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Luxury Island Hopping in the Cyclades

Embark on a journey through Greece’s most iconic destinations, beginning with a private guided tour of the Acropolis, Acropolis Museum, and Plaka district in Athens. Head to Mykonos to explore its stunning beaches and enjoy a private RIB boat cruise to Delos and Rhenia. In Naxos, experience a small-group wine tour and discover its beautiful beaches. Conclude in Santorini with a private food and wine tasting tour.

Highlights

Experience Greece’s rich history and natural beauty on this immersive journey. Begin in Athens with a private tour of the Acropolis, Acropolis Museum, and the charming Plaka district. Travel to Mykonos to relax on its stunning beaches and enjoy a private RIB boat cruise to the ancient ruins of Delos and the secluded Rhenia. Continue to Naxos for a small-group wine tour, where you’ll taste local wines and explore the island’s gorgeous beaches. End in Santorini, known for its breathtaking views and sunsets, with a private food and wine tasting experience. Wrap up your adventure with an exclusive sunset caldera cruise, a luxurious way to take in Santorini’s dramatic landscape. This trip blends culture, relaxation, and authentic Greek experiences.

Price from
6500 per person
Best for
Luxury Travelers
Best time to visit
May - September
Adventure level
Easy

Talk to an expert

Eleni-300x300
Eleni
Travel Specialist

My name is Eleni, a social bee and art enthusiast buzzing in the hospitality sector for 15 vibrant years. As a passionate traveler, crafting unforgettable journeys through the enchanting lands of Greece, Italy, and Turkey is not just my job; it’s my joy. Picture sipping espresso in Rome’s bustling piazzas, diving into the azure waters of Santorini, or unraveling the mysteries of Istanbul’s ancient bazaars. With every itinerary I design, I weave together culture, history, and pure adventure, ensuring your trip is a masterpiece of discovery. Let’s turn your wanderlust into wander-must! Welcome to a world where every moment is an opportunity for adventure and every destination a canvas for your dreams.

Itinerary

Day1
Athens
Arrival in Athens

Begin your adventure in Athens, a city where history meets modernity. Athens, the heart of Western civilization, offers a blend of historical landmarks like the Acropolis and contemporary attractions. Your journey begins with a private transfer from Athens International Airport to your hotel. Spend time discovering the charm of the Plaka district or walking on Dionysiou Aeropagitou, Athens’ longest pedestrian street. For dining and entertainment options, consult your expert Insider Travel Designer.

Day2
Athens
Acropolis, Acropolis Museum & Plaka Guided Tour - Private Tour

Acropolis, Acropolis Museum & Plaka Guided Tour – Private Tour

You will begin your adventure by meeting your knowledgeable, state-licensed guide, who will lead you on a captivating historical journey to Greece’s most iconic landmark, the Acropolis, as well as the stunning New Acropolis Museum followed by an hour leisure walk in the old town Plaka passing by some important ruins on the way!

As you ascend to the summit of the sacred rock of the Acropolis, prepare to be awed by the Parthenon, one of the most important architectural masterpieces in history. Once at the top, your guide will provide an enlightening tour that unveils the grandeur of Athens and the profound cultural achievements of Greek civilization during its Golden Age.

Next, you will visit the renowned Acropolis Museum, a global attraction celebrated for its impressive collection. Each floor is a treasure trove of exquisite artifacts, sculptures, and antiquities, inviting you to explore the depths of Athens’ rich heritage.

Concluding your journey, you will wander through Plaka, the picturesque old neighborhood of Athens, characterized by its charming whitewashed houses and narrow cobbled streets. Here, you can soak in the vibrant atmosphere, where history and modernity seamlessly blend, creating a truly magical experience.

If you wish to continue exploring the city, feel free to ask your guide for recommendations to perfect your day in Athens. Athens is an ancient city that has evolved into a contemporary metropolitan, continuously keeping up with the new trends of the modern world. However, Greece’s capital is immensely proud of its important heritage; it has successfully integrated the ancient sections into the contemporary scene, creating a unique blend.

Inclusions

  • 5-hour private guided tour
  • Hotel pick-up (walking)
  • 2-hour visit to the Acropolis Site
  • 2-hour visit to the New Acropolis Museum
  • 1-hour Plaka guided walking tour
  • Private services of a state-licensed guide
  • Entrance fees
Day3
Mykonos
Flight to Mykonos & Enjoy an Afternoon at Leisure

Your private luxury transfer will take you to Athens Airport to catch your flight to Mykonos. Mykonos Town is a dreamy destination for couples seeking romance. Lose yourselves in the maze of narrow, whitewashed streets, where charming boutiques and hidden cafés invite you to linger. Take a sunset walk by the famous windmills and enjoy a romantic dinner in Little Venice, with the sea lapping gently against the buildings. The town’s vibrant atmosphere and intimate charm make it an unforgettable setting for romantic moments.

