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 30​min
3
Milos
— 2 nights
Fly:  2​h 30​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): delve into the distant past at The Palace of Knossos, then meet the residents at Cretaquarium - Thalassocosmos, and then ponder the design of Morosini Fountain (Lion's Fountain). Keep things going the next day: test your team's savvy at popular escape rooms, 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 get engrossed in the history at Heraklion Archaeological Museum.

For ratings and other tourist information, read our Heraklion trip itinerary maker tool .

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. Traveling from Washington DC to Heraklion, you'll lose 7 hours due to the time zone difference. In May in Heraklion, expect temperatures between 75°F during the day and 60°F at night. Wrap up your sightseeing on the 9th (Sat) to allow 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, take in the dramatic natural features at Skaros Rock, awaken your taste buds at some of the top wineries in the area, and make a trip to Sunset in Oia.

To see photos, ratings, other places to visit, and other tourist information, use the Fira travel planner .

Traveling by ferry from Heraklion to Fira takes 2 hours. In May, plan for daily highs up to 75°F, and evening lows to 63°F. Cap off your sightseeing on the 14th (Thu) early enough to go by car to Milos.

Things to do in Fira

Parks Outdoors Beaches

Side Trips

Oia, Kamari, Akrotiri, Imerovigli, Perissa Black Sand Beach
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): examine the collection at Milos Mining Museum, stroll through Firiplaka Beach, and then kick back and relax at Kleftiko Beach. Get ready for a full day of sightseeing on the 16th (Sat): enjoy the sand and surf at Pollonia Beach and then enjoy the sand and surf at Sarakiniko Beach.

For more things to do, where to stay, reviews, and other tourist information, read Milos vacation tool .

Getting from Fira to Milos by car takes about 4.5 hours. May in Milos sees daily highs of 74°F and lows of 62°F at night. Finish your sightseeing early on the 16th (Sat) to allow enough time to fly to Mykonos Town.

Things to do in Milos

Outdoors Parks Beaches
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.
Change things up with a short trip to Portara in Naxos Town (about 1h 25 min away). There's still lots to do: take a stroll through Little Venice, take an in-depth tour of Archaeological Museum of Mykonos, make a trip to Matoyianni Street, and contemplate in the serene atmosphere at Paraportiani Church.

To see reviews, photos, maps, and more tourist information, go to the Mykonos Town vacation app .

You can fly from Milos to Mykonos Town in 2.5 hours. Another option is to ride a ferry. May in Mykonos Town sees daily highs of 73°F and lows of 63°F at night. Wrap up your sightseeing on the 20th (Wed) early enough to travel back home.

Things to do in Mykonos Town

Outdoors Parks Beaches

Side Trips

Paradise Beach, Portara, Platis Gialos Beach, 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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