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Ruins, Wine, Scenic Hikes and The Sea

14 Days / 13 Nights

Athens, Mykonos, Santorini, Heraklion, Chania

from$3,375 per person

Travel and LeisureFodorsUSA TodayNew York TimesNational GeographicWashington PostVogue
If a combination of history and culture, delicious food and superb wine, being active in the outdoors, and lazing under the bright sun is what you're dreaming of for your next vacation, this two-week itinerary across Greece is exactly what you've been looking for. Starting from vibrant Athens, make a stop in cosmopolitan Mykonos before you surrender to the utter beauty of Santorini. End your two-week itinerary in Greece with a trip to Crete, the country's largest island. 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 with data 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 3- to 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, Mykonos, Santorini, Heraklion, Chania tour

3 Nights in Athens

3 Nights in Athens

4 days in Athens
4 days in Athens

3 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 accommodations. The drive takes about 45 minutes, depending on traffic.

Our representative will then meet with you to answer any questions you have and to get you settled for the rest of your trip.

Day 2

Day 2 - Your First Full Day in Athens

Athens Highlights Mythology Small Group Tour

Athens Highlights Mythology Small Group Tour

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 - Your Second Full Day in Athens

Indulge in Local Cuisine

Suggested activities for an additional cost, depending on your choice

Olive oil, vegetables, fish, and feta are key ingredients in Greek cuisine. Fresh vegetables, honey, fish, lamb, and cheese are added to create typically Greek flavors. Tzatziki, souvlaki, gyros, dolmathakia, spanakopita, loukoumades, authentic Greek yogurt, and amygdalota are just a few options to be enjoyed in local cafes and restaurants. We've picked some of the most delicious food tours for you to choose from.

Athens by Night Food and Wine Tasting Private Tour

Athens by Night Food and Wine Tasting Private Tour

Suggested activities for an additional cost, depending on your choice

Seeking an extraordinary Greek culinary experience to tease your senses? Follow an expert food guide on a quest to discover Athens by night, and experience exquisite Athenian delicacies. Enjoy the best views of Athens after dusk and explore sophisticated eateries to devour the finest of authentic Greek cuisine, including the best souvlaki in town! And to top it all off? A wine tasting focused on indigenous local varieties (plus ouzo!)


Activity Level : Easy
Duration : 4 hours

Delicious Athens Food Small Group Tour

Delicious Athens Food Small Group Tour

Suggested activities for an additional cost, depending on your choice

Eat your way through Athens! Discover Greek flavors and their history, with a walk through some of the city’s most interesting neighborhoods, rarely visited by tourists. Taste olive oils, Greek cheeses, tsipouro drink, honey, souvlaki, tapenades, baklava, Greek coffee, sweets, and a variety of Greek tapas.


Activity Level : Light
Duration : 3 hours 30 minutes

The Great Eats and Streets Private Tour

The Great Eats and Streets Private Tour

Suggested activities for an additional cost, depending on your choice

Athens came together through a mixture of cultures across the centuries, and there’s still a lot of that history around, in the food as well as in the city's neighborhoods. This tour explores the city's complex heritage, and its effects on contemporary Greek culture and cuisine. 


Activity Level : Light
Duration : 5 hours

Day 4

Day 4 - Traveling to Mykonos by Ferry

The Cycladean island of Mykonos awaits you today! A driver will pick you up from from your accommodation and take you to the port of Piraeus, where you'll catch your ferry to Mykonos. Although there are several departures each day, they're all very early so you'll need to be up with the lark for this leg of the journey. The ferry journey itself takes at least two and a half hours up to five and a half, depending on which departure is available.

Mykonos by Ferry
We also offer the following excursions in Athens

Acropolis for Families Private Tour
Moderate2 hours
Ancient Corinth Tour & Nemea Wine-Tasting Private Tour
Moderate9 hours
Athens Highlights Mythology Private Tour
Moderate4 hours
Athens Markets and Chronicles Small Group Tour
Light4 hours

2 Nights in Mykonos

2 Nights in Mykonos

3 days in Mykonos
3 days in Mykonos

2 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 4

Day 4 - Arrival in Mykonos

Upon arrival at Mykonos' main port, you'll be taken to your accommodations.

Day 5

Day 5 - Your First Full Day in Mykonos

Mykonos Town Small Group Walking Tour

Be Enchanted By Mykonos Town

Please ask your travel advisor for the cost to add this to your package

Mykonos is probably the most famous Greek Island, and getting to know its vibrant capital, Mykonos Town, is the best introduction to the so-called Island of The Winds. Chora, as Mykonos Town is also known, feels like the setting of a movie with its whitewashed alleys, quaint churches, and iconic windmills. Your expert guide will walk you through the town's secrets, local tastes, and best photo spots, such as the gorgeous Little Venice.


Activity Level : Light
Duration : 2 hours

Day 6

Day 6 - Traveling to Santorini by Ferry

Scenic Santorini awaits you today! A driver will pick you up from your accommodations and take you to Mykonos' port where you'll catch your ferry to Santorini. The duration of the journey is around 2 hours / 3 hours 30 minutes based on your preferred departure time.