Day4
Mykonos
Delos - Rhenia RIB Boat Cruise from Mykonos - Private Experience

Delos – Rhenia RIB Boat Cruise from Mykonos – Private Experience

Explore Mykonos, along with Delos, Rhenia, and other rocky islets, which together form a captivating island complex. These islets are a must-visit for anyone discovering Mykonos, offering a blend of history and unforgettable beaches.

Our journey begins at Ornos Beach, heading first to Delos, a UNESCO World Heritage archaeological site of profound beauty. According to Greek mythology, this sacred island emerged from the Aegean Sea at the command of Poseidon, providing refuge to Leto as she gave birth to Apollo and Artemis.

Continuing on, we’ll reach the nearby Rhenia Island and anchor near one of its renowned beaches, Skinos Beach, famously known as the “Blue Lacuna.” Here, you’ll have the opportunity to swim in the crystal-clear waters, wander along the coastline, and savor our delicious snacks and drinks.

Inclusions

  • 3-hour Luxury RIB boat cruise
  • Hotel pick up and drop off (Vehicle)
  • Expert, English-speaking captain
  • Fresh fruit and snacks
  • Cool beverages (soft drinks, water, juices)
  • Wi-Fi internet connection,
  • Snorkeling equipment
  • Beach towels

Exclusions 

  • Delos entrance fees
  • Seabob – Jet rental
  • Brunch on board from private chef
  • Alcohol beverages
  • Premium drinks (champagne/malt,…)
  • Additional hostess
Day5
Mykonos
Discovering Mykonos' Stunning Beaches

Whether you’re seeking relaxation or adventure, Mykonos beaches have something for everyone. Popular spots like Psarou and Paradise Beach offer vibrant atmospheres with beach clubs and water activities, while quieter options like Elia and Kalo Livadi are perfect for unwinding. Explore the island’s coastline and discover the clear blue waters and golden sands that make Mykonos a beach lover’s paradise. From sunbathing to snorkeling, these beaches provide the perfect getaway for any traveler.

Day6
Naxos
Ferry Transfer to Naxos & Enjoy an Afternoon at Leisure

Your driver will pick you up from your hotel and transfer you to Mykonos port.

After about 1 hour you will be in Naxos port!

Upon arrival, your driver will be awaiting you with a sign with your name on it.

You will be transferred to your hotel.

Naxos Town, the bustling capital of the island, is a must-see for any visitor. Stroll through its historic old town, where Venetian architecture blends with Cycladic charm. Visit the ancient Portara, the symbol of Naxos, and enjoy stunning views of the Aegean Sea. The town is filled with shops, restaurants, and cafés, making it the perfect place to enjoy a mix of culture, history, and local cuisine. Whether you’re looking to explore or relax, Naxos Town offers a vibrant yet laid-back experience.

Day7
Naxos
Naxos Wine Tour & Beyond - Small Group

Naxos Wine Tour & Beyond – Small Group

Embark on an enchanting journey, immersing yourself in the authentic world of viticulture that has gracefully upheld a centuries-old tradition— the very tradition that birthed the ancient Greek god of wine and revelry. This intimate small-group wine tour is tailor-made for enthusiasts who seek to intertwine their passion for fine wines with the art of savoring and embracing local culture.

Dive into the captivating history of Naxos wine, tracing its roots to ancient vine cultivations dating back three thousand years to the prehistoric era. Venture into the heart of the Naxian countryside, traversing enchanting landscapes adorned with vine terraces and ancient olive trees. Your private Mercedes van will escort you to the sanctuary of Dionysus, the ancient god of wine, where your expert certified guide will illuminate the origins of early vine cultivation, the rituals of wine drinking, and the legendary banquets of antiquity. Delve into the myths surrounding this elixir and explore how wine shaped the evolution of philosophy, art, poetry, music, and political life.

The journey continues with an iconic drive to the first contemporary local Naxian winery, renowned for producing some of the finest wines on the island. Wander through the vineyards of this small family estate as the wine producer unveils the secrets of local viticulture and the rich history of winemaking in Naxos and the Aegean islands. Indulge in a sensory experience as you sample a curated selection of exquisite Naxian wines from the family cellar, perfectly paired with delectable Naxian treats. Nestled in the serene vineyard, far from the bustling tourist spots and staged spaces, this wine-tasting experience promises to be an iconic and immersive journey through the history and flavors of Naxos.

Inclusions

  • 3-hour small group experience (max 12 pax)
  • Services of an English speaking licenced guide
  • Visit to local vineyard with presentation by wine producer & sommelier
  • Tasting of 4 wines paired with local cheeses, cold cuts, homemade sourdough bread and “moustokouloura” – special cookies made from the local grapes must
Day8
Naxos
Exploring the Beaches of Naxos

Naxos boasts some of the most beautiful and diverse beaches in Greece, offering something for every type of traveler. Agios Prokopios and Agia Anna are popular spots with clear waters and plenty of amenities, perfect for a day of swimming and sunbathing. For a quieter escape, visit Plaka or Aliko Beach, where you can enjoy the natural beauty of Naxos’ coastline. Whether you’re looking for family-friendly beaches, secluded spots, or water sports, Naxos has it all, making it a top beach destination in the Cyclades.

