An Odyssey in the Cyclades
This sample 11-day itinerary focuses on the highlights of Greece's most beloved islands, the Cyclades. Touch down in Mykonos and see why it has attracted jetsetters for decades and before you leave, you'll enjoy the extraordinarily dramatic scenery and charming architecture of Santorini. You'll also enjoy the rural authenticity of Naxos (the ancient world's favorite source of marble) and quiet, paradisiacal Paros. If you have some time to spare, we recommend adding Crete to this trip. Greece's largest island, Crete has retained its own culture, as well as the ruined palaces of the Minoans, who flourished in the Bronze Age, when the Greeks were still obscure.
One of our team members in the region 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 that you can use to reach your local JayWay contact (who you will meet in person) throughout your trip. In all of our destinations, we offer a variety of memorable 2-5 star accommodation options, including boutique hotels, charming B&Bs, and spacious apartments. With our firsthand experience, we can ensure they are all clean, comfortable, and centrally located, with local ambience.
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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.
Mykonos
Naxos
Paros
Santorini
package excludes:
- Flights from and to your home country.
- 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
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 destination-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.3 Nights in Mykonos
3 Nights in Mykonos
3 Nights in Mykonos
Although Mykonos is mainly known for its glamorous nightlife and summer beach party scene, which has made it the center of attention among the world’s most affluent travelers and celebrities, who come to the island to enjoy its nights, the island has managed to preserve its historical charm. Mykonos’s unique architecture has long been a source of inspiration for architects, photographers and designers across the globe. The island’s architectural diversity and history are reflected in the hundreds of whitewashed churches and monasteries which are scattered across its barren landscape, the imposing windmills that once played a crucial role in the island’s economy, and its colorful pirate houses, which point to its turbulent past. Apart from the famed beaches that make headlines for their extravagant champagne parties and prices, there are plenty of natural, quieter beaches to savor and explore. Those looking to escape crowds can also find their paradise on Mykonos. Foodies find much to adore in the island's flavors, aromas, and sights. The island caters to the most discerning palates -- from dining in family-owned beach tavernas with your toes touching the sand, to renowned international establishments serving award-winning cuisine, or indulging on freshly grilled seafood prepared by a private chef on a secluded beach.
Although Mykonos is mainly known for its glamorous nightlife and summer beach party scene, which has made it the center of attention among the world’s most affluent travelers and celebrities, who come to the island to enjoy its nights, the island has managed to preserve its historical charm. Mykonos’s unique architecture has long been a source of inspiration for architects, photographers and designers across the globe. The island’s architectural diversity and history are reflected in the hundreds of whitewashed churches and monasteries which are scattered across its barren landscape, the imposing windmills that once played a crucial role in the island’s economy, and its colorful pirate houses, which point to its turbulent past. Apart from the famed beaches that make headlines for their extravagant champagne parties and prices, there are plenty of natural, quieter beaches to savor and explore. Those looking to escape crowds can also find their paradise on Mykonos. Foodies find much to adore in the island's flavors, aromas, and sights. The island caters to the most discerning palates -- from dining in family-owned beach tavernas with your toes touching the sand, to renowned international establishments serving award-winning cuisine, or indulging on freshly grilled seafood prepared by a private chef on a secluded beach.
Day 1
Day 1 - Arrival in Mykonos
Upon arrival at the airport, our driver will pick you up and take you to your accommodation.
Catch a Sunset at the Windmills
Stroll around the little streets of the Mykonos Chora (Old Town) and enjoy the sunset from the windmills with a romantic view of the Little Venice district. A few of the ancient mills still exist as a testament to the rich past and history of the island. In use for centuries, the windmills ceased to mill grain during the 20th century and now mostly contribute to the island's economy by helping create a special atmosphere, especially during sunset. On your way back into town, have a drink at one of the bars in the lively Little Venice.
Day 2
Day 2 - Your First Full Day in Mykonos
Mykonos Highlights Half-Day Group Tour
On this half-day tour, explore all the highlights of Mykonos, starting with iconic landmarks in the main town like the windmills, Little Venice Beach, and Agia Paraportianni church. Drive past villages to key sites, including the 16th-century monastery in Ano Mera, the seaside village of Agios Ioannis, and serene Agrari Beach. Conclude the tour at a famous spot perfect for capturing panoramic photos of Mykonos town.
