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Hop around the Greek Cyclades on this 10-day cruise. Set sail from Santorini aboard a gleaming 52-foot (16-meter) yacht and cruise around the sun-baked archipelago, which is known for its glamorous beach resorts, ancient sites, rugged landscapes and postcard-perfect blue-and-white architecture. Travel to Ios, Amorgos, Small Cyclades, Naxos, Syros, Mykonos, Sifnos and Folegandros, spending a day or two on each island. Enjoy both a mixture of free time and guided tours, and relax with included cabin accommodation as well as daily breakfast and lunches. This small-group tour is limited to just eight people.


  • 10-day sailing tour of the Greek Islands from Santorini
  • Travel by comfortable sailboat to eight of the famous Cyclades Islands
  • Visit Ios, Amorgos, Small Cyclades, Naxos, Syros, Mykonos, Sifnos and Folegandros
  • Learn about local culture and history from your expert skipper, who'll give you recommendations on what to do and see during your excursions
  • Enjoy plenty of free time to explore on your own and soak up the exquisite Mediterranean atmosphere
  • Daily breakfasts and lunches included
  • Small-group tour limited to eight people ensures a more personalized experience

Why Our Insiders Chose This Tour

This is an awesome way to experience one of the most scenic of the Greek island groups. Admire iconic whitewashed houses, enjoy gyros and ouzo galore, and swim in the turquoise waters of the Mediterranean. Sleeping on the boat lets you save money while providing a fun and unique experience.

What You Can Expect

10-Day Greek Islands Tour: Small-Group Cyclades Islands Sail from Santorini

Leave Santorini and spend seven nights traveling through the Greek islands to Mykonos!

Spend 10 days exploring the Cyclades, one of the six groups of Greek islands. Start in Santorini and make your way to Ios, Amorgos, Small Cyclades, Naxos, Syros, Mykonos, Sifnos and Folegandros, spending a day or two on each island. You'll travel in a 52-foot yacht; for smaller groups, a slightly smaller yacht will be used.

The skipper of your yacht will act as a guide by taking the hassle out of your travels, managing trip logistics and making sure everything runs smoothly. Armed with knowledge of the historical, cultural and social aspects of each of your destinations, your skipper will provide suggestions on what to do and see during your shore excursions, as well as suggest local restaurants to enjoy some classic Greek food. Daily breakfasts and lunches are included.

You'll spend the night on the boat in one of the five twin/double cabins, each shared by two people. Though this isn't a spacious luxury cruise, you'll get to revel in the adventure of an authentic sailing trip, and your cozy sailboat features all of the necessary amenities needed for a comfortable experience, including three shared bathrooms, two showers and a common area.

See below for a sample itinerary (the exact itinerary is subject to change due to inclement weather and/or seasonal changes to local transport routes/timetables).


Day 1: Santorini – Ios (L)
Your 10-day Greek islands tour departs from the sands of Santorini, an iconic Greek Island (officially named Thira) that was formed by a huge volcanic explosion. Today, it's instantly recognizable by its blue and white buildings, fascinating ruins and spectacular natural beauty.

After meeting your skipper and small group at the Vlychada Marina, hop in the sailboat and feel the rush of the ocean breeze as you make your way across the Aegean Sea to the island of Ios. Upon arrival, you'll be charmed by this exciting island that is a both a haven for party-goers from all over Europe and a true historic gem.

Enjoy free time to walk around, admire the classic Aegean architecture, and visit some of the 365 churches, one for each day of the year. Take advantage of the nightlife by grabbing some drinks from the nearby bars. At the end of the day, relax on the boat's deck and appreciate the serenity of life atop the water.

Overnight: Boat

Day 2: Ios – Amorgos (B,L)
Cast away from Ios in the morning to the mountainous shores of Amorgos, the easternmost island of the Greek Cyclades island group. This rugged, ancient island has a long history of colonization and occupation dating back as far as 4,000 BC.

During your free time here, admire the classic Greek architecture as you walk around and learn about the island’s colorful past on a visit to Gayros Tower, housing many interesting cultural relics. Then, enjoy a lovely meal with your guide and fellow travelers at a waterside restaurant in Katapola.

Overnight: Boat

Day 3: Amorgos – Small Cyclades (B,L)
With clear waters, beautiful beaches, quiet tavernas and quaint fishing villages to explore, the Small Cyclades island group is an ideal location to drop anchor for the night.

Journey across the glistening Aegean Sea and visit one of these secret, secluded islands. With a much slower pace than its more touristy neighbors, the Small Cyclades islands invite you to kick back, unwind, and soak up the beauty of the unparalleled scenery.

Overnight: Boat

Days 4-5: Small Cyclades – Naxos (B,L)
After another morning of exhilarating sailing, land on charismatic Naxos, the largest and most fertile of the Cycladic Islands home to picturesque villages, Byzantine churches, lush valleys, ancient citrus groves and wonderful beaches.

Admire medieval buildings on a visit to the Venetian Kastro, check out an old Romanesque church, and meet the locals on a country excursion. During your two days here, you’ll have plenty of time to sample a host of beaches and indulge in the vibrant nightlife.

Overnights: Boat

Day 6: Naxos – Syros (B,L)
Your next destination is Syros, where you’ll discover authentic island life with a rare opportunity to see the islands as the Greeks do. Admire Syros’s typical whitewashed houses, terraced fields and fabulous sandy beaches.

Explore narrow stairwells and whitewashed squares that open out onto breathtaking coastal vistas. See the stonewalled village of Ano Syros and sample classic Greek fare in Ermoupolis.

Overnight: Boat

Day 7: Syros – Mykonos (B,L)
Next, travel to one of the most enigmatic and famed of all the Greek Islands, Mykonos. Legendary in both ancient and modern times, Mykonos was the mythical battlefield where Zeus fought the Gigantes, but today it's best known for its decadent nightlife.

Spend the day exploring the island’s many wonders on your own and then head down to Little Venice to watch a sunset from a restaurant balcony.

Overnight: Boat

Day 8: Mykonos – Sifnos (B,L)
On the ancient island of Sifnos, enjoy floating atop the blue waters off Kamares, mingle with locals and travellers alike in Apollonia, and perhaps get a taste of culture at the Museum of Popular Art.

Known for its production of high-quality ceramics, the island getaway of Sifnos boasts fertile valleys of wild juniper, terraced olive groves, sweeping beaches and buzzing waterside tavernas, where the Greek cuisine is as authentic and fresh as it gets.

Overnight: Boat

Day 9: Sifnos – Folegandros (B,L)
On your ninth day, set sail for the bold cliffs and striking landscapes of Folegandros. With its dramatic cliffs and wild landscapes, the tranquil charm of Folgandros belies its history as a place for the exiled and imprisoned, during both ancient and recent times.

While wandering around this scenic island, take in the scent of fresh bougainvilleas that line the walled pathways and head up to the hillside church in time for sunset.

Overnight: Boat

Day 10: Folegandros – Santorini (B,L)
Your unforgettable 10-day Greek islands adventure comes full circle back in Santorini. If time permits, stay a little longer here to soak up more of the cultural, social and culinary delights of this tourist hotspot.

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