Sail from Mykonos to Santorini on this Greek Island adventure

Move between the boat, the beach and inviting Greek villages on this relaxing Greece sailing adventure between Mykonos and Santorini. Wile away days swimming in turquoise waters, lazing on white-sand beaches, sampling mouth-watering local cuisine and exploring coastal villages seeped in history, mythology and beauty. Visit the beautiful islands of Amorgos, Naxos, Small Cyclades and Ios, watch a host of spectacular sunsets and enjoy Greek hospitality before returning to the boat to be rocked gently to sleep at night.

Mykonos, Greece
Santorini, Greece
Physical rating
Cultural rating
Min 15
Group size
Min 1 Max 11
Carbon offset
50kg pp per trip


  • Eat at lively Greek tavernas
  • Join locals for a shot of lemony kitron
  • Swim in pristine turquoise waters
  • Wander the cobblestone streets of whitewashed Amorgos
  • Enjoy the pumping nightlife of Ios
  • Relax on Santorini's black-sand beaches


This itinerary is valid for departures from 01 January 2016 to 31 December 2016. View the itinerary for departures between 01 January 2015 - 31 December 2016

Welcome to Mykonos, Greece. Your adventure begins with a welcome meeting at 4 pm. Insurance details and next of kin information will be collected at this meeting, so ensure you bring these details to provide to your leader. The first port of call is the local supermarket to buy supplies for your trip as a group (we call this a ‘starter park’). The starter pack will include provisions for breakfast, lunch and/or snacks for the whole trip. If you have any special dietary requirements, please make sure you notify us at the time of booking so we can accommodate your requests.

Before and after the meeting, perhaps head out to enjoy Mykonos and unwind on one of the island’s sandy beaches. Navigate the town's narrow streets, visiting the Church of Panagia Paraportiani or browse chic galleries, restaurants and boutiques. In the evening, possibly wander down to Little Venice to enjoy a cocktail by the water at sunset. The old town areas of Hora are perfect for a stroll or partake in the vibrant nightlife. The best beach choices are to the south, where water-sports are also on offer. Tonight, you’ll spend the night aboard the boat.

Notes: If you can't arrange a flight that will arrive in time, you may wish to arrive a day early so you're able to attend. We'll be happy to book additional accommodation for you (subject to availability).

***The beauty of sailing is that each day is unique and, while we have a destination to reach, if the weather changes or something takes the group’s fancy, we are flexible on the day's itinerary***

Sail to the Bay of Gaidharos for breakfast and a swim. Continue across the Aegean to Naxos where the boat will anchor for the next two nights. Possibly go on an optional day trip around the island or hike up to the Roman Catholic neighbourhood of Kastro, where winding laneways, mansions and churches retain a medieval feel. Stop by the cathedral in the square and visit the nearby Archaeological Museum. Soak up the sun and take part in optional water sports on the southern beaches of Naxos. Dependent on time, perhaps visit the unfinished temple of Portara and look out over the islands from its vantage point.

Maybe even join an optional jaunt out into the countryside - glimpse local rural life, visit one of the oldest temples in Greece and then chill out up in the hills with lunch at a family tavern. Get a taste of the local brew with a shot of Kitron, which is best described as lemon liquor. There are plenty of things to see and do over the next couple of days, but your crew will steer you in the right direction if you're a bit stuck.

Small Cyclades

It's time to feel the wind in your hair once again as you sail along the coast of Naxos. After around five hours drop anchor in the Small Cyclades. This group of islands feature great beaches and small fishing villages filled with friendly locals. While all of the islands harboured communities in ancient times, the middle ages saw this reduced to just pirates and goats. Today, only Koufonisia, Iraklia, Shinousa and Donousa have permanent residents with the largest population said to be somewhere around 300.
Featuring clear waters, great beaches, friendly locals and sleepy tavernas that are all built around quaint fishing villages, the islands are an ideal overnight anchorage and exploration. Indulge in fresh seafood in a quiet taverna and sit back to enjoy a taste of traditional Mediterranean life.


There's a brief three hour sail to reach the rugged, mountainous island of Amorgos. This island is packed with a history of colonisation, with influences of the Venetians, Byzantines and Ottomans. Katapola, the island's main port, boasts classic Cycladic architecture with windmills and an old Venetian castle. The waterfront is an excellent place to relax with its restaurants, cafes and bars. Perhaps drive up to the 11th-century monastery, Moni Hozoviotissis, where you can examine historical relics and indulge in breathtaking views of the Aegean Sea. You’ll also have the chance to visit the nearby Minoan settlement or visit the mountain village of Hora. The Amorgos Archaeological Collection is housed nearby in Gavros Tower, which is one of the few remaining towers on the island.


The isle of Ios is thought to be the burial place of epic Greek poet, Homer. Wander the old town or relax on the popular beaches of Gialos and Mylopotas. These sands offer water sports during the day and a hub for nightlife in the evening. If you’re after something quieter, head to the beaches of Valmas, Kolitsani or Tsamaria. Enjoy sunset views from the hilltop Panagia Gremiotissa (Church of the Virgin). The distinctive single palm tree next to the church makes it an instantly recognisable icon throughout town.


Sail through the remarkable caldera into Santorini, which is your final stop. In 1,500 BC, a volcanic eruption changed the landscape of the Mediterranean and caused the island of Santorini to sink in the middle - creating the caldera. Although you’ll sleep on board the boat tonight, you’re free to enjoy this majestic island however you like. A walk along the volcanic rim from Fira to Oia offers breathtaking views of the caldera and surrounding villages (the sunsets of Oia are world famous). Check out Santorini's volcanic beaches, such as Red Beach or the black beaches of Perissa, Vlychada, Perivolos and Agios Georgios.
Your adventure from Mykonos to Santorini comes to an end today. Depart the boat around 10 am or any time before. We recommend you consider booking an extra night's accommodation after this trip to see all the sights of Santorini.

Notes: Please note the itinerary above is subject to change and may vary depending on weather or berth availability. Your skipper will make the final call to ensure your safety at all times.
View trip notes to read full itinerary


4 breakfasts, 3 lunches
Overnight boat (7 nights)


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Important notes

The trip commences on day 1 in Mykonos at 4pm.

Trip notes

Want an in-depth insight into this trip? Your trip notes provide a detailed itinerary, visa info, how to get to your hotel, what’s included - pretty much everything you need to know about this adventure and more.

View trip notes


Our Sail Greece - Mykonos to Santorini trips score an average of 4.86 out of 5 based on 43 reviews in the last year.

Sail Greece - Mykonos to Santorini , September 2015

Sail Greece - Mykonos to Santorini , September 2015