Crete, Mykonos & Santorini

Greek Isles Cultural Walking Tour

7 DaysStarting at $6,895


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 Oia 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.

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


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• Soak in the Venetian and Ottoman architecture on a guided walk through the streets of the Cretan capital of Heraklion. 

• Step back in time on an exploration on foot at eye level of the Minoan Palace of Knossos. 

• Punctuate spectacular walks with in-person visits to 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.

• Go island-hopping, Greek style, to Mykonos to explore Little Venice and learn the art of cheese-making from a local dairy craftsman and sample some fresh specialties.

• Walk through shimmery green olive groves and between mountain villages to do an oil tasting with a maker at his mill on Naxos.

• Cross the sea to Santorini, to roam the ancient and picturesque streets to explore, shop, and visit artisans.

• Luxuriate at your perfectly-sited hotel overlooking the caldera and the deep blue sea. 

• Walk on the slopes of the famous volcano to a local vineyard for a tasting with views of the sunset over the crater.

Download Full Daily Itinerary


  • Starting Point:

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

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

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Walking Level

  • Daily Mileage Options: 2-8 miles

  • Route Notes:

    The terrain on this trip includes a mix of paved and cobblestone streets in Heraklion, Mykonos town, Fira and Oia; as well as well-maintained countryside and coastal trails; vineyard, olive grove and shepherds’ paths of compressed dirt and stone; and even crushed lava rock on the volcanic trails. The footpaths offer a selection of level, rolling and hilly terrain with some elevation gain and loss.

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 Greek Isles on foot and at eye level. Each day, join your guide on the most cinematic footpaths in the islands.
  • 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 islands.
  • Small groups that provide you unrivaled access. An average of 10 guests per departure means we can offer you special ‘only with Classic Journeys’ access Knossos so you experience the ancient ruins on a personally guided exploration, in-person visits with bakers, shepherds and olive oil makers that other companies cannot arrange because of larger group sizes, and vineyard walks with a winemaker on Santorini.
  • Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in the Greek Islands, including a cave hotel perched on the cliffs above the caldera in Santorini.
  • Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of the places you visit with us in Greece. From gourmet picnics to coveted restaurants and tastings of local specialties, 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 the Greek Isles 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.
  • Regenerative Travel that supports the history, culture, people and places you’re visiting with us in the Greek Islands. 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.


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.

Lagos Mare

Lagos Mare Boutique Hotel is an elegant property located in a charming seaside village on Naxos. Enjoy upscale accommodations with modern amenities, a spa, an outdoor pool, and warm Greek hospitality during your stay.

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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