Amazing Day Trips to Take Around the Cyclades by Boat

Milos is just one of the many stunning destinations to explore on a day trip around the Cyclades
Milos is just one of the many stunning destinations to explore on a day trip around the Cyclades | ©  Vasilis Tsikkinis photos / Getty Images
Photo of Judy Cogan
24 November 2021

Strewn across the Aegean Sea in southern Greece, the Cyclades comprise 39 islands, which include some of the country’s most popular spots – with Mykonos and Santorini being two – as well as lesser-known gems such as Serifos and Kythnos. This archipelago makes for a seriously idyllic spot to set sail, with whitewashed villages and azure bays to dip into as you go. Here we reveal some of the must-sail highlights from this enchanting string of islands.

To navigate the Cyclades at your own pace there are hundreds of boat charter options via SamBoat.

Rhenia Island

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Sailboat moored at jetty of Greek island. Whitewashed houses waterfront. Summer sunshine, vacations, adventures. Mykonos, Delos and Rhenia, Greece.
© Natallia Pershaj / Alamy Stock Photo
Yachts regularly leave from Mykonos Old Port to make the 45-minute crossing to the beautiful, uninhabited island of Rhenia. Spend a peaceful morning relaxing on a deserted beach or diving off the boat into the clear sun-dappled waters of a sandy cove. Swing by Delos island, a Unesco World Heritage site next door with ancient Greek ruins. It’s steeped in mythology and history and thought to be the birthplace of Greek gods Apollo and Artemis.


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Overlooking the old town of Naoussa, Paros, Greece
© Joana Kruse / Alamy Stock Photo
The island of Paros is fringed by beautiful beaches such as Kolymbithres, with its distinctive granite rock formations, and the local favourite in the quaint fishing village of Ambelas – a sandy spot to taste fresh seafood cooked in the cute seafront tavernas. For a lively end to a day’s sailing, try Santa Maria Beach. It draws a young crowd for its watersports and the fun-loving Santa Maria Beach Bar, where one of the most popular sunset libations is the Pink Flamingo – a refreshing blend of rosemary-infused vodka, fresh strawberries, vanilla syrup, lime and basil.


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Santorini, Greece. The picturesque Oia village at sunrise.
© Sorin Colac / Alamy Stock Photo
A volcanic explosion engulfed Santorini some 3,500 years ago, leaving black-sand beaches, steep lava-sculpted cliffs in psychedelic hues and a scattering of smaller islands in its wake. Make the trip from Santorini to two of the neighbouring lava islands: first Nea Kameni, with its dramatic dark landscape, and then on to Palea Kameni, where you can feel the rejuvenating effects of natural hot springs. Most cruises sail below the beautiful village of Oia, giving you a view of its white houses trickling down towards the ocean.


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Traditional windmill looming over the town of Mykonos at sunset
© agefotostock / Alamy Stock Photo
Sail on a catamaran around Mykonos and soak up its stunning coastline, peppered with secluded beaches and dramatic cliff features. For dinner, hop ashore and venture to the whitewashed Roca Cookery Restaurant in the Old Port. Expect uninterrupted ocean and island views, along with an appetising menu making use of local ingredients with Italian and Greek influences. The Mykonian spaghetti with tomato, cured meats and local cheese is a must-try, as are the moreish loukoumades (bite-size fluffy sweet honey balls).


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Traditional fishermen houses with the impressive boat shelters, also known as ?syrmata? in Klima of Milos, Greece
© Constantinos Iliopoulos / Alamy Stock Photo
The luminous Greek island of Milos has some of the region’s best beaches, with more than 70 white sand spots to explore. Other highlights include the charming fishing villages of Mandrakia and Klima. It’s on this largely undiscovered treasure of an island that the Venus de Milo – an ancient Greek sculpture – was found in pieces and transported to the Louvre in Paris. Sail around the white cliffs at Sarakiniko and dip into the bottle-green swimming hole at Papafragas. If you choose to stay more than one night, take a break from the water and check into the whitewashed boutique hotel Salt, with its sunbeds shaped like billowing sails and a wooden terrace.


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Street with colorful buildings in town center of Ermoupoli, Syros, Greece.
© NAPA / Alamy Stock Photo
One of the most popular day sailing trips is to venture from the west coast of Mykonos to the island of Syros, which has a long tradition of shipbuilding. The journey can take from 30 minutes to an hour and a half depending on the vessel. Italian influences run throughout the island, with whitewashed houses swapped out for colourful buildings, marble piazzas and even a miniature replica of La Scala theatre. The best beaches are in the north – namely Delfini, Varvarousa and Aetos, and seaside tavernas are in abundance.


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authentic Greece - Serifos island, Chora village and windmills.
© freeartist / Alamy Stock Photo
On Serifos, you’ll find high-end second homers who have invested in the island for its blissful solitude and unspoiled landscape. There’s also a fast and free nudist collective who skinny dip in secret coves. For your circumnavigation of the island, mark the rugged Kalo Ambeli beach and pristine Vagia beach on the south coast on your itinerary. From here, sail up to the peaceful climbs of Skala beach on the north coast, next to Sykamia beach and 10km (6mi) from the village of Chora.


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An ocean bay of Kynthos
© Konstantinos_K / Getty Images
If you’re looking for some real escapism, head to Kythnos. This little-known Greek island has barely changed for centuries, and has scarcely been touched by tourism. You’ll see donkeys carrying loads up hills blooming with wildflowers, and locals pottering around chalk-white villages chit-chatting in Greek. It’s a walkers paradise with more than 60 beaches – only reachable by foot or by boat – thermal springs, tiny white chapels and one of Greece’s largest caves. In terms of cuisine, must-tries include the local thyme honey sfouggato (deep-fried balls fashioned out of eggs and garden vegetables) and the traditional cheese pies.

Explore some of the amazing coastal spots around the Cyclades by choosing from hundreds of charter options via SamBoat.

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