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The Cyclades Uncovered

12 Days / 11 Nights

Athens, Milos, Naxos, Santorini

Travel and LeisureFodorsUSA TodayNew York TimesNational GeographicWashington PostVogue

Spend 12 days exploring the treasures of some of the most incredible Greek Islands. After a short stay in Athens, during which you'll check the city's highlights off your list, your Cyclades adventure begins in quaint Milos, an island with authentic vibes and spectacular scenery. Your journey continues in Naxos, the largest of the Cyclades Islands, renowned for its history and gastronomy. Before you leave Greece behind, head to Santorini for unique moments in the most gorgeous setting. After this first taste of the Cyclades, you'll certainly be coming back for more.

One of our team members in Greece will be available to you leading up to and during your trip to answer any questions and arrange local services. You will receive access to your Guest Page, with its information on the best these destinations have to offer, including things to see and do, and other inside tips from restaurant recommendations to tipping advice. Upon arrival, we will provide you with a local SIM card or eSIM with data that you can use to reach your local JayWay contact throughout your trip. In all of our destinations, we offer a variety of memorable 3-5 star accommodation options, including boutique hotels and charming B&Bs. With our firsthand experience, we can ensure they are all clean, comfortable, and centrally located, with local ambiance.

Route for Athens, Milos, Naxos, Santorini tour

2 Nights in Athens

2 Nights in Athens

3 days in Athens
3 days in Athens

2 Nights in Athens

Although it's hard to not keep craning your head to take in the spectacle of the Acropolis at the center of town (especially when it's lit up at night), there's more to Athens than its dense concentration of ancient ruins. Athens is a center for contemporary art, with modern galleries sitting beside museums stuffed with art dating back millennia. This combination of the old and new is especially clear at the Odeon of Herodes Atticus, a spectacular open-air theater that has hosted concerts and plays for nearly 2,000 years. The city's culture is also reflected in its diverse food and drink, which combines traditional Greek favorites with influences from across the Mediterranean, and the world, as fitting Athens' deep history as a humming harbor hub. While Athens' variety is enough to keep you busy, from the hidden back alleys of the center, to the city's showy coast, the city works well as a base for day trips, whether down the coast, or to the Peloponnese. Head to oracular Delphi, or hunt for where Lord Byron's carved his name into the monumental Temple of Poseidon at the tip of Cape Sounion.

Although it's hard to not keep craning your head to take in the spectacle of the Acropolis at the center of town (especially when it's lit up at night), there's more to Athens than its dense concentration of ancient ruins. Athens is a center for contemporary art, with modern galleries sitting beside museums stuffed with art dating back millennia. This combination of the old and new is especially clear at the Odeon of Herodes Atticus, a spectacular open-air theater that has hosted concerts and plays for nearly 2,000 years. The city's culture is also reflected in its diverse food and drink, which combines traditional Greek favorites with influences from across the Mediterranean, and the world, as fitting Athens' deep history as a humming harbor hub. While Athens' variety is enough to keep you busy, from the hidden back alleys of the center, to the city's showy coast, the city works well as a base for day trips, whether down the coast, or to the Peloponnese. Head to oracular Delphi, or hunt for where Lord Byron's carved his name into the monumental Temple of Poseidon at the tip of Cape Sounion.

Day 1

Day 1 - Arrival in Athens

Upon your arrival in Athens, a driver will meet you and drive you to your centrally located accommodation. The drive takes about 45 minutes, depending on traffic.

Day 2

Day 2 - Your First Full Day in Athens

Athens Highlights Mythology Small Group Tour

Explore Athens' Highlights

Included in your vacation package price.

Discover the myths behind the greatest landmarks in Athens. Learn about Greek gods and heroes, and discover what really hides behind ancient myths. At the same time visit the best landmarks and sites in Athens, such as the Acropolis (Parthenon, theater of Dionysus, temple of Athena Nike, temple of Erechtheion, and the sanctuary of Asclepius), Olympian Zeus’ temple, the Ancient Agora, and the temple of Hephaestus.


Activity Level : Moderate
Duration : 4 hours

Day 3

Day 3 - Traveling to Milos by Ferry

Milos awaits you today! A driver will pick you up from from your accommodations and take you to the port of Piraeus, where you'll catch your ferry to Milos. The duration of the journey is around 3 hours 30 minutes.

