7-Night Sailing Adventure in the Greek Islands from Santorini to Mykonos

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8 Days (approx.)
Tour Details

Set sail from Santorini to Mykonos on this 7-night yacht cruise around the dreamy Cyclades archipelago. This independent sailing adventure gives you the opportunity to test your sailing skills while visiting some of the region’s most charming islands. Make the most of free time to swim, sunbathe and sightsee, and dock each night on Santorini, Ios, Amorgos, Naxos, Mykonos and another of the Cyclades’ smaller islands. Cabin accommodation as well as daily breakfasts and lunches are included. Numbers are limited to just nine participants, ensuring a small-group experience.


Departure & Return Location

Akrotiri Area, Santorini (Google Map)

Departure Time

4pm on Day 1

Price Includes

  • 7 nights accommodation on board a yacht
  • Meals as per itinerary (B=breakfast, L=lunch, D=dinner)

Price Excludes

  • Food and drinks, unless specified
  • Optional excursions and activities
  • Gratuities (optional)
  • Dinners


  • 7-night sailing adventure around the Cyclades, from Santorini to Mykonos
  • Visit Santorini, Ios, Amorgos, Naxos and Mykonos, plus a smaller island in the archipelago
  • Dock each night and enjoy sunset vistas and beachside bars
  • Enjoy optional activities such as a day trip to Delos from Mykonos
  • Help the crew on board and get involved with the sailing of the yacht
  • Small-group cruise with a maximum of nine people ensures personalized attention
What to Expect

Your 7-night sailing adventure cruises north through the Cyclades islands, docking each night so that you can enjoy the nightlife, if you wish. Travel and sleep each night on board a comfortable yacht; it’s small and intimate with just five cabins and three shared bathrooms that are also used by the crew. The tour is a sailing adventure, so an emphasis is put on pitching in and helping the crew. No experience is necessary, just a desire to participate and help out with anything from clearing tables after meals to assisting out on deck. Breakfasts and simple lunches are included on board, but evening meals are taken in town at your own expense with the exception of Day 1. Once on the islands, how you spend your time is up to you; all activities and excursions are payable at your own expense. Prearranged excursions are on offer on Mykonos and Naxos, should you wish to do them, and your crew will happily offer tips for places to see each day.



Day 1Santorini

Board your yacht in the afternoon and meet your crew and fellow passengers during a welcome meeting to learn about the finer details of your itinerary. How you spend the rest of your afternoon is then up to you. Perhaps take a walk to around the stunning capital of Fira, seeing the glorious Dominican Convent and other attractions, or bask on the island’s dramatic black-sand beaches such as Perissa or Agios Georgios. In the evening, head to Dimitris Tavern for a traditional dinner with the crew and the rest of your group, and admire the sunset vista against the sea. Overnight: boat docked at Santorini Port

Day 2Santorini - Ios

Sail away from port in the early morning, and pass Santorini’s caldera, an incredible geological formation that was the result of a colossal volcanic eruption around 1500 BC. Sit out on deck and soak up the sun’s rays, and after roughly four hours on the water, dock on Ios, a large and lively island that’s popular with holidaying Greeks who come for come for watersports, bars and an abundance of beaches. Follow the sunbathing masses to Gialos or Milopotas, escape the crowds at Valmas or Tsemaria or explore the shops at Chora – the island’s pretty Old Town. In the evening, visit one of Ios’ many beach bars or take a stroll up the hill to Panagia Gremiotissa, a popular spot to see the sunset. Overnight: boat docked at Ios Port

Day 3Ios - Amorgos

Enjoy breakfast as you sail southeast to the mountainous island of Amorgos, an idyll immortalized in Luc Bresson’s 1988 film, The Big Blue. With impressive history to equal its rugged beauty, the island was ravaged by pirates in the Middle Ages before being ruled in succession by the Venetians, Byzantines, Ottomans and, finally, the Greeks. Dock at Katapola Port, and head out to discover Amorgos’s delights at leisure. Take a stroll to an ancient Minoan settlement or relax in a waterfront cafe and gaze out at the white Cycladic architecture and windmills that dot the coastline. Overnight: boat docked at Katapola Port, Amorgos