Day9
Santorini
Ferry Transfer to Santorini & Enjoy an Afternoon at Leisure

Your next stop is the world-famous island of Santorini, a place that truly speaks for itself. After a smooth morning transfer, the rest of the day is yours to relax or discover the island at your leisure.

Oia is a must-see destination for any visitor to Santorini, known for its iconic sunset views and charming Cycladic architecture. Take time to explore its narrow streets lined with art galleries, shops, and cafés, or visit the famous blue-domed churches. Whether you’re enjoying a leisurely stroll or indulging in delicious local cuisine, Oia’s beauty and relaxed atmosphere make it a highlight of any trip to Santorini.

Day10
Santorini
Santorini Greek Food & Wine Tasting - Private Tour

Santorini Greek Food & Wine Tasting – Private Tour

Savor the essence of Santorini’s gastronomy on our Greek Food & Wine Tasting Tour.
Explore two wineries and relish a delightful Greek meze-style meal at a charming traditional restaurant. Gain insights into Santorini’s food and wine culture and receive tips on Greek gastronomy.

Perfect for foodies, wine enthusiasts, adventurers, and those seeking a comprehensive culinary journey in Santorini.

Inclusions

  • 4-hour private experience
  • Pick-up and drop-off at a meeting point in close proximity to your accommodation
  • Private services of an experienced sommelier
  • Tasting of 10 award-winning wines
  • Traditional diner at a picturesque village
Day11
Santorini
Exclusive Platinum Sunset Caldera Cruise - Private Cruise

Exclusive Platinum Sunset Caldera Cruise – Private Cruise

With this experience, you will have the unique opportunity to view the sunset with your loved ones from the comfort of your catamaran.

You will be transferred to the port of Vlychada to embark on your catamaran, where the captain and crew will greet you with a welcome drink.

Dive into the crystal-clear waters of Red Beach and ask the crew for the snorkeling equipment, as you should definitely explore the seafloor! Then, you will stop by the White Beach for swimming and BBQ, where you will enjoy a variety of Greek dishes, all cooked and served on board. You will pass by the Lighthouse, south of the Caldera, and enjoy a dip at the Hot Springs.

Heading toward Ammoudi port, you will view Oia and the most colorful and romantic sunset you’ve ever seen. As the sun slowly dips into the sea, creating a scenery straight out of a painting, admire another picture-perfect town, Fira.

Finally, the catamaran will be anchored to the port, where your transfer will be waiting for your return.

Inclusions

  • 5-hour private boat excursion
  • Hotel pick up and drop off (Vehicle)
  • Dinner and drinks on board
  • 2-3 swimming stops
  • Snorkeling equipment
  • Towels (to be returned to the crew)
  • Blanket (to be returned to the crew)
  • Map with extensive info on the landmarks and destinations
  • Floating devices
  • WC & facilities for washing seawater off
Day12
Departure
Depart from Santorini to Athens by plane

As your incredible journey from Athens to Mykonos, Naxos, and Santorini wraps up, savor one last breakfast before checking out from one of the dreamy Santorini. A private driver will escort you to Santorini’s airport for your flight back to Athens, marking the end of this beautiful chapter.

Athens: Grande Bretagne

Myconian Deos

Mykonos: Deos

Deos stands out among Mykonos’ luxury hotels, offering the perfect balance between proximity to town and a sense of secluded tranquility. Its distinct atmosphere is shaped by breathtaking views, a deep connection to the island’s natural beauty and culture, and the sophisticated design of its suites, complete with private pools. The hotel features a world-class spa, gym, and a panoramic deck where guests can enjoy some of the island’s best views, cocktails, and fine dining. With its seamless blend of sea and sky, Deos invites guests to experience time differently—moving between the serene sanctuary it offers and the vibrant energy of Mykonos Town.

Sundunes Naxos

Naxos: Sundunes

Experience the allure of the newly unveiled Plaka Beach Luxury Hotel, a shining addition to Naxos Island’s luxury offerings. As our doors open for the first time, we welcome you to immerse yourself in a realm of refined elegance and modern luxury. Here, contemporary design meets classic charm, creating an atmosphere where every detail is crafted to delight the senses and every moment promises unforgettable indulgence.

andronis_boutique

Santorini: Andronis Boutique Hotel

Retreat to the Andronis Boutique Hotel, a luxurious escape set high on Santorini’s stunning cliffs. With 25 newly renovated suites and villas, each offering spectacular views of the Aegean, every moment here promises to be extraordinary. Unwind on private terraces with soothing hot tubs, enjoy exquisite cuisine at Lauda Restaurant, rejuvenate at the Mare Sanus spa, and let romance bloom under the stars. In this serene haven, the timeless beauty of Santorini surrounds you, making every experience a cherished memory.

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