Two-Week Cycladic Island Hopping in Greece Itinerary + Map

I’ll be honest, planning a trip to the Greek Islands can be challenging. There is so much to consider when crafting a fun, yet relaxing, island-hopping itinerary in Greece.

As a seasoned travel agent (yep, we still exist), I’ve figured out how to strike the perfect balance between adventure and relaxation.

This two-week island-hopping itinerary through the Cyclades is all about soaking up Greece’s best, from dreamy beaches and crystal-clear waters to charming villages and ancient ruins.

Greece is packed with natural beauty, history, and serious good vibes. Each island on this route has its own personality, and together they create an unforgettable journey.

2 Week Greek Island Hopping Itinerary

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Day 1-3: Athens

Whilst Athens might seem like a strange place to begin your island-hopping adventure, it’s not an island after all, it’s the best place to start.

Athens International Airport is much larger than the island airports and has direct flights from most major cities across the world.

Depending on where you’re flying from, tickets also tend to be a lot cheaper. Once you arrive in Athens, you can catch the ferry to the first island on our itinerary. 

However, whether you’re solo in Athens or with friends,  it would be a shame to fly through here without seeing everything it has to offer.

Aim to spend a few days exploring Athens and discovering the incredible history of this city. 

Be sure to hit the main attractions in Athens, and visit the Ancient Agora before walking up to the Acropolis to explore the ruins of the infamous Parthenon.

Make sure to stop by Areopagus Hill at sunset or sunrise to get a great view of Athens and the Parthenon.

Be sure and visit Plaka, an old neighborhood in Athens made up of narrow streets, traditional Greek restaurants, and small boutique shops for you to browse.

Then spend your evening relaxing in the local bars, or delve into the lively nightlife in the Psiri neighbourhood. 

Athens Day Trip Idea

If you are feeling ready to explore something amazing just outside Athens take a day trip to Delphi.

Delphi, the centre of ancient Greece, has some of the best ruins in Greece, such as the amphitheater and Temple of Apollo.

On your way back, visit the mountain village of Arachova, a beautiful place on the hills of Mount Parnassus. 

Sleep in Athens

• Coco-Mat Athens BC ($$$)
• Hotel Grande Bretagne Spa ($$$$)
• AthensWas Hotel ($$$)

Eat in Athens

• Atlantikos ($$)
• Varoulko ($$$)
• Vezené ($$$$)

Day 4-6: Mykonos

To begin your island-hopping adventure, catch the early ferry from Athens to Mykonos.

Ferries out of Piraeus Port depart daily starting around 7 am. The faster ferry takes around 2 1/2 hours and costs between €56-€87.

The slower but cheaper ferries take an average of 4.5 – 5 hours and cost around €35-€45.

On Mykonos, you’ll find picturesque villages like you see in magazines and beautiful landscapes.

Getting around in Mykonos is fairly easy with the public transport, but for full freedom, rent a car. Keep in mind that one of the things you want to avoid in Mykonos is relying on taxis. They are very expensive and hard to find.

Begin your day at Mykonos Town, a quick 8-minute drive up the coast from Mykonos port.

Explore the narrow streets full of cute, but expensive shops, and visit the iconic windmills. Just a heads up, Mykonos is one of the most expensive islands in Greece.

When you start to get peckish, grab some lunch at Pepper Souvlaki & More for some of the best street food on the island. 

In the afternoon, explore the Mykonos Folklore Museums. The museums showcase the island’s history and culture, with displays of traditional clothing, tools, and ancient artifacts.

During the first evening in Mykonos, try some of the traditional food at M-Eating.

This restaurant has a relaxing atmosphere and serves all the best traditional Greek food, from favorites such as souvlaki to the much-loved gyros. 

Day 2 in Mykonos is all about capturing those stunning Instagram moments and lounging on its picturesque beaches.

Don’t miss out on the beauty of Paradise Beach and Elia Beach, among the island’s top spots for sun, sea, and sand.

However, if you want something a little quieter, take the bus 25 minutes north to Agios Stefanos.

Or, head south to Korfos, where the shallow waters and strong winds make it the perfect place for surfing.

You can hire equipment here, or simply take the time to relax on the white sands.  

Mykonos Day Trip Idea

There are a lot of great day trips from Mykonos, but since you only have a couple of days, I would check out the Island of Delos. It’s perfect for the afternoon via an organized tour.

It’s most well known for the archaeological site where buildings have been discovered from over 2000 years ago and is said to be the birthplace of the gods Apollo and Artemis.

It’ll take you a few hours to explore the island, so make sure to bring plenty of sunscreen, water, and snacks to keep you fueled and ready to go. 

Sleep in Mykonos

• MyCocoon Hostel ($$)
• Myconian Korali ($$$)
• Santa Marina A Luxury Collection ($$$$)

Eat in Mykonos

• Captain’s ($)
• La Petite Taverne ($$)
• Thioni Restaurant ($$$$)

Day 7-9: Naxos

To hop over to the second island on your itinerary, take a short ferry ride from Mykonos port to Naxos.

These ferries run every day and take about 1 hour 20 minutes, costing between €36 and €80.

Aim to arrive by mid to late morning, so you can spend the rest of your day exploring Chora, the main town on Naxos.  

