Bespoke Greek Islands Hopping – 14 days Itinerary (Luxury Edition)

Curated Islands Hopping: A Premier Aegean Escape Among Greece’s Finest Islands

Imagine a Greece beyond the guidebooks. A place of warm hospitality, hidden coves, and villages untouched by time. Our passion is crafting journeys that reveal this authentic side of the Aegean, and we are thrilled to invite you on a 14-day, premium island-hopping EPIC adventure.

We’ve personally curated a route across four stunning islands and Athens, weaving together rich history, vibrant local culture, and unforgettable moments of pure relaxation. Together, we’ll venture off the beaten path. You’ll share stories with fishermen in a quiet taverna, learn age-old crafts from local artisans, and discover a responsible and sustainable way to travel that supports the communities we visit.

Consider every detail cared for, from your arrival at the airport. This all-inclusive, bespoke tailor-made trip is our invitation to experience the true warmth, beauty, and spirit of Greece with us.

Suggested Itinerary 13 nights/ 14 days

Athens – Evia – Tinos – Naxos – Santorini

Day 1: Arrive in Athens and travel to Evia Island

Upon arrival in Athens, meet your private driver and travel across the Evripos Bridge to Evia, Greece’s second-largest island and one of its most authentic destinations. Enjoy the scenic drive through coastal landscapes and pine-covered hills as you make your way to South Evia. Check in at your accommodation and relax after your journey.

Overnight at Heromylos Resort or similar

Day 2: Discover the Flavors of Evia

Evia is an untouched island full of hidden gems and local treasures. Begin your day exploring the fig farms that produce Evia’s famous PDO dry figs and enjoy a delightful food pairing experience with homemade products. Later on, visit a 150-year-old traditional stone olive mill to learn about the art of olive oil making and enjoy tastings of fresh, aromatic olive oil.

Overnight at Heromylos Resort or similar

Day 3: The Dragon Houses of Styra

Today’s adventure takes you to the mysterious Dragon Houses of Styra, an archaeological enigma that continues to puzzle experts. Enjoy a scenic hike up the mountain slopes, surrounded by stunning nature and breathtaking panoramic views of the Aegean Sea. The trail offers fantastic photo opportunities and a genuine connection to Evia’s wild landscape.

Overnight at Heromylos Resort or similar

Day 4: Cooking Class with Georgia

Experience the warmth of Greek hospitality in a hands-on cooking class hosted by Georgia in her family homestead. Learn how to prepare traditional Greek dishes such as tzatziki, Greek salad, moussaka, and baklava in an intensive yet fun culinary session. The day includes an abundance of food, laughter, wine, and even dancing — a true immersion into Greek culture.

Overnight at Heromylos Resort or similar

Day 5: Discover Ancient Athens

Embark on a journey through history with a licensed guide, starting at the Acropolis of Athens, where the Parthenon and other enduring monuments stand as symbols of classical Greece. Continue to the Ancient Agora, the heart of ancient public life, where Socrates once spoke and Plato once walked. Conclude your exploration at the Acropolis Museum, where masterpieces and artifacts from the Acropolis are beautifully displayed, offering a deeper understanding of the ancient citadel. Round off the experience in the charming Plaka district, with its cobblestone streets, traditional tavernas, and authentic Athenian atmosphere. 

Overnight at Electra Palace or similar

Day 6: Immersive Athens Experience
Take a day to further explore the historical center of Athens at your own pace. Visit the National Archaeological Museum to delve deeper into Greece’s ancient past, stroll through the charming Anafiotika neighborhood with its Cycladic-style houses, or relax at a traditional café in Syntagma Square. This is a perfect opportunity to reflect on the city’s rich history and soak in its unique atmosphere.

Overnight at Electra Palace or similar

Day 7: Travel to Tinos – A Cycladic Gem

Begin your day with an early ferry from Rafina to Tinos, an island that embodies the authentic beauty of the Cyclades. After checking into your boutique hotel, delve into the island’s unique charm with a guided food and walking tour through Tinos town, sampling local products and learning about its rich history and culture.

