Greece – Island Hopping Vacation

  • 12 Days , 5 Cities
  • From $4,740
Customizable Itinerary This sample itinerary was created by our destination specialist to inspire you. It can be customized to your exact preferences and budget.
Crete is the largest island in Greece territory and the fifth-largest island in the Mediterranean Sea, with a rich historical and cultural background. The island is a beautiful place with distinctive differences in customs, daily life, and nature from the rest of the country.
Countries Visited Greece
Places Visited Athens, Chania, Thera, Milos
Suggested Duration 12 days
Travel Styles Cultural Tours, Family Vacations, Food Tours, Hiking & Trekking Tours
  • DAY 1

    Welcome to Athens, Greece!

    Upon arrival, your driver will be awaiting you at the airport with a sign with your name on it. Private transfer to your hotel.

    Athens’ heyday was around 400 years BC; that’s when built most classical monuments. During the Byzantine and Turkish eras, the city decayed into just an insignificant little village, only to become the capital of newly-liberated Greece in 1833. Ahead of the 2004 Olympics, it transformed almost the entire infrastructure: the Metro, trams, new ring roads, and viaducts have eased the pressure of the heavy traffic.

    Athens is still a rather messy and chaotic place—it wouldn’t be Athens otherwise—and despite all the improvements, it still retains a great deal of its oriental charm. The whole coastal stretch from Piraeus to the old Hellenikon airport has been improved with new plantings, viaducts, and paths for walking. The Plaka district is becoming more and more popular, and it is on the way to catching up with Psyrri, Gazi, and Rouf regarding restaurants. Discover the beauties of the Anafiotika district at the feet of the Acropolis, and visit the ancient village still housed amid the city. In Exarchia, there is still a somewhat in-your-face anarchic atmosphere around the Technical University. Meanwhile, Kolonaki is becoming chicer and chicer.

    What's included?

    • Accommodation Accommodation
    • Transfer Transfer
    View on map
  • DAY 2

    Athens - Acropolis & Flavors of the city

    A perfect tour to get an authentic feel of Athens! Ascend to the top of the sacred rock of the Acropolis to be confronted by one of the world’s most essential structures in history, the Parthenon. Once there, you will enjoy a guided tour that will reveal the magnitude and the rich heritage of Athens and the cultural achievements of the Greek civilization of the Golden Age.

    Sense the intriguing Greek cuisine and local food culture through an experiential food tour in the heart of the bustling capital of Greece. After visiting Acropolis, get ready for a 3-hour food tour that will truly make you feel like an Athenian! Wander through authentic corners of the city and visit many dedicated artisans that have perfected their recipes over the decades, specialized food stores sourcing the best products from all over Greece, and the vibrant central food market.

    You will enjoy a leisurely walk through the city's old quarter to marvel Plaka neighborhood with its picturesque cobbled streets, quaint restored buildings, and distinct and atmospheric architecture. You will walk by the Roman Agora, the Tower of the winds, Hadrian’s Library, Lycicrates Monument, Fethiye Mosque, beautiful neoclassical buildings, and many more Roman, Byzantine, and Ottoman traces of the old city.

    What's included?

    • Breakfast Breakfast
    • Accommodation Accommodation
    • Tour Tour
    View on map
  • DAY 3

    Welcome to Chania, Crete

    After breakfast, your driver will deliver you to Athens Airport. A short domestic flight from Athens to Chania, and you will find yourselves on the majestic island of Crete!

    Upon arrival, your driver will be waiting for you with a sign with your name. You will be transferred to your hotel. Walkthrough the stone paths and the narrow streets of the Old Town and discover the hidden spots of the Venetian Harbor. You will enjoy a stroll in the puzzled alleys where the Venetians, the Ottomans, and the old Cretans lived and occupied. Enjoy this tremendous flower-decorated neighborhood, meet the locals, and eat like locals! The unique Cretan gastronomy is something you would not want to miss!

    What's included?

    • Breakfast Breakfast
    • Accommodation Accommodation
    • Transfer Transfer
    • Flight Flight
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  • DAY 4

    Chania - Unique hiking experiences of Samaria Gorge

    The gorge of Samaria is the gem of the White Mountains! Hidden in the south part of the Chania district, it is the enormous gorge in Europe, covering an area of 18 km (11 miles) in length. The gorge of Samaria is counted among the top destinations of the Chania district, and a journey to Chania can never be considered complete unless you visit the Gorge. Therefore, you should believe us when we say that its beauty will not let you down! The state park of Samaria was added to the World Network of Biosphere Reserves (MAB: Man & Biosphere) by UNESCO in 1981 to give prominence to and protect valuable habitats for man and the rest of the biosphere.

