On a sailing vacation in Greece, you will experience what many call the world’s most beautiful islands from a small yacht.  You will have plenty of free time for hiking, snorkeling, and relaxing. On your sailing adventure in Greece, you will explore ancient archaeological sites and taverna-lined harbors, dine on fresh seafood and don’t forget to try the ouzo!

Sailing Adventure Vacation in Greece

Experience what many call the world’s most beautiful islands from a small yacht

Sample 10 Day Itinerary for a Sailing Vacation in Greece

Day 1 Santorini

You will arrive at the meeting point mid-morning for an important group meeting.  You will meet the Chief Experience Officer (CEO) skipper and the other group members. You will be departing today, so if you’d like to explore Santorini we recommend arriving a day early.

Sailing Adventure Vacation in Greece

Explore Santorini on a sailing adventure in Greece

Santorini Island is a 1 million-year-old volcano that remains in an active/dormant state. Its breathtaking beauty, both historically and geologically, is awe-inspiring making it one of life’s true highlights.

The features rich volcanic soil and the wines, tomatoes, and cucumbers are super tasty due to the soil composition and low rainfall. Visitors can make their way from sea level to the crater rim either by bus, gondola or even a donkey ride. Fira, the main town, sits perched on the edge of the caldera with breathtaking views of multi-coloured cliffs, sugar-cube architecture and great local markets for shopping.

Day 2-4 Ios/Small Cyclades/Naxos

Possible island stops include: Ios, Small Cyclades, Naxos

Explore Ios, Small Cyclades, Naxos on a sailing adventure in Greece


Located in the central and southern part of the Aegean Sea, there are 39 islands in the Cyclades of which 24 are inhabited. On these small islands where the past meets the present, one can find both peace and tranquility and colorful nightlife. The white heat of July and August is often relieved by the meltemi, a strong northerly wind that sweeps across the eastern coast of mainland Greece and the Cyclades. Narrow paths full of flowers, whitewashed houses, blue windows and white churches under the dazzling sun and complimented by golden beaches: this is one of those magical places where the reality outstrips the postcards.


Port Ios is situated at the far end of the excellently sheltered Ormos Iou on Ios’ western side. Its very pretty, and the town port is in fine condition with considerable space. Take the enjoyable 25 minute walk to the old town of Charos at the top of the hill. Other options include visiting Homer’s tomb or relaxing on the famous south-side beach, Magganari.


Naxos town is a pretty, typical Greek Island town offering the usual charm. Visit the monument to Apollonius (Bacchus) situated on the headland as you approach the port from the NE. The monument was started in 530BC, but strangely never completed. The town also has a Venetian castle on the hill, and was once ruler of its surrounding islands leaving legacies of aristocracy. The ‘labyrinth’ street patterns exist here as a testament to the cunning of local inhabitants in their efforts to confuse and ward off piracy in past times. But that´s not all folks! Around the island you will find a lot of interesting places and we are offering to you a special roundtrip in Naxos just follow your skipper and you will see hidden areas and feel the atmosphere of Naxos!!

The highlight of Naxos is going on an optional day trip guided by your CEO skipper. Rent cars (remember to bring your license) and explore the inns and outs of the the island. Stops include the Temple of Dimitra, visiting a local microbrewery, the Church of Drosiani – which has wall paintings dating back to the 6th century, stopping to take in the views of Mt. Zeus at Zas Cave, enjoying a meal at a local tavern owned by the town butcher, and finally ending the day at Apollonas beach.

Please note: While it is our intention to adhere to the route described above, there is a certain amount of flexibility built into the itinerary and on occasion it may be necessary, or desirable to make alterations. On Day 1 of your tour you will be advised of any amendments.

Day 5 Mykonos

Legendary both in ancient and modern times, Mykonos is one of the best-known Greek islands, and provides ample entertainment for history and party buffs alike. Just a short boat ride away from the main port lies Delos, legendary birthplace of Apollo and home of the Gods. As the most sacred island in the Aegean for ancient Greeks, Delos gave name to the Cyclades – that is, the islands encircling (kyklos) Delos. Mykonos town, as typical a whitewashed Greek island town can be, has long been famous for its nightlife, with bars and clubs filled with the beautiful of Europe rocking till dawn every night. And during the days, a short bus and boat ride takes you to some of the best—and craziest—beaches in all of Europe.

Sailing Adventure Vacation in Greece

Explore Mykonos on a sailing adventure in Greece

Day 6-9 Syros/Paros/Sifnos/Folegandros

Possible Island stops include: Syros, Paros, Sifnos, Folegandros.

8 passenger yachts make for an exciting and intimate adventure!


In Syros you experience authentic Greek culture, great eating, and a handful of small but pleasant beaches. Ermoupoli is capital of Cyclades and Syros. The main square of the town is called Plateia Miaouli. Surrounded by Town hall, cafeterias, bars and palm trees. Commonly described:”probably the most elegant square in Greece.” Town hall is designed by German architect Ernest Tchiller. You will find Archaeological museum inside Town Hall. Syros has the first ever opera house of Greece, the Apollon theatre located close to main square. Apollon theatre is made from marble and limestone. Enjoy options of going on short hikes, visiting local markets and going SCUBA diving.


Livadhi is a small town on the east coast of Paros, easily accessible from the channel between Paros and Naxos. It’s quaint, and provides a respite from other busier ports in the region. Sample the local cuisine at one of the various tavernas commanding superb views over the strait between these two large islands. Naousa lies centrally at the base of its very large bay on the north east end of Paros. It’s another idyllic island town, with a historical port, featuring Venetian ruins.


An ideal island for walking, head for the trails and admire the views of olive groves and wild juniper. The island hosts a number of small, locally-owned and operated ceramic workshops, some of which are open to the public. It’s well worth it to take something unique and authentic home with you.


One of the must see islands in the Cyclades, famous for one of the most breathtaking cities around, Hora. The capital town, located up in the hills, boasts a traffic-free main street with plenty of green spaces to explore. A great island for hiking and snorkeling opportunities. Photographers will love the classic whitewashed houses decorated with colorful bougainvillea.

Day 10 Santorini

Departure day, depart at any time upon arrival to Santorini. If you would like extra time in Santorini after your sailing journey is finished, we recommend booking extra time on the island.

Ready for a Sailing Vacation in Greece?

Be sure to give luxury travel advisor, Margi Arnold a call to discuss your vacation. With over 25-years’ experience in the travel industry Margi, is an expert that will help you personalize your trip and will ensure a worry-free vacation. Start by completing a vacation request or call Margi at 303-694-8786.

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