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Crete, Mykonos & Santorini

Greek Isles Cultural Walking Tour

7 DaysStarting at $7,595
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Overview

Island-hopping in the Greek Isles is an odyssey through sunlight and history, where whitewashed villages cling to cliffs above sapphire seas and every breeze carries the scent of thyme and salt. Across Mykonos, Crete, and Santorini, you’ll walk amid olive groves and vineyards, cobbled lanes and ancient ruins, meeting artisans, winemakers, and guides whose families have called these islands home for generations. Classic Journeys has thoughtfully crafted an adventure that balances cultural discovery and coastal serenity—where mythology meets Mediterranean life. From quiet trails overlooking the Aegean to farm lunches and hillside sunsets, each day reveals the authentic heart of Greece, shared in the company of locals who make you feel less like a traveler and more like an honored friend.

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

Itinerary Highlights

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• Experience Venetian and Ottoman architecture on a guided walk through the vibrant heart of Crete.

• Explore the legendary Minoan Palace of Knossos at eye level, tracing the footsteps of ancient history.

• Visit a restored Byzantine monastery, welcomed by a community of nuns eager to share their centuries-old weaving tradition.

• Meet George, a traditional baker who demonstrates how he creates phyllo dough by hand—and sample delicacies fresh from his oven.

• Island-hop to Mykonos and stroll the iconic lanes of Little Venice, then learn cheese-making from a third-generation local craftsman, tasting farm-fresh specialties in his company.

• Amble through sunlit olive groves and countryside trails to a family-run mill for a memorable olive oil tasting.

• Journey to Santorini, wandering picturesque streets, shopping for handcrafted goods, and observing artisans at work.

• Walk famed caldera trails with panoramic Aegean views, then toast the sunset at a family-run vineyard high above the crater.

Download Full Daily Itinerary

Map

  • Starting Point:

    Mykonos – 10:00 am – Hotel Lobby

  • Ending Point:

    Oia, Santorini – 11:00 am – Hotel Lobby
Itinerary Map

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Walking Level

  • Daily Mileage Options: 2-6.5 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.
To See Mileage Daily, Download Full Itinerary

Dates & Prices

The earlier you book, the more options you’ll have and the lower your price. Secure your spot with a deposit of just $500 per person at the time of reservation. Plus, you can always change your mind — there’s no fee 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.

Hotels

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. 

Belvedere Hotel Mykonos

A five‑star member of The Leading Hotels of the World, this serene retreat in the heart of Mykonos Town blends whitewashed Cycladic charm with modern elegance. Terraced sea‑view rooms, a tranquil pool, and world‑class cuisine create a relaxing oasis just steps from the island’s iconic windmills.

Fanari Villas

An award‑winning luxury sanctuary named Best Scenic View Hotel in Greece, this cliffside gem offers unforgettable views of Santorini’s caldera. Elegant cave‑style suites, heartfelt service, and magical sunsets create an atmosphere of timeless serenity rooted in authentic island charm.

Manili Boutique Suites & Villas

Recipient of a MICHELIN Key distinction, this intimate boutique property in Archanes blends Cretan tradition with refined modernity. Serene courtyards, inviting pools, and warm, family‑style hospitality make it a graceful base amid Crete’s vineyards and mountain landscapes.

What’s Included

  • Meals: All breakfasts, four lunches, and three dinners.
  • Hotels: Award-winning boutique properties, thoughtfully selected for their exceptional location, design, history, and regional character.
  • Tour Leader(s): Expert guides who are your well-connected local friends and provide you access to people and places you wouldn’t find on your own.
  • Supplemental Experts: Additional regional guides and specialists on select tours.
  • Transportation: All land transportation as listed in the daily itinerary, including fares for trains, ferries, and other modes of travel.
  • Perfect Pairings Dinner: A special dinner prepared by one of our favorite chefs with a procession of wines tailored to each course.
  • Privileged Access Events: One-of-a-kind access to remarkable people, places, and experiences arranged just for you, as noted in the daily itinerary.
  • Admissions & Entry Fees: Entry to tastings, historic sites, and other scheduled activities listed in the daily itinerary.
  • Baggage Transfers: Upon arrival, we whisk you and your bags directly to your room—no waiting, no tipping.
  • Gratuities: All gratuities at hotels, restaurants, and for baggage handling.
  • Dedicated Guest Services Coordinator: Your pre-trip concierge and tour expert, available to answer questions and ensure you’re fully ready to get the most out of your tour.
Not Included: Tour Leader gratuities, travel to and from your trip’s start and end points, and any meals or activities taken independently.

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.

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FAQs

What is the best month to go to Greece?

May through October is the sweet spot for Greece—think sun-warmed villages, crystal-clear seas, and perfect walking weather. Classic Journeys times your adventure for these prime months, so you wander ancient ruins and whitewashed villages when the scenery is at its most dazzling and the crowds are fewest.

How much does an average trip to Greece cost?

The cost of visiting Greece varies, but with Classic Journeys, your luxury walking tour includes boutique accommodations, expert guides, many local meals, and immersive excursions—all with no hidden fees. You get exceptional value and total ease, with every detail seamlessly handled so you can just enjoy the magic of Greece.

What is the best part of Greece to go to?

The best part of Greece is island hopping in the Aegean Sea—exploring Crete’s Minoan ruins, wandering olive groves, and soaking up village life on Mykonos and Santorini. With Classic Journeys, you discover iconic sites, share meals with local families, and relax in perfectly sited hotels—all with the insider access of your well-connected guide.

Is Greece safe to travel to right now?

Greece is one of Europe’s safest countries and welcomes travelers year-round. With Classic Journeys managing your hotels and daily logistics, you simply lose yourself in ancient alleyways, sunny harbors, and hillside trails—exploring at your own relaxed pace, knowing every detail is covered.

What is the prettiest Greek Island to visit?

Greece has plenty of stunning islands, and while some say Santorini is best, others swoon for the shores of Crete. Classic Journeys’ walking tour leads you to the most beautiful spots on Santorini, Crete, and Mykonos—breathtaking cliffs, hidden coves, and charming villages—each with its own magic, history, and time for you to soak it all in like a local.