    The gorge’s trial starts at Ksyloskalo (Omalos plateau, 1.227 meters - 4 feet altitude), and after following the river bed, it ends up at the littoral village of Agia Roumeli. The trail of Samaria is the most visited in the whole of Greece; it is excellently equipped with signals and signs which eliminate the danger of getting lost; it is comfortable and very well cared for, mostly with stones and soil. It is not considered a challenging hike, vividly proof that hundreds of people cross it daily from the opening (in May) till the closing of its visiting season (in October). It is an enjoyable hike, not a strenuous one, with many landscape alternations and a versatile environment. However, one should always keep in mind that though the trail is not tricky, one should be more careful during some trek parts.

    What's included?

    • Breakfast Breakfast
    • Accommodation Accommodation
    • Tour Tour
    • Transfer Transfer
    View on map
  • DAY 5

    Chania - Knossos & Heraklion

    Enjoy the morning at leisure in Chania old town. Explore the waterfront and streets just behind. Walk along the harbor wall to the Venetian Lighthouse and enjoy your lunch before heading to Heraklion.

    Your driver will pick you up and take you to Heraklion's capital. After a 2-hour drive, you will reach Knossos. Knossos, the largest and most famous of the Minoan palaces, the residence of the mythical King Minos and the monster Minotaur, a multi-acre complex of royal apartments, elaborate staircases, storage, and craft areas, the first European theater, and a throne room with the original Bronze Age throne. Replicas of many frescoes grace the palace. After lunch, head to Knossos and enjoy a guided tour.
    Discover the cradle of the Minoan civilization; this evocative Bronze Age site is believed to be Europe's oldest city. Learn about its history and mythology, including the story about the labyrinth, the mythical Minotaur, and the trick Theseus pulled to kill the beast with the help of Ariadne; however, he could not avoid a tragedy, the one that gave the name to the Aegean sea.

    After the guided tour, you will continue your journey to Heraklion. After you take in the breathtaking views over the Old Port, you can discover the city's historical center, the most remarkable attractions of Heraklion, or visit some of the most important museums. Heraklion has the liveliest shopping, dining, and nightlife venues and the freshest and most creative Cretan cuisine! Everything is within reach!

    What's included?

    • Breakfast Breakfast
    • Accommodation Accommodation
    • Tour Tour
    • Transfer Transfer
    View on map
  • DAY 6

    Chania - Jeep safari with Dikteon Cave visit

    Explore Crete by Land Rover on a full-day adventure along the Minoan Path, and experience a blend of ancient myths, spectacular landscapes, and a traditional Cretan lunch.
    Following a pick-up from your hotel, drive through spectacular mountains en route to the Lassithi Plateau, and enjoy a bird’s-eye view of the Lassithi Plateau and north coast. Continue to Dikteon Cave to marvel at the birthplace of Zeus before heading to a traditional olive mill.
    Visit a traditional olive mill in the Protected Designation of Origin Archanes, Heraklion, Crete. Here, the locals produce their oils exclusively from their olive groves, with 2000 trees surrounding the olive mill. Making extra virgin olive oils using the most ancient and modern methods of olive oil extraction with a telling effect and olive oil tasting here is something you would not want to miss! Work up an appetite before your lunch at a local taverna.

    What's included?

    • Breakfast Breakfast
    • Lunch Lunch
    • Accommodation Accommodation
    • Tour Tour
    View on map
  • DAY 7

    Welcome to Santorini!

    Private transfer to the Heraklion Port. Transfer with hydrofoil boat in two hours to Santorini. Your driver will deliver you privately to the hotel in Santorini.
    Free day at leisure in Santorini.

    The island's beauty has been waxed lyrical over the years, fully earning the epithet "kalliste" (the most beautiful). Along with "Strogili," one of the former names lent to the island over its troubled history.
    Its history is one of the battles and conquers, of a tragic eruption and a blossoming renaissance – events that haven't altered Santorini's charm, but that undoubtedly scarred it. Together with the inhabited Therania and five other smaller islands, Thera (Santorini's Greek name) belongs to the namesake archipelago, the vestige of a volcanic caldera. Places of unspoiled nature and postcard-like views, the islands are reachable by boat and bear the original appeal of the old-fashioned Santorini. The main island is split into picturesque villages masterly painted in dazzling blue and white hues, outlining the holiday resort's multi-faceted personality and its extraordinary landscapes.

