Experience quintessential Greek islands and the warm breeze of the Cyclades on this first-class, two-week sailing vacation. After a 5-star welcome at one of Athens' top hotels, explore the city with private tours before jetting off to Santorini for sunset wine tasting and a spa afternoon. Sail to Paros and Mykonos via your own private yacht, with luxurious stays on each, while experiencing the best of the archipelago's beaches, charming towns, and snorkeling spots.


  • Dine "in the sky" with panoramic views of the Greek capital 
  • Follow in the footsteps of Socrates and Plato as you tour Athens' ancient sights
  • Sip wine at sunset from Santorini's highest point at Prophet Elias
  • Sail around the Cyclades with your own private yacht and crew
  • Learn to cook traditional Mykonian cuisine at a local's home

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens, Neighborhood Gems Tour, Sunset Dinner Athens
Day 2 Tour of Ancient Athens, Anafiotika & Plaka, Dinner in the Sky Athens
Day 3 Fly to Santorini, Kallos Spa Experience, Sunset Wine Tour Santorini
Day 4 Day Cruise Around the Caldera with Swimming & Snorkeling  Santorini
Day 5 Day Cruise to Ios, Relax on Maganari Beach & Explore the Island  Santorini
Day 6 Day Cruise to Anafi, Explore the Island, Sunset Wine Tasting  Santorini
Day 7 Day Cruise to Folegandros, Megalochori Sunset Wine Tasting  Santorini
Day 8 Sail to Paros, Explore Naousa, Local Dinner in Paros Paros
Day 9 Day Cruise to Antiparos via Panteronisia & Despotiko Paros
Day 10 Day Cruise to Naxos, Visit the Small Cyclades Paros
Day 11 Sail to Mykonos via Rhenia & Delos Mykonos
Day 12 Cruise Mykonos' Best Beaches, Lunch at Kalafatis Bay, Island Village Tour Mykonos
Day 13 Traditional Greek Cooking Experience, Mykonos Walking Tour Mykonos
Day 14 Depart Mykonos  

Detailed Itinerary

Day 1: Arrive in Athens, Neighborhood Gems Tour, Sunset Dinner

Welcome to Athens
Settle in with a drink at your hotel's terrace or take a dip in the inviting pool (photo courtesy of Grande Bretagne)

Welcome to Athens! With over 5,000 years of history and an eclectic mix of ancient and modern, Greece's buzzy capital acts as an outdoor museum to some of the world's most historic landmarks. Upon arrival at the airport, you'll take a private transfer to your downtown hotel. Your destination is the 5-star Grande Bretagne Hotel, whose neoclassical facade and opulent interior have graced the central Syntagma Square since 1874.

Check in, and you'll immediately be transported back to the Belle Époque with the hotel's glimmering marble floors and furnishings, elaborate chandeliers, and pristine vintage furniture. Deluxe rooms and suites continue the lavish 19th-century feel, while the restaurant and pool offer some of the best Acropolis views in the city. When you're ready, head out for a private city tour with a twist. You'll spend the next four hours experiencing Athens like a local, focusing on the city's neighborhood gems, hidden courtyards, and independent cafés off the regular tourist trail.

Unearth local creativity with visits to artisanal workshops, cultural spaces, and several galleries, then discover the capital's world-leading street art scene. You'll also get an introduction to Greek cuisine and snack on delicious meze, traditional sweet pastries, and excellent Greek coffee and spirits. After your tour, head to dinner at one of the city's most mesmerizing spots, known for its modern Greek fare and beautiful views over the Acropolis. 

Day 2: Tour of Ancient Athens, Anafiotika & Plaka, Dinner in the Sky 

See the world's oldest theater, which hosted plays by Sophocles and Euripides, with a visit to the Theater of Dionysus

Spend the day exploring Greece's capital and follow in the footsteps of Cleisthenes, Socrates, and Plato with a private tour of the Acropolis and the Parthenon. Along the way, your guide, an esteemed archaeologist, will share how the concept of democracy first developed in sixth-century BCE Athens and the vital role the ancient city played in the story of civilization. Visit the New Acropolis Museum and see the Theater of Dionysus and the Asclepius Sanctuary, among other ancient sights.

