800-200-3887
FIND A TOUR
FIND A TOUR
All Tours
Crete, Mykonos & Santorini

Greek Isles Cultural Walking Tour

7 DaysStarting at $7,295
Download itinerary Book Now

Overview

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 on our small-group Greece tours. 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

Itinerary Highlights

Download Full Daily Itinerary

• 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

Map

  • 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

Click map to enlarge

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.

Talk to an expert
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. 

Greece-Liana-Hotel-Spa

Liana Beach Hotel & Spa

Situated on the pristine coastline of Naxos, the Liana Beach Hotel is a luxurious property with breathtaking sea views. Enjoy the beachfront access, fine dining, wellness spa, pool, and relaxing atmosphere while staying at this upscale retreat.

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 Santorini’s caldera with ringside seats for sunset. Lovely rooms are decorated in a sparse classic style.

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.

What’s Included

  • Meals: All breakfasts, two lunches, and four 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.

Guest Reviews

Trustpilot

Similar Tours

See All Tours

From the Blog

All Posts

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 Aegean Sea—exploring Crete’s Minoan ruins, wandering olive groves, and soaking up village life on Naxos 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 Naxos or the shores of Crete. Classic Journeys’ walking tour leads you to the most beautiful spots on Santorini, Naxos, 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.