Mykonos, Delos, Chora, Naxos, Santorini, Oia, Firostefani, Fira, Kamari, Akrotiri, Crete, Heraklion, Chania, Topanas, Hora
Dates are flexible and customizable for private departures.
Explore and experience iconic beaches and enchanting panoramas during your 14-day Greece island-hopping vacation. You will travel to four islands known for their combination of pink and white beaches, whitewashed villages, and fascinating ancient ruins. Your tour will be custom-tailored to immerse you in Greece’s history and heritage as you traverse the marvels of Crete, Mykonos, Naxos, and Santorini for an unforgettable Mediterranean getaway.
Mykonos – Diving Straight Into the Island Adventure
Mykonos has become all glitz and glamour during the last two decades with super-yachts laying anchor beneath the cliffs and a famous jet-set crowd filling the bars. It is popular and chic, with trendy continental ideas mixing into what remains of the tradition. Find popup boutiques down narrow cobbled lanes, dapper cafes alongside church bells, Venetian mansions turned to glamorous seafood restaurants, and cocktail bars along the beaches. You will touch down and dive straight into the island adventure, Mykonos whisking you off with its atmosphere. Even after a long flight, it’s a destination that will immediately fill you with energy.
Mykonos – Feet in the Sand and Dinner in a Mykonian Household
Head away from the bustle this morning and give yourself space to unwind. Agios Sostis beach is just the place, soft sand flowing gently in lagoon-like waters. Palm trees sway softly here, and at high tide, you can be sat at a beach terrace with your feet in the sea. There’s snorkeling and sunbathing, plus some easy walks to quiet nearby coves. Transfers to and from the beach are included, but nothing else is planned for the day. Then, as the sun starts to set you will be taken to a countryside Mykonian household to meet a local family. Sit on their garden terrace and hear their stories, with free-flowing wine causing many a tongue to sing. Authentic dishes come from the kitchen, and you feast on both food and tradition, getting a sense of what Mykonos was like before it became popular.
Mykonos – The Magnificent Ancient Ruins of Nearby Delos
Sculpted lions guard an avenue through Delos, and they stand majestic, beneath the shadow of Corinthian columns, above an expanse of sun-baked sand. Apollo was born here, and you will visit the god’s sanctuary where marble beasts dominate excavated ruins. Doric temples are dotted elsewhere, their columns rising in postcard-perfect unison. There are three agoras to explore, each its own archaeological site and story, one of them the center of the known trading world back in 200 BC. The entire island is a UNESCO World Heritage Site, and there are no more important Greek ruins outside Athens. And as you explore you will find that Ancient Greece wasn’t one but many civilizations, with the island also taking you through Egyptian, Syrian, Naxian, and Hellenistic periods. It will be a full-day private tour, and you will be back in Mykonos early-evening time.
Naxos – Expansive Beaches and Island Escapism
Many feel that Naxos is how the Cyclades islands used to be before tourism. But that suggests the islands are all the same, and Naxos has always been a small, mostly unpopulated island. It does not have the ancient history of its neighbors, nor the variety of villages. However, it does have superb beaches. Check in to a Chora hotel, and your guide will provide a map and some good advice, as from here you can walk the cliffs to mostly deserted strips of sand, or grab a quick taxi to some very expansive and windswept beaches. After the action of Mykonos, Naxos is where you fully unwind. So kick back and soak up the sun.
Naxos – Temple Highlights of Naxos and More Beach Time
Historical highlights also dot the island, so you can head inland with your local guide ad stop at the Temple of Demeter, where sculpted deities to fertility often evoke emotion. Tour the old market at Chalki and taste sublime olive oils and fruit liqueurs along the way. Stroll down the 2,600-year-old entrance to the Temple of Apollo, but there is no temple, and there never was, but the entranceway is Naxos’s most iconic attraction. After half a day with a local guide, you will have covered most of the sights, so get dropped off on a small beach and do nothing for the rest of the day. For authentic dining, you can head to Kastro in Chora for the best Naxos tavernas.
Naxos – Cyclades Cooking Class and Village Life
Olive groves and fruit plantations fringe Kaloxylos, a tiny village on the island. They entice you with fragrances and fabulous colors, not to mention the shade they provide. Joining the local guide you go foraging here, picking organic produce to be used in a home-based cooking lesson. You will learn and taste the Naxos way, particularly how it is distinguished from other Greek cuisines, and how seasonal the menu should always be. After lunch, there will be plenty of time to relax in the village and see how slowly life moves here. Later in the day, it will be worth visiting Portara for the best Naxos sunset views.