    The scent of wine grapes and vineyards stretching lazily down Santorini's unrefined hills; the unique taste of tomatoes grown solely on volcanic soil and the soaring temperature of the island; the subtle sand or the smoothness of white pebbles and turquoise waters of some of Europe's most suggestive beaches; the upbeat sound of the buzzing nightlife; the spectacle of the sun setting behind the village of Oia and the caldera to finally plunge into the skyline. Santorini gratifies all five senses, treating the traveler to enchanting views and thousands of colors.

    What's included?

    • Breakfast Breakfast
    • Accommodation Accommodation
    • Transfer Transfer
    • Cruise/Boat Cruise/Boat
    View on map
  • DAY 8

    Santorini - Enjoy Caldera Sunset Cruise

    In the morning, explore Santorini at your own pace. Without mentioning dazzling panoramas, and the mesmerizing sea of vibrant villages, Santorini's culinary tradition would be something worth experiencing. Borrowing a pronounced Mediterranean diet from the mainland, Santorini tends to use vegetables, quality olive oil, meat, and fresh seafood generously, creating its cuisine by adding products that are cultivated solely on its fertile soil.

    Santorini is in all aspects a work of art, and its souvenirs and local produce doubtlessly reflect the island's beautiful facets. Try the island's peculiar white eggplants with mozzarella, or sample the unique "Tomatokeftedes," tomato fritters made of Santorini's produce, with a glass of Vinsanto. Oia and, above all, Fira is the island's major shopping destination, with unrivaled charm where traditional shops line up neatly down narrow streets.

    In Santorini, a visit to one of the local art galleries is a must: evocative handicrafts, folk art, and jewelry can be bought at accessible prices, guaranteeing a souvenir that mirrors the authenticity of the villages. Another worthy shopping experience is all about local produce. The diversity of products makes it hard to choose from the numerous delicacies grown on volcanic soil. The Greek version of split peas, Fava, is particularly unique in Santorini and makes a down-to-earth yet scrumptious puree. The island's grapes make a heavenly wine exported worldwide and can buy in any local wineries. Last comes Santorini's trademark tomato, the locals' pride and a must-try for food enthusiasts - wonderfully flavorful and juicy.

    In the afternoon, you admire the Caldera Sunset Cruise. Starting from the port of Vlychada port, the cruise passes by Red and White Beach, with a stop at Black Mountain. It will then pass by the Lighthouse South of the Caldera and the Hot Springs at the Volcano. The next stop is Thirassia, where lunch will be served. You will then sail towards the port of Ammoudi for a spectacular view of Oia. The return route will offer beautiful Fira views and sunset views before entering the port of Vlychada.

    What's included?

    • Breakfast Breakfast
    • Lunch Lunch
    • Accommodation Accommodation
    • Cruise/Boat Cruise/Boat
    View on map
  • DAY 9

    Santorini - Eat & Walk Food Tour

    Our goal is to showcase the flavors and ingredients of Mediterranean cuisine from a local standpoint in a fun & informative manner to let you experience Greek food as the locals do!
    Start your day with a traditional Greek coffee. Our fun local food expert will meet you at a starting point in Firostefani and lead you through the traditional towns of Firostefani and Fira, following a pebbled downhill footpath right on the edge of the world-famous Santorini caldera. Follow your guide through the historical alleyways and hidden paths of Fira with several stops for samplings of local treats, including an olive oil tasting and a quick bite of souvlaki - the ultimate Greek street food.

    During the tour, you will have the opportunity to taste Santorini & Greek food, street food, samples of local beer, wine, and raki, Cycladic cheeses & cold cuts, olive oil tasting, delicacies from the bakery, and traditional sweets. Of course, lunch at a caldera view restaurant combined with some local wine is a 'must'!

    What's included?

    • Breakfast Breakfast
    • Lunch Lunch
    • Accommodation Accommodation
    • Tour Tour
    View on map
  • DAY 10

    Welcome to Milos!

    Private transfer to the Santorini port.
    Two hours transfer with hydrofoil boat from Santorini to Milos. Upon arrival, your driver will be awaiting you with a sign with your name. You will be transferred to your hotel.

