Sail the Greek Islands between Santorini and Mykonos

Dreaming of crystal-clear sapphire waters, whitewashed villages, history laden ruins, lively Greek culture and delectable cuisine straight off the land or from the sea? Then sailing from Greece's Santorini to Mykonos may just be what the doctor ordered. Spend eight blissed-out days under sun drenched skies enjoying the best the Greek Islands of Santorini, Ios, Amorgos, Small Cyclades, Naxos and Mykonos have to offer.

Santorini, Greece
Mykonos, Greece
Physical rating
Cultural rating
Min 15
Group size
Min 1 Max 9
Carbon offset
58kg pp per trip


  • Enjoy stunning coastal views in Santorini
  • Swim in the warm turquoise waters off the island of Amorgos
  • Eat fresh seafood off the boat at a taverna in Small Cyclades
  • Wander the olive groves of Naxos
  • Explore the Church of Panagia Paraportiani in Mykonos


Kalimera. Welcome to Santorini, Greece. Your adventure begins with a welcome meeting at 1.30 pm. Meet your skipper at the self-service beachfront restaurant, which is right in front of Akrotiri Hotel that's located at Akrotiri Beach. 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 skipper will then give you a detailed trip briefing aboard the yacht. Get acquainted with your new shipmates, as you sail for four hours to the island of Ios. In the evening, enjoy your first dinner with the group and spend your first night on the boat, strengthening your sea legs for the week ahead.

It’s worth arriving into Santorini a few days before the trip begins to enjoy some time on the island. If you do arrive early, visit the volcanic red and black beaches, explore the cobbled alleys, restaurants and shops of exuberant Fira or walk along the island’s volcanic rim to Oia at sunset.

Notes: The marina in Santorini is currently closed for dredging. Until further notice you will be met at the existing meeting point and transferred to the yacht by vehicle or water taxi. 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***

Inhabited since early Cycladic times the Ionians settled Ios around 1050 BC, suffering similar periods of occupation and foreign rule as many of its neighbours. The isle of Ios is also 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.


Sailing for around four hours, reach the rugged, mountainous island of Amorgos - known as the stunning location of Luc Bresson's film, 'The Big Blue'. 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.

Small Cyclades

It's time to feel the wind in your hair once again, as you sail along for around three hours to 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.


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 need any recommendations.
Lifting anchor, set off on a short three hour sail to Mykonos where you'll spend your final evening. This classic Mediterranean island is packed with excitement, beauty and glamour. White-washed architecture clings to the labyrinth of narrow streets and laneways in the town's old area. The hum of the nightlife, chic cafes, restaurants, galleries and boutiques give way to the island's wonderful sandy beaches.

Check out the Church of Panagia Paraportiani - its unique array of lines and angles are simply fascinating. Soak in the atmosphere by joining fellow sun-seekers and party-goers on the beach or take a day trip to the sacred island of Delos, birthplace of Apollo and Artemis. Little Venice has colourful wooden balconies that hang precariously over the sea - the perfect spot to sit back with a cocktail and enjoy a magical Aegean sunset.

Depart the boat on the final day at 10 am, as there are no more activities planned. We recommend booking an extra night's accommodation after this trip, so you have plenty of time to explore Mykonos.

Notes: This itinerary is subject to change depending on weather and 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

This trip starts on Day 1 in Santorini at 1.30pm.

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 - Santorini to Mykonos trips score an average of 4.81 out of 5 based on 32 reviews in the last year.

Sail Greece - Santorini to Mykonos , July 2015

Sail Greece - Santorini to Mykonos , August 2015