Milos by Ferry
We also offer the following excursions in Athens

Acropolis for Families Private Tour
Moderate2 hours
Ancient Corinth Private Tour with Transfer from Athens to Nafplio
Light6 hours
Ancient Corinth and Nemea Private Day Trip
Moderate9 hours
Athens Markets and Chronicles Small Group Tour
Light3 hours

3 Nights in Milos

3 Nights in Milos

4 days in Milos
4 days in Milos

3 Nights in Milos

Tucked away in the Western Cyclades subgroup, Milos Island owes its otherworldly lunar landscapes to its volcanic past. Alongside its dramatic rock formations, Milos is known for its crystal-clear turquoise waters, century-old catacombs, and easy-going vibes. Unlike other Greek Islands, Milos remains irresistibly unspoiled, a haven of insanely blue waters, whitewashed villages, and cotton candy sunsets. With several remote beaches and sea caves to explore, Milos is also the ideal destination for sailing and cruising enthusiasts.

Tucked away in the Western Cyclades subgroup, Milos Island owes its otherworldly lunar landscapes to its volcanic past. Alongside its dramatic rock formations, Milos is known for its crystal-clear turquoise waters, century-old catacombs, and easy-going vibes. Unlike other Greek Islands, Milos remains irresistibly unspoiled, a haven of insanely blue waters, whitewashed villages, and cotton candy sunsets. With several remote beaches and sea caves to explore, Milos is also the ideal destination for sailing and cruising enthusiasts.

Day 3

Day 3 - Arrival in Milos

Upon your arrival to the Milos port, our driver will wait for you and take you to your accommodation.

Day 4

Day 4 - Your First Full Day in Milos

East Milos Jeep Safari Private Tour

East Milos Jeep Safari Private Tour

Included in your vacation package price.

Today's a day for sun, sea and history! After departing Adamas Port, you will have the chance to admire volcanos, sulphur mines, monasteries and secluded beaches!


Activity Level : Light
Duration : 4 hours

Day 5

Day 5 - Your Second Full Day in Milos

Adamantas, Kleftiko, Agia Kiriaki Private Morning Cruise

Adamantas, Kleftiko, Agia Kiriaki Private Morning Cruise

A half-day private cruise during which you'll marvel at traditional fishing villages with colorful houses, lava rocks, and stunning sea caves. Enjoy swimming in crystal clear waters and a full traditional lunch with local products on board.


Activity Level : Light
Duration : 6 hours

Day 6

Day 6 - Traveling to Naxos by Ferry

Today you will travel from Milos to Naxos by ferry. A driver will pick you up at your accommodations and take you to the port. Then you will take ferry to Naxos, which takes up to 4 hours.

Naxos by Ferry (Adamas Port)
We also offer the following excursions in Milos

Adamantas, Kleftiko and Agia Kiriaki Small Group Morning Cruise
Light6 hours
Adamantas, Kleftiko, Poliegos and Pollonia Small Group Cruise
Light9-10 hours
Amazing Beaches Small Group Tour
Light4 hours
Instagram Small Group Tour of Milos
Light3 hours

3 Nights in Naxos

3 Nights in Naxos

4 days in Naxos
4 days in Naxos

3 Nights in Naxos

The largest island in the Cyclades, Naxos frequently appears lists of the most authentic Greek islands and for good reason, as it is large enough to not rely solely on tourism. Gracefully lying in the heart of the Aegean, this dazzling Greek jewel is an ideal destination for those who wish to indulge in life's simple pleasures, great food, and gorgeous sandy beaches. What visitors love most about Naxos is the genuine rural charm found in the island’s picturesque mountainous villages, which dot the rugged landscape. Naxos has been the source of quality marble for centuries, and its ancient marble quarries, and their products, are some of the island's many highlights. Naxian marble was used to create the extraordinary sculptures that can be admired on the island of Delos and the archaeological site of Delphi. At sunset, enjoy a leisurely walk along the harbor of Chora (Naxos' old town) towards the island's most imposing landmark: the Portara. This massive marble doorway dates back to 530 B.C. and was built to honor the god of light, Apollo, although it was never fully completed. The myths and legends surrounding the island of Naxos are worth the trip alone. After sunset, head to one of the local tavernas found inside the fortified walls of the Venetian castle, the Kastro.

