Greece Island Hopping Tour in 10 Days

A 10 day trip to Greece 
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Explore six exquisite islands on this 10-day tour through the Cyclades and beyond. Each island has its own appeal, be it the quiet beaches on Naxos, Santorini’s whitewashed villages, the history of Crete, the waters around Elafonisi, chic Mykonos or the archaeological Delos. Handcrafted to provide the complete island hopping experience for those relatively short on time, these are ten days of endless highlights and impressions. And just like the Aegean Sea, it’s as laid-back as it can be.

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Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Cyclades Islands, Aegean Sea, Hora (Mykonos Town), Panagia, Paraportiani, Little Venice, Delos, Archaeological Site of Delos, Cynthus, Catacombs, Chora, Naxos,  Santorini, Fira, Oia, Imerovigli, Firostefani, Red Beach, Kamari, Perissa, Pyrgos, Thirassia, Akrotiri, Crete, Heraklion, Chania, Palace of Knossos, Elafonisi

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Hora (Mykonos) – Windmills, Villages and Sunset

Mykonos looks like a vacation everywhere you turn. Blissful Aegean waters surround the island, so calm and peaceful until they dramatically reflect sunset hues. The villages are small and mazy, with hardly any of the streets wide enough for motorized vehicles. Most of the hills are lush and rugged, their green colors complementing the sea. There are beaches, a classic vacation image, along with sights that prove you are very far from home – the Hora windmills just one example. Mykonos has an international airport, so you fly directly into the Cyclades. Within an hour of landing, you will have checked into a boutique hotel in Hora, the main Mykonos town.

From your suite, you can gaze over the Aegean for your first glance of what this island hopping tour will be about. The afternoon will be at your leisure, and it is easy to get around the key Mykonos highlights. Take a walk through the town, your footsteps on cobbles as you come across small cafes and restaurants. Head out to the windmills for the famous Mykonos photo, and then keep walking a little further for some initial beach time. Head back to the hotel for sunset as you have a perfect view from your suite, before checking out the chic, indulgent atmosphere that dominates a Mykonos evening.

What’s Included: airport transfer, accommodation

Day 2: Hora – The Archaeological Wonder of Delos

At first, Delos appears to be a classic Greek island. Your boat will drop anchor in a quiet blue bay alongside golden sand and a rugged cliff-lined backdrop. Jump in for a swim and all is how it is supposed to be. But you are not visiting Delos for the swimming, as you will step onto the island to enter the mythologized birthplace of Greek gods. Apollo and Poseidon have their stories here, along with other legendary names like Artemis. Delos was a myth at first, but a handful of the archaeological remains point to its godly past, these best understood in the excellent Archaeological Museum of Delos.

Your local guide will provide eye-opening stories as you move back outside and connect the centuries. Delos rose to become the world’s most important trading center, around 400 – 300 BC. Amid the vast archaeological ruins, you will find an avenue of sculpted lions. Around the Delos summit, you can look down on temples and Corinthian columns. At the Temple of Hercules and House of Cleopatra, you can trace the Delos history between civilizations. There are many Hellenistic remains, some of them relatively new as they only show two millennia of history. Delos is the most important Greek historical site outside Athens, and you can spend the whole day on the island before returning to Mykonos and a different side to Greece.

What’s Included: accommodation, tour, breakfast

Days 3 – 4: Chora (Naxos) – Relaxing on a Mostly Undiscovered Island

On the fast catamaran, you will cruise to Naxos and its largest village, Chora. Barely 5,000 people live on the entire island, and you will soon find yourself alone on the coast. The wind whispers softly in your ear, there is sand between your toes, and the waters are fresh, more like a lagoon than a sea. Naxos is a mostly undiscovered island, passed over by almost everyone visiting the Cyclades. What it does not have in terms of tourist-focused restaurants, it makes up for in pure serenity and tradition. This is where the menus do not come in English, and the coastline is not populated by superyachts.

This will be an island escape, made all the better by the lack of crowds. So take your time, take a stroll, relax on a beach and wile away an evening in one of the tavernas. Then wake up the next morning and do the same again. A stop in Naxos is chance to explore what the Greek islands used to be before they grew popular with tourists over the eighties and nineties. You will enjoy this island as you meet the locals, dine beneath clear skies, take a hike to hidden beaches, and indulge with the many small pleasures.

What’s Included: accommodation, tour, breakfast

Day 5: Oia (Santorini) – Wandering Villages and Vineyards

Keep cruising, continuing on the same Cyclades ferry route that connects Mykonos with Santorini. You will disembark and transfer to Oia, the largest and the most charming of the island’s villages. Accommodation is hard to come by here, which means it’s mostly visited by day-trippers, especially those who come for the world-famous sunsets. You will have a jacuzzi suite overlooking the sunset, a place of tranquility for watching a whitewashed facade change color with the sun. Oia is also a good place to start your guided Santorini exploration, the guide telling you why the church domes and window shutters are painted blue.