Continue down the hill, and you'll pass landmarks, including the National Observatory of Athens, before arriving in the historic Plaka neighborhood. Hear from your guide how the district developed over the millenniums and pass key landmarks, including the Lysicrates Monument, before strolling to the top of the Anafiotika neighborhood. Admire the Cycladic style architecture and whitewashed cubic houses with brightly painted shutters before pausing for a café at a local haunt. Part ways with your guide, and the rest of the afternoon is yours to spend at leisure. 

In the evening, you'll dine on a six-course modern Greek tasting menu at Dinner in the Sky. With incredible views over the Acropolis, mountains, and sea, you'll appreciate the beautiful Athenian cityscape from your slowly rotating table, suspended 165 feet (50 m) in the air, with seating for just 22. Gaze at the panoramic vistas while sipping excellent Greek wines as you toast your final night in Athens.

Day 3: Fly to Santorini, Kallos Spa Experience, Sunset Wine Tour

Toast your arrival on the volcanic island with a glass of Santorini wine on a sunset wine tour

Your sailing tour of the Cyclades begins today! After a private transfer to the airport and a short flight, you'll arrive in Santorini, known for its magnificent Caldera, volcanic beaches, and cosmopolitan feel. Upon arrival, your driver will transfer you to your accommodation in Oia. You'll stay at the 5-star Canaves Oia Epitome, the island's only property that offers sea and sunset views from each of its luxury suites and villas. Impeccably furnished with natural and earthy materials and a modern, elegant design, each accommodation has its own heated or plunge pool. 

After check-in, enjoy a dip in the hotel's large infinity pool or a welcome drink on your private balcony overlooking the Aegean, then take a private transfer to nearby Imerovigli. The next few hours are yours to indulge in the Kallos Spa, where you can unwind with a massage or spa treatment and unwind in the hammam area or one of the two serene pools. 

You'll finish your first day on the island with a private wine tour and discover Santorini's 400-year-old vines with visits to three wineries. Start at a 19th-century canava (an underground cave used for grape storage and winemaking) and try a selection of varietals. Your next tasting is an interactive musical wine tasting where you'll taste three different ancient varietals while listening to ancient Greek wind and string instruments. Your final tasting takes you to a terrace with sunset views, which you'll admire while sipping wine and feasting on local meats and cheeses. 

Day 4: Day Cruise Around the Caldera with Swimming & Snorkeling 

Drop anchor and admire Santorini's red volcanic cliffs that give the beach its name 

This morning, it's time to check out your yacht, which will be for your private use during your sailing trip. Meet your driver and head to the port to board your luxury Beneteau Oceanis 45 yacht, fully equipped with everything you might need for a day's sailing and more, including plenty of refreshments. After a warm welcome from your captain, who'll be with you for the next nine days, set off for your first excursion around the Caldera. Relax with a refreshing drink as you sail past the tiny island of Aspronisi, the archaeological site at Akrotiri, and Indian Rock.

Drop anchor at Santorini's Red Beach and White Beach, where you can swim or snorkel in the turquoise waters and admire the beaches' distinctive colored pebbles. Return to Oia and disembark in time to watch the island's famed sunset. It's the best spot on the island to catch the oranges, reds, and pinks of the setting sun and see the caldera transform into a sea of twinkling lights as night falls. Either dine in the privacy of your balcony, head to the hotel's restaurant, or explore Oia's dining scene. You'll find plenty of options that showcase the island's fresh produce and abundant seafood. 

