Island Hopping in the Cyclades

Santorini, Smaller Cyclades Islands

Duration: 10 nights

Price: From $2,100 per person in low season based on two adults travelling together and including accommodation on a bed and breakfast basis, private transfers, ferry transportation and taxes

On this romantic escape in Greece, visit three of its most beautiful islands, from its biggest hitters to its best-kept secrets, experiencing some of its most beautiful views, villages and ports, and food and wine - all while staying in hotels we have handpicked for their sheer luxury, romance, style and exclusiveness, including stunning accommodation and clifftop infinity pools overlooking the Aegean.
Perfect forCouples and honeymooners looking for an unabashedly romantic holiday in Greece.
In the knowExtend your holiday in Greece with some more idyllic island hopping and visit beautiful Mykonos

Best for

  • Honeymoon
  • Landscapes & Scenery
  • Off the Beaten Track
  • Couples

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All itineraries on our website are designed as a starting point. Tell us your budget/wishlist/preferred length of stay and we'll help you select the best hotels and experiences, so your holiday is totally personalised.

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Itinerary details



Your honeymoon begins on the idyllic island of Santorini, where whitewashed houses tumble down to the sea and the legendary sunsets paint the sky at dusk. The award-winning Perivolas sits on a cliff above the Aegean, offering an intimate and stylish escape, yet it’s just a short walk from the pretty village of Oia, and down to the port of Ammoudi, where you can tuck into fresh seafood in a waterfront taverna. If you fancy a longer walk, enjoy the scenic trek from Oia to Fira, which has endless perfect photo opportunities.

Don’t miss the sunsets – best enjoyed with a cocktail in hand, or on a private cruise around the island, discovering hidden coves and fishing ports with houses carved into the walls of the caldera. Return for a swim in the floodlit infinity pool at the edge of the cliff, accompanied only by the sounds of church bells and fishing boats, followed by a chilled glass of wine in the candlelit bar.
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After drinking in the pleasures of Santorini, enjoy a scenic ferry ride to the neighbouring island of Folegandros. While it has become increasingly popular, it remains one of Greece’s most unspoilt and authentic islands, with a more wild, untamed beauty, where you can immerse yourself in the Greek way of life. Some parts are closed to traffic, meaning that you can explore its atmospheric medieval towns, its Venetian castle and its pretty coastlines in relative solitude, and find a secluded bay all to yourself – it’s no accident that Folegandros is known as the ‘island of peace’. On Karavostasi harbour, sample the fresh local bread and some matsata, a local pasta dish.

Your base for three nights, Anemi, showcases traditional Cycladic architecture in its striking white-cubed design, with signature Grecian interiors of white and blue. In the evenings, enjoy live music, or settle down to watch a classic movie at the open-air cinema.
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3 nightsSIFNOS

From Folegandros, it’s another ferry ride to the historic island of Sifnos, named by National Geographic as one of the world’s top ten ‘islands under the sun’. It’s also notable for its night-time stars: the Verina Astra hotel takes its name from the Greek word for stars (and each suite is named after a constellation) - this is a fantastic spot for some night-time stargazing from your villa as the sky is covered in a blanket of lights. In the morning, relax with some yoga under the olive trees.

Sifnos is characterised by its steep cliffs, mountainous terrain and deep bays. There are some lovely walking trails, and you should take some time to discover this little-known gem, including the castle you can see from the hotel, the mountaintop churches and the nearby village of Artemonas, with its classic mansions and villas with gardens of flowers. If you have a sweet tooth, pop into one of the bakeries for a treat, and learn how to make local specialities at a pastry making workshop, or dip into the craft shops, and if you’re feeling inspired, try your hand at pottery – an ancient tradition on Sifnos that’s many thousands of years old. Meanwhile, if the sparkling waters are still luring you, hire a private boat and skipper for a day at sea.
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