Sailing the Greek islands for a week sounds amazing for good reason. Board a catamaran with an experienced crew to hop from island to stunning island in the Cyclades. Along the way, explore the best of Mykonos and watch the sunset from Santorini, see ancient ruins, and swim in the azure Aegean waters before bedding down in your boat each night.

Upcoming Departures

Date Duration Availability Cost per person
Apr 13, 2019 4 days Available $1,280 USD Inquire


  • Go sailing with an experienced crew
  • Swim in the Aegean Sea 
  • Explore the best of Mykonos
  • Catch the sunset on Santorini

Brief Itinerary

Day Highlights Overnight
Day 1 Meet your crew at Naxos Marina Naxos 
Day 2 Sail from Naxos to Mykonos Mykonos
Day 3 Explore Mykonos Mykonos
Day 4 Visit Paros Paros
Day 5 Swim at Antiparos Ios
Day 6 Explore Ios or hop to Santorini Santorini or Ios
Day 7 Sail to Koufonissi Koufonissi
Day 8 Departure  

Detailed Itinerary

Day 1: Naxos 


Start off in Naxos to meet the crew who'll guide you on your yachting adventure. Relax for the evening at one of the tavernas around Naxos Marina, order a Greek salad (or ten), and get ready to sail those brilliantly blue waters in the morning. 

Day 2: Sail from Naxos to Mykonos

Sailing in the Mediterranean

Good, strong sailing breezes are common in this part of the Aegean Sea and they should help propel you north from Naxos to Mykonos. You should reach the marina by late afternoon, giving you time to explore this famously lively island by night. Or, if you'd prefer to just chill on the deck of your yacht and play cards, go for it. It's your trip! 

Day 3: Explore the Best of Mykonos


Today you get to spend a full day getting to know Mykonos. You'll have the option of a quick trip to the nearby island of Delos, which was sacred to the ancient Greeks. Or maybe you'd like to spend the day at one of the best beach clubs on the Mediterranean. If you want to do both, that's an option as well.

Day 4: Sail from Mykonos to Paros


Your crew will prepare the catamaran (you're on vacation, after all) and set you all up for an early sail from Mykonos so you can arrive on the island of Paros by about noon. Make the most of your time by visiting the pretty main town of Paroikia and, of course, taking a dip in the Aegean Sea. 

Day 5: Swim at Antiparos and Spend the Night in Ios


Time to leave Paros and sail one nautical mile south to Antiparos. Here you'll find an ancient acropolis and azure waters. Once you're done checking out the area, cross the Aegean Sea once again to set up for the night on the island of Ios. Known for its sandy golden beaches, its parties, and for being the birthplace of the ancient poet Homer, this is one island you don't want to miss. 

Day 6: Explore Ios or Hop Over to Santorini


It's up to you what you'd like to do today. Maybe you want to sleep in after a big night out, perhaps you'd like to explore a bit more of Ios, or maybe Santorini is calling? Take a ferry over to that famous island of blue-domed Byzantine churches and epic sunsets to see what all the fuss is about. 

Day 7: Sail to Koufonissi


Today you'll sail on over to Koufonissi. On the way, stop for lunch before arriving at port in the early evening. This little island is known for its secret coves, crystal clear waters, and for covering only 10 square miles! Basically, it's as charming as anywhere on Earth. 

Day 8: Departure

The Portara in Naxos

Having spent the night on the peaceful island of Koufonissi, it's time to get back to it and sail over to Naxos. This is your final stop, and after crossing its southern coasts and then turning north to arrive at the main port, this part of your Greek adventure is over. Head home, or extend your trip and see the Acropolis in Athens, or hike in a giant gorge on the island of Crete. 


Map of Sailing the Greek Cyclades Islands - 8 Days
Map of Sailing the Greek Cyclades Islands - 8 Days

Upcoming Departures

Date Duration Availability Cost per person
Apr 13, 2019 4 days Available $1,280 USD Inquire