Spend your day walking the winding streets and browsing the small but quaint shops of Chora.

Make sure to visit the Portara, an ancient marble gateway that is all that remains of the unfinished Temple of Apollo.

Then head across the town to explore the Kastro, one of the most well-preserved castles on the Cyclades, built by the Venetians in 1207.

In the evening, grab a cocktail in one of my favorite bars in Chora, Naxos Cafe, to relax and rest after a day of walking. 

Naxos Day Trip Idea

On your second day in Naxos, head out of the main town to explore some of the smaller villages on the island.

It’s best to rent a car for the day so you can quickly move about the island and make the most of your time here. If you don’t want to drive then I recommend a Naxos bus tour to take you to the sites.

Spend your day driving between the mountain villages of Chalkio, Filoti, and Apeiranthos, before heading back to Chora.

If you have time, head for a dip in the sea at beautiful and sandy Maragas Beach. Just 7km south of Chora, it’s the perfect final stop on your final day in Naxos.

Plus, despite being so close to the town, this beach is much quieter than the more touristy beaches such as Agios Prokopios Beach. 

Sleep in Naxos

• Nastasia Village ($$)
• Nissaki Beach Hotel ($$$)
• Panorama Hotel ($)

Eat in Naxos

• Metaxi Mas ($$)
• Labyrinth Wine Restaurant ($$)
• Ellinko Restaurant ($$)

Day 10-13: Santorini

The third and final Greek island on your itinerary is the stunning and iconic island of Santorini.

It’s very easy to get between the two islands, and the ferry takes around 2 hours, prices range from €31 and €100. 

When you arrive in Santorini, you’ll be in the beautiful town of Fira. Take the afternoon to explore this town, and relax after a morning of travelling.

This town sits on the edge of Santorini’s caldera and is made up of classic white buildings.

Walk through its streets and admire the iconic blue-domed churches scattered throughout before spending the evening sipping on a few cocktails and relaxing by the coast. 

On your second day in Santorini, head to the ancient site of Akrotiri. This Minoan settlement was buried under volcanic ash in around 1600 BC, preserving the ruins of multistory buildings, frescoes, and pottery. 

Once you have your fill of the island’s history, spend your afternoon relaxing on one of Santorini’s beaches such as the beautiful Kamari or Perissa Beach.

Both beaches are beautiful, however, Perissa is a longer beach and tends to feel less crowded and touristy, whilst Kamari has more amenities like restaurants for you to enjoy.  

In the evening, grab a taxi or take the bus to save some pennies, to the north of the island to see another beautiful village in Santorini.

Oia is known for having some of the most beautiful sunsets, so make sure you get a good spot near the top of the village to witness the sky light up with burning hues of orange.

You’ll find plenty of restaurants to have dinner and sip on some cocktails as you watch the sun go down. 

Santorini Day Trip Idea

For your third day in Santorini, head on a boat tour to explore the volcanic islands of Nea Kameni and Palea Kameni. Whilst Nea Kameni is an active volcano, it has been dormant since the 1950s.

On your trip, you’ll hike up the volcano before taking a relaxing swim in one of the hot springs found in Palea Kameni.

These islands can only be reached by boat trip, and take around 3 hours. 

Continuing with the theme of volcanoes, in the later afternoon, head to the Red Beach. Striking because of its, you guessed it, red sand, this beach is one of the most unique beaches in the Cyclades Islands.

The journey takes about 20 minutes from the main bus station in Fira, or you can grab a taxi. 

Sleep in Santorini

• Andronis Boutique Hotel ($$$)
• Katikies Hotel ($$$)
• Grace Hotel Santorini ($$$)

Eat in Santorini

• Metaxy Mas ($$)
• Selene ($$$)
• To Psaraki ($)

Day 14: Return to Athens

On your final day, head back to Athens. Whilst you can get the ferry, it takes around 7 hours and costs between £45-160.

The best way to travel from Santorini to Athens is actually by flying. The flight itself is just 50 minutes, and tickets start from around £35.

It also means you’ll already be in the airport, ready to fly off to your next destination or return home for some well-deserved rest. 

Do You Need To Rent A Car for The Greek Islands?

For this itinerary, you don’t need to rent a car. It is true that a rental car comes in handy when visiting islands like Milos and Crete, and even some of the islands in this itinerary, but since you are making short stays, I don’t recommend getting a car.

Island Hopping in Greece Wrap-Up 

With this two-week island-hopping adventure, you’ll visit some of Greece’s most beautiful islands on a dream holiday.

The Cyclades Islands are filled with ancient history, surrounded by stunning blue waters, and covered in beautiful Greek villages just waiting to be explored. 

Whilst you start your itinerary in the bustling city of Athens, you soon delve into the calm atmosphere of island life, visiting the beaches of Mykonos, the mountain villages of Naxos, and the volcanoes of Santorini.

Each island offers a unique experience that will make these weeks completely unforgettable.

And of course, the islands are filled with restaurants serving fresh seafood and traditional Greek cuisine, so make sure there’s plenty of room in your budget to indulge in the food on offer.

Whether you’re a history buff, beach lover, or food enthusiast, the Cyclades Islands offer it all. Prepare for two weeks of relaxation, adventure, and indulgence as you hop between them with this perfect 14-day itinerary! 

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