14 days in Greek Isles Itinerary

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.

Go for a jaunt from Corfu Town to Paleokastritsa to see Paleokastritsa Beach about 36 minutes away. There's lots more to do: deepen your knowledge of military history at Old Fortress Corfu, admire the striking features of Corfu Museum of Asian Art, stop by Sweet 'N Spicy Bahar Shop, and identify plant and animal life at Corfu Donkey Rescue.

For where to stay, traveler tips, photos, and tourist information, you can read our Corfu Town travel route planner.

Chicago, USA to Corfu Town is an approximately 17-hour flight. Traveling from Chicago to Corfu Town, you'll lose 8 hours due to the time zone difference. In September, daytime highs in Corfu Town are 82°F, while nighttime lows are 65°F. Wrap up your sightseeing on the 25th (Sat) early enough to travel to Lindos.

A medieval settlement on the island of Rhodes, Lindos provides a mix of ancient history and modern attractions.

On the 26th (Sun), delve into the distant past at Acropolis of Lindos, stroll through Lindos Beach, and then stroll through Tsambika Beach. On the 27th (Mon), you'll have a packed day of sightseeing: delve into the distant past at Village of Lindos.

For more things to do, photos, traveler tips, and other tourist information, read Lindos trip planner.

Getting from Corfu Town to Lindos by combination of flight and bus takes about 7.5 hours. Other options: do a combination of bus and ferry; or do a combination of bus, train, and ferry. Traveling from Corfu Town in September, Lindos is a bit warmer at night with lows of 73°F. Finish your sightseeing early on the 27th (Mon) to allow enough time to travel 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.

Kick off your visit on the 28th (Tue): contemplate the long history of Venetian Walls and Tomb of Nikos Kazantzakis, get a new perspective on nature at The Natural History Museum of Crete, then take in the architecture and atmosphere at Church of Saint Titus, then examine the collection at Kazantzakis Museum, and finally observe the fascinating underwater world at CRETAquarium. Here are some ideas for day two: take an in-depth tour of Heraklion Archaeological Museum, look for gifts at Nerium Oleander, then take an in-depth tour of Historical Museum of Crete, and finally explore the ancient world of The Palace of Knossos.

For traveler tips and more tourist information, you can read our Heraklion trip planning tool.

Getting from Lindos to Heraklion by combination of bus and flight takes about 5.5 hours. Other options: do a combination of taxi and ferry. In September in Heraklion, expect temperatures between 82°F during the day and 69°F at night. Finish up your sightseeing early on the 29th (Wed) so you can catch the ferry to Fira.

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

Fira is known for nightlife, wineries, and museums. Your trip includes some of its best attractions: delve into the distant past at Akrotiri, enjoy the sand and surf at Red Beach, make a trip to Sunset in Oia, and get a dose of the wild on Santorini Sailing.

For traveler tips, maps, more things to do, and other tourist information, refer to the Fira trip itinerary planner.

Ride a ferry from Heraklion to Fira in 2.5 hours. September in Fira sees daily highs of 82°F and lows of 70°F at night. Wrap up your sightseeing on the 3rd (Sun) early enough to ride a 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.

On the 4th (Mon), take in the spiritual surroundings of Paraportiani Church, then make a trip to The Windmills (Kato Milli), and then wander the streets of Little Venice. Here are some ideas for day two: kick back and relax at Platis Gialos Beach and then kick back and relax at Paradise Beach.

Take the guesswork out of planning a Mykonos Town vacation by using our trip itinerary maker.

You can ride a ferry from Fira to Mykonos Town in 2.5 hours. Another option is to fly. In October, daily temperatures in Mykonos Town can reach 71°F, while at night they dip to 63°F. Wrap up your sightseeing on the 5th (Tue) early enough to fly back home.