15 Days
6 Stops
Private transfer
Your tailor-made itinerary – No cost, no commitment
Experience the essence of Greece on this two-week itinerary—a little over 14 days of ancient landmarks, breathtaking landscapes, and idyllic island life. Begin in Athens, where the Acropolis, Parthenon, and charming Plaka district reveal the cradle of Western civilization. Venture north to the dramatic monasteries of Meteora, perched atop towering rock formations, before returning south to follow the call of the Aegean.More...
Day 1 - 4
Dominating the Attica region of Greece, the country’s capital, Athens, is one of the oldest cities in the world. For over two and a half centuries, the astonishing Greek temples and monuments of Athens have continued to intrigue and amaze visitors from around the world. This icon of western civilization seamlessly combines ancient history with modern architecture and a surprisingly lively atmosphere. This is particularly apparent in areas at the foot of the Acropolis, Anafiotika, Plaka, Monastiraki, and Thissio where visitors will find numerous extraordinary Neoclassical buildings, trendy and traditional cafes, and shops, and narrow winding streets with historical treasures at every turn. Once you have enjoyed a history and art fix, try some mouth-watering Greek cuisine at one of the city’s fine local restaurants before indulging in the insatiable nightlife at the chic cocktail bars and waterfront dance clubs.
The Athenian Callirhoe Exclusive Hotel is perfectly situated in the heart of Athens City, Greece, near the Kallimarmaro Stadium, the Acropolis, the Brand New Acropolis Museum, and Plaka. The hotel’s cosy and elegantly decorated rooms and suites feature tea/coffee-making facilities, central heating/cooling, workspaces, private bathrooms, minibars, hairdryers, flat-screen TVs, and laptop-sized safes. Accommodations with balconies are available. Facilities and services include restaurants, a bar, daily housekeeping, a sauna, a gym, and Wi-Fi.
Short on time but want to see everything that Athens has to offer? We know how to get you around all the ‘must see’ sites and sights. Our Athens city tour takes you to the most important sites of the historic capital. The Panathenaic Stadium was the site of the first Olympic Games of modern times in 1896. The Prime Minister's residence (ex. Royal Palace) is guarded by the Evzones in their colorful uniform. The Temple of Olympian Zeus,Hadrian's Arch, Parliament, and the memorial to the Unknown Soldier, the Academy, the University, the National Library, and Omonia Square. We make a short stop at each place. Of course, we can’t leave out the Acropolis, home to the Architectural Masterpieces of the Golden Age of Athens: The Propylaea, the Temple of Athena Nike, the Erechtheion and ‘the harmony between material and spirit’, the monument that ‘puts the order in the mind’, the Parthenon and the Theatre of Dionysus'. Concluding the tour, we will visit the new Acropolis Museum and admire the wonders of the classical era.
Day 5 - 6
Picturesque white-washed villages cover the dramatically carved landscape of the volcanic Greek island of Milos or Melos, the southwesternmost island of the Cyclades, found just north of the Sea of Crete. For history enthusiasts, be sure to visit the Archaeological Museum, with artefacts from the Neolithic to the Byzantine periods, The Ancient Roman Theater of Milos, The Venetian Castle, The Mining Museum in Adamas and the early-Christian Catacombs, a glorious archaeological spectacle dating from the 1st to the 5th century AD. For a more leisurely exploration, swim in the crystal-clear turquoise waters that lap gleaming white rock formations, rugged cliffs and sea caves on the many secluded beaches. Plaka, a hilltop town and the de facto capital, is where to find several inviting restaurants, quaint cafes, Greek and European pastries, coffee and sweets. End the day by unwinding with a leisurely soak in the mineral springs, which physicians have recommended since the time of Herodotus.
Melian Boutique Hotel & Spa is a romantic haven of serenity, built at the waterfront of Milos, in the enchanting island complex of the Cyclades. A luxury hotel in Milos endowed with elegance and breathtaking views to the most captivating sunset of the island and the emerald waters of the Aegean Sea. The 15 luxury rooms and sea view suites offered by this unique hotel next to the beach provide all modern amenities while combining traditional handmade furniture with art objects to create a wonderfully romantic setting. In the hotel’s cocktail lounge overlooking the Aegean sea, guests can enjoy the sun as it sets over the azure while sipping on cocktails. Guests can dine at the on-site restaurant or relax and unwind at the spa.
