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SIGNATURE ITINERARY

Greece: Islands of Surprises

11 NIGHTS · FLEXIBLE DATES · PRICES FROM $6,890 pp

20 YEARS OF CRAFTED TRAVEL

6,000+ TRAVELLERS SERVED

PERSONALLY VETTED BY OUR TEAM

92% REPEAT AND REFERRAL CLIENTS

Greece: Islands of Surprises · 11 nights
From · $6,890 pp
ABOUT THIS JOURNEY

For travelers who want to feel ancient wonder, wander through whitewashed villages, and dive into the Aegean’s impossibly blue waters.


Have you ever pictured the Acropolis on a hilltop, a Santorini sunset, or volcanic sand between your toes and thought … “Could it really look like that?” This is Greece: island by island, at exactly the right pace. Experience a journey where each stop feels distinctly different from the last. You’ll begin in Athens, a city of antiquity, whose millennia-old sites, stone alleys, and rooftop bars create an atmosphere that is as historic as it is electric. Next is Paros, where quaint harbors, hidden coves, and Cycladic charm welcome you with open arms. Naxos is something else entirely, with green rolling hills and the best homegrown food in the Greek Isles. In a dramatic finish, gaze out upon the caldera as you stay in a breathtaking resort perched high on Santorini’s cliffside.

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DAYS 1 - 2

Athens

Moments after landing, you find yourself in the heart of the old town with a rooftop pool and the Acropolis shining before you like a beacon. Your hotel is the perfect place to rest, recover, and let the city settle around you. Enjoy wandering at leisure, soaking in the atmosphere, and dining at a rooftop restaurant whose views are second to none. Next, you’ll embrace a slow morning before meeting your guide to discover Athens’ most captivating sights. As the Parthenon stands before you, let it sink in that this soaring monument has survived for two and a half thousand years. You’ll also visit the Erechtheion and the Theatre of Dionysus, each offering a new layer of ancient wonder. On the second night, as the sun sets over Athens, you'll already feel the pull of the Greek Isles waiting ahead.

DAYS 3 - 5

Paros

A short flight brings you to Paros, and you settle in within walking distance of Naoussa, one of the prettiest harbor towns in the Cyclades. The first afternoon is yours to comb the beach, trace cobbled streets, then have dinner with your feet in the sand. If you're in the mood, the island has a vibrant nightlife, livelier than that of its neighbors. A private tour of Paros awaits the next day, as a local guide introduces you to the hilltop village of Kostos, the traditional charm of Lefkes, Prodomos' marble alleys, and the shores of Golden Beach. Your lunch at a tavern in Piso Livadi is the kind of meal that makes you understand why no one around seems to be in a hurry.

DAY 6 - 8

Naxos

Naxos welcomes you with a sea-view balcony and Agios Prokopios: the island's most beautiful beach. With the golden sand just steps from your door, the first moments are built for simple pleasures: to relax, swim, and do as little as possible. A delicious adventure greets you the next day as you travel the countryside to a family farm. Led by a Naxian chef, you'll pick vegetables and fruit straight from the garden and hear stories of those who have worked these lands for generations. A cooking class follows, then an evening of authentic Greek cuisine and dancing. It is an experience that has nothing to do with sightseeing and everything to do with why we travel in the first place.

DAYS 9 - 11

Santorini

The final leg of the journey is one of legend; what most of us picture when we think of Greece. Your room sits on the edge of the caldera with a private jacuzzi and views so enchanting, you can't look away. The next morning, embark on a shining catamaran as you discover Santorini's volcanic cliffs, Black Beach, Red Beach, and warm Aegean waters. You'll even savor a traditional barbecue on board, with plenty of wine and fabulous conversation. Back on shore, the revelry continues as a Greek wedding show brings a party's worth of energy, dancing, and plate smashing. For the final day, indulge in Cycladic luxury by lounging poolside, then cruising the island for a food-and-wine tasting tour. Your trip ends in the only way it could: watching the sun dip behind the caldera, the sky turning every shade of orange, pink, and yellow.

DAY BY DAY

The highlights

  • DAY 1

    Arrive in Athens for a two-night stay in the historic capital.