Santorini – Whitewashed Cubist Streets and the Famous Caldera Walk
Take the fast ferry to Santorini, and you will disembark onto the most famous of the Greek islands. A short, uphill walk and a short road transfer brings you to Oia, the largest and most beautiful of all the whitewashed villages. Oia is much quieter than Fira as there is a relative lack of accommodation, so your experience is relaxing and calm. Wander the cubist streets, where blue shutters and domes shimmer in the sun, and church bells tell the passing of time. As the afternoon heat fades, you can take a guided walk along the caldera, footsteps along the cliffs on route to Fira, where you’re led into a traditional taverna for an evening of seafood, mezze, and plate smashing.
Santorini – Exploring Fira Before an Afternoon Catamaran Cruise
Wake up late and gaze over the Aegean from your suite. Dip into the infinity pool, walk the artisanal streets and visit a couple of boutiques. Drink coffee on your seaside terrace and generally settle into the Santorini way of life. Around midday your guide will take you to Fira for a guided tour, explaining the cubist architecture and island history. From here, it will be a quick descent to the port and an afternoon of catamaran cruising. Go swimming at the aptly named Red Beach, stop to admire the sands at White Beach. Dine on barbecue as you sail past Indian Rock, the old lighthouse, and the hilltop remains of Akrotiri. Jump off into the Nea Kameni hot springs then set sail back towards Fira, a spectacular sunset bouncing off the Aegean.
Santorini – Old-World Santorini and Wine Tasting
Vineyards carpet much of Santorini, their green hues punctuated by small, near-decaying farmhouses. The wine is so revered it could be traded freely during almost five centuries of prohibition. Meet with a cellar-master and tour a vineyard before a wine tasting experience that takes you through different varietals and vintages. Another winery is next door, and its views are endless, the perfect place for a leisurely wine and food pairing lunch. After being made soporific by the wine, you go touring Santorini’s medieval villages, Megalochori, Pyrgos, and Firostefani, and see that all are quite different from the most popular – Oia and Fira. While Santorini is now world-famous, today’s private tour reveals its local side. And after the sunset crowds subside, you’ll have another laid-back evening in the mazy streets of Oia.
Crete – Historic Island Highlights on a Private Tour from Heraklion to Chania
Continue on the fast ferry as the trip from Santorini to Crete takes just under two hours. You will disembark in Greece’s fifth-largest city, a rather industrial looking destination that most people run far from when they arrive. However, if you know which way to turn, Heraklion is studded with historical treasures including fort walls, Venetian art, ancient temples, Ottoman architecture, and Egyptian sculptures. So you will spend half a day before traveling onwards, the highlight being the suburb Palace of Knossos. From here, it will be a two-hour transfer to old-world Chania, where you are soon immersed in an old Venetian city where winding alleys lead to a charming 14th-century harbor.
Crete – Deserved Coves and the White Sand of Elafonissi
Crete is huge, and its secrets are dotted around. The journeys are long yet beautiful, memorable for barren landscapes that suddenly burst into life with a monastery or mountain. Today you will head southwest and across mountain passes to find churches hidden inside caves. Your destination is Elafonisi, where the sand is both pink and white, the waters are opaque turquoise, and the vibe is as escapist as it comes. It might feel as if you are on a Caribbean island, such is the fine sand and warm, tropical waters. Despite being named one of the world’s top 25 beaches, there is enough space on Elafonisi for a very relaxed afternoon. It is then a winding journey back to Chania, and an evening in the local neighborhoods.
Crete – Guided Through the Colorful Chania Neighborhoods
To understand Crete's history and style, you will need to explore the little neighborhoods, including Topanas, Splantzia, Kasteli, and Kolombo. Here, mythology and tradition guide every day as flowers decorate houses and avenues, stone paths take you through Ottoman and Venetian architecture. A great Minoan city with high walls looks down on these neighborhoods, casting a shadow across food markets and cobbled stone paths. With your local guide, you can explore and come to know how Crete very much feels like its own country, especially when you learn the lunchtime traditions. After lunch, the day is left free, and you can find a number of decent beaches within reach of the hotel.
Crete – The Pink Sands of Balos and Gramvousa
Two weeks of island hopping has to end on the Aegean. Set sail on a small-group catamaran tour this morning, wind power taking you west to the pink sands of Balos and Gramvousa. These beaches are lined by cafes or bars, but hidden inside a protected area. Seals swim past the coast, and the catamaran docks at very private places for swimming. The sun beats down, and you laze away on the deck. Then in Gramvousa, you can hike to a Venetian castle and beachside shipwreck. Sailing back to Chania, you will probably drift off on the deck, which is just another of the highlights of Greek island hopping. Tonight is your final chance for a taverna meal, and like the last three days, you will taste how Crete is different from the other islands.
