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.
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.
DAYS 3-4 – NAXOS / MYKONOS
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.
Starting Point:Heraklion, Crete – 9:00 am – Lobby of GDM Megaron Heraklion
Ending Point:Oia, Santorini – 12:00 pm – Oia hotel lobby
Why Choose Classic Journeys
We believe in creating authentic connections by immersing you into the history and culture of a people and place. So we find the most well-connected local guides who share their relationships and knowledge with us. And with them, we handcraft walking tours in cinematic settings that allow you to see the world on foot and at eye level.
It's why Travel + Leisure magazine has named Classic Journeys as the #1 World's Best Tour Operator multiple times, and the editors of T+L say, "Classic Journeys provides unbeatable access to experiences around the globe." Here's what that access means for you every time you travel with us.
- 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.
Dates & Prices
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Select our “Family Departure” to travel with other families.
- 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.
- When your group arrives, we whisk you and your bags to your room immediately. No waiting – no tipping.
Extend Your Trip
Greece: Athens & Delphi
Are you considering extra time in Athens as part of your trip to Greece? What better way to make it happen than with a seamless extension in handcrafted Classic Journeys style. From Santorini, we’ll coordinate your flight to Athens and arrange guided visits to the essential sights in the city where...View trip
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- Starting at $5,895
- 7 days
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