17 days in Greece Itinerary

The place where Cretan and Venetian cultures merged in the 13th century, Chania Town attracts throngs of tourists with its well-preserved medieval harbor.

Bring the kids along to Rethymnon Old Town and Agia Marina Beach. Get some cultural insight at Lighthouse of Chania and Archaeological Museum of Chania. Explore Chania Town's surroundings by going to Lake Kournas (in Kournas) and St. Nicholas Church (in Georgioupolis). There's much more to do: enjoy the sand and surf at Agii Apostoli Beach, delve into the distant past at Archaeological Site of Ancient Aptera, explore the different monuments and memorials at German Military Cemetery, and discover the deep blue sea with a scuba or snorkeling tour.

For photos, maps, where to stay, and other tourist information, use the Chania Town trip planner.

Chicago, USA to Chania Town is an approximately 15.5-hour flight. Traveling from Chicago to Chania Town, you'll lose 8 hours due to the time zone difference. Plan for somewhat warmer temperatures traveling from Chicago in September, with highs in Chania Town at 84°F and lows at 68°F. Finish your sightseeing early on the 9th (Fri) to allow enough time to take a shuttle to Heraklion.

Crete's largest city, Heraklion remains best known for its proximity to a sprawling Bronze Age archaeological site, once the center of a vanished Minoan civilization.

On the 10th (Sat), explore the ancient world of The Palace of Knossos, then step into the grandiose world of Castello del Molo (Koules), then take in the architecture and atmosphere at Church of Saint Titus, and finally take an in-depth tour of Heraklion Archaeological Museum. Get ready for a full day of sightseeing on the 11th (Sun): examine the collection at Kazantzakis Museum, get up close and personal with brilliant marine life at CRETAquarium, then get a new perspective on nature at The Natural History Museum of Crete, and finally stroll through Ligaria Beach.

For traveler tips, ratings, reviews, and other tourist information, read Heraklion online trip builder.

Take a shuttle from Chania Town to Heraklion in 2 hours. Alternatively, you can drive; or take a bus. In September in Heraklion, expect temperatures between 82°F during the day and 69°F at night. Finish your sightseeing early on the 11th (Sun) so you can ride a ferry to Fira.

Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.

Take a break from the city and head to Kamari Beach and Perissa Black Sand Beach. You'll explore and learn at Museum of Prehistoric Thira and Wine Museum Koutsogiannopoulos. The adventure continues: explore the striking landscape at Skaros Rock, enjoy the sand and surf at Red Beach, get a dose of the wild on Santorini Sailing, and relax and rejuvenate at some of the best spas.

For other places to visit, more things to do, reviews, and other tourist information, refer to the Fira journey maker app.

You can ride a ferry from Heraklion to Fira in 2.5 hours. In September in Fira, expect temperatures between 82°F during the day and 70°F at night. Cap off your sightseeing on the 15th (Thu) early enough to catch the ferry to Naxos Town.

Naxos Town tops the itinerary of most visitors exploring the Aegean islands, drawing their attention with taverns, shops, beaches, and ancient ruins.

Start off your visit on the 16th (Fri): delve into the distant past at The Temple of Apollo – Portara, then steep yourself in history at Old Town, then explore the galleries of Fish & Olive, and finally stroll through Mikri Vigla Beach. Get ready for a full day of sightseeing on the 17th (Sat): take a stroll through Kastro, enjoy the sand and surf at Plaka Beach, and then enjoy the sand and surf at Agios Prokopios Beach.

For where to stay, more things to do, maps, and more tourist information, read our Naxos Town trip planning app.

Getting from Fira to Naxos Town by ferry takes about 2.5 hours. Other options: fly. In September, daily temperatures in Naxos Town can reach 81°F, while at night they dip to 70°F. Cap off your sightseeing on the 17th (Sat) early enough to catch the ferry to 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.

Start off your visit on the 18th (Sun): kick back and relax at Martselo beach, then contemplate the long history of Lefkes, then pause for some serene contemplation at Panagia Ekatondapiliani, and finally head off the coast to Parikia Town.

For other places to visit, reviews, maps, and more tourist information, read Paros trip planner.

You can ride a ferry from Naxos Town to Paros in an hour. Expect a daytime high around 81°F in September, and nighttime lows around 70°F. Finish up your sightseeing early on the 18th (Sun) so you can catch the ferry to 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.

You'll visit kid-friendly attractions like Little Venice and Agios Stefanos Beach. Relax by the water at Paradise Beach and Paralia Kalafati. The adventure continues: tour the pleasant surroundings at Panormos Beach, kick back and relax at Kalo Livadi Beach, don't miss a visit to The Windmills (Kato Milli), and see the interesting displays at Aegean Maritime Museum.

For where to stay, traveler tips, photos, and more tourist information, refer to the Mykonos Town day trip planning app.

Ride a ferry from Paros to Mykonos Town in 2 hours. Expect a daytime high around 79°F in September, and nighttime lows around 69°F. Wrap up your sightseeing on the 22nd (Thu) to allow time to fly back home.