As the ultimate sailing adventure through Greece's coveted Cyclades Islands, this tour combines bustling city life with tranquil villages nestled in the Aegean Sea. From some of Europe's best nightlife to humble fishing towns and secluded beaches, travelers will enjoy Greece's rich and varied heritage. Enjoy sunsets and local seafood while discovering important and ancient archeological sites, all from the comfort of a private yacht.

Highlights

  • Swim at secluded beaches
  • Discover the birthplace of Artemis and Apollo
  • Dance the night away in Mykonos
  • Watch the sun set next to iconic windmills
  • Explore tiny villages and indulge in the daily catch

Brief Itinerary

Day Highlights Overnight
Day 1 Welcome to Paros Paros
Day 2 Enjoy the glitz of Mykonos Mykonos
Day 3 Step back in time on Syros Syros
Day 4 Feel like a local on Serifos Serifos
Day 5 Sail to Sifnos Sifnos
Day 6 Discover Milos Milos
Day 7 Go caving in Antiparos Antiparos
Day 8 Say goodbye to Greece  

Detailed Itinerary

Day 1: Welcome to Paros

Classic Greek island architecture
Classic Greek island architecture

Welcome to Cyclades Islands! Your sailing adventure begins aboard your own yacht on the small island of Paros. Often overlooked due to its ritzy neighbor, Mykonos, you'll quickly learn that Paros has a special charm of its own. It may be small, but it's packed with exceptional beauty and activity. Some say Paros is what Mykonos once was, so enjoy all the Greek charm without the crowds and tourist prices. Suggested activities include:

  • Visit Panagia Ekatontapiliani, a 4th-century Byzantine church;
  • Discover Kolimbithres, a secluded beach with natural swimming holes;
  • Enjoy a meal in Parikia, the island's buzzy port town;
  • Get active at Golden Beach, where you can paddle board, wind surf, or kayak. 

Day 2: Enjoy the glitz of Mykonos

Mykonos, Greece
Mykonos, Greece

The gentle winds of the Aegean Sea will push you towards Mykonos, one of Greece's most coveted islands. The island is an idyllic getaway for cosmopolitan fun-lovers, acting as a magnet to the world’s most posh personalities since the 1970s. Today, Mykonos attracts all kinds of adventure-seekers, including nature lovers, foodies, and sports-enthusiasts.

You'll enjoy a sunset sailing tour to the nearby island of Delos. As a Unesco World Heritage Site, Delos is rich in ancient Greek history. It's one of the most important archaeological sites in Greece and the birthplace of Apollo and Artemis.

Suggested activities on Mykonos include:

  • Swim or sunbathe at some of the country's most remarkable beaches;
  • Get your blood pumping with adrenaline-rich water sports;
  • Watch the fishing boats return as you sample local cuisine;
  • Grab a drink in the island's impressive bar scene;
  • Enjoy picturesque architecture and wander the maze-like streets up the hill for island views;
  • Watch the sun melt into the sea next to iconic windmills.

Day 3: Step back in time on Syros

Syros, Greece

Take a break from the party scene and sail back in time to the island of Syros. Legends, traditions, and untold stories define this elegant Cycladic island. Suggested activities include:

  • Explore the aristocratic, 19th-century mansions of the Vaporia neighborhood in the main town of Ermoupolis;
  • Enjoy a local beer in the old town;
  • Swim at one of the many beaches;
  • Meander the steep, narrow alleys of Ano Syros and the celebrated nearby seaside settlement of Posidonia;
  • Walk the golden streets of Miaouli Square at dusk.

Day 4: Feel like a local on Serifos

Cyclades Islands
Cyclades Islands

Known for both secluded and bustling beaches, mouth-watering food, and a main town of unparalleled beauty, Serifos leaves a lasting impression on visitors. The island's main town is one of the most idyllic in the Cyclades. With typical and traditional whitewashed architecture, it’s studded with charming churches and twisting alleyways. Suggested activities include:

  • Tour Aghios Athanasios square;
  • Enjoy or a beer or raki (a traditional distilled spirit) like a local;
  • Admire the famous windmills;
  • Hike to the Hilltop Chora or the old mining trail;
  • Swim at a quiet beach.

Day 5: Sail to Sifnos

Greek Islands

Sifnos is one of the most popular of the Cyclades Islands. With gorgeous whitewashed villages and an abundance of traditional foods, plus plenty of unspoiled sandy beaches with clean, shallow waters, it's obvious why Sifnos is an ideal getaway. This island appeals to all travelers. Chic and cosmopolitan—but at the same time decidedly familial and low-key—it’s an island perfect for long days at the beach. Suggested activities include:

  • Visit the famous Chrysopigi Monastery and the Church of Seven Martyrs;
  • Relax on a sandy beach;
  • Meander Kastro, a quaint medieval village;
  • Go snorkeling or diving in one of the best spots in the world;
  • Hike one of the many trails around the island;
  • Nosh on locally caught seafood;
  • Enjoy traditional architecture in Apollonia.

Day 6: Discover Milos

Waters of Milos, Greece

Milos is rumored to be the next luxury destination in Greek tourism, with its outstanding beaches, crystal-clear water, and gorgeous sunsets. Milos offers over 70 beaches ideal for swimming and is home to a dormant volcano. Its power may be experienced at Kalamos, one of the island’s oldest volcanic centers. Enjoy this best-kept-secret with these suggested activities:

  • Climb the hilltop in Plaka;
  • Hike to the cliff-diving spots in Sarakiniko;
  • Swim at some of the best beaches in Greece;
  • Visit the prehistoric village of Fylakopi;
  • Be charmed by the idyllic fishing villages of Mantrakia, Klima, and Filopotamos.

Day 7: Go caving in Antiparos

Caving adventures in Antiparos

Today you'll ditch the crowds for the small island of Antiparos, an anti-mainstream island that has stood its ground as an alternative offshoot to places like nearby Mykonos and Paros. Thanks to its tranquility, Antiparos houses holidays for many celebrities. Here you'll find famous scenes like octopus drying on a line and white-washed boathouses lining the rocky port. Suggested activities include:

  • Visit the Venetian Castle district;
  • Admire the old town ruins, perfectly complemented by the signature blue-on-white color scheme;
  • Discover the cave of Antiparos;
  • Eat lunch at a traditional fish tavern;
  • Go swimming at one of the many beaches.

Day 8: Say goodbye to Greece

Greece
Greece

Enjoy your last leisurely morning on the sea before packing your bags. A transfer to either the airport or to the port will be arranged for your journey back home or to your next destination.