Day 5: Day Cruise to Ios, Relax on Maganari Beach & Explore the Island 

Pass the delightful Ammoudi Bay as you sail to Ios

The first full day of your sailing adventure begins with a day trip to Ios, a dream of an island in the southern Cyclades. In the morning, your driver will transfer you to Vlychada Port, where you'll step back on board and set sail, passing Thirassia and the picturesque Ammoudi Bay before mooring at Ios harbor.

The rest of the day is yours to do as much or as little as you like. There are over 46 miles (75 km) of golden sands and turquoise coastline to explore, including one of the Cyclades' best beaches, Maganari, featured in Luc Besson's "The Big Blue." Head inland, and you'll find 365 churches, cubist Cycladic architecture, and plenty of tavernas, where you can savor the view over local specialties and a glass of local wine.

You'll return to Santorini at the end of the afternoon in time to witness the sunset from your yacht. After a private transfer back to your hotel, the rest of the evening is yours to enjoy at leisure. 

Plan your trip to Greece
Chat with a local specialist who can help organize your trip.

Day 6: Day Cruise to Anafi, Explore the Island

Anafi's beaches combine golden sands with crystal-clear waters, perfect for a snorkel or a swim 

Today's cruise is to Anafi, a tiny island 16 nautical miles (25 km) east of Santorini, which remains beautifully undeveloped. Legend has it that Anafi rose to provide shelter for the Argonauts and protect them from the sea. It's a gentle two-hour sail, and the yacht is yours to sunbathe on the deck or relax in the shade. Drop anchor at the port of Agios Nikolaos, where you'll find some wonderful tavernas and restaurants for a delicious lunch after a morning on the beach.

Spend a few hours resting on the golden sands at Klisidi, Megas Potomos, or Megalos Roukonas, all tranquil beaches with crystal-clear waters, perfect for swimming or snorkeling. After refreshments back at the harbor, try out a different beach or explore the island's main (and only) village. Located at the top of the hilly terrain, Chora's houses are built on the mountain's slopes and surrounded by small churches. It's an easy walk from the harbor, and you'll be rewarded with views from the Venetian Castle as you approach the top. 

Day 7: Day Cruise to Folegandros, Megalochori Sunset Wine Tasting 

Accessible only by boat, Katergo Beach on Folegrandos remains a hidden gem

The beautiful island of Folegrandos, located in the center of the Cyclades, next door to Santorini, is today's scenic sailing destination. Filled with charming churches and wild landscapes, the island has several gorgeous beaches. Your destination is Katergo Beach, a secluded spot only accessible by boat. After a gentle sail around Santorini's caldera, you'll arrive at the island. The rest of the day is yours to swim and sunbathe while your crew gets to work preparing a delicious lunch served on deck.

In the afternoon, you'll sail back to Santorini in time for a private sunset wine tour. Start in Megalochori, a quiet village with charming alleyways and ornate bell towers. The island's famous Wine Museum is your next stop, where you'll enjoy a tasting of local varietals and delve into Santorini's fascinating wine history, all inside a labyrinthine cave 26 feet (8 m) underground. After the tour, select your favorite wine and enjoy it, overlooking the island's sunset from Prophet Elias Mountain, the highest point on Santorini. 

Day 8: Sail to Paros, Explore Naousa, Local Dinner in Paros

Explore Paros
Paros' beautiful harbor in the island's capital, Naousa

Wave goodbye to Santorini this morning; you're off to Paros! One of the largest islands in the Cyclades, Paros' pretty villages are filled with blue and white houses and steep, cobbled streets that are never far from a great stretch of beach. With a Byzantine footpath connecting the villages, there's plenty to explore inland, too. You'll spend the day cruising the small islands of the Cyclades en route. It's around a seven-hour trip, so enjoy the views and kick back on deck as your crew serves an al fresco lunch accompanied by local wines.

Arrive at the harbor, and your driver will transfer you to your accommodation—Hotel Andronis Minois. Designed in classic Cycladic architectural style, suites are elegantly furnished in white and neutrals, warmed with earthy reds and blues, with touches of Moroccan decor. Opt for the Minois Blue or Essence Suite, and you can relax in your private infinity pool and enjoy sweeping sea views.

