Immersive 2-Week Greece Vacation: Food, Culture & History

A 14 day trip to Greece 
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This is an iconic Greek island hopping vacation with visits to four islands in two weeks and a complete variety of experiences on land and water. White cubist villages, ancient temple ruins, pink and white beaches, catamaran sailing, local cooking, strolling neighborhoods and savoring flavors are all yours to enjoy on this custom vacation. Handcrafted to celebrate the best of the Cyclades and Crete, this two-week tour shows you how every Greek island is completely unique and home to its own culture, history, and experiences.

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General Information

Detailed Itinerary

Places Visited 

Mykonos, Hora (Mykonos Town), Panagia Paraportiani, Little Venice, Delos, Archaeological Site of Delos, Cynthus, Catacombs, Chora, Naxos, Santorini, Oia, Imerovigli, Firostefani, Fira, Red Beach, Kamari, Perissa, Pyrgos, Thirassia, Akrotiri, Crete, Heraklion, Chania, Palace of Knossos, Elafonisi, Falassarna, Topanas, Kolombo, Monastery of Karolos, Balos, Gramvousa

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Hora (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.

What’s Included: airport transfer, accommodation

Day 2: Hora – 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.

What’s Included: accommodation, tour, breakfast

Day 3: Hora – 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.

What’s Included: accommodation, tour, breakfast

Day 4: Chora (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.

What’s Included: accommodation, tour, breakfast

Day 5: Chora – 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.

What’s Included: accommodation, tour, breakfast

Day 6: Chora – 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 your 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.

What’s Included: accommodation, tour, breakfast

Day 7: Oia (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 village.  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.

What’s Included: accommodation, tour, breakfast

Day 8: Oia – 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.

What’s Included: accommodation, tour, breakfast

Day 9: Oia – 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 quite different to 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.

What’s Included: accommodation, tour, breakfast

Day 10: Heraklion to Chania (Crete) – Historic Island Highlights on a Private Tour

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.

What’s Included: accommodation, tour, breakfast

Day 11: Chania – 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.

What’s Included: accommodation, tour, breakfast

Day 12: Chania – Guided Through the Colorful Chania Neighborhoods

To understand Creten history and style, you will need to explore the little neighborhoods, including Topanas, Splantzia, Kasteli, and Kolombo. Here, mythology and tradition guides the 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.

What’s Included: accommodation, tour, breakfast

Day 13: Chania – 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.

What’s Included: accommodation, tour, breakfast

Day 14: Chania – 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.

What’s Included: airport transfer, breakfast



Please inquire for a custom quote. The price is customized based on final accommodation choices, travel dates, and other custom preferences.