14 days in Athens, Santorini & Monolithos Itinerary

14 days in Athens, Santorini & Monolithos Itinerary

Created using Inspirock Greece trip itinerary maker

Make it your trip
Fly
1
Athens
— 2 nights
Fly
2
Oia
— 2 nights
+2
Drive to Santorini Airport, Fly to Diagoras Airport, Drive to Monolithos
3
Monolithos
— 7 nights
Drive to Diagoras Airport, Fly to La Guardia Airport

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Athens

— 2 nights

The Birthplace of Democracy

One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
Start off your visit on the 14th (Sat): get engrossed in the history at Acropolis Museum, then catch a live event at Panathenaic Stadium, then look for gifts at Amazing Chocolate, and finally take an in-depth tour of National Archaeological Museum. Keep things going the next day: steep yourself in history at Acropolis of Athens and then get into the urban bustle at Stavros Niarchos Foundation Cultural Centre.

To see where to stay, photos, maps, and more tourist information, you can read our Athens vacation maker app.

New York City, USA to Athens is an approximately 13.5-hour flight. Traveling from New York City to Athens, you'll lose 7 hours due to the time zone difference. In September in Athens, expect temperatures between 84°F during the day and 69°F at night. Wrap up your sightseeing on the 16th (Mon) to allow time to travel to Oia.

Things to do in Athens

Museums · Shopping · Historic Sites

Side Trips

Find places to stay Sep 14 — 16:

Oia

— 2 nights
Every day hundreds of visitors come to Oia just to experience its sunsets.
Kick off your visit on the 16th (Mon): stop by Atlantis Books E.E., examine the collection at Wine Museum Koutsogiannopoulos, then learn about winemaking at Venetsanos Winery, and finally delve into the distant past at Akrotiri. Get ready for a full day of sightseeing on the next day: contemplate the long history of The Castle of St Nicholas, pause for some serene contemplation at Cathedral of Saint John the Baptist, explore the galleries of Ernesto Workshop & Gallery, then examine the collection at Monastery of Profitis Ilias, then see the interesting displays at Cultural Village, and finally contemplate in the serene atmosphere at Orthodox Metropolitan Cathedral.

Planning Oia trip won't be overwhelming when you use Inspirock's itinerary maker.

You can fly from Athens to Oia in 5 hours. Other options are to do a combination of car and ferry; or do a combination of ferry and taxi. In September in Oia, expect temperatures between 82°F during the day and 70°F at night. Wrap up your sightseeing on the 18th (Wed) early enough to travel to Monolithos.

Things to do in Oia

Museums · Historic Sites · Wineries · Shopping

Side Trips

Find places to stay Sep 16 — 18:

Monolithos

— 7 nights
Give yourself a bit of retail therapy at Art Park Rhodes and Marias House. Koskinou Traditional House and Folklore Museum of Lardos Village will appeal to museum buffs. Get out of town with these interesting Monolithos side-trips: Ancient Kamiros (in Kalavarda), Eleousa (Campochiaro & Agios Nikolaos Fountoukli) and Bee Museum (in Pastida).

For ratings, where to stay, traveler tips, and tourist information, go to the Monolithos driving holiday planning site.

Use the Route module to find suitable travel options from Oia to Monolithos. In September, plan for daily highs up to 83°F, and evening lows to 73°F. You'll set off for home on the 25th (Wed).

Things to do in Monolithos

Historic Sites · Parks · Outdoors · Beaches

Side Trips

Find places to stay Sep 18 — 25:

Santorini travel guide

4.1
Beaches · Landmarks · Ruins
Wine Island
Known for dramatic views and romantic sunsets, the island of Santorini draws visitors with its long string of black, white, and red beaches. The largest and most significant of a small group of volcanic islands located just 200 km (120 mi) southeast of Greece's mainland, Santorini boasts just over 15,000 permanent residents. Created by a massive volcanic eruption that likely destroyed a single large island, the archipelago still features an active volcano, which saw its last eruption in the 1950s. The easiest way to explore Santorini's craggy coastline is on foot. Start by visiting the archaeological sites on the island's southwestern side, which offer a chance to discover the area's ancient past with unobstructed views of the famed volcano.