The largest island in the Cyclades, Naxos frequently appears lists of the most authentic Greek islands and for good reason, as it is large enough to not rely solely on tourism. Gracefully lying in the heart of the Aegean, this dazzling Greek jewel is an ideal destination for those who wish to indulge in life's simple pleasures, great food, and gorgeous sandy beaches. What visitors love most about Naxos is the genuine rural charm found in the island’s picturesque mountainous villages, which dot the rugged landscape. Naxos has been the source of quality marble for centuries, and its ancient marble quarries, and their products, are some of the island's many highlights. Naxian marble was used to create the extraordinary sculptures that can be admired on the island of Delos and the archaeological site of Delphi. At sunset, enjoy a leisurely walk along the harbor of Chora (Naxos' old town) towards the island's most imposing landmark: the Portara. This massive marble doorway dates back to 530 B.C. and was built to honor the god of light, Apollo, although it was never fully completed. The myths and legends surrounding the island of Naxos are worth the trip alone. After sunset, head to one of the local tavernas found inside the fortified walls of the Venetian castle, the Kastro.

Day 6

Day 6 - Arrival in Naxos

Upon arriving at the port, you'll be taken to your accommodations in Naxos.

Naxos Old Town and Castle Private Walking Tour

Naxos Old Town and Castle Private Walking Tour

Included in your vacation package price.

Meandering through the paths of history & mythology this immersive walk will take you back in time. You will experience many sensations at every step of the way in the Old town of Naxos where every corner, every coat of arms has a story to tell.


Activity Level : Moderate
Duration : 2-3 hours

Day 7

Day 7 - Your First Full Day in Naxos

The Best of Naxos Private Tour

The Best of Naxos Private Tour

Included in your vacation package price.

Enjoy an immersive tour of the island. Together with your professional expert guide you will visit famous landmarks of Naxos connecting the island’s rich ancient past evenly with the present. While unraveling the rich history of Naxos, from ancient through byzantine and medieval times, you will experience the local culture of Naxos today.


Activity Level : Moderate
Duration : 6 hours

Day 8

Day 8 - Your Second Full Day in Naxos

Private Hiking Tour

Private Hiking Tour

Without any doubt, hiking on Naxos is a fantastic “all five senses” experience! You will experience the rich and magnificient nature of the island and learn about the history and traditions, plants and herbs and their healing powers. And of course, you will enjoy the local cuisine


Activity Level : Strenuous
Duration : 5 hours

Day 9

Day 9 - Traveling to Santorini by Ferry

Today you will travel from Naxos to Santorini by ferry. A driver will pick you up at your accommodations and take you to the port. Then you will take the ferry to Santorini, which takes around 1 hour 30 minutes / 3 hours based on your preferred departure time.

We also offer the following excursions in Naxos

All the Marble Private Tour
Moderate7 hours
Catamaran Group Day Cruise
Easy8 hours
Cheese and Wine Trails Private Half-Day Tour
Light5 hours
Cheese, Wine and Sightseeing Private Tour
Light8 hours

3 Nights in Santorini

3 Nights in Santorini

4 days in Santorini
4 days in Santorini

3 Nights in Santorini

“Intelligent adults come here and turn into infants,” Craig Walzer, owner of the Atlantis Bookstore. Santorini is every traveler's dream. The whitewashed houses and blue domed churches perched atop of soaring cliffs, the narrow cobblestone streets and unsurpassed views of crystal-clear blue waters -- these all greet you as you step foot on this fairytale land. Intertwining myth and reality, Santorini is every bit as beautiful as the countless postcards, magazine covers, and Instagram photos claim. The village of Oia is world-famous for its sunset, where thousands of spectators line up every evening to witness the magic as the sun bids farewell to the sky and the canvas lights up in fierce hues. Fortunately, the sunset can be enjoyed from much of the rest of this crescent-shaped island. Santorini is also home to Akrotiri, the Greek take on Pompeii. Inhabited since Neolithic times, this city was built up by the Minoans, a seafaring civilization that predated the ancient Greeks, only to be destroyed in the catastrophic eruption that shaped Santorini, which forms part of a massive volcanic caldera. Covered in ashes for millennia, Akrotiri is still being uncovered. We suggest visiting the neighboring center of the caldera, where you can enjoy hot springs, visit the volcanic crater, and enjoy stunning views of Santorini itself. Santorini’s unique ecology, climate and volcanic ash soil paved the way for a flourishing wine industry. Its indigenous varietals will make your stay even more enjoyable.

