20 days in Greece Itinerary

20 days in Greece Itinerary

Created using Inspirock Greece trip maker

Make it your trip
Fly
1
Athens
— 3 nights
Drive
2
Kranidi
— 2 nights
Drive
3
Milos
— 2 nights
Fly
4
Heraklion, Crete
— 2 nights
Ferry
5
Oia, Santorini
— 3 nights
Taxi
6
Fira, Santorini
— 2 nights
Ferry
7
Mykonos Town, Mykonos
— 3 nights
Fly

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Athens

— 3 nights

The Birthplace of Democracy

One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
Get some cultural insight at Acropolis of Athens and National Archaeological Museum. Take a break from the city and head to Glyfada Beach and Legrena Beach. There's much more to do: get engrossed in the history at Acropolis Museum, pause for some photo ops at Temple of Olympian Zeus, wander the streets of Monastiraki, and look for gifts at Old Orient Jewelry.

To find maps, photos, other places to visit, and other tourist information, refer to the Athens trip itinerary planning website.

New York City, USA to Athens is an approximately 12.5-hour flight. The time zone difference when traveling from New York City to Athens is 7 hours. In September in Athens, expect temperatures between 84°F during the day and 69°F at night. Wrap up your sightseeing on the 7th (Mon) early enough to travel to Kranidi.

Things to do in Athens

Outdoors · Parks · Beaches · Tours

Side Trips

Kranidi

— 2 nights
On the 8th (Tue), Head underground at Franchthi Cave, Head underground at Didyma Caves, then enjoy the sand and surf at Paralia Lepitsa, and finally examine the collection at Ermionis - Bairaktaris Apiary. On the 9th (Wed), you'll have a packed day of sightseeing: tour the pleasant surroundings at Petrothalassa Beach and then trek along Devil's Bridge.

To find where to stay, photos, traveler tips, and tourist information, refer to the Kranidi trip itinerary site.

You can drive from Athens to Kranidi in 2.5 hours. Traveling from Athens in September, you can expect nighttime temperatures to be little chillier in Kranidi, with lows of 54°F. Wrap up your sightseeing on the 10th (Thu) early enough to travel to Milos.

Things to do in Kranidi

Parks · Outdoors · Beaches · Trails

Side Trips

Milos

— 2 nights

Island of Colors

The result of thousands of years of volcanic activity, the island of Milos features a craggy coastline interspersed by shallow beaches.
On the 11th (Fri), examine the collection at Milos Mining Museum, kick back and relax at Sarakiniko Beach, then get engrossed in the history at Archaeological museum of Milos, then delve into the distant past at Ancient Roman Theatre - Milos, and finally steep yourself in history at Venetian Castle of Milos. Get ready for a full day of sightseeing on the 12th (Sat): stroll through Paliochori Beach and then enjoy the sand and surf at Kleftiko Beach.

To find more things to do, other places to visit, and other tourist information, go to the Milos trip itinerary builder tool.

You can drive from Kranidi to Milos in 8.5 hours. Traveling from Kranidi in September, expect somewhat warmer with lows of 70°F in Milos. Wrap up your sightseeing on the 12th (Sat) to allow time to fly to Heraklion.

Things to do in Milos

Parks · Outdoors · Beaches · Museums

Heraklion, Crete

— 2 nights
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 13th (Sun): take in the waterfront activity at Old Venetian Harbor of Heraklion, take in the architecture and atmosphere at Church of Saint Titus, get engrossed in the history at Historical Museum of Crete, then get a new perspective on nature at The Natural History Museum of Crete, and finally take an in-depth tour of Heraklion Archaeological Museum. Get ready for a full day of sightseeing on the next day: test your problem-solving skills at popular escape rooms, explore the ancient world of The Palace of Knossos, then do a tasting at Domaine Paterianakis, and finally learn about winemaking at Lyrarakis Winery.

To find maps, more things to do, photos, and other tourist information, go to the Heraklion day trip app.

Fly from Milos to Heraklion in 5 hours. Alternatively, you can ride a ferry. Expect a daytime high around 82°F in September, and nighttime lows around 69°F. Cap off your sightseeing on the 14th (Mon) early enough to catch the ferry to Oia.

Things to do in Heraklion

Museums · Historic Sites · Wineries · Fun & Games

Side Trip

Oia, Santorini

— 3 nights
Every day hundreds of visitors come to Oia just to experience its sunsets.
Start off your visit on the 15th (Tue): enjoy the sand and surf at Katharos Beach, contemplate the waterfront views at Amoudi Bay, and then do a tasting at Domaine Sigalas. Here are some ideas for day two: take in the exciting artwork at Mnemossyne Gallery, make a trip to Sunset in Oia, and then race across the water with a speed boat tour.

To see maps, traveler tips, other places to visit, and other tourist information, go to the Oia attractions planning app.

Traveling by ferry from Heraklion to Oia takes 2.5 hours. Alternatively, you can fly. Expect a daytime high around 82°F in September, and nighttime lows around 70°F. Wrap up your sightseeing on the 17th (Thu) early enough to drive to Fira.

Things to do in Oia

Outdoors · Parks · Tours · Nature

Fira, Santorini

— 2 nights
Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
Start off your visit on the 17th (Thu): explore the ancient world of Akrotiri, kick back and relax at Red Beach, and then indulge your senses at some of the top wineries in the area. Keep things going the next day: take in the architecture and atmosphere at Orthodox Metropolitan Cathedral, stroll through Perissa Black Sand Beach, and then trek along Ekklisia Theoskepasti hiking trail.

For maps, traveler tips, more things to do, and other tourist information, read Fira travel itinerary planner.

Fira is just a stone's throw from Oia. September in Fira sees daily highs of 82°F and lows of 70°F at night. Finish up your sightseeing early on the 19th (Sat) so you can catch the ferry to Mykonos Town.

Things to do in Fira

Parks · Outdoors · Beaches · Wineries

Side Trips

Mykonos Town, Mykonos

— 3 nights

Chora Mykonos

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.
Get some cultural insight at Little Venice and Paraportiani Church. Visit Paradise Beach and Elia Beach for some beach relaxation. And it doesn't end there: enjoy the sand and surf at Panormos Beach, tour the pleasant surroundings at Super Paradise Beach, and don't miss a visit to The Windmills (Kato Milli).

To see ratings, other places to visit, more things to do, and tourist information, use the Mykonos Town trip planner.

Traveling by ferry from Fira to Mykonos Town takes 2.5 hours. Alternatively, you can fly. In September, daily temperatures in Mykonos Town can reach 79°F, while at night they dip to 69°F. Cap off your sightseeing on the 22nd (Tue) early enough to catch the flight back home.

Things to do in Mykonos Town

Parks · Outdoors · Beaches · Neighborhoods

Side Trips

Greece travel guide

4.2
Beaches · Ruins · History Museums
Few places manage to capture the world's imagination quite like Greece, a land of sun-kissed coastlines, tranquil whitewashed villages, lively seaside towns, and well-preserved ancient sites. One of the world's top tourist destinations since ancient times, the country draws nearly 20 million visitors each year. Athens, the birthplace of Western civilization, continues to attract the biggest crowds and serves as a base for exploring the country and its 227 inhabited islands. Away from its cities, Greece features a picturesque countryside of olive groves, vineyards, and tiny settlements nestled against rolling hills and rugged mountain ranges. Explore the old mainland on foot and discover the islands on a guided boat or ferry tour.