Catch a Sunset at the Windmills
Stroll around the little streets of the Mykonos Chora (Old Town) and enjoy the sunset from the windmills with a romantic view of the Little Venice district. A few of the ancient mills still exist as a testament to the rich past and history of the island. In use for centuries, the windmills ceased to mill grain during the 20th century and now mostly contribute to the island's economy by helping create a special atmosphere, especially during sunset. On your way back into town, have a drink at one of the bars in the lively Little Venice.
Day 3
Day 3 - Your Second Full Day in Mykonos
Sunset South Coast Small Group Sailing Cruise
Sail into the sunset! Swim at Mykonos South Coast famous beaches and fall in love with the colored sunset with a view of Delos island.
Delos and Rhenia Half-Day Small Group Sailing Cruise
Setting sail from the cosmopolitan Ornos Bay, you will travel to the UNESCO-listed archaeological site of Delos to admire the sacred island from the sea and learn the site’s ancient history from the knowledgeable crew. You will then sail to the neighboring secluded island of Rhenia, stopping at one or two different beaches for swimming or snorkeling in the crystal clear waters before you indulge in a delicious Greek lunch with beverages onboard.
Day 4
Day 4 - Traveling to Naxos by Ferry
Naxos awaits you today! A driver will pick you up from from your accommodations and take you to Mykonos' port where you'll catch your ferry to Naxos. The ferry journey itself takes between 30 minutes and an hour and a half depending on which departure you choose. There are several ferry departures every day from morning to late afternoon.
2 Nights in Naxos
2 Nights in Naxos
2 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 4
Day 4 - Arrival in Naxos
Upon arriving at the port, you'll be taken to your accommodations in Naxos.
Portara, the Great Door of Naxos
Portara is the symbol of the island. If you come to Naxos by ferry, it is one of the first things you see as you approach the island. This marvelous, massive marble door frame is what’s left of a portal to an Ionic temple devoted to Apollo, which started in the 6th century BC but was never finished. It's located on a small promontory overlooking the island of Delos, the mythological birthplace of Apollo and Artemis. It is a memorable location, and we find it incredibly photogenic at sunset, so we recommend visiting after your first dinner on the island.
Day 5
Day 5 - Your First Full Day in Naxos
Naxos Town Group Food Tour
On this tour, indulge in a culinary adventure, savoring local delights like fine Naxian cheeses paired with wine, traditional Naxian potatoes, and savory phyllo snacks. Traverse from the historical port to the majestic castle, winding through the charming Venetian Old Town adorned with vibrant fruit stands, aromatic herb stalls, and quaint alleyways. Delight in various traditional mezes and local delicacies, all while gaining insights into Naxos's rich culinary heritage and the people behind its regional cuisine.
Dine Like a God
According to Greek mythology, Dionysus, the god of wine, blessed the island of Naxos with fertility. Unique among the dry Cyclades, Naxos produces a rich harvest of cheeses, meats, butter, potatoes, oil, honey, spices, and Kitron, a local spirit made from the citron tree. Cows graze coastal fields, free-roaming goats and sheep gnaw wild oregano and thyme, and roosters and rabbits help themselves to locals’ veggie-heavy compost. It’s easy to find superb traditional dishes in the town of Naxos, but we highly recommend enjoying dinner in the mountain villages, exploring their culture and culinary favorites such as "kokoras me makaronia" (rooster braised in red sauce), "kouneli riganato" (wild rabbit), or goat stew.
Day 6
Day 6 - Traveling to Paros by Ferry
Today, the island of Paros awaits! The ferry ride is fairly brief, 30-60 minutes, depending on which departure you take. We've included a port transfer to get you to the port of Naxos in comfort.
2 Nights in Paros
2 Nights in Paros
2 Nights in Paros
Paros offers a quintessential Greek island experience. Located in the heart of the Cyclades, this fisherman's paradise historically famed for its marble now attracts landlubbers. Paros combines all the necessary elements for a memorable vacation: captivating landscapes, heavenly beaches with turquoise waters, picturesque villages with whitewashed cube houses and colorful shutters framed with beautiful bougainvillea, traditional island flair, and a distinctive character. The town of Parikia is home to the impressive church of Panagia Ekatontapiliani (the Church of a Hundred Doors), one of Greece's main pilgrimage points. Once a quaint fisherman's village, Naoussa is the place to be, offering a more laidback and affordable take on neighboring Mykonos. Naoussa houses narrow maze-like alleyways, cute shops, and a plethora of fish taverns serving fresh food. At night, the picturesque harbor, with its traditional fishing boats, offers a new side, thanks to its bustling nightlife.