The Full Day Around Milos tour is available on three different boats to suit any preference and offers the most comprehensive way to explore the island, visiting its most secluded and stunning spots. Starting from Adamas, the tour sails either clockwise or counterclockwise, allowing you to swim and relax at the most famous locations around Milos. You will stop at Polyegos Island, Sulphur Mines or Firligos Beach, Gerakas Beach, Kleokio, take a photo stop at the breathtaking Sykia Cave, and enjoy the crystal-clear waters of Kalogries Beach.
Day 7 - 8
Situated in the Aegean Sea, the Greek island of Naxos is the largest of the Cyclades Archipelago. Its fertile landscape features ancient ruins, quaint mountain villages with sheep-dotted slopes, and vast stretches of magnificent beaches. With their crystal-clear waters, soft white sands and watersports such as swimming, windsurfing, kitesurfing and surfing on offer, the beaches here provide the ultimate holiday experience, while the island’s lush interior makes it an ideal destination for hiking and mountain biking enthusiasts. Make sure to visit the mysterious Cave of Zas, filled with incredible stalactite formations and dedicated to Zeus in ancient times. The wide variety of historic attractions includes breathtaking Venetian mansions, Byzantine country churches, and the medieval old quarter of Kastro, with its centuries-old stone paving, arches and buildings.
Porto Naxos Hotel is located just minutes from the heart of Naxos old town and the sandy beach of Agios Georgios. The accommodation features a selection of rooms and suites, each equipped with air conditioning, minibars, hairdryers, LCD TVs and safety deposit boxes. Guests can enjoy delicious dishes at the on-site restaurant. Other amenities available to guests include a pool bar, swimming pools, a tennis court, a sauna and a fitness centre.
Begin your adventure at Ai-Giannides Beach, conveniently located near Naxos Town (Chora). This beautiful spot is just a stone's throw away from the iconic Portara, the massive marble gateway of an unfinished temple dating back to 530 BC.
Once familiar with your kayaking gear, you'll embark on a thrilling paddle around the peninsula. Along the way, enjoy the opportunity to swim and have a light snack, making the most of this stunning setting.
Your qualified guide will provide an underwater camera, so you can capture every exciting moment. Families are welcome—children under 16 can join the fun by paddling in a tandem kayak with a parent.
Day 9 - 10
Set in the Cyclades Archipelago at the heart of the Aegean Sea, the paradise-like Paros Island is renowned for its spectacular beaches, idyllic traditional villages, and exciting nightlife. The island boasts 38 magnificent soft, sandy beaches, characterised by white sand, crystal-clear turquoise waters, and superb restaurants and beach bars. The eastern beaches are perfect for windsurfing and kite surfing, and there are numerous magnificent scuba diving spots, as well as guided trips to the uninhabited islets of the Aegean Sea, with close reefs and old wrecks on offer. Historic attractions include intriguing castles, ancient monasteries, a Mycenaean Acropolis, Byzantine Museums, two folklore museums, a wine museum, and more. Nature lovers will delight in the chance to explore the Valley of Butterflies, where butterflies put on a spectacular display in summer.
The Saint Andrea Seaside Resort is located on the north side of Paros island near the cosmopolitan town of Naousa. The resort offers luxurious rooms and suites equipped with LCD TV, air-conditioning, Wi-Fi, a safe deposit box, a minibar, and a balcony. Guests can enjoy a hearty buffet breakfast served each morning in the breakfast room. Facilities include a 24-hour reception, restaurant, swimming pool, a lobby bar, free Wi-Fi, and parking.
Embark on unforgettable new adventures aboard our traditional Kaiki, a wooden motorboat typically used by fishermen, as we explore the stunning islands of Antiparos and Despotiko. We'll arrange a convenient transfer from your hotel (or a nearby stop) to the port of Pounta.
