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.

Change things up with these side-trips from Corfu Town: Canal D'Amour (in Sidari), St. Spyridon First Beach (in Agios Spyridonas) and Paleokastritsa Beach (in Paleokastritsa). There's much more to do: explore the ancient world of Old Fortress Corfu, admire the striking features of Corfu Museum of Asian Art, explore the historical opulence of Mon Repos Palace, and make a trip to Spianada Square.

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

Washington, USA to Corfu Town is an approximately 16.5-hour combination of flight and car. You'll lose 7 hours traveling from Washington to Corfu Town due to the time zone difference. Traveling from Washington in September, expect a bit warmer with lows of 65°F in Corfu Town. Finish your sightseeing early on the 5th (Tue) so you can fly 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.

Kick off your visit on the 6th (Wed): take in the spiritual surroundings of Paraportiani Church, make a trip to The Windmills (Kato Milli), then wander the streets of Little Venice, and finally make a trip to Rarity Gallery. Get ready for a full day of sightseeing on the next day: discover the deep blue sea with GoDive Mykonos PADI Diving Resort, enjoy the sand and surf at Paradise Beach, and then enjoy the sand and surf at Platis Gialos Beach.

To see where to stay, reviews, other places to visit, and other tourist information, refer to the Mykonos Town trip planner.

Traveling by flight from Corfu Town to Mykonos Town takes 5 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of bus and ferry. In September, daytime highs in Mykonos Town are 79°F, while nighttime lows are 69°F. Wrap up your sightseeing on the 7th (Thu) early enough to ride a 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, kick back and relax at Red Beach, tour the pleasant surroundings at Perissa Black Sand Beach, and indulge your taste buds at Food & Drink.

Plan a trip to Fira easily and quickly by telling Klarna Trips to suggest an itinerary.

You can ride a ferry from Mykonos Town to Fira in 2.5 hours. Another option is to fly. Expect a daytime high around 82°F in September, and nighttime lows around 70°F. Finish your sightseeing early on the 11th (Mon) to allow enough time to ride a ferry 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 12th (Tue): take an in-depth tour of Heraklion Archaeological Museum, then steep yourself in history at The Palace of Knossos, and then indulge in some personalized pampering at Aegeo Spas. Here are some ideas for day two: observe the fascinating underwater world at CRETAquarium, learn more about the world around you at The Natural History Museum of Crete, then take an in-depth tour of Historical Museum of Crete, then explore the historical opulence of Castello del Molo (Koules), and finally take in the architecture and atmosphere at Church of Saint Titus.

To see reviews, more things to do, photos, and more tourist information, use the Heraklion trip itinerary planning site.

You can ride a ferry from Fira to Heraklion in 2.5 hours. In September in Heraklion, expect temperatures between 82°F during the day and 69°F at night. Finish your sightseeing early on the 13th (Wed) to allow enough time to fly to Tsilivi (Planos).

A growing favorite with international vacationers, Tsilivi sits on the northern coast of Zakynthos.

Kick off your visit on the 14th (Thu): kick back and relax at Laganas Beach, take some stellar pictures from Bochali View Point, then take a tour by water with Boat Tours & Water Sports, and finally stop by Medusa Boutique.

To see traveler tips, other places to visit, where to stay, and other tourist information, you can read our Tsilivi (Planos) trip builder.

You can fly from Heraklion to Tsilivi (Planos) in 4.5 hours. Alternatively, you can do a combination of ferry and bus; or do a combination of ferry and bus. In September, plan for daily highs up to 83°F, and evening lows to 65°F. On the 15th (Fri), wrap the sightseeing up by early afternoon so you can travel back home.