    You will have a day to explore and enjoy Milos freely. Here are some suggestions:

    Beaches
    The beaches of Milos, some of the most beautiful in the Cyclades, await Palaiochori, Papafragas, Gerontas, Firiplaka, Tsigrado, and Plathiena. Yellow, orange, red, and dazzling white rock formations are even more vibrant against the background of turquoise waters. Milos’ volcanic soil has created a sight beyond one’s imagination. Jump into a sailboat or speedboat and take in the kaleidoscope of the island’s beaches.

    Pirates’ caves at Kleftiko, Papafragas, Sarakiniko, and Katergo.
    The formidable pirates of the Middle Ages had their hideouts in Milos. Traces of their existence can be found in Kleftiko, where the pirates’ bollards for their ships can be found sculpted on the spectacular rocks, beside blue-green water next to the caves. In Sarakiniko, the landscape is from another world: all-white stones in mesmerizing shapes dominate the cove. Get lost in the deep blue of the Aegean and feel nature embrace you.

    Little Venice
    In the afternoon, take a stroll in the quaint, colorful hamlet above the water, where the old port of Ancient Milos used to be. It is one of the unique towns you’ll encounter in the Cyclades. What makes it unique? The 35 sirmata in a row – cave-like structures that used to store boats and are now holiday homes. Wander around the little town, level with the water, and wait for the sunset.

    What's included?

    • Breakfast Breakfast
    • Accommodation Accommodation
    • Transfer Transfer
    • Cruise/Boat Cruise/Boat
    View on map
  • DAY 11

    Milos - Boat trip to around Milos and to Kleftiko

    The yacht will depart from the village of Pollonia at 09:45 daily, setting a course to the beach of Gerakas. Close to a significant deposit of perlite (one of the most famous minerals of Milos), Gerakas is only accessible by the sea. Long white sand slides of perlite meet the sea, offering an impressive setting. After 30 minutes of swimming, we start sailing again, destination Kleftiko! The yacht will cruise along the south side of Milos, where you will witness the coastline with the beaches of Paliochori, Aghia Kyriaki, Tsigrado, and Fyriplaka. Provatas, Gerontas reach about 1,5hr later to Kleftiko!

    Kleftiko is the famous landmark of Milos. Here we will have a more extended stop allowing plenty of time for snorkeling. Onboard is available the equipment, underwater pictures with the action camera, and a cave tour with a small tender boat to the sea caves of Kleftiko. The area here is full of sea caves, and it’s impossible to swim along all of them (they are too many and far apart), so with our tender boat navigated by one of our crew members, you will get to see most of them! Lunch will be served during the stop in Kleftiko. Traditional dishes such as chicken with lemon sauce accompanied by Greek salad. Alternative options are provided for those with special dietary requirements. Greek bottled dry white wine will complete this gastronomical journey.

    Once we have enjoyed Kleftiko, the yacht will return to Pollonia via the south side with the last swim stop in Tsigrado or Fyrligos beach. The boat then will stop at the south coast of Provatas, from where you will be transferred by minibus back to Pollonia.

    What's included?

    • Breakfast Breakfast
    • Lunch Lunch
    • Accommodation Accommodation
    • Tour Tour
    • Cruise/Boat Cruise/Boat
    View on map
  • DAY 12

    Depart to Milos Airport to fly back home

    Your driver will deliver you to Milos Airport for a short flight to Athens!
    Today, you will have to say goodbye to beautiful Greece.

    What's included?

    • Breakfast Breakfast
    • Transfer Transfer
    View on map

Starting from $4,740 per person

Price per person in double occupancy
The rate is based on 4-star accommodation
Price excluding international flights
This trip is customizable for your private travel.


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What’s Included?

  • 11-Night 4-star hotel accommodation centrally located
    2 nights in Athens
    4 nights in Crete
    3 nights in Santorini
    2 nights in Milos
  • Daily buffet breakfast
  • Lunch in Crete, Santorini, and Kleftiko.
  • Private airport transfers in Athens, Crete, and Milos.
  • Private port transfers in Crete, Santorini, and Milos
  • Heraklion to Santorini ferry tickets
  • Santorini to Milos ferry tickets
  • Domestic flight from Athens to Chania
  • Domestic flight from Milos to Athens
  • English-speaking guide during the tours

Sightseeing Highlights Included

  • Visit the Acropolis & flavors of Athens tour
  • Unique hiking experiences of the Samaria Gorge
  • Explore the ancient city of Knossos in Crete
  • Jeep safari with Dikteon cave visit
  • Caldera Sunset Cruise in Santorini
  • Full-day boat trip to around Milos and to Kleftiko

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