After a refresh, head out to explore Paros. Stretch your legs after a day sailing with a trip to nearby Naousa, a colorful, authentic village that's retained its traditional charm. You'll find the ruins of a Venetian fortress at the entrance to its small harbor, and several excellent tavernas line the waterfront (as you'd expect, fish and seafood are a specialty). Try the local kakavia (fisherman's soup) flavored with lemon, celery, tomatoes, olive oil, and parsley, or opt for classic grilled or fried octopus washed down with a glass of moraitis sillogi, the local white wine. 

Day 9: Day Cruise to Antiparos via Panteronisia & Despotiko

Snorkel in the inviting turquoise waters around Antiparos

Today, it's back on board your yacht for a cruise to the neighboring island of Antiparos. There are several sights to see on the way, and first up is the blue lagoon on Panteronisia, where you'll drop anchor and enjoy a swim and snorkel in the turquoise waters. Next is Despotiko, a tiny uninhabited island with long stretches of golden sands, where you'll have a couple of hours to sunbathe and swim. Afterward, sail to Antiparos, where you'll hug the coastline to admire the island's famous Sea Caves.

Alight on the island, and the rest of the day is yours to explore. The village of Kamobos, in the island's center, is home to just a dozen inhabitants, and its whitewashed churches set the scene for the traditional atmosphere. Don't miss the nearby beaches of Glyfa and Livadia if you're looking for a secluded sandy hideaway. Away from the beaches, there's plenty for nature lovers, too, with several hiking trails that wind through rugged landscapes, lush forests, and pristine coastline. You'll return to Paros in time for the evening and enjoy dinner at your hotel or in town.

Day 10: Day Cruise to Naxos, Visit the Small Cyclades

Discover Naxos' world-class beaches and natural beauty on today's cruise 

Your destination this morning is Naxos, the largest and most fertile of the Cyclades, known for its expansive white-sand beaches, archaeological treasures, and laid-back charm. As you sail past the island's famous Portara (Temple of Apollo), you'll discover the hidden beaches of the southeast coastline, with some only accessible by boat. Your exact location will depend on the weather forecast and wind destination, but you can relax knowing you'll be met with secluded sands, shallow waters, and beautiful scenery. 

You'll drop anchor at three different bays, each acclaimed for its tranquility, abundant sea life, and natural beauty. Spend the morning swimming, snorkeling, or soaking up the views, and when hunger strikes, your crew will provide a memorable lunch on deck accompanied by local wine or beers. Afterward, you'll sail to the idyllic island of Schinoussa, a remote paradise in the Small Cyclades, where you'll have the afternoon to spend at leisure. You'll return to Paros in the early evening, ready to spend your final night on the island. 

Day 11: Sail to Mykonos via Rhenia & Delos

Mykonos' whitewashed houses, blue doors, and pink bougainvillea are the archetypal Cyclades

It's the final leg of your sailing adventure, and no tour of the Cyclades would be complete without a stay on Mykonos. Renowned for its cosmopolitan atmosphere and the fetching blue and white buildings of its Little Venice neighborhood, the island has several Michelin-starred restaurants and plenty of designer shops and nightlife. Set sail from Paros and anchor en route at Rhenia, an uninhabited island with a deserted beach perfect for a midmorning swim. 

Before you reach Mykonos, you'll moor at the sacred island of Delos, said to be the birthplace of twin deities Apollo and Artemis and home to an incredible UNESCO-listed archaeological site. In around an hour, just as the sun sets, you'll reach Mykonos and transfer to your accommodation—a suite at the 5-star Myconian Villa Collection. Occupying a gorgeous location nestled into the hillside above Elia Bay, suites are stylishly furnished with the discrete luxury of a private house and have their own saltwater pool or Jacuzzi with plenty of space to unwind. 

