Greek Islands Sailing Tour
10 Days | 1 Country | 5 Cities
Explore Athens and the historic Acropolis, then set sail around Santorini to witness a breathtaking sunset in Oia. Relax on the turquoise beaches of Mykonos, marvel at the unique landscapes of Milos, and encounter playful dolphins off the shores of Naxos.
10 Days | 1 Country | 5 Cities
Explore Athens and the historic Acropolis, then set sail around Santorini to witness a breathtaking sunset in Oia. Relax on the turquoise beaches of Mykonos, marvel at the unique landscapes of Milos, and encounter playful dolphins off the shores of Naxos.
10 Days | 1 Country | 5 Cities
Explore Athens and the historic Acropolis, then set sail around Santorini to witness a breathtaking sunset in Oia. Relax on the turquoise beaches of Mykonos, marvel at the unique landscapes of Milos, and encounter playful dolphins off the shores of Naxos.
Book with only €100 deposit
Whats Included:
Explore Athens on tour, wandering through historic streets and vibrant neighborhoods. Visit iconic landmarks such as Syntagma Square and the Parliament, then stroll through the lively Plaka district with its cobblestone alleys, quaint shops, and traditional tavernas. Ascend to the Acropolis to admire the magnificent Parthenon and learn about the ancient history that shaped Western civilization.
From Naxos, embark on a full-day sailing adventure through the crystal-clear waters of the Small Cyclades. Cruise to hidden beaches and secluded coves, perfect for swimming and snorkeling, while enjoying a delicious onboard lunch accompanied by refreshing drinks. Keep an eye out for playful dolphins that often accompany the boat, adding magic to your journey.
Spend a free day exploring Milos, a volcanic island known for its unique landscapes and colorful harbors. Discover pristine beaches, charming villages, and dramatic cliffs at your leisure, immersing yourself in the island’s natural beauty and relaxed atmosphere.
Sail around the stunning Santorini caldera aboard a comfortable catamaran, stopping to swim in warm volcanic hot springs and visit the quiet island of Thirassia. Take in panoramic views of the active volcano and the iconic villages of Oia, with their whitewashed houses and blue domes. Enjoy a delicious barbecue feast on board, complemented by local wine, water, and soft drinks.
On Mykonos, venture beyond the bustling tourist areas to explore remote villages, quiet harbors, and magnificent beaches. Wander through the enchanting Old Town’s narrow cobblestone streets, admire the famous Windmills, and stroll along the picturesque waterfront of Little Venice. Soak up the authentic island atmosphere as you visit local shops, cafes, and charming neighborhoods.
Accommodation: Handpicked 4 & 5 star hotels in great locations.
Meals: Daily breakfasts at all hotels during the tour.
Airport Meet and Greet with all intercity transfers including hotel pick-up and drop-off.
Transport: Ferry, boat.
OPTIONAL ACTIVITIES
Mykonos full day sailing tour - from 120 EUR
Athens: Full-Day Rail Tour to Meteora - from 100 EUR
UPGRADES
Hotels 5 stars - price on request
Private tours - price on request
Day 1-2 Athens
Arrive in Athens before noon, where a private airport transfer will greet you and take you comfortably to your centrally located hotel. After settling in, begin Day 1 with a guided walking tour through the vibrant streets of the city. Stroll across elegant Syntagma Square, witness the ceremonial changing of the guards at the Hellenic Parliament, and wander through the charming Plaka district, where cobblestone alleys, neoclassical architecture, and traditional tavernas offer a taste of authentic Athens. As the afternoon unfolds, enjoy panoramic views of the Acropolis before ascending to the ancient citadel itself. With your expert guide, explore monumental landmarks such as the Parthenon, the Temple of Athena Nike, and the Erechtheion, while learning how this sacred hill shaped the birth of democracy and Western philosophy.
Hotel: Grand Hyatt Athens or similar.