Overnight at Odera or similar

Day 8: Discover Traditional Villages of Tinos

Embark on a private tour to explore the hidden gems of Tinos’ inland. Visit charming traditional villages, stop at a local marble workshop, and meet the island’s only remaining basket maker, preserving a centuries-old craft. This immersive experience offers a deep connection to the island’s heritage.

Overnight at Odera or similar

Day 9: Travel to Naxos – Relax and Recharge in Naxos

Take a ferry to Naxos, the largest and most fertile island in the Cyclades. After checking into your hotel, explore the island’s treasures, from its quaint villages and artisan shops to its pristine beaches.

Overnight at Laguna Coastal Resort or similar

Day 10: A Blend of Tradition and Natural Beauty

Your private guide will lead you through the rich tapestry of Naxos, beginning at the iconic Temple of Apollo, the island’s most famous landmark. From there, journey into the heart of the island to the picturesque traditional village of Chalki, where you will wander through quiet alleys adorned with neoclassical mansions and Byzantine churches. The experience culminates with a visit to a local store specializing in the production of Kitron, the unique citron liqueur of Naxos, where you will learn about its distillation process and enjoy a tasting of this celebrated spirit.

Overnight at Laguna Coastal Resort or similar

Day 11: Travel to Santorini 

Board a scenic ferry ride from Naxos to Santorini, the crown jewel of the Cyclades. Upon arrival, transfer to your hotel, perched dramatically on the edge of the caldera. In the afternoon, enjoy a private visit to Santorini’s renowned wineries, including a tasting experience at Santo Wines, where volcanic soil imparts unique flavors to local varietals like Assyrtiko.

Spend the evening relaxing and soaking in panoramic views of the caldera and the Aegean Sea from your terrace or a local cliffside café.

Overnight at Katikies Santorini or similar

Day 12: A Santorini Sunset at Sea 

Enjoy a leisurely morning—perhaps stroll through Fira’s or Oia’s cobblestone streets, browse artisan boutiques, or savor a relaxed brunch overlooking the caldera. In the afternoon, set sail on a luxury catamaran cruise. The cruise includes swimming stops at Red Beach and White Beach, snorkeling opportunities, and a delicious onboard meal of fresh local cuisine. As the sun begins to set, position yourself on deck with a glass of wine and take in the world-famous Santorini sunset from the sea.

Overnight at Katikies Santorini or similar

Day 13: Akrotiri & Village Charms 

Step back in time with a guided tour of the Akrotiri Archaeological Site, often referred to as the “Minoan Pompeii.” This remarkably preserved Bronze Age settlement offers a fascinating look into ancient life, with multi-story buildings, frescoes, and advanced urban planning. Continue your exploration with a visit to Pyrgos, a charming inland village filled with traditional Cycladic architecture, quiet alleys, and panoramic views from its hilltop castle. Cap off your day in Fira, where you can wander the postcard-perfect streets, visit art galleries, and enjoy a final sunset over the caldera from one of the island’s most iconic spots.

As a memorable finale to your Santorini journey, you are invited to a complimentary sunset dinner at one of the island’s caldera-view restaurants. Savor local delicacies and fine wine while the sun melts into the Aegean, painting the sky with a palette of gold, rose, and violet.

This is more than just a meal — it’s a celebration of your journey, an experience to be remembered long after you’ve returned home.

Overnight at Katikies Santorini or similar

Day 14: Farewell to Greece 

Enjoy a final breakfast before checking out of your hotel. Depending on your departure time, take the opportunity for a leisurely stroll or some last-minute shopping. Transfer to the airport for your onward journey, taking with you unforgettable memories of Greece’s rich history, vibrant culture, and breathtaking landscapes. Safe travels!

Important Notice:

Greece, together with the other countries belonging to the Schengen area, has started using the new EU Entry/Exit System (EES) since 12 October 2025, replacing manual passport stamps with a digital border control system for third-country nationals.

The EES records travellers’ biometric data (such as fingerprints and facial images) as well as dates and locations of entry/exit, with the aim of simplifying border controls and preventing overstays. The system is gradually implemented across the Schengen Area from October 2025 to April 2026, with Greece being one of the first countries to implement it.

Please find more info here: The New Entry/Exit System (EES) in Athens International Airport