The Fabulous Tour: 14-Day Greek Island Hopping

Itinerary at a Glance:

Day 1: Athens
Day 2: Athens
Day 3: Athens – Mykonos
Day 4: Mykonos
Day 5: Mykonos
Day 6: Mykonos – Naxos
Day 7: Naxos
Day 8: Naxos – Paros
Day 9: Paros
Day 10: Paros – Santorini
Day 11: Santorini
Day 12: Santorini
Day 13: Santorini – Athens
Day 14: Athens

Detailed 14-Day Greek Island Hopping Itinerary

Day 1: Athens

Welcome to Athens, where your Greek journey begins among ancient monuments, lively neighbourhoods and the unmistakable energy of the modern city. Upon arrival at Athens International Airport, you will be transferred to your hotel.

The rest of the day is yours. Take a first walk through Plaka, pause beside ancient Greek and Roman landmarks, browse the small shops or find somewhere inviting for your first taste of Greek cuisine. There is no need to see everything today. Athens will still be waiting for you tomorrow. Overnight in Athens. 

Day 2: Athens

Today, begin discovering the city that has shaped so much of Greece’s story. Your guided coach tour takes you to the Acropolis, where the Parthenon and Erechtheion rise above modern Athens. Continue past the Panathenaic Stadium, the Temple of Olympian Zeus and the Greek Parliament before visiting the Acropolis Museum.

By the time the tour ends, ancient Athens will have begun to feel less like a chapter in a history book and more like part of the city around you.

Afterward, the afternoon is free. Stay in the historic centre for lunch, explore another neighbourhood or simply find a café and enjoy Athens at your own pace. Overnight in Athens. (B)

Day 3: Athens – Mykonos

This morning, leave the mainland behind. A private transfer takes you to Piraeus Port, where you board the ferry to Mykonos and watch Athens gradually give way to the open Aegean.

Upon arrival, you will be transferred to your hotel. Then it is time for your first Cycladic island.

Wander through the whitewashed lanes of Mykonos Town, find the famous windmills and continue towards Little Venice, where old houses meet the edge of the sea. As evening approaches, choose a favourite café, bar or restaurant and enjoy the feeling that the island journey has truly begun. Overnight in Mykonos. (B)

Day 4: Mykonos

Today belongs entirely to Mykonos.

Return to the lanes of Mykonos Town when they catch the morning light, browse the boutiques, spend time by the sea or settle into a café and simply watch the island move around you.

Later, the choice is yours again. Perhaps a relaxed dinner and a walk beneath the evening lights, or perhaps a glimpse of the livelier Mykonos that emerges after dark.

There is no timetable to chase today.

Overnight in Mykonos. (B)

Day 5: Mykonos

Your final full day in Mykonos offers a very different possibility. If history calls, take the optional boat trip to Delos, an uninhabited island and one of Greece’s most important archaeological sites.

There, ancient ruins spread across a landscape that feels worlds away from cosmopolitan Mykonos, although the two islands lie close together.

Later, return across the water for one final Mykonos evening. By tomorrow, the journey changes mood again. Overnight in Mykonos. (B)

Day 6: Mykonos – Naxos

This morning, transfer to the port and board the ferry to Naxos. The crossing takes approximately 30 minutes, and the atmosphere on arrival feels distinctly different.

After your transfer to the hotel, the rest of the day is free. Begin discovering Naxos slowly. Spend time by the sea, wander through town or let your first encounter with the island come through its food and local products.

Mykonos has been left behind. Now the journey settles into a gentler Cycladic rhythm. Overnight in Naxos. (B)

Day 7: Naxos

Today gives you time to discover more of Naxos and its long history.

You can begin at the Portara, the monumental gateway of the unfinished Temple of Apollo, standing above the sea and greeting travellers as they approach the island. From there, wander into Chora and explore the Castle.

For a deeper look into Naxos’ past, you can also visit the temporary exhibition of the Archaeological Museum of Naxos while the main museum is being renovated.

Afterward, change history for the sea. You can head to a sandy beach, or simply enjoy the coast until the light begins to soften. In the evening, enjoy dinner at a traditional taverna and let Naxos provide another flavour of Cycladic life. Overnight in Naxos. (B)

Day 8: Naxos – Paros

Another island waits this morning.

Transfer to the port and board the ferry to Paros, an approximately 30-minute journey across the Aegean. Upon arrival, you will be transferred to your hotel.

Follow narrow lanes between whitewashed houses, browse local shops or find a table by the water. Your first day in Paros does not need a grand plan. Sometimes the pleasure of island hopping is simply arriving somewhere new and allowing the place to introduce itself. Overnight in Paros. (B)

Day 9: Paros

You have a full day to discover Paros in whichever way suits you.

Use local buses to reach some of the island’s traditional villages, or rent a car and follow your own route. Stop when something catches your attention. Stay longer when somewhere feels right.

This is one of the quieter pleasures of the journey: not every day needs to be filled from morning to evening. Overnight in Paros. (B)

Day 10: Paros – Santorini

Today, the final island crossing brings you to Santorini.

After your transfer to the port, board the ferry and continue across the Aegean. On arrival, you will be transferred to your hotel, and the rest of the day is free.

The landscape has changed again. You may choose a boat excursion towards the volcanic islands or begin exploring Fira. Later, find somewhere overlooking the caldera and watch the colours change as the sun sinks and evening settles over Santorini. Overnight in Santorini. (B)

Day 11: Santorini

Santorini deserves more than one hurried day, so today is entirely yours.

Perhaps begin with the prehistoric settlement of Akrotiri, where another chapter of the island’s history lies beneath layers of volcanic material. You may spend part of the day beside one of its black-sand beaches. Preshistoric settlement of Akrotiri ↗.

Later, wander through one of the island’s towns without a particular destination in mind. Here, the views have a habit of interrupting the itinerary anyway. Overnight in Santorini. (B)

Day 12: Santorini

Your final full day on the island is an invitation to choose whatever Santorini has left you curious about.

You might visit Ancient Thera, the mountaintop city overlooking the island, or join a winery tour and discover the wines shaped by Santorini’s distinctive volcanic landscape.

Alternatively, do less. Return to a favourite village, linger over lunch, seek out another caldera view or simply enjoy knowing that today you do not have to move on yet.

Tomorrow, the islands begin to recede behind you. Overnight in Santorini. (B)

Day 13: Santorini – Athens

Enjoy your morning in the island before transferring in the early afternoon to Santorini Port.

Board the ferry to Piraeus and watch the beautiful Aegean.

Upon arrival, you will be transferred to your hotel in Athens. Your final evening brings you back to where the journey began, but after Mykonos, Naxos, Paros and Santorini, Athens may now feel a little different too. Overnight in Athens. (B)

Day 14: Athens

After breakfast, a private taxi transfer will take you to Athens International Airport. End of services. (B)

Have a pleasant and safe trip home.

N.B. B: Breakfast, L: Lunch, D: Dinner