Day 2-4 Mykonos
After breakfast, enjoy a comfortable transfer to the port and board a scenic ferry to Mykonos, one of the Cyclades’ most iconic islands. Upon arrival, a private transfer will take you to your boutique hotel, where you’ll have time to settle in before beginning your Mykonian adventure. Later, embark on a half-day guided tour that takes you off the beaten path and deep into the authentic heart of the island. Venture beyond the bustling beaches and postcard-perfect spots to explore remote villages, secluded harbors, and hidden coves that reveal the island’s untouched beauty. Your guide will share local stories and cultural insights as you uncover Mykonos’ traditional side, a world away from the lively party scene.
In your free time, explore the enchanting Old Town of Mykonos (Chora). Lose yourself in the maze of narrow cobblestone alleys, where whitewashed buildings are brought to life by vibrant bougainvillea and colorful doors. Stumble upon charming chapels, local boutiques, and cozy cafés nestled in picturesque corners. Don’t miss a visit to the iconic Mykonos Windmills, the romantic Little Venice district with its waterfront views, and the atmospheric Alefkandra quarter, filled with artistic flair and island charm.
Hotel: Aphrodite Beach Resort Hotel or similar.
Day 4-6 Naxos
After breakfast, enjoy a seamless transfer to the port and board a ferry to Naxos, the largest and greenest of the Cyclades islands. Upon arrival, a private transfer will take you to your charming seaside hotel. On Day 4, enjoy free time and delve into the rich cultural heritage and island charm of Naxos. Wander through the maze-like streets of the Old Town, where Venetian architecture and whitewashed houses blend seamlessly into the historic landscape. Make your way to the iconic Portara, the towering marble gate of an unfinished temple dedicated to Apollo, perched dramatically on the islet of Palatia. As the sun begins to set, the Portara offers one of the most magical viewpoints in the Aegean. In the evening, dine in a traditional taverna, where the flavors of Naxian cheese, grilled meats, and local wine offer a true taste of the island’s culinary soul.
On Day 5, set off on a full-day sailing adventure across the azure waters surrounding Naxos and the Small Cyclades. Climb aboard a comfortable yacht and cruise to secluded beaches, hidden coves, and unspoiled bays only accessible by boat. Dive into the crystal-clear sea for swimming and snorkeling, bask in the Mediterranean sun, and enjoy the possibility of spotting playful dolphins as they dance alongside the boat. Your journey includes a delicious onboard lunch, refreshing drinks, and local snacks, creating a day of pure relaxation, light adventure, and unforgettable views over the Aegean.
Hotel: Naxos Palace Hotel or similar.
Day 6-7 Milos
After breakfast, enjoy a comfortable transfer to the port and board your ferry to the enchanting island of Milos, a hidden gem in the Cyclades celebrated for its surreal landscapes, striking geology, and quiet authenticity. The remainder of the day is yours to uncover Milos at your own pace. Begin your exploration at Sarakiniko Beach, one of the most extraordinary natural wonders in the Aegean. With its lunar-like white volcanic rock formations and turquoise sea, Sarakiniko offers a breathtaking contrast and a photographer’s paradise. Walk along its carved stone crests, explore hidden coves, or dive into the crystal-clear waters from smooth rock ledges. Continue your journey through history with a visit to the ancient Catacombs of Milos, one of the most important early Christian sites in Greece. Not far from here lies the site where the iconic Venus de Milo—now housed in the Louvre—was discovered in 1820. As you stand among the ruins, imagine the island’s long and layered history stretching from the ancient Greek world to today. In the afternoon, head to one of Milos’ famous beaches like Palaiochori, with its vivid red cliffs and thermal springs, or Agia Kyriaki, a tranquil stretch of coast with fine pebbles and shallow waters perfect for swimming. Enjoy a refreshing dip, followed by a relaxing moment in a seaside café where you can sip local wine or freshly pressed juice while gazing at the serene sea. As evening falls, stroll through the winding alleys of Plaka, the island’s charming capital. Watch the sunset from Castro, the Venetian hilltop fortress offering panoramic views over the Aegean, then dine in one of Plaka’s traditional tavernas serving fresh-caught seafood, fava, and locally made cheeses.