Crete – Departure
Crete’s main international airport is just a 20-minute transfer from your hotel. After a morning in the old town, you will depart, taking two weeks of escapist memories back home.
- Relax on the expansive beaches of Naxos, an island that helps you escape the world
- Indulge in the beauty of Santorini, an island that connects you to Greek tradition
- Discover Ancient Greece on a day trip to Delos, the most important archaeological ruins outside Athens
- Explore the contemporary chic of Mykonos, an island that’s all about the Greek vacation style
- Walk across astonishing pink and white sands around the island of Crete, the island where beach time meets ambient neighborhoods
- Gain an intimate understanding of the food, the tour including a household dinner in Mykonos and a cooking class on Naxos
- Enjoy all the history, like Venetian harbors, iconic windmills, ancient temples, and small whitewashed villages
- Cruise around Santorini on a catamaran, just one of the Aegean Sea highlights on this tour
The highlight of the Greek islands is how each one feels completely different. Sure, you can look at photos of blue and white villages and imagine the islands are very similar. Or you can spend an evening in a taverna and think it’s quintessentially Greek, without initially noticing the island individualism. But when you get to know the country you experience its nuance. Mykonos and Naxos are neighbors but are absolutely distinct in atmosphere and style. Delos is all archaeological ruin while Santorini is dominated by the dramatic work of nature, and these islands are all in the Cyclades chain. When you travel to Crete, the changes are even more distinctive as if you are exploring a different country entirely.
It is this individualism and inimitability that has made Greek island hopping such a famous vacation experience. A short ferry west, and everything changes. A quick hop south, and there is a new collection of treasures to find. This two-week tour is handcrafted to incorporate four corners of the Greek experience with Mykonos, Naxos, Santorini, and Crete. These are not only the most diverse islands, but they are neatly connected on the ferry route south. Over the two weeks, you will take day trips to smaller islands, including the birthplace of Apollo – Naxos – and the breathtaking white sand of Elafonisi.
Fly to Mykonos, the most developed and contemporary of the islands. Chic cafes meet with swanky seafood restaurants and languid beaches. It is an island populated by jet-setters, less authentic than the others but packed with beautiful streets and sights. Spend three nights amid the bustle of Hora, easing into the sultry island atmosphere. On day two you have dinner at a small Mykonian country household while day three is dedicated to the ruins of Delos nearby. Mykonos is an incredibly easy first stop, and by day four you will be looking forward to something a little more traditional.
So enter Naxos, an undeveloped island with just a handful of boutique hotels. Walk to deserted, expansive beaches during the day, feeling the escapism that the Cyclades can provide. Sink your toes into cooling sand, feel the salty breeze through your hair and visit a handful of temple ruins devoid of tourists. Go on a Cyclades cooking class, and spend your evenings in tiny whitewashed villages that have not yet been populated by souvenir shops. Naxos is the unsung gem of the Cyclades, and after three days you will realize why people don’t like to shout too loudly about its riches, as some islands are best left as they always have been.
Take the ferry south to Santorini and the most photogenic of Greece’s islands. It has the quintessential Greek island image many people are expecting, where blue domes and window shutters enliven the whitewashed cubist villages. Think breathtaking sunsets, turquoise waters, swathes of vineyards and getting lost in the mazy villages. You will be staying in the largest village Oia, which is linked to Fira by a stunning walk along the old volcanic caldera. Enjoy an afternoon of catamaran cruising on day eight, stopping at caves and lagoon-like waters to swim. Then spend day nine in the vineyards and small villages, getting to know parts of Santorini that have not yet been popularized by Instagram.
Crete is an enormous island, comfortably larger than all the other previous three put together. Disembarking in Heraklion, you spend a day amid historical highlights, like a medieval old city and vast Mycenaean ruins. You spend four nights in Chania, a charming Venetian-styled harbor city that’s packed full of alleys and cobbles. From here you make excursions to the white sands of Elafonisi and pink sands of Balos, plus get guided through local neighborhoods that seem frozen in the 17th and 18th centuries. Chania is a relaxed yet exciting destination to end on, and when you need to be alone, there are some great beaches within easy reach. Consider learning more about our travelers’ best Greece vacation experiences by reading their Greece travel reviews.
$3,495 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
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Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
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