Cyclades Island Hopping - Greek Style

Great For: Foodie Escapes, Hidden Gems, Luxury Adventure, Special Offers Breaks

A sun-drenched journey through Greece’s most iconic islands

from £1260pp

your escape

Sail between handpicked Cycladic islands on a journey that blends beach time, boutique charm, and local culture. Begin in Paros for laidback luxury and golden beaches, hop to Naxos for authentic village life, and end in Santorini with cliffside dinners and endless views. We’ll handle the transfers, timings, and hidden gems - so you can just follow the sun.

included highlights

7 nights split across 3 curated island stays Premium ferry transfers and private ground transport Cliffside suite in Santorini with caldera views Sunset sailing experience with onboard mezze Local dining recs and Loupr concierge support throughout

why this trip works

It’s the best of the Greek islands - without the stress of planning or overcrowded hot