Hotel: Santa Maria Village or similar.
Day 7-9 Santorini
After breakfast, enjoy a transfer to the port and board a high-speed ferry to the iconic island of Santorini, renowned for its breathtaking caldera views, cliffside villages, and whitewashed houses topped with blue domes. On Day 8 prepare for an unforgettablecatamaran cruise through the enchanting caldera, a highlight of any trip to Santorini. Your cruise includes a stop at the healing hot springs near the Palea Kameni islet, where you can soak in warm, mineral-rich waters known for their therapeutic properties. Continue sailing to the volcanic beaches of Red Beach and White Beach, where you can swim, snorkel, and admire the unique rock formations sculpted by ancient lava flows. Later, cruise past the legendary village of Oia, perched dramatically on the edge of the caldera. From the water, take in one of the most breathtaking perspectives of Santorini’s sunset, as the sky transforms into brilliant hues of gold and pink. During the cruise, you’ll be treated to a delicious onboard barbecue, featuring fresh local ingredients, grilled meats, salads, and traditional Greek dishes, all accompanied by unlimited wine, water, and soft drinks. Whether you’re lounging on deck, swimming in secluded bays, or enjoying the flavors of the islands, this journey offers a perfect blend of luxury, adventure, and Aegean beauty.
Hotel: La Maltese Estate or similar.
Day 9-10 Athens
After breakfast, enjoy a smooth transfer to the Santorini port and board your comfortable ferry back to Athens, taking in the final views of the Aegean as you sail toward the mainland. Upon arrival in Athens, a private transfer will bring you to your hotel. Take advantage of your free time in Athens to revisit your favorite spots or uncover new ones. You might wander through the vibrant streets of the Monastiraki district, known for its flea markets, rooftop bars, and eclectic shops. Stop for a coffee or a final taste of Greek cuisine in the hip Psiri neighborhood, or explore Anafiotika, a hidden village-like quarter tucked beneath the Acropolis, where Cycladic-style houses evoke the feeling of the islands.
On your departure day, enjoy a private airport transfer, arranged seamlessly for your convenience, ensuring a relaxed and stress-free conclusion to your Greek adventure.
Hotel: Grand Hyatt Athens or similar.
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€100 DEPOSIT
Only €100 deposit to book your tour today
EASY PAYMENT
Full payment not required until 60 days before travel
NO CHANGE FEE
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General FAQ
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An independent tour means you have the freedom to explore cities at your own pace, breaking away from the constraints of a group. Connect with local guides and a small group of fellow travelers exclusively during our captivating sightseeing tours and activities, ensuring a personalized experience tailored just for you!
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If you are travelling solo, then a single supplement is mandatory and you will get your own room at our designer’s hotels. We do not offer shared rooms with other travelers that you are not acquainted with. Please click "Book Now" to see the price.
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Yes, it’s possible to customize the adventure to fit you just right. Add more days to your trip, modify cities on the itinerary, add additional sightseeing tours, or explore specific destinations – simply share your travel plans with us, and we'll make it happen.
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Each tour encompasses comfortable 4 or luxurios 5-star hotel stays, efficient transportation via trains or planes, captivating sightseeing tours, and entrance tickets. We meticulously plan for the fastest and most comfortable routes to ensure a seamless and enjoyable travel experience for you.
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Flights to and from your starting and ending points, city tax are not included in the trip cost. Additionally, it's essential to check whether you require a visa for your journey. Travel insurance is also not covered in the trip cost and should be arranged separately.
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Yes, you can add your pre/post accommodation as well as optional sightseeing tours during the booking.
