved ancient sites. One of the world's top tourist destinations since ancient times, the country draws nearly 20 million visitors each year. Athens, the birthplace of Western civilization, continues to attract the biggest crowds and serves as a base for exploring the country and its 227 inhabited islands. Away from its cities, Greece features a picturesque countryside of olive groves, vineyards, and tiny settlements nestled against rolling hills and rugged mountain ranges. Explore the old mainland on foot and discover the islands on a guided boat or ferry tour.