Paros offers a quintessential Greek island experience. Located in the heart of the Cyclades, this fisherman's paradise historically famed for its marble now attracts landlubbers. Paros combines all the necessary elements for a memorable vacation: captivating landscapes, heavenly beaches with turquoise waters, picturesque villages with whitewashed cube houses and colorful shutters framed with beautiful bougainvillea, traditional island flair, and a distinctive character. The town of Parikia is home to the impressive church of Panagia Ekatontapiliani (the Church of a Hundred Doors), one of Greece's main pilgrimage points. Once a quaint fisherman's village, Naoussa is the place to be, offering a more laidback and affordable take on neighboring Mykonos. Naoussa houses narrow maze-like alleyways, cute shops, and a plethora of fish taverns serving fresh food. At night, the picturesque harbor, with its traditional fishing boats, offers a new side, thanks to its bustling nightlife.
Day 6
Day 6 - Arrival in Paros
Upon arrival to Paros island you'll be met in the port by our driver who will take you to your accommodation.
Naoussa's Peaceful Atmosphere
Day 7
Day 7 - Your First Full Day in Paros
Paros Highlights Half-Day Private Tour
Discover over 6,000 years of Paros' history on this guided tour, highlighting the island's culture and landscapes. Start in Parikia, where you’ll visit the Ekatontapyliani, the "Church of a Hundred Doors," and explore the Venetian Kastro. Continue to Lefkes, the ancient capital, set in lush mountains, and enjoy a relaxing break at a traditional Kafenio if desired. The tour ends in Naousa, a picturesque village with charming streets, before you return to your accommodations.
Keep Active by the Beach
Day 8
Day 8 - Traveling to Santorini by Ferry
Today you will travel from Paros 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 45 minutes / 3 hour 20 minutes based on your preferred departure time.
3 Nights in Santorini
3 Nights 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 8
Day 8 - Arrival in Santorini
Upon arrival to Santorini's port, you'll be taken to your hotel in Fira.
Blindingly White
Day 9
Day 9 - Your First Full Day in Santorini
Highlights Small Group Tour
From the world-renowned Oia with its caldera-facing cave houses to lesser-known villages lost in time to a tasting of exquisite local wines, this tour of Santorini has it all and is sure to make you fall in love with the most iconic Greek Island.
A Perfect Date Night
Santorini is a perfect destination for romance, drawing couples from around the world for honeymoons and anniversaries. Naturally, Santorini Island is full of romantic options, from sunset bars overlooking the caldera to wineries offering local wine tasting with breathtaking views of the volcanic caldera. We recommend taking it slow at the end of a memorable day by visiting an open-air cinema. Kamari, a village on the eastern part of the island, perhaps has the country's best theater.
Day 10
Day 10 - Your Second Full Day in Santorini
Premium Group Catamaran Cruise
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.
Santorini Shopping Spree
Need some retail therapy? Explore vibrant Santorini with a shopping spree. Dive into the island's charming boutiques and artisanal shops, where every corner holds a treasure waiting to be discovered. From unique souvenirs to high-end fashion, a Santorini shopping experience is a celebration of its eclectic style. Experience the thrill of finding that perfect keepsake against the backdrop of the island's iconic white-washed architecture and the azure Aegean Sea. Some of the best places to shop include Fira, Oia, Pyrgos, Emporio, and Kamari, including stores such as Andronis Stores (fashion), Ammos Stores (fashion), Faros Market near Akrotiri (family-run store full of handmade goods), Epilekton (decorative items and knick-knacks), La Bohème Santorini (handmade jewelry and accessories), and Atlantis Books.
Day 11
Day 11 - Departure Day
Today a driver will pick you up from your accommodation and take you straight to Santorini's airport.
Glowing Reviews from Our Guests
Average of our Guest's Ratings of tour packages including these destinations
Very efficient and well planed. Everything worked as planned.
– Ruth & Lisa, New Jersey
Visited : Greece, Croatia
Itinerary : Athens, Naxos, Paros, Athens, Dubrovnik, Split
Rating :
Very easy to work with. Great guest page. Very knowledgeable staff.
– Leslie & Constantine, Connecticut
Visited : Greece
Itinerary : Athens, Naxos, Santorini
Rating :
I have recommended JayWay to several friends and we will travel with JayWay again!
– Beth, Timothy, Dean & Susan, Minnesota
Visited : Greece, Turkey
Itinerary : Santorini, Naxos, Chania, Athens, Nafplio, Athens, Istanbul
Rating :