Day 4Amorgos - small Cyclades island

After breakfast, enjoy a drive out to Moni Hozoviotissis, an 11th-century monastery stacked into the cliffs overlooking the sea. Browse its collections of historical artifacts and soak up views of the Aegean Sea before returning to the water to continue sailing. Feel the wind in your hair as you set sail from Amorgos around lunchtime, and head off to discover some of the smaller islands that comprise the Cyclades chain. After roughly five hours at sea, moor up at one of the unspoiled, almost-uninhabited islands – perhaps Koufonisia, Iraklia, Shinousa or Donousa – and make the most of the island seclusion by swimming in the clear waters, sunbathing on the beaches or enjoying fresh seafood in a quiet waterfront taverna. Overnight: boat docked at a small Cyclades island

Day 5Small Cyclade - Naxos

Leave the peaceful solitude of your island after breakfast, and sail north to Naxos, where more sandy beaches and olive grove-framed villages await. The largest of Greece’s Cycladic islands, Naxos has a colourful mythological history, with many considering it to be the place where Zeus hid from his destructive father. Dock at the port, enjoy lunch on board, and then spend the rest of your day doing whatever you please. Maybe explore Naxos’ scenic Old Town, or wander along the southern shores of the island to scout out the best beaches. Overnight: boat docked at Naxos Port

Day 6Naxos

After breakfast, enjoy a full day of free time to get to know the island. Naxos has plenty to offer besides its beautiful beaches, so perhaps take a stroll to the impressive Venetian Castro of Naxos to wander around the medieval mansions, monuments and churches that are etched into the hillside. Pay a visit to the Archaeological Museum of Naxos for an insight into island life thousands of years ago and see a white marble figurine that’s said to be the earliest example of sculpture in Greece. If you want to experience more of Naxos’ culture, join a day trip around the island to visit one of the oldest temples in Greece – the Temple of Demetra – and spend time at a family-run tavern in the hills. The excursion also includes a shot of kitron, the local lemon liquor, plus a walk along one of the finest beaches on the island. Overnight: boat docked at Naxos Port

Day 7Naxos - Mykonos

Enjoy breakfast and cruise away from port toward your final destination: the gorgeous party island of Mykonos. On arrival, perhaps take a walk to admire Mykonos’ chic whitewashed architecture with sights such as the Church of Panagia Paraportiani or take a day trip (own expense) to the sacred island of Delos, the alleged birthplace of Apollo and Artemis. Later on, make the most of your final night on one of the liveliest Greek islands and check out the hedonistic bars and bustling restaurants; Mykonos nightlife is legendary. Overnight: boat docked at Mykonos Port

Day 8Mykonos

Sit down for a final breakfast on board your yacht, and then say goodbye to your crew and fellow passengers as your 7-night cruise finishes.


Additional Information
  • 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
  • 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.
  • Travel insurance that covers medical expenses, including emergency repatriation, is required to participate on this tour; proof of insurance must be shown to your tour leader on the first day.
  • We suggest bringing one medium-size suitcase or backpack per person, weighing no more than 15kg/33lb.
  • Not wheelchair accessible
  • A minimum of 2 people per booking is required
  • Voucher info: You can present either a paper or an electronic voucher for this activity.
  • Local operator information: Complete Operator information, including local telephone numbers at your destination, are included on your Confirmation Voucher. Our Product Managers select only the most experienced and reliable operators in each destination, removing the guesswork for you, and ensuring your peace of mind.
  • Cancellation Policy If you cancel at least 7 day(s) in advance of the scheduled departure, there is no cancellation fee. If you cancel between 3 and 6 day(s) in advance of the scheduled departure, there is a 50 percent cancellation fee. If you cancel within 2 day(s) of the scheduled departure, there is a 100 percent cancellation fee.