Best for those interested in seeing Greece by boat, this sailing adventure combines bustling and ancient Athens with some of the country's most beautiful islands: the Cyclades. Set on a yacht, you'll sail the turquoise waters of the Aegean Sea in search of the region's rich heritage, including gorgeous beaches, iconic windmills, exotic plant life, and beautiful sunsets. The days are yours to indulge in rich, local cuisine, as well as discover archaeological sites, step back in time while meandering small villages, and enjoy some of the best nightlife in Greece.


  • Eat like a local with plates full of fresh seafood
  • Swim in crystal-clear, turquoise waters
  • Watch the sun melt into the sea next to iconic windmills
  • Dance the night away in Mykonos
  • Tour Athen's ancient architecture

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Explore Athens: a private tour at the Acropolis Athens
Day 3 Discover the glamorous island of Mykonos Mykonos
Day 4 Set sail for Naxos Naxos
Day 5 Feel like a local in tranquil Heraklia Irakleia
Day 6 Sail to the Island of the Sun Schinoussa
Day 7 Go caving in Antiparos Paros
Day 8 Get active in Paros Paros
Day 9 Trace the footsteps of Apollo and Artemis Mykonos
Day 10 Say goodbye to Greece  

Detailed Itinerary

Day 1: Arrive in Athens

Athens, Greece

Welcome to Athens! Greece's capital city is a vibrant hub brimming with ancient landmarks and intriguing side-streets at every turn. The day is yours to enjoy all that Athens has to offer, including its ultramodern museums, multi-arts spaces, local shops, and hip cafes. Suggested activities include:

  • Take a leisurely stroll and explore the beating heart of the city;
  • Lose yourself in the colorful network of streets in the town center;
  • Wander the island-like paths of the Anafiotika neighborhood near the Acropolis;
  • Enjoy an elegant Greek dinner at a scenic restaurant overlooking the beautifully-lit Parthenon.

Day 2: Explore Athens: a private tour at the Acropolis

The Acropolis

Today is all about ancient Athens. The focal point of this iconic city is the famous Acropolis, perched high atop a hill overlooking the city. Join a private tour of the area, admiring all the famous sites of the ancient and modern Athens city.                                          

During this 4-hour tour, you'll start at the Archaia agora, the Areopagus hill from which Apostle Paul spoke to the Athenians. Next, you'll follow your guide to the Propylaea, the Temple of Athena Nike, the Parthenon, and the Erechtheion. The tour ends with a pleasant walk by the Herodion and Dionysos Theaters and a visit to the Acropolis museum.

The rest of the day is yours to continue exploring this vibrant city.

Day 3: Discover the glamorous island of Mykonos

Traditional windmills on Mykonos

Welcome to Mykonos, one of Greece's most glamorous and popular 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. Suggested activities 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.
Plan your trip to Greece
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Day 4: Set sail for Naxos

Naxos, Greece

Say goodbye to Mykonos (for now) and set sail while enjoying the amenities on your yacht. Cruise the iconic blue waters of the Aegean Sea before arriving in nearby Naxos. The day is yours to explore the island known for its private beaches and pure relaxation. Suggested activities include:

  • Shop and enjoy a meal in the island's bustling town center;
  • Admire the historical, Venetian architecture;
  • Wander the Kastro (castle) area;
  • Swim or wind surf at secluded beaches;
  • Hike to the Apollo Temple.

Day 5: Feel like a local in tranquil Heraklia

Waters of Heraklia

Heraklia is a diamond-shaped island set just south of Naxos. This small, charming oasis is home to just over 150 inhabitants and has nearly avoided all tourism, making it the perfect stop for a quiet and picturesque evening. Just like its residents, you'll enjoy Heraklia's permanent tranquillity and unmatchable beauty.

Your yacht will arrive at the port of Agios Georgios, where you may feel like you have traveled back to a simpler time. White buildings and colorful sailboats dot the shore as locals meander around the small town center. Suggested activities include:

  • Enjoy a leisurely day at the beach;
  • Hike through the island's western half, a protected green space;
  • Taste local seafood.

Day 6: Sail to the Island of the Sun

Schinoussa, Greece

Today you'll set sail for Schinoussa, known as the Island of the Sun. Close to Naxos, Irakleia, Koufonisia, and Keros, it's nestled in the Small Cyclades and is known as one of the most beautiful islands in the Aegean. The entire island is part of the program Natura 2000, as it hosts many endemic plants and is an important migratory station for many birds.

The small island is home to only two villages, Chora and Messaria. Together, the two towns house about 256 inhabitants who work in agriculture, farming, fishing, and tourism. Schinoussa owes its name to the mastic tree shrub that grows all over the island. Suggested activities include:

  • Swim, swim, swim. This island is home to some of the best beaches in Greece, all perfect for swimming and sunbathing;
  • Enjoy traditional fava at one of the town's cafes;
  • Sip a beer at the port while watching the sun set.

Day 7: Go caving in Antiparos

Tranquil island of 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.

On your way to Paros, you'll enjoy views of neighboring islands, such as Despotiko, Tsimintiri, and Stroggylo.

Day 8: Get active in Paros

Classic Greek island architecture
Classic Greek island architecture

Paros is one of the Cyclades Islands' best kept secrets. 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.

You'll quickly learn that Paros has a special charm of its own. 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 9: Trace the footsteps of Apollo and Artemis

Discovering archaeological sites in the Cyclades Islands

The gentle Aegean winds will guide you back to Mykonos, where you can sail along stunning  coastline and beaches. From here you'll take a sunset sailing tour to the nearby island of Delos where you'll enrich your knowledge of ancient Greek history. The Cyclades Islands (kyklos meaning circle) get their name by encircling the sacred island of Delos, which is a Unesco World Heritage Site. It's one of the most important archaeological sites in Greece and the birthplace of Apollo and Artemis.

Day 10: Say goodbye to Greece

The Cyclades Islands

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.