Get ready to uncover the hidden gems of the Aegean Sea that are only accessible by boat. With crystal-clear waters, you'll truly feel like you've stepped into paradise! Our journey begins at 10:00 am from the Pounta port, where we will guide you to breathtaking beaches, sea caves, and small islands, leaving you in awe of the exotic destinations around you. This cruise offers a unique opportunity to reconnect with the untamed beauty and natural wonders of the area.
While the following itinerary is indicative, our captain will select the best locations for each cruise based on the weather conditions, ensuring you have an extraordinary experience around Antiparos and Despotiko islands. Discover the enchanting Panteronissi, where the turquoise waters will make you feel as if you're swimming in a vast pool crafted by nature herself. The wild landscapes of the southeast coast feature cliffs that dive into the sea, creating a chain of caves, including the captivating cave of Mastichari. Enjoy several stops for swimming in these crystal blue waters!
During the trip, we'll provide morning coffee, a snack, and a BBQ lunch featuring either chicken or pork skewers, paired with two types of salads, tzatziki, pita bread, and of course, local beverages such as white house wine, soft drinks, and mineral water. For dessert, indulge in delicious fresh fruits. We'll return to the port of Pounta at 4:30 pm, followed by a transfer back to your hotel or a nearby stop.
Day 11 - 13
Perched on a 220-metre-high cliff overlooking the vivid blue waters of the Aegean Sea, Fira is Santorini's cultural and commercial capital that beckons those in search of breathtaking views, stunning sunsets, delectable local cuisine, and unforgettable cultural experiences. Facing the volcano on the island's western edge, Fira is a bustling cosmopolitan town characterised by a mixed sample of Cycladic and Venetian styles woven together by labyrinth streets that cater to daytime adventures and nighttime sprees. Embark on a fascinating exploration of the town's local museums, restaurants, coffee shops, and archaeological sites by hopping on a cable car heading to remarkable churches and iconic landmarks. For a deep dive into local history, visit the Museum of Prehistoric Thira, the Archaeological Museum, and the Santozeum. End the day with a leisurely cruise to the volcano from the Old Port on a luxury yacht or traditional wooden sailing boat.
Located in Fira, Santorini, Aressana Spa Hotel and Suites provides guests with a fairytale-like vacation. Accommodation options consist of a selection of rooms and suites that are comfortably furnished and equipped with air conditioning, Wi-Fi, TVs, mini-fridges, tea/coffee-making facilities, and complimentary soft drinks, mineral water, and homemade preserves. Guests can start the day with a Santorinian breakfast buffet, enjoy delicious traditional cuisine, and relax with drinks at the on-site restaurant and bar. Facilities and services include a lobby lounge, a swimming pool, poolside cabanas, daily cleaning, and a turndown service.
Enjoy a private hotel pick-up and set sail on a catamaran cruise around the stunning Santorini Caldera. On this 5-hour tour, relax as you sail to the volcanic islands and take the opportunity to swim or snorkel in the deep blue, crystal-clear waters. Visit the spectacular Red Beach and White Beach, and stop at the Hot Springs to enjoy a therapeutic mud bath. A delicious barbecue is served on board, accompanied by unlimited Santorinian white wine and soft drinks.
After returning to the port, meet your guide for the second part of the tour. Begin with a visit to Santo Wines Winery, where you can taste three distinctive local wines while admiring breathtaking views of the volcano. Continue to the Wine Museum, a family-run winery with a long tradition of winemaking. The tour concludes in Oia at the Sun Spirit Cocktail Bar, one of the best spots on the island to enjoy a sunset. Relax with a glass of wine as the sun slowly sinks into the Aegean Sea, creating an unforgettable end to your day.
Day 14 - 15
Dominating the Attica region of Greece, the country’s capital, Athens, is one of the oldest cities in the world. For over two and a half centuries, the astonishing Greek temples and monuments of Athens have continued to intrigue and amaze visitors from around the world. This icon of western civilization seamlessly combines ancient history with modern architecture and a surprisingly lively atmosphere. This is particularly apparent in areas at the foot of the Acropolis, Anafiotika, Plaka, Monastiraki, and Thissio where visitors will find numerous extraordinary Neoclassical buildings, trendy and traditional cafes, and shops, and narrow winding streets with historical treasures at every turn. Once you have enjoyed a history and art fix, try some mouth-watering Greek cuisine at one of the city’s fine local restaurants before indulging in the insatiable nightlife at the chic cocktail bars and waterfront dance clubs.