Santorini by Ferry
We also offer the following excursions in Mykonos

Ancient Delos Small Group Tour
Light4 hours
Armenistis Lighthouse Group Sunset Visit
Light2 hours
Armenistis Lighthouse Private Sunset Tour
Easy2 hours
Authentic Mykonos in a Nutshell Bike Group Tour
Strenuous4 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 6

Day 6 - Arrival in Santorini

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

Day 7

Day 7 - Your First Full Day in Santorini

Santorini Wanderlust Private Tour

Santorini Wanderlust Private Tour

Included in your vacation package price.

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 ( or a mystical music show or a meze style lunch) !


Activity Level : Moderate
Duration : 4 hours

Day 8

Day 8 - Your Second Full Day in Santorini

Volcanic Caldera Private Hike

Scenic Hikes from Shore to Springs

Please ask your travel advisor for the cost to add this to your package

If you're looking to stay active, we recommend hiking. Our favorite trail runs for 6.5 miles, between Fira and Oia, and we're sure you'll enjoy every minute of it. On the way, you'll pass through the beautiful towns of Firostefani and Imerovigli. If you're looking for more of a challenge, head from the village of Pyrgos, through Santorini's highest point (home to the Prophet Elias Holy Monastery), and on to ancient Thira. For a more rough and ready path, walk to the the Old Port, where you can hop aboard a boat tour that will take you across the caldera to the volcano on Nea Kameni. A spectacular hike up over this dormant mountain is moderately challenging but worth the effort for its breathtaking views. Back on the boat, you can circle around to the other side of the volcano, where your weary legs will relish a chance to soak in the thermal hot springs at Palia Kameni before looping back to Fira.


Activity Level : Strenuous
Duration : 4 hours 30 minutes

Day 9

Day 9 - Traveling to Heraklion by Ferry

Heraklion awaits you today! A driver will pick you up from from your accommodations and take you to the port where you'll catch your ferry to Heraklion. The journey takes around 2 hours.

Heraklion by Ferry (Fira)
We also offer the following excursions in Santorini

Anydro Small Group Tour
Light5 hours 30 minutes
Best of Santorini Private Tour
Light5 hours
Flying Dress Private Photo Shoot
Light1 hour
Highlights Small Group Tour
Light5 hours 30 minutes

2 Nights in Heraklion

2 Nights in Heraklion

3 days in Heraklion
3 days in Heraklion

2 Nights in Heraklion

Visitors to Heraklion, Crete's capital, are greeted by the imposing Venetian Koules Fortress, a reminder of the importance of this historic gateway to the rest of the island. A vibrant university town, Heraklion is home to some of the island's most important landmarks, such as the Knossos Palace, with its striking Bronze Age ruins, complete with colorful, stunning frescoes. Heading to the center, the bustling Old Town has many markets and cafes, along with neoclassical buildings and a 10th century church with impressed stained glass. Heraklion is a great base for exploring the island, but before you hit the road, take the time to stroll along its Venetian harbor, lined with traditional fishing boats and offering spectacular views of the Koules Fortress.

Visitors to Heraklion, Crete's capital, are greeted by the imposing Venetian Koules Fortress, a reminder of the importance of this historic gateway to the rest of the island. A vibrant university town, Heraklion is home to some of the island's most important landmarks, such as the Knossos Palace, with its striking Bronze Age ruins, complete with colorful, stunning frescoes. Heading to the center, the bustling Old Town has many markets and cafes, along with neoclassical buildings and a 10th century church with impressed stained glass. Heraklion is a great base for exploring the island, but before you hit the road, take the time to stroll along its Venetian harbor, lined with traditional fishing boats and offering spectacular views of the Koules Fortress.

Day 9

Day 9 - Arrival in Heraklion

Upon your arrival in Heraklion Port, a driver will meet you and drive you to your centrally located accommodations.

Day 10

Day 10 - Your First Full Day in Heraklion

Heraklion Bites and Sights Group Tour

Discover Crete's Capital

Included in your vacation package price.

Bypass the concrete and head straight for the heart of Heraklion. Hit the backstreets and hidden pathways, checking out the highlights, sampling local treats, and discovering the forces that combined to make Heraklion the city it is today. This tour will help you get to know the city not just as it is now, but also as it was centuries ago, uncovering remnants of occupations by the Byzantines, Arabs, Venetians, Turks, and, yes, pirates.


Activity Level : Light
Duration : 4 hours

Day 11

Day 11 - Traveling to Chania by Private Transfer

Today you're heading further west, to Chania. To make a day of it, and making the journey much more interesting we've included a stop on the way. We'll arrange for a driver to pick you up in the morning. En route, you'll visit the old town of Rethymno, an hour from Heraklion. There you will have a two-hour stop for exploration of the city. From there you'll continue your journey to your final destination in Chania. The total journey time, with stops, is around four hours.