Spend the evening dining in style at the hotel's restaurant or head out to sample Mykonian or international cuisine at one of the nearby restaurants. Depending on your mood, seek out one of the island's upscale bars or wander through the bougainvillea-clad cubic houses in the Old Town.

Day 12: Cruise Mykonos' Best Beaches, Lunch at Kalafatis Bay, Island Village Tour

Blue seas, skies, and sandy stretches abound on today's tour of Mykonos' southern coast

It's the last full day of your sailing vacation, and you'll spend it sailing around Mykonos and visiting the famous sandy stretches on the south of the island. See the beaches at Ornos, Psarou, Platys, and Gyalos before crossing over to uninhabited Dragonissi to discover the island's beautiful sea caves and rock formations. Be sure to keep your eyes peeled for the wild mountain goats and eagles often spotted here. Your next stop is the Bay of Frangias, where you'll stop for refreshments on the beach and swim in one of Mykonos' most picturesque spots. 

If you've worked up an appetite from a morning spent swimming and snorkeling, you can refuel with lunch at a beachside taverna at your next stop, Kalafatis Bay. Afterward, either make the most of the watersports on offer or sit back and relax with a coffee at one of the sea view bars. Your final stop is the lively Super Paradise Beach, where you can relax on the sand or head to the Tropicana Bar, recently voted one of the world's top beach bars. 

You'll return to Mykonos in the early evening, where you'll say your goodbyes to your captain and crew. Then, spend the next few hours in the company of a local private guide, discovering Mykonos' authentic side in the charming villages and quaint harbors that give the island its soul. Drive through the agricultural heartland to the village of Ano Mera to explore a small farm and stop for a cold drink in the village square. Then, continue past picturesque Kalo Livadi and wrap up your tour on the narrow streets of Mau, home to the Mykonos dam. 

Day 13: Traditional Greek Cooking Experience, Mykonos Walking Tour

Learn to make Greek classics, such as stuffed tomatoes, on today's tour 

Today, you'll discover the meaning of the Greek word spíti (home) in its truest sense, with a warm welcome into a local cook's home for an authentic Greek cooking experience. Over five or so hours, you'll experience traditional Greek and Mykonian hospitality and learn the cooking methods and secrets of traditional Mykonos cuisine. 

Start with appetizers such as dakos (toasted bruschetta) with kopanisti cheese and tomato, and louza, a pork cold cut famed as the "prosciutto of the Aegean" and local to the Cyclades. Over a glass of wine, you'll learn about local culture and life on the island. Help pick herbs and vegetables from your host's organic vegetable garden and then set to work on making lunch. You'll be guided throughout on how to create classics such as tzatziki, spinach pie, stuffed peppers and tomatoes, and beef with orzo. Afterward, you'll dine together on your freshly prepared creations. 

Complete your Mykonos experience with a 1.5-hour private walking tour through the island's capital, Mykonos Town. Wander through the labyrinthine whitewashed streets with your guide and tour the Lakka neighborhood, where you'll stop for Ellikinos kafes (Greek coffee) at a spot favored by locals. Browse the independent boutiques on picturesque Matoyianni Street and visit the beautiful, atmospheric Greek Orthodox Church of Panagia Paraportiani. You'll finish at the famous Kato Milli, Mykonos' landmark windmills, where you'll part ways with your guide, ready to enjoy your final night on the island.

Day 14: Depart Mykonos

Depart - Time to say farewell to Greece !
Enjoy one last coffee with a view of Mykonos before heading to the airport

It's time to say goodbye to the Aegean. In the morning, you'll transfer to Mykonos airport in time for your flight back to Athens, ready for your onward journey. Kaló taxídi! (safe travels!)

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Map of Luxury Sailing in the Cyclades: Santorini, Paros & Mykonos - 14 Days
Map of Luxury Sailing in the Cyclades: Santorini, Paros & Mykonos - 14 Days