Escape to the Greek Islands for a week of sun, sand, and sailing in luxurious style. With a private yacht and crew, you'll spend your days cruising the glittering Aegean while nights are spent on land in some of the Cyclades' finest hotels. Start with astonishing sunsets in Santorini and finish in laid-back Paros and cosmopolitan Mykonos—discovering a paradise of secluded islets, tiny villages, and secret coves in between.


  • Explore the Cyclades each day with a private sailing yacht and crew
  • Sip wine at sunset from Santorini's highest point, Prophet Elias Mountain
  • Relax on the famous sands of Maganari Beach, featured in "The Big Blue"
  • Follow in the footsteps of the Greek Gods with a visit to the ancient island of Delos

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Santorini, Cruise Around the Caldera Santorini
Day 2 Day Cruise to Ios, Relax on Maganari Beach & Explore the Island  Santorini
Day 3 Day Cruise to Anafi, Explore the Island, Sunset Wine Tasting  Santorini
Day 4 Sail to Paros, Explore Naousa Paros
Day 5 Day Cruise to Antiparos via Panteronisia & Despotiko Paros
Day 6 Sail to Mykonos via Rhenia & Delos Mykonos
Day 7 Depart Mykonos  

Detailed Itinerary

Day 1: Arrive in Santorini, Cruise Around the Caldera

Savor the sight of Santorini's blue-domed churches and white cubist houses

Welcome to Greece! Your flight lands in Santorini, the southernmost island in the Cyclades, known for its magnificent caldera, volcanic beaches, and cosmopolitan feel. Upon arrival at the airport, meet your driver and transfer 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 combined with a modern and 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. When you're ready, meet your driver and head to the port to board your luxury Beneteau Oceanis 45 sailboat, fully equipped with everything you might need for a day's sailing, including plenty of refreshments. After a warm welcome from your captain, who'll be with you for the next six days, set off for your first excursion around the caldera. Relax with a sundowner 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 2: Day Cruise to Ios, Relax on Maganari Beach & Explore the Island 

Ammoudi Bay
Sail to Ios, where you'll step ashore and explore the island for the day

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 beautiful golden sands and turquoise coastline to explore, including one of the Cyclades' best beaches, Maganari, which featured in Luc Besson's "The Big Blue." Head inland, and you'll find 365 churches, stark 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. 

Day 3: Day Cruise to Anafi, Explore the Island, Sunset Wine Tasting 

Return to Santorini in time for a sunset wine tasting experience

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, either 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. 

You'll sail back to Santorini in the afternoon in time for a sunset wine tour. Start in Megalochori, a quiet village filled 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 4: Sail to Paros, Explore Naousa

Spend the day hopping between small Cycladic islands on your way to Paros

Wave goodbye to Santorini this morning; you're off to Paros! One of the largest islands in the Cyclades, Paros' pretty villages filled with blue and white houses and steep, cobbled streets 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 a delicious 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 a number of 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. 

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Day 5: Day Cruise to Antiparos via Panteronisia & Despotiko

Drop anchor in hidden coves and turquoise bays as you cruise to 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 west of Antiparos 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 Sea Caves of Antiparos.

Alight on the island, and the rest of the day is yours to explore. The village of Kamobos, in the center of the island, 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 dinner at your hotel or in town.

Day 6: Sail to Mykonos via Rhenia & Delos

Relax in your own private pool on Mykonos
Savor the views from your private pool (photo courtesy of Myconian Villa Collection)

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 vibrant and 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 that's perfect for a midmorning swim. 

Before you reach Mykonos, you'll moor at the sacred island of Delos, 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 begins to set, you'll reach Mykonos, where you'll say your goodbyes to your captain and crew and transfer to your accommodation—a suite at the luxury 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. As the night unfolds, either raise a toast to your trip at one of the island's upscale bars or wander through the bougainvillea-clad cubic houses in the Old Town for a final evening stroll. 

Day 7: Depart Mykonos

Depart - Time to say farewell to Greece !
Your Cyclades adventure comes to a close today

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

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Map of Luxury Sailing in the Cyclades: Santorini, Paros & Mykonos - 7 Days
Map of Luxury Sailing in the Cyclades: Santorini, Paros & Mykonos - 7 Days