Greek Isles
Crete, Mykonos & Santorini

Greek Isles Cultural Walking Adventure

7 DaysStarting at $6,595


Island-hopping in the Aegean is an odyssey beyond anything you dreamed it would be. This remarkable adventure includes spectacular islands in vivid blue seas, the finest sites of antiquity, white beaches beyond compare, and time with locals who welcome you with wide-open arms. You explore Crete with its Minoan ruins, rolling olive groves and Byzantine churches, and Naxos, the greenest of the Cyclades. You also enjoy a leisurely multi-night stay in red-cliffed Santorini, settling into a charming hotel with incredible sunset views of the extinct volcano’s caldera. From Mykonos to Delos and beyond, we draw on local connections to provide you with insider access and show you Greece at its best. You meet phyllo bakers, olive growers, archeologists and villagers – the contemporary Greeks who live amid some of the loveliest scenery and finest historical treasures on earth. You’ll head home with a deep and very personal feel for this wonderful culture and the islands that have cradled it for millennia.

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Classic Journeys provides unbeatable access to experiences around the globe.”
Travel + Leisure


You meet in the Cretan capital of Heraklion (2 nights) a town, studded with Venetian and Ottoman architecture. From here, you make a memorable visit to the Minoan Palace of Knossos. Your spectacular walks will be punctuated by meetings with olive-oil makers, a traditional baker who still makes phyllo dough by hand, and a small community of nuns who welcome you to their home that is a restored Byzantine monastery.
Get ready for a couple of days of island-hopping, Greek style. Your home base is Naxos (2 nights) where you’ll leave the beaten path near Kourounohori to see a remarkable statue abandoned by its sculptor more than 2,500 years ago. You’ll also experience the true archeological wonders of Delos, mythological birthplace of Apollo, on a guided visit to the temples, amphitheater, homes and more.
DAYS 5-7 – OIA
Crossing the sea to Santorini, you travel to Oia (2 nights). Roam the ancient and picturesque streets to explore, shop, visit artisans, sip something cold at a table overlooking the sea, or just linger poolside at your hotel. Next day, a morning walk on the slopes of the famous volcano precedes an invitation to a local vineyard for a tour and tasting with views of the sunset over the crater.
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  • Starting Point:

    Heraklion, Crete – 9:00 am – Lobby of GDM Megaron Heraklion
  • Ending Point:

    Oia, Santorini – 11:00 am – Lobby of Fanari Villas

Dates & Prices

The earlier you book, the more choice you’ll have and the lower your price. And you can always change your mind — you won’t be charged to transfer to a different trip before your final payment is due. Talk with one of our travel experts at 800-200-3887.

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Family Departure

Select our “Family Departure” to travel with other families.

Why Choose Classic Journeys

Travel + Leisure has awarded Classic Journeys the #1 World’s Best Tour Operator multiple times and says, "Classic Journeys provides unbeatable access to experiences around the globe." Here’s what that access means for you.

  • Experience the world on foot and at eye level. Each day, join your guide on the most cinematic footpaths in the region.
  • Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, share their lifelong connections as well as engaging anecdotes about the history and culture of the region.
  • Small groups that provide you unrivaled access. An average of fewer than 10 guests per departure means we can offer you special access to sites like Stonehenge so you experience the stone circle when it’s closed to the general public, a guided visit to Zion Narrows that other companies cannot arrange because of larger group sizes, and vineyard walks with a count and countess in Tuscany.
  • Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in the region you’re exploring, including rainforest lodges, 16th century villas, and award-winning properties that show up on World’s Best and Gold lists.
  • Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of the places you visit with us. From gourmet picnics to coveted local restaurants, our meals offer you opportunities to explore native food traditions and fine dining.
  • Handcrafted itineraries with all activities included. With our long-term friendships, we know our walking tour regions more personally than anyone else. So you get thoughtfully curated itineraries that combine explorations of the villages, organic farms, archeological sites and the people who know them best.
  • Sustainable travel that supports the places you’re visiting. We put our local currency into the pockets of the people who live where we travel. It’s your guarantee that you’ll have authentic, up-close experiences on your trip. Best of all, our person-to-person approach helps sustain their ways of life.


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We spend years cultivating personal relationships with our hoteliers to provide you thoughtfully selected accommodations that reveal the true character of the region. Here is a sampling of our favorite hotels on this tour. 

Fanari Villas

The pinch-yourself views at this all-suite hotel are utterly remarkable. The classic white-washed building sits right on the edge of the Santorini’s caldera so you can marvel at the sunsets during your stay at this luxurious property.

GDM Megaron Heraklion

This landmark 5-star hotel is a commanding historic monument in the heart of Heraklion. There’s an open-air pool on the roof. High-ceilinged rooms and public spaces are beautifully decorated in a warm modern style.

Naxos Island Hotel

Naxos Island Hotel is designed in traditional Cycladic style. The hotel is a miniature of Naxos Island where each room retains the features of a village and it is made of marble, emery, and plaster.

What’s Included

  • Award-winning boutique hotels that provide you unlimited access to the people and places, culture and history you came to experience
  • All breakfasts, 2 lunches and 4 dinners
  • Full-time experienced guide(s) who are with you throughout the trip and handle behind-the-scenes logistics
  • Admissions to tastings, historic sites and other scheduled events as noted in the detailed daily itinerary
  • Gratuities for hotels, meals, and baggage
  • All land transportation during the trip

Above & Beyond Benefits

Privileged Access Events

  • One-of-a-kind access to remarkable people, places and activities arranged just for you.

Wine on Us

  • In many regions, we uncork wonderful local wines at every dinner, compliments of Classic Journeys.

Invisible Check-In

  • When your group arrives, we whisk you and your bags to your room immediately. No waiting – no tipping.

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