  • DAY 2

    Uncover the city’s ancient wonders on a small group tour, including the Acropolis and its surrounding treasures.

  • DAY 3

    Fly to Paros for a three-night stay on this laid-back Cycladic island.

  • DAY 4

    A leisure day to explore the charming harbor village and beaches of Naoussa.

  • DAY 5

    Discover Paros’s villages, views, and beaches on a private tour with a local driver-guide.

  • DAY 6

    Sail by ferry to Naxos for a three-night stay, the largest and greenest of the Cyclades.

  • DAY 7

    Get hands-on with a small group Naxian cooking class, capped with dinner and wine.

  • DAY 8

    A leisure day to explore the island's sandy beaches.

  • DAY 9

    Sail by ferry to Santorini for a three-night stay overlooking the caldera.

  • DAY 10

    Sail the caldera on a small group catamaran tour with lunch and refreshments on board, then take in a lively evening of Greek dance and music with VIP seats and a pre-show party.

  • DAY 11

    Savor the island’s flavors on a small group food and wine tour.

  • DAY 12

    Fly to Athens and connect onward for your flight home.

WHAT’S INCLUDED

Everything taken care of

  • Private drivers for every airport and port transfer
  • Ferries with reserved seats throughout
  • Boutique hotels, carefully chosen, in the heart of each destination
  • Daily breakfast included
  • A cooking class dinner, catamaran lunch, wedding show dinner, food and wine tour dinner
  • Small group and private tours led by expert local guides
  • Skip-the-line access at keys sites
PRICING

Prices from

  • 2 people travelling
    $7,490 pp
  • 4 people travelling
    $6,990 pp
  • 6 people travelling
    $6,890 pp

Prices are subject to change depending on your preferred dates of travel. Price does not include international flights.

WHAT OUR CLIENTS SAY

Thank you for doing all of the heavy lifting for our recent WAC planned trip to Greece. It was absolutely wonderful… The two tours you planned for us while in Athens were most enjoyable. The family table cooking experience you suggested and planned for us just outside of Chalkio was one of the highlights of Naxos… The ferry to Paros from Naxos was an adventure… Paros was quaint and beautiful.

DOUG S.  ·  GOOGLE REVIEW

Hilary planned us an absolutely amazing Greece honeymoon that went flawlessly! All of the transfers and hotels were booked with absolutely no hiccups. The suggested excursions were so much fun (the Catamaran tour in Santorini can’t be topped!)

KATHRYN D.  ·  GOOGLE REVIEW
COMMON QUESTIONS

Everything you want to know

A selection of questions about this itinerary and planning a trip to Italy. For more, visit our full FAQ page.

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THE PEOPLE BEHIND YOUR TRIP

Meet the team

Every WAC journey has a dedicated travel designer and a whole team working in the background. From booking suppliers, reconfirming every transfer and reservation, preparing your travel documents, and making sure nothing is left to chance, we’ve got you covered.

Hilary Altman

FOUNDER & CEO
I match travelers with their dream places. The best trips are fun, life-changing, and leave you connected to the world and each other in new ways.

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Christine Turoczi

TRAVEL DESIGNER
Travel has always been part of who I am. I love helping people turn dream trips into unforgettable memories they’ll cherish for a lifetime.

Grace Campagna

PRODUCT MANAGER
I studied history, so I love researching places. Finding hidden gems in ancient cities and staying in historic hotels are my favorite parts of travel.

Kimberly Espinosa

TRAVEL DESIGNER
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Joy Cunanan

BOOKING ASSISTANT
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Emma Wallace

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In Genoa, a pesto class host told me her dream was to visit New York, where my sister lives. It reminded me that we’re all living someone’s dream.

Venice King

ACCOUNTING ASSISTANT
Travel introduces me to people I’d never meet otherwise. On one trip, our local guide became our friend and even invited us to his daughter’s baptism!

Faye Canillo

OPERATIONS ASSISTANT
My favorite place is Siargao, our first-ever family trip. The beaches were beautiful, but the memories we made together are what I’ll always cherish.

Sarah Kanavos

PRODUCT EXECUTIVE
I lived in Andalucía for two years and made friends from all over the world. Now I help others plan trips that build connections like the ones I made!
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