Chania by Private Transfer with a Stop in Rethymno
We also offer the following excursions in Heraklion

Archaeological Museum and Knossos Palace Private Tour
Light4 hours
Heraklion by Catamaran Group Cruise
Easy5 hours
Heraklion by Catamaran Group Sunset Cruise
Easy5 hours
Horse Riding Group Experience
Light4 hours

3 Nights in Chania

3 Nights in Chania

4 days in Chania
4 days in Chania

3 Nights in Chania

Crete’s most romantic destination offers an irresistible sense of charm. Chania’s Old Town is undeniably captivating, with winding alleyways lined with charming boutique stores, fragrant jasmine trees and bougainvillea, and picturesque squares dotted with local taverns serving Cretan delicacies. The Venetian harbor opens up to panoramic views of the Aegean and the striking Egyptian Lighthouse, which once guided ships safely into the harbor. Traces of centuries of conquests are evident in the amalgam of cultures that intertwine in the cobblestone streets and historical districts of this enchanting town. The district of Splantzia is lined with reminders of the town's Ottoman period. In the afternoon, take a walk along the marina, lined with Venetian boathouses reborn as exhibition spaces and cafes. At sunset people gather by the harbor to witness the magical sunset or simply stroll along the esplanade.

Crete’s most romantic destination offers an irresistible sense of charm. Chania’s Old Town is undeniably captivating, with winding alleyways lined with charming boutique stores, fragrant jasmine trees and bougainvillea, and picturesque squares dotted with local taverns serving Cretan delicacies. The Venetian harbor opens up to panoramic views of the Aegean and the striking Egyptian Lighthouse, which once guided ships safely into the harbor. Traces of centuries of conquests are evident in the amalgam of cultures that intertwine in the cobblestone streets and historical districts of this enchanting town. The district of Splantzia is lined with reminders of the town's Ottoman period. In the afternoon, take a walk along the marina, lined with Venetian boathouses reborn as exhibition spaces and cafes. At sunset people gather by the harbor to witness the magical sunset or simply stroll along the esplanade.

Day 11

Day 11 - Arrival in Chania

Upon arrival to Chania you'll be taken directly to your accommodation.

Day 12

Day 12 - Your First Full Day in Chania

Street Stories of Chania Group Tour

A Place to Rest & Be Happy

Included in your vacation package price.

Experience the real Crete with a walk through one of its most picturesque cities. Chania is a kaleidoscope of different elements: ancient ruins, strong local culture and traditions, and delectable cuisine (and yes, you’ll get to taste some!). Escape the tourist traps and dive into secret corners and local neighborhoods — each stop has a story to tell!


Activity Level : Light
Duration : 4 hours

Day 13

Day 13 - Your Second Full Day in Chania

Explore the European Hiking Path

Please ask your travel advisor for the cost to add this to your package

Crete offers plenty of options for lovers of the great outdoors, especially hikers. In nearly any direction, you'll find traditional villages, high mountains, and beautiful beaches. Whether on your own or on a guided tour, hiking is a wonderful way to see the stunning beauty of the island’s natural landscape. Chania is surrounded by 150 hiking trails, but our favorite takes you through Samaria Gorge, a beloved gorge in the National Reserve of Lefka Ori, about an hour's drive from Chania. This gorge forms part of Crete’s most famous hiking route, the E4 trail, part of an EU-wide system of paths. Imbros Gorge is also worth a visit, as it's regularly ranked among the island's most beautiful and famous gorges.

Explore the European Hiking Path

Day 14

Day 14 - Departure Day

Sadly the time has come to leave Crete behind. We'll arrange for a driver to take you to Chania airport for your departing flight. The drive to the airport is about 30 minutes.

We also offer the following excursions in Chania

Balos and Falassarna Beach Small Group Jeep Tour
Light7-8 hours
Chania Wine, Food & Sunset Group Tour
Light4 hours
Elafonisi Beach and Milia Mountain Retreat Small Group Tour
Moderate8-9 hours
Olive Oil Tasting Small Group Tour
Light7 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

3 Nights Accommodation
Breakfast (hotels only)
Athens Airport Transfer
Athens Highlights Mythology Small Group Tour
Piraeus Port Transfer
Athens (Piraeus) - Mykonos Ferry

Mykonos

2 Nights Accommodation
Breakfast (hotels only)
Mykonos Port Transfer
Mykonos Port Transfer
Mykonos - Santorini Ferry

Santorini

3 Nights Accommodation
Breakfast (hotels only)
Santorini Fira Port Transfer
Santorini Wanderlust Private Tour
Santorini Fira Port Transfer
Santorini - Heraklion Ferry

Heraklion

2 Nights Accommodation
Breakfast (hotels only)
Heraklion Port Transfer
Heraklion Bites and Sights Small Group Tour
Heraklion - Chania Private Transfer with a stop in Rethymno

Chania

3 Nights Accommodation
Breakfast (hotels only)
Street Stories of Chania Small Group Tour
Chania City - Chania Airport Private 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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