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How to Spend 2 Weeks Island Hopping in Greece


How to Spend 2 Weeks Island Hopping in Greece

A trip to Greece is a fantastic way to see where democracy, the Olympics and philosophy truly began. Add in stunning historic architecture, a warm climate, endless beaches and a welcoming people, and it is easy to see the appeal of a Greek getaway. While the mainland offers a variety of magnificent spots, including the capital of Athens, the Greek islands are also an amazing way to enhance your next vacation.

This two-week island hopping itinerary takes you to 7 of the most beautiful Cyclades islands. The Cyclades, so named because of the archipelago’s islands are set up in a circle around Delos, played important roles in Greek mythology. They are a great place to enjoy the beautiful scenery, just relax on a beach, go hiking in the mountains or tour historic ruins.

1. Athens (1 night)


Many travelers will arrive and depart at the Athens Eleftherios Venizelos International Airport, which is why this itinerary begins in the capital city. Athens, of course, has plenty to offer travelers, and it is also a popular departure point for those flying to some of the gorgeous Greek islands. During your time in Athens, be sure to see landmarks like the Acropolis, or the high city of Athens, where you’ll find the 2,500 year-old Parthenon, the Temple of Athena Nike and the extensive collection of artifacts at the New Acropolis Museum. At the base of the Acropolis, explore the charming districts of Plaka and Thissio, where you can tour ancient Roman ruins.

Accommodation: Where to Stay in Athens

See also: Top Athens Attractions

2. Mykonos (2 nights)

Windmill of Mykonos

Take a ferry from Athens to Mykonos to enjoy this wildly popular Greek island in the heart of the Aegean Sea. Mykonos is well known for its nonstop nightlife, so plan for a few evenings of dancing, live music and plenty of delicious cocktails. Of course, there is also plenty to do during the day. In Mykonos, you can see the charming 16th century windmills that overlook the charming Little Venice district, or you can explore the 15th century Byzantine church called Panagia Paraportiani right in Mykonos Town. Don’t forget about the world-famous beaches like the party beach called Paradise, the beach called Elia that boasts jet ski rentals, the secluded Fokos beach and the family beach of Ornos.

Accommodation: Where to Stay in Mykonos

See also: Top Mykonos Attractions

3. Delos (day trip from Mykonos)

The island of Delos

While you’re in Mykonos, spend half a day exploring the nearby island of Delos. The island is completely uninhabited, but you can still visit thanks to boats that depart daily from Agios Nikolaos in the morning and return in the afternoon. In Delos, you will be delighted to find an enormous collection of archeological sites and ruins. Some of the most notable landmarks on the island include the ruins of three temples dedicated to Apollo, the detailed mosaics in the House of Dionysos, a building called Cleopatra’s House thanks to busts of the iconic woman found within and what remains of a large marble theater.

4. Paros (3 nights)

Parakia, Paros

Another of the Cyclades Islands is Paros, which is a quieter island where travelers of all ages come to relax on the beach, explore historic sites and dine on the local cuisine. A highlight of any stay in Paros is a visit to the Panagia Ekatontapiliani, a church that was originally built 1,6000 years ago and then rebuilt in the late 18th century. You’ll also be able to make a splash at the Aqua Park, a water-based theme park, tour the rustic taverns and fishing spots in the village of Naousa and dance the night away at the bars on Lower Market Street. Don’t leave without tasting the local seafood doused in vinegar, a true island delicacy.

5. Antiparos (day trip from Paros)

Antiparos, Cyclades

On one of your days in Paros, set aside some time to visit the island of Antiparos. More than 1,000 people live on the island, and it is accessible by ferry several times a day from the ports of Parikia and Pounta on Paros. Antiparos is best known for its incredible cave, a grotto that you reach by walking more than 300 steps underground into an atmosphere that feels out of this world. Antiparos is also home to the gorgeous Sostis Bay, a popular beach spot for visitors, and several traditional wooden boats that provide short tours around the island.

6. Naxos (2 nights)


The largest of the Cyclades, Naxos offers more variety than many of the other islands, with picturesque towns, high mountains, lush green valleys and attractive beaches. You can still see what remains of the Castro, or walled city, that is located just above the island’s main harbor. Other top things to do in Naxos include swimming at the Agios Prokopios Beach, seeing Dionysus’ Temple in the village of Glinado and dining at one of the taverns at the harbor of Lionas.

Accommodation: Where to Stay in Naxos

7. Santorini (3 nights)


Perhaps the best-known of all the Greek islands is Santorini, and for good reason. Santorini is a picturesque spot and a place where you can enjoy dramatic views and some of the best sunsets on the planet. The town of Fira is often featured in photographs, thanks to its unusual perch right on the edge of a cliff leading down to the sea. From Fira, you can walk right along the perimeter of a volcanic caldera to the town of Oia. Other spots you don’t want to miss in Santorini are the lighthouse of Faros, the pebbled coastline of Black Beach and the town of Akrotiri, which is more than 3,5000 years old and was covered in volcanic ash just like Pompeii in Italy.

Accommodation: Where to Stay in Santorini

See also: Santorini Attractions

8. Milos (2 nights)

Sykia Cave at Milos

Although the island of Milos has a winning combination of dozens of gorgeous beaches and lots of historic statues, it is off the radar for many travelers. For the intrepid visitor, this only makes Milos that much more appealing. Some of the ways you can pass the time in Milos include watching the sunset from the perfectly-positioned village of Plaka, seeing the village of Tripiti, where the iconic Venus de Milo statue was found, trying horseback riding right on the beach or exploring Sikia cave on a guided tour.

Athens (1 night)

Evzoni regiment arrival

End your island-hopping adventure by heading back to the capital of Athens. If you’ve already done the Acropolis on the first part of your vacation, spend some time exploring the city’s incredible museums. Some of the top picks for culture enthusiasts will be the National Archeological Museum, the National Art Gallery and the Museum of Cycladic Art. Then, make your way to the National Garden, which could be considered the heartbeat of the city, to admire the Greek Parliament Building and spot ancient ruins among a lush green garden. Round out your stay in Greece by snagging some souvenirs from the street vendors and shops found in the Monastiraki district.


Day 1: Arrive in Athens, sleep in Athens

Day 2: Ferry to Mykonos, sleep in Mykonos

Day 3: Delos half-day trip, sleep in Mykonos

Day 4: Ferry to Paros, sleep in Paros

Day 5: Antiparos day trip, sleep in Paros

Day 6: Explore Paros, sleep in Paros

Day 7: Ferry to Naxos, sleep in Naxos

Day 8: Explore Naxos, sleep in Naxos

Day 9: Ferry to Santorini, sleep in Santorini

Day 10: Explore Santorini, sleep in Santorini

Day 11: Explore Santorini, sleep in Santorini

Day 12: Ferry to Milos, sleep in Milos

Day 13: Explore Milos, sleep in Milos

Day 14: Ferry to Athens, sleep in Athens

Day 15: Fly Home