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

BOOK THIS TRIP

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.

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.

DAYS 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 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

WHAT’S INCLUDED

Everything taken care of

Door to door, from the moment you land until you fly home. Private drivers meet you at every airport and port, and your flights and ferries within Greece are booked for you, so there are no tickets to buy and no connections to figure out.

Private drivers for every airport and port transfer
Flights within Greece
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, and food and wine tour dinner
Small group tours led by expert local guides
Skip-the-line access at key sites

Meals not listed above are yours to enjoy wherever you like. International flights are not included.

PRICING

From $6,890 PER PERSON

Based on six people traveling together

2 people traveling

$7,490 pp
4 people traveling

$6,990 pp
6 people traveling

$6,890 pp

WHY THE PRICE CHANGES

Private drivers and many of your arrangements are priced per vehicle or per booking, not per person. The more of you who travel together, the more those costs are shared, so the lower the price for each person.

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

BOOK THIS TRIP

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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.

How is a signature itinerary priced compared to a bespoke trip?

Signature itineraries have an established starting price based on the fixed itinerary. Bespoke trips are quoted individually, starting at approximately $20,000 per group, and scale with destination, length, and access.

What happens if our luggage is delayed or lost?

As soon as you land, head to your airline’s lost luggage desk and fill out a report. They’ll be tracking your bag and can usually tell you exactly where it is, and it’s typically shipped to your hotel within 24 hours. Hold onto the receipt with the phone number and confirmation number so you can follow up if needed, and this is one of several reasons we recommend travel insurance for every trip.

What happens if we need to file a claim while traveling?

Your travel designer can help you understand next steps, but the claim itself is handled directly through your insurance provider.

How can we use our phone internationally?

We’d recommend carrying a phone for missed connections or emergencies, and downloading WhatsApp before you go, since it’s the standard for local calls and texting in much of Europe and Africa. An eSIM app like Airalo is a straightforward option our own team has used and liked. Otherwise, call your carrier about an international plan, and if you have an iPhone, turn off data roaming beforehand to avoid a surprise bill. Since options change often and we’re travel specialists rather than phone specialists, your carrier is the best source for what’s currently available.

Do US citizens need a visa for Greece?

No. Greece is part of the Schengen Agreement, and US travelers can stay visa-free for up to 90 days within a 180-day period.

Is there a hotel tax we should know about?

Yes, Greece charges a Climate Crisis Resilience Fee per room per night, collected directly at your accommodation rather than included in the room rate. It’s higher in peak season (April through October) and at higher-category hotels, and cruise passengers pay a separate small port levy. We’ll note the approximate amount for your specific properties and dates.

Should we fly or take the ferry between islands?

For nearby islands within the same group, the ferry is scenic and part of the experience. For longer jumps, or if time is tight, a short domestic flight is usually the smarter choice, and we’ll route your itinerary accordingly.

Can we combine Athens with the islands in one trip?

Yes, this is one of our most requested itinerary shapes, a few days of history and food in Athens followed by island time. We’ll sequence it so the transitions feel seamless.

ASK US DIRECTLY

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When your vision calls for something entirely custom, it deserves to be designed from the ground up. Our bespoke process begins with an unhurried discovery conversation.

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WHY TRAVEL WITH US

The details that make the difference

We’ve been there.

Every hotel, tour, and experience we recommend has been personally vetted by our team. We don’t send you somewhere we wouldn’t go ourselves.

Our connections are yours.

Years of relationships with exceptional guides, trusted drivers, and the right people on the ground across Europe and Africa.

Nothing gets left to chance.

Before you travel, we reconfirm every booking, every transfer, and every detail to make sure the pieces fit together exactly as planned. You’ll also receive your full itinerary, hotel confirmations, guide contacts, and emergency support loaded into your personal travel app before departure.

Someone picks up the phone.

While you’re away, we’re available. If something shifts, we handle it so you don’t have to.

Your time is the point.

We’ve been arranging travel across Europe and Africa for 20 years, and more than 92% of our clients come back or refer a friend.