14 days in Greek Isles & Milos Itinerary

14 days in Greek Isles & Milos Itinerary

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Route & dates

14 days in Greek Isles & Milos Itinerary

Start: Washington DC
+2
subway + bus + Fly:  18​h
1
Heraklion, Crete
— 1 night
ferry:  2​h
2
Fira, Santorini
— 5 nights
Drive:  4​h 15​min
3
Milos
— 2 nights
Fly:  2​h 15​min
4
Mykonos Town, Mykonos
— 4 nights
Fly:  15​h 30​min
End: Washington DC

1
night
Heraklion, Crete

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 8th (Fri): explore the ancient world of The Palace of Knossos, then meet the residents at Cretaquarium - Thalassocosmos, and then ponder the design of Morosini Fountain (Lion's Fountain). On the 9th (Sat), you'll have a packed day of sightseeing: test your problem-solving skills at popular escape rooms, then take an in-depth tour of Ιστορικό Μουσείο Κρήτης - Historical Museum of Crete, then learn more about the world around you at The Natural History Museum of Crete, and finally take an in-depth tour of Heraklion Archaeological Museum.

Before you visit Heraklion, use our trip planner to discover what you can do and see there.

Washington DC, USA to Heraklion is an approximately 18-hour combination of subway, bus, and flight. You can also do a combination of train, bus, and flight; or do a combination of train and flight. The time zone difference moving from Eastern Standard Time (EST) to Eastern European Time (EET) is 7 hours. In May, plan for daily highs up to 75°F, and evening lows to 60°F. Finish your sightseeing early on the 9th (Sat) to allow enough time to ride a ferry to Fira.

Things to do in Heraklion

Museums Historic Sites Fun & Games

Side Trips

The Palace of Knossos, Cretaquarium - Thalassocosmos
Find places to stay May 8 — 9:
Highlights from your plan
Heraklion Archaeological Museum ©
Heraklion Archaeological Museum
The Palace of Knossos ©
The Palace of Knossos
Cretaquarium - Thalassocosmos ©
Cretaquarium - Thalassocosmos

5
nights
Fira, Santorini

Fira ©
Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
Fira is known for nightlife, museums, spas, historic sites, and wineries. Your plan includes some of its best attractions: delve into the distant past at Akrotiri, indulge your senses at some of the top wineries in the area, kick back and relax at Perissa Black Sand Beach, and steep yourself in history at Ancient Thera.

To see maps, reviews, where to stay, and other tourist information, use the Fira trip maker .

Getting from Heraklion to Fira by ferry takes about 2 hours. May in Fira sees daily highs of 75°F and lows of 63°F at night. Finish up your sightseeing early on the 14th (Thu) so you can catch the ferry to Mykonos Town.

Things to do in Fira

Parks Outdoors Beaches

Side Trips

Oia, Kamari, Akrotiri, Imerovigli, Ekklisia Theoskepasti hiking trail
Find places to stay May 9 — 14:
Highlights from your plan
Sunset in Oia ©
Sunset in Oia
Akrotiri ©
Akrotiri
Kamari Beach ©
Kamari Beach

2
nights
Milos

Milos ©
The result of thousands of years of volcanic activity, the island of Milos features a craggy coastline interspersed by shallow beaches.
Kick off your visit on the 15th (Fri): see the interesting displays at Milos Mining Museum, then enjoy the sand and surf at Firiplaka Beach, and then enjoy the sand and surf at Kleftiko Beach. Get ready for a full day of sightseeing on the 16th (Sat): tour the pleasant surroundings at Pollonia Beach and then tour the pleasant surroundings at Sarakiniko Beach.

To see photos, reviews, traveler tips, and more tourist information, you can read our Milos trip itinerary maker .

Getting from Fira to Milos by car takes about 4.5 hours. In May in Milos, expect temperatures between 74°F during the day and 62°F at night. Cap off your sightseeing on the 16th (Sat) early enough to catch the flight to Mykonos Town.

Things to do in Milos

Outdoors Beaches Parks
Find places to stay May 14 — 16:
Highlights from your plan
Kleftiko Beach ©
Kleftiko Beach
Sarakiniko Beach ©
Sarakiniko Beach
Firiplaka Beach ©
Firiplaka Beach

4
nights
Mykonos Town, Mykonos

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.
Take a break from Mykonos Town with a short trip to Portara in Naxos Town, about 1h 25 min away. Next up on the itinerary: take a stroll through Little Venice, enjoy the sand and surf at Panormos Beach, take an in-depth tour of Archaeological Museum of Mykonos, and tour the pleasant surroundings at Elia Beach.

For more things to do, reviews, maps, and tourist information, read Mykonos Town trip planner .

You can fly from Milos to Mykonos Town in 2.5 hours. Alternatively, you can ride a ferry. In May, daily temperatures in Mykonos Town can reach 73°F, while at night they dip to 63°F. Wrap up your sightseeing on the 20th (Wed) early enough to travel back home.

Things to do in Mykonos Town

Outdoors Beaches Parks

Side Trips

Platis Gialos Beach, Paradise Beach, Portara, Elia Beach, Panormos Beach
Find places to stay May 16 — 20:
Highlights from your plan
Little Venice ©
Little Venice
The Windmills (Kato Milli) ©
The Windmills (Kato Milli)
Aegean Maritime Museum ©
Aegean Maritime Museum

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