It can be cool on these cobbled streets, most of them in shadow for most of the day. From Oia. you then ascend onto rugged hills, with a short drive bringing you to a patchwork of olive groves and vineyards. Go on a food and wine tasting, with many local delicacies experienced in just two hours, before continuing to the village of Fira. Like Oia, this is another mazy place where you are guided by sounds and smells, as well as the sights. The tour ends here, and you may choose to walk back to Oia, along a famous cliffside path. But of course, you might want to be back in Oia quickly, meaning more time to enjoy the jacuzzi sunset.

What’s Included: accommodation, tour, breakfast

Day 6: Oia – Catamaran Sailing, Ancient Ruins and Another Iconic Sunset

Santorini has many secrets, but it is only a small island. Unlike Crete or Mykonos, you can get around everything in just a couple of days. So head off with your guide and feast on the ruins, an excavated city your first stop today. Travel to the unusual red and black beaches, not really places to sunbathe but destinations to appreciate the diversity of nature. Grab lunch in the island’s highest village, the blue and white facade complemented by volcano views, and then walk off the indulgent food on a volcano. If you are feeling adventurous, then it is possible to walk to the volcano’s conical summit. But just a few steps on the rugged slopes may be enough. Take it slow in the afternoon, and watch that sunset once more.

What’s Included: accommodation, tour, breakfast

Day 7: Oia – An Afternoon of Cruising Around Santorini

Enjoy a relaxed morning on the Greek islands, drinking your morning coffee with a view and a quiet walk through a whitewashed town. This afternoon you can set off on a small-group catamaran sailing cruise. Rest on the deck as turquoise waters extend in all directions. Jump off at quiet swimming spots, beneath the entrances to cliffside caves. Cruise alongside the cliffs, gazing up at the villages you explored yesterday, and then stay out for sunset, a different perspective as the catamaran glides back to port. Like yesterday, you will find Oia to have many excellent dining spots this evening, from coastal seafood restaurants to small local haunts within the maze.

What’s Included: accommodation, tour, breakfast

Day 8: Heraklion to Chania (Crete) – From Minoan to Venetian Histories

Crete is an island of convoluted and complex history. Take the fast boat to Heraklion, and you can step back to the time of early Minoan culture, Crete being the island from which this civilization spread. Vast crumbling ruins are found in Knossos, including a palace that really evokes ancient power. The world’s greatest collection of Minoan art is found at the nearby archaeological museum, from vases to sculptures and surreal friezes. Then you step forward into a medieval period, jumping the classical times to explore old town Heraklion. It’s here that you find a vast fortress and colorful cobbled lanes, along with all the tradition that’s been taken forward into the 21st century.

Heraklion is ugly at first glance but beautiful with a local guide. You must sidestep the busy streets and know how to enter the old town, where there is respite from noise and many cafe terraces. After lunch, it’s a two-hour transfer along the coast to Chania, where the style is intimately Venetian. Chania was an integral part of the Venetian Republic, and the avenues have an artisanal style, with colorful townhouses lining the water and gastronomy that straddles nations and eras. After a busy day of historical sites, Chania is good for self-exploration, especially in the early evening. You can walk without a map and without a plan, enjoying whatever Venetian remains you stumble upon.

What’s Included: accommodation, tour, breakfast

Day 9: Chania – The Clearest Waters in Europe on a Elafonisi Day Trip

Elafonisi appears to be more Caribbean than European, the color of the water like something from a dream. When the sun shines, the water is more translucent than turquoise, as if the Aegean coast houses jewels instead of sand. Take a day trip here, and you bask in the tranquility. Mountain streams and rugged vistas dominate the morning, a road taking you through the remote landscapes of southwestern Crete. Follow a green coastline then stop in the tiny village of Topolia, a starting point for finding a church in the middle of a dripstone cave.

Head back towards the water, and the ineffable colors take over. A shimmering pink beach is back-dropped by pine and juniper covered dunes. From here, the translucent lagoon extends, and you will walk to Elafonisi, spending the whole afternoon on the island’s white-sand beaches. There is no history here, and really there is not really anything here other than the beach and the lagoon. It is this that is the highlight. After nine days of island hopping, you will have found the most exquisite of all island scenes. And while you can never have Elafonisi completely to yourself, the island is large enough to absorb its fascinated visitors. Return to Chania by dusk, where there is one final Greek sunset and probably a final taverna dinner.

What’s Included: accommodation, tour, breakfast

Day 10: Chania – Departure

It is just a 20-minute transfer from Chania to the international airport. After traveling via the ferries all week, you are now back in the sky without having to return two hours by road to Heraklion. The morning is at your leisure, and there is a good chance you will be taking a final stroll through the old Venetian town.

What’s Included: airport transfer, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.