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

Santorini, Cyclades Islands, Greece
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10-Day Greek Islands Tour: Small-Group Cyclades Islands Sail from Santorini
24 hours
10 days
Guide Language
Non Cancellable
Starts From
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US$1817.63 US$ 1935.00
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Adult(s) x (Age 15 To 99)
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  • Multi-Day Trip
  • Lunch included
  • Breakfast included
  • Small-group tour


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.


  • Meals as per itinerary (B=breakfast, L=lunch, D=dinner)
  • 9 nights of accommodation on the boat
  • Professional skipper/guide
  • Bed linens
  • Food and drinks, unless specified
  • Gratuities (optional)
  • Entrance fees
Additional Info:
  • Confirmation will be received within 48 hours of booking, subject to availability
  • Minimum age is 18 years. Children traveling with an adult must be 15 years or older.
  • Adult pricing applies to all travelers
  • Please advise any specific dietary requirements at the time of booking
  • Passport information and date of birth must be provided at time of booking
  • Rooms are allocated upon arrival by the skipper according to the group's composition, which means it is not possible to reserve or guarantee any specific berth or cabin.
  • Please note that on days in which no activities are planned, you are free to explore at your leisure; all activities and purchases will be at your own expense. You will have your tour guide's cell phone number in case of emergency.
  • Travel insurance that covers medical expenses, including emergency repatriation, is required to participate on this tour; proof of insurance must be shown to your skipper on the first day.
  • We suggest bringing one medium-sized suitcase or backpack per person weighing no more than 33 lbs (15 kg)

Meeting Point

Vlychada Marina, Santorini
Departure Time:
11am on Day 1
Return Details:
Returns to original departure point about 1pm


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