Your Cyclades sailing adventure begins at the port of Parikia on the island of Paros, known for its golden beaches and white-washed shops and houses decked with bougainvillea. Ferry or fly to the island on your own in time for boarding your deluxe catamaran in the late afternoon. Your captain and trip leader welcome you aboard with refreshments and appetizers and will assign you to your cabin with private bathroom for the week. Meet your fellow travelers and get oriented to Paros’ many attractions, including  Ekatontapiliani (the “church with 100 gates”). Stroll back into town for dinner and drinks at your leisure; then tuck into your catamaran for the night.

Wake up to a typical Greek breakfast buffet of yogurt, coffee, fresh fruits and pastries and set sail for Sifnos. You’ll have the whole afternoon and evening to discover the island. Sifnos is a hiker’s paradise, with dozens of trails to explore and experience Greece off the beaten path. There are many other great options besides hiking… Borrow a snorkel and mask from your catamaran and dive into the warm, crystal clear waters. Stroll the maze of narrow streets and shops, rent a bicycle, or visit the archaeological museums. Pause for a prayer at the beautiful Church of the Seven Martyrs and explore the antiquities in Kastro, the old capital. Tonight, dine near the harbor or head inland to the tavernas of lively Apollonia, a town dedicated to the god Apollo. Apollonia is known for its fun yet unpretentious atmosphere and is the perfect place to enjoy Greek nightlife.

Leave lively Sifnos for the striking rock formations, caves and hot springs dotting unspoilt Milos. As you approach the island, you’ll be greeted by a colorful spread of boathouses; venture further to visit the Christian catacombs and the ancient amphitheater, built to hold 7,000 people. We can recommend several of the island’s dozens of beaches to laze upon, and point you to the hot springs. Head to the capital town of Plaka to visit its museums and castle. A popular way to experience Milos is by renting a scooter or ATV to tour around the island! As the sun sets, return to the port of Pollonia for a gorgeous view and lovely setting for dinner.  Watch the stars slowly reveal themselves as you return to your cabin and doze off to the gentle lapping of the sea.

After a leisurely breakfast, we take a quick trip to the nearby island of Kimolos before setting sail to Folegandros, said to be “as beautiful as Santorini” with its cliffside setting and white-washed houses pouring down to the sea. Only 12 square miles, this gem of an island has less than 700 full-time residents. Venture to Chora (the main town), closed to cars but bustling with tavernas and shops under the trees. Take the bus or hike to find secluded beaches and villages. Time travel to the Middle Ages as you stroll along the Kastro, a small fortress built by the Venetians in 1210. Feel the magic of old Greece as you walk up the hill to the Orthodox church of Panagia for a panoramic view of the Chora and coast as the sun sets. Return to your catamaran to sip a glass of wine or grappa and watch the sunset from the deck.

Today’s exciting destination is Ios, in the heart of the Cyclades. Known for its great beaches, fun bars and tavernas, you will love this beautiful island. The main town, also called Ios, is located on a hillside marked by a double windmill. Explore the island’s numerous churches and chapels encircled within its crumbling medieval walls. Or, seek out the beautiful, domed 17th century Church of Ayia Irini  on the west coast of the island. Archaeology enthusiasts can hire a taxi to visit the terraced ruins of Skarkos, an early Bronze settlement and one of the most important prehistoric sites in the Aegean. If you would prefer to relax and let loose, enjoy the ocean breezes and excellent people watching from a thatched roof cabana at one of Ios’ beach clubs where you can eat, drink, jet ski, kayak, and more! Tonight, join the party in town with a shot of grappa and some Greek dancing – or just relax onboard.

Catch the steady breeze and set sail for lively Naxos, one of the largest and greenest islands in the Cyclades. Wander through the old town’s market and meander around the Venetian castle, or join your trip leader and rent a bike or hike to a traditional village or particularly gorgeous beach. Venture further by renting a scooter or car to visit the island’s attractions (like the giant unfinished statue of Apollo in Apollon) as you wish. You can even partake in a marble carving class where you learn to create masterpieces using tools similar to those used by the Ancient Greeks. Your carved marble stone makes for the perfect souvenir to take home! Drop into the church of Panagia Mirtidiotissa and Saint Georgios Diasorites to take in the artwork and beautiful frescoes. Walk through the Portara, the gateway to the unfinished Temple of Apollo.  Head to the old town for dinner and an evening stroll or partake in an optional cooking lesson with a local Greek chef before returning to your peaceful cabin on the Aegean.

Your last day sailing returns you to the island of Paros and the port of Naoussa where you’ll have a full afternoon to explore this beautiful island – its white marble quarries were used to create the famed Venus de Milo. Set off on your own to seek out one of several incredible beaches, such as Alykí beach with its ancient ruins, where you can laze on the beach and dive into the clear waters to cool off. If you enjoy wine, visit one of several wineries on the island where you can sample varieties of wine found only in this region! Tonight, toast your captain and traveling mates to your weeks’ adventures. Opa!

After one last hearty Greek breakfast, disembark your catamaran. You can extend your stay in Paros for the day or continue to other Greek destinations such as Santorini, Mykonos, Athens, or Crete, or journey homeward.