The Athenian Callirhoe Exclusive Hotel is perfectly situated in the heart of Athens City, Greece, near the Kallimarmaro Stadium, the Acropolis, the Brand New Acropolis Museum, and Plaka. The hotel’s cosy and elegantly decorated rooms and suites feature tea/coffee-making facilities, central heating/cooling, workspaces, private bathrooms, minibars, hairdryers, flat-screen TVs, and laptop-sized safes. Accommodations with balconies are available. Facilities and services include restaurants, a bar, daily housekeeping, a sauna, a gym, and Wi-Fi.
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For this extensive itinerary that covers both the mainland and the islands, the shoulder seasons of late spring (April to June) and early autumn (September to October) are ideal. You will enjoy excellent weather for exploring the ancient sites in Athens and the monasteries of Meteora, while the Cyclades islands will be warm with fewer crowds than in high summer.
The overall cost of this trip is highly dependent on your travel style, as it covers both the Greek mainland and more exclusive islands like Santorini. Generally, a comfortable, mid-range week-long trip to Greece starts at approximately $1,100, excluding international flights. Budgeting for higher costs in popular destinations like Santorini is recommended.
The key highlights of this journey include exploring the historical heart of Athens, culminating at the Acropolis, and witnessing the dramatic, cliff-top monasteries of Meteora. For the islands, don't miss a boat tour of Milos's sea caves and beaches, a wine tasting in Santorini, or trying watersports like kayaking on Naxos and Paros.
When visiting the monasteries of Meteora, be sure to wear clothing that respects the local customs, often requiring shoulders and knees to be covered. For island hopping, factor in potential ferry delays caused by high winds, especially during the Meltemi season, and always book your ferry tickets in advance, particularly for the longer journeys between Milos and the other Cyclades.
Give us a few details like destination, travel preferences, and budget to receive a free personalized travel itinerary in minutes.
In a one-on-one consultation, we pair you with an English-speaking, native-European travel expert to customize your trip even more, making it unique to you and providing in-depth knowledge on every destination.
Or better yet, we’ll book it for you. Every detail is covered by us and you’ll have dedicated guides with you every step of the way, so you can focus on the fun. No action needed — just enjoy the ride.
Tourlane brings out your inner explorer. As your personal travel expert, we’ll help plan a tailor-made trip full of unforgettable moments. Tourlane services aren’t available in all U.S. states. Check your state’s eligibility during the booking process.
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4,421Reviews
About Tourlane
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4.5 of 5
4,421Reviews
4.5 of 5
4,421Reviews
Island hopping Cyclades Islands
We took a trip with tourlane in May 2024. We came across tourlane by chance. We went island hopping in the Greek Cyclades with a flight and organized transfer from island to island by ferry and private transfer to the hotels. Everything was perfectly organized and planned.
Island hopping Greece
Hello dear Tourlane Team!
Family trip to Greece
We had Tourlane plan a vacation with island hopping in Greece. Rental cars on every island, interesting hotels plus ferries and domestic flights. It was great how such a package was put together from our wishes. We are now looking forward to our vacation. Highly recommended.
Greece ISLAND HOPPING START: Athens, then we took the ferry to Paros, 4 days later to Naxos and finally 3 days to Santorini! You were so great! The island hopping went really well thanks to you! From cab, ferry to 3-star hotel, the whole organization! EVERYTHING TOP! And booking the trip was also super easy! I just want to say thank you, it was the best 14 days for a long time
We planned and carried out a family trip with Tourane. The entire planning went smoothly and all our wishes were taken into account. What was particularly pleasant were the very well organized transfers and hotels. Everything went very smoothly so that we could concentrate on the family vacation experience. We will be happy to use the Tourlane service for future family trips.