Luxury Sailing in the Cyclades: Santorini, Paros & Mykonos - 10 Days

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

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, which 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. 

Day 4: Day Cruise to Anafi, Explore the Island, Santorini Sunset Wine Tasting 

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, the highest point on Santorini. 

Day 5: Sail to Paros, Explore 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 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, this 5-star boutique hotel's 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 6: Day Cruise to Antiparos via Panteronisia & Despotiko

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 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 7: Day Cruise to Naxos, Visit the Small Cyclades

Day 8: Sail to Mykonos via Rhenia & Delos

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 begins to set, 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, either seek out one of the island's upscale bars or wander through the bougainvillea-clad cubic houses in the Old Town.

Day 10: Depart Mykonos