“Intelligent adults come here and turn into infants,” Craig Walzer, owner of the Atlantis Bookstore. Santorini is every traveler's dream. The whitewashed houses and blue domed churches perched atop of soaring cliffs, the narrow cobblestone streets and unsurpassed views of crystal-clear blue waters -- these all greet you as you step foot on this fairytale land. Intertwining myth and reality, Santorini is every bit as beautiful as the countless postcards, magazine covers, and Instagram photos claim. The village of Oia is world-famous for its sunset, where thousands of spectators line up every evening to witness the magic as the sun bids farewell to the sky and the canvas lights up in fierce hues. Fortunately, the sunset can be enjoyed from much of the rest of this crescent-shaped island. Santorini is also home to Akrotiri, the Greek take on Pompeii. Inhabited since Neolithic times, this city was built up by the Minoans, a seafaring civilization that predated the ancient Greeks, only to be destroyed in the catastrophic eruption that shaped Santorini, which forms part of a massive volcanic caldera. Covered in ashes for millennia, Akrotiri is still being uncovered. We suggest visiting the neighboring center of the caldera, where you can enjoy hot springs, visit the volcanic crater, and enjoy stunning views of Santorini itself. Santorini’s unique ecology, climate and volcanic ash soil paved the way for a flourishing wine industry. Its indigenous varietals will make your stay even more enjoyable.

Day 9

Day 9 - Arrival in Santorini

Upon arrival to Santorini's port, you'll be taken to your hotel in Oia

Santorini Sunset Small Group Food Adventure

Santorini Sunset Small Group Food Adventure

Included in your vacation package price.

See Santorini at its tastiest, glitziest best with a local guide by your side! On this food-focused sunset adventure, you’ll spend the evening enjoying some of the best local dishes and drinks the island has to offer while walking along the beautiful Santorini caldera. Learn about the culinary culture, admire some of the island's best sights, and visit a mix of famous spots, historic haunts, and hidden gems as you eat and sip your way through Santorini.


Activity Level : Light
Duration : 4 hours

Day 10

Day 10 - Your First Full Day in Santorini

The Wine Island

Suggested activities for an additional cost, depending on your choice

Santorini is the most popular of the Greek islands and boasts a unique landscape. The famous caldera, amazing red and black volcanic beaches, and the volcano’s crater in Nea Kameni all remind one of its origins. Santorini, because of its unique climate and the mineral content of its volcanic soil, probably has the best wine in Greece. Assyrtiko is the most popular grape variety, rich in minerals and very tasty, and used in most of the white wines produced on the island. We offer a variety of island tours, the best one for you depends on your interests, and how much time you have to devote.

Santorini in a Nutshell Private Tour

Santorini in a Nutshell Private Tour

Suggested activities for an additional cost, depending on your choice

Santorini is a place like no other, full of hidden gems and wonders that are hard to find without a local by your side. Explore off the beaten path, as you visit traditional villages, discover whitewashed back alleys, visit Greece’s Pompeii, the Akrotiri archaeological site, and end on a delicious note by tasting local wines and seasonal tapas.


Activity Level : Light
Duration : 8 hours

Best of Santorini Private Tour

Best of Santorini Private Tour

Suggested activities for an additional cost, depending on your choice

This private tour of Santorini shows you around the best of the island in a day. Visit Santorini's must-see sites and landmarks while nibbling on local delicacies and sipping on Greek wine along the way. Discover the most photogenic parts of the island and create memories to last a lifetime.


Activity Level : Light
Duration : 5 hours

Santorini Wanderlust Private Tour

Santorini Wanderlust Private Tour

Suggested activities for an additional cost, depending on your choice

Experience the absolute splendor of Santorini while strolling through some of the island's most scenic and quiet villages. Walk alongside beautiful mansions, explore quaint rural houses and discover the charm of Santorini’s abandoned neighbourhoods. With this tour, you will also get to visit a traditional winery to taste the local volcanic wines!


Activity Level : Moderate
Duration : 4 hours

Santorini Private Tour for Families

Santorini Private Tour for Families

Suggested activities for an additional cost, depending on your choice

Santorini is a special place like no other ,and this tour captures the best of the island, along with tons of hidden gems you might not get to see without a local by your side. Explore off the beaten path as you visit traditional villages, discover whitewashed back alleys, see an amazing beach with a spectacular lunar-like landscape, and end on a delicious note with a picnic on the beach!


Activity Level : Light
Duration : 6 hours

Day 11

Day 11 - Your Second Full Day in Santorini

Catamaran Premium Small Group Cruise

Catamaran Premium Small Group Cruise

Included in your vacation package price.

Santorini’s volcanic landscape is best explored from the water, so set sail on this top-rated catamaran cruise, which will bring you to the island’s best beaches, viewpoints, and even directly inside the caldera, with a small group of fellow travelers. Along the way, you'll soak in natural hot springs, swim and snorkel off the Red Beach, and take in views of nearby Cyclades islands. An open bar and buffet lunch served right onboard keep you refreshed and energized throughout the voyage.


Activity Level : Easy
Duration : 5 hours

Day 12

Day 12 - Departure Day

Today a driver will pick you up from your accommodations and take you straight to Santorini's airport.

We also offer the following excursions in Santorini

Anydro Small Group Tour
Light5.5 hours - 6.5 hours
Caldera Private Hike
Strenuous4 hours 30 minutes
Highlights Small Group Tour
Light5,5 hours
Oia’s Hidden Treasures Private Tour
Light4 hours

What's Included

Here are all the services provided as part of your complete vacation package. See what every JayWay trip includes.
Please let us know if you'd like to upgrade any transfers or add any additional tours or excursions to your itinerary.

Athens

2 Nights Accommodation
Breakfast (hotels only)
Athens Airport Transfer
Athens Highlights Mythology Small Group Tour
Piraeus Port Transfer
Athens (Piraues) - Milos Ferry

Milos

3 Nights Accommodation
Breakfast (hotels only)
Adamas Port Transfer
East Milos Jeep Safari Private Tour
Adamas Port Transfer
Milos - Naxos Ferry

Naxos

3 Nights Accommodation
Breakfast (hotels only)
Naxos Port Transfer
Naxos Old Town and Castle Private Walking Tour
The Best of Naxos Private Tour
Naxos Port Transfer
Naxos - Santorini Ferry

Santorini

3 Nights Accommodation
Breakfast (hotels only)
Santorini Oia Port Transfer
Santorini Sunset Small Group Food Adventure
Catamaran Premium Small Group Cruise
Santorini Oia Airport Transfer

package excludes:


  • Flights to and from Europe.
  • Tips for Tour Guides, Drivers and Local Reps.
  • Meals (other than breakfast if included in room rate and meals listed as included in food tours and excursions, unless explicitly stated otherwise).
  • Parking fees for your Rental Car (if you are booking one with us) unless otherwise indicated. Some hotels provide free parking facilities.
  • Travel Insurance. See the insurance link on our website
Benefits of Traveling with JayWay

A JayWay vacation is more than the sum of its parts. Our team work tirelessly to ensure your experience is memorable for all the right reasons. Your trip is personalized to maximize your enjoyment. You're taken care of every step of the way.

A Travel Advisor who speaks your language

We will make sure that all your requirements and interests are taken into account in preparing your itinerary.

A totally tailored itinerary for your vacation

Your trip is customized for you by  an experienced trip planner and an expert on the region.

A choice of hand-picked hotels and excursions

We've personally inspected and tested all the hotels and local tour providers we work with to ensure quality.

Detailed pre-trip preparation to make the most of every day

Your Europe-based Tour Manager will be in touch by email and phone a month before you arrive to finalize timings.

On-trip Concierge Service to smooth out any bumps in the road

Your tour manager is at your service throughout your journey. We'll provide a local SIM so you can stay connected.

Personalized Guest Page to make sure you're not missing out

Packed with detailed information and recommendations curated by locals on the best things to do, see and eat.
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