We spend a great deal of time thinking about other people's Greek holidays. After 25 years, we have crafted thousands of them — each one different, each one shaped by the particular person or couple or family who asked us to help.
But occasionally, clients ask us a different question: what would you book for yourselves?
It is a question we love, because it forces us to be honest. Not about what is popular, or what photographs well, or what is easy to sell — but about what we genuinely believe makes an extraordinary Greek holiday.
Here are seven itineraries we would book without hesitation.
1. The Romantic Escape
Santorini + Paros — 10 nights
This is the itinerary we recommend most often to couples, and it is the one we would choose ourselves.
Santorini (5 nights): Not in Fira or Oia in August — but in Imerovigli, in a cave hotel carved into the caldera cliff, with a private plunge pool and a view that changes colour every hour. Dinner at Selene in Pyrgos, which serves the finest modern Greek food on the island. A morning at the ancient site of Akrotiri, the Minoan city preserved under volcanic ash. A wine tasting at Santo Wines as the sun goes down over the caldera.
Paros (5 nights): The fishing village of Naoussa, with its Venetian castle and its harbour tavernas. Days at the beaches of Santa Maria and Kolymbithres. An afternoon in the marble-paved lanes of Lefkes, the island's mountain village. A boat trip to Antiparos, the smaller island just offshore, with its extraordinary cave and its perfect beach.
The combination works because Santorini provides the drama and Paros provides the ease. Together, they give you the full range of what the Cyclades can offer.
2. The Food Lover's Journey
Athens + Crete — 12 nights
Greece has become, in the last decade, one of the world's great food destinations. This itinerary is designed for those who want to eat their way through it.
Athens (4 nights): The city's food scene has been transformed. Monastiraki and Psirri for street food and mezze. Diporto, the legendary basement restaurant near the central market, for the kind of lunch that lasts four hours. The central market itself — the Varvakios Agora — for an hour of sensory overload. A cooking class in a Plaka kitchen. Dinner at Varoulko Seaside, where Lefteris Lazarou has been serving the finest seafood in Greece for thirty years.
Crete (8 nights): Split between the west (Chania, with its Venetian harbour and its extraordinary covered market) and the east (the Lasithi Plateau, the wine villages of Heraklion, the fishing harbours of Elounda). A cooking class in a Cretan farmhouse. A morning at the Minoan palace of Knossos. Dinner at Peskesi in Heraklion, which serves traditional Cretan food made entirely from ingredients sourced from the restaurant's own farm.
This is a holiday that will change how you think about Greek food — and probably how you cook when you get home.
3. The Greek Discovery
Symi + Halki + Leipsoi — 12 nights
This is the itinerary for those who want to go beyond the obvious. Three small Dodecanese islands, each one extraordinary, none of them crowded.
Symi (4 nights): The most beautiful harbour in Greece. Excellent swimming at Agios Georgios and Nanou Bay. The monastery of Panormitis. Fresh fish at the harbour tavernas every evening.
Halki (4 nights): No cars. One village. Complete peace. The walk to the abandoned hilltop village of Chorio. The best swimming of the trip at Ftenagia Beach.
Leipsoi (4 nights): The clearest water in the Aegean. A handful of beaches, all uncrowded. Evenings so quiet you can hear the sea from your room. A day trip to Patmos, the island of the Apocalypse.
This itinerary requires a little more logistical planning than a two-island trip — the ferry connections between these islands are not always straightforward — but that is exactly what we are here for. The reward is a Greece that most visitors never find.
4. The Family Adventure
Corfu + Kefalonia — 14 nights
Greece is one of the world's great family destinations, and the Ionian islands are particularly well suited to families with children. The sea is calmer than the Aegean, the beaches are excellent, and the islands are large enough to offer real variety.
Corfu (7 nights): The old town, a UNESCO World Heritage Site, with its Venetian architecture and its cricket pitch (a legacy of British rule). The beaches of the north — Paleokastritsa, Sidari, Kassiopi — which are among the most beautiful in the Ionian. A boat trip to the Blue Caves. Cycling through the olive groves of the interior.
Kefalonia (7 nights): Myrtos Beach, which is simply one of the most beautiful beaches in the world. The sea caves at Melissani. The wine of the island — Robola, grown in mountain vineyards — which is excellent and almost unknown outside Greece. A day trip to Ithaca, the island of Odysseus, which is just a short ferry ride away.
The combination gives families two weeks of variety — different landscapes, different beaches, different experiences — without the complexity of too many moves.
5. The Solo Traveller's Greece
Athens + Thessaloniki + Samos — 14 nights
Greece is one of the world's best destinations for solo travellers — safe, sociable, and endlessly interesting. This itinerary combines two of the country's great cities with one of its most underrated islands.
Athens (4 nights): The Acropolis at dawn. The National Archaeological Museum. The neighbourhood of Exarcheia, which is the city's most interesting and least touristy area. Walking tours of the street art, the Byzantine churches, the Ottoman-era bazaar.
Thessaloniki (4 nights): Greece's second city is, in our view, the country's most underrated destination. The Byzantine churches — there are fifteen UNESCO-listed ones — are extraordinary. The food scene is arguably better than Athens. The waterfront, with its White Tower and its promenade, is beautiful. The city has an energy and an authenticity that Athens, for all its magnificence, sometimes lacks.
Samos (6 nights): A large, green, mountainous island in the eastern Aegean, just off the Turkish coast. The birthplace of Pythagoras and Epicurus. Excellent wine (Samos Muscat is one of Greece's great wines). Beautiful beaches at Kokkari and Tsabou. A hiking trail through the island's interior that is one of the finest walks in Greece.
6. The Culture Seeker
Athens + Rhodes + Patmos — 12 nights
For those who want to understand Greece — its history, its religion, its extraordinary depth of civilisation — this is the itinerary.
Athens (4 nights): The Acropolis and the Acropolis Museum (which houses the Parthenon sculptures and is one of the finest museums in the world). The ancient Agora. The Byzantine Museum. A guided tour of the city's lesser-known archaeological sites — the Kerameikos cemetery, the Temple of Hephaestus, the Tower of the Winds.
Rhodes (5 nights): The Old Town, which is the best-preserved medieval city in Europe. The Street of the Knights. The Palace of the Grand Masters. The ancient city of Lindos, with its acropolis above a perfect bay. The Valley of the Butterflies, which is exactly what it sounds like.
Patmos (3 nights): The island of the Apocalypse, where St John wrote the Book of Revelation. The monastery of St John, which dominates the island from its hilltop, is one of the most important religious sites in the Orthodox world. The cave of the Apocalypse, where the revelation is said to have occurred. And, away from the religious sites, some of the most beautiful swimming in the Dodecanese.
7. The Ultimate Luxury Week
Mykonos + Santorini — 10 nights, with private yacht
This is the itinerary for those who want Greece at its most extraordinary. It is not cheap. But it is, in our experience, worth every penny.
Mykonos (4 nights): A suite at the Myconian Collection or the Belvedere. Dinner at Nobu. A day at Nammos Beach Club. Shopping in the lanes of the old town. A sunset cocktail at Little Venice.
Private yacht (3 nights): A crewed sailing yacht, departing from Mykonos, sailing south through the Cyclades. Anchoring in deserted bays. Swimming off the back of the boat in water so clear you can see the seabed ten metres below. Eating lunch on deck. Arriving at Santorini by sea — which is, without question, the finest way to arrive.
Santorini (3 nights): A cave suite at Canaves Oia or Mystique. Private caldera tours. Dinner at Selene. A morning at Akrotiri. A final sunset that you will remember for the rest of your life.
The yacht element is what makes this itinerary genuinely extraordinary. There is a freedom to arriving at an island by sea, dropping anchor in a bay that has no road access, swimming in water that no one else has reached that day — a freedom that no hotel, however magnificent, can replicate.
A note on these itineraries
These are not templates. They are starting points — ideas that we would adapt, refine and personalise for every client who asked us to help. The best Greek holiday is always the one that is built around you: your pace, your interests, your idea of what a perfect day looks like.
If any of these itineraries resonates with you — or if you want to tell us what you love and let us build something entirely new — we would love to hear from you.
Written by
The Greeko Team
Greeko has been crafting bespoke Greek holidays for over 25 years. Every article is written from genuine first-hand knowledge of the islands, the culture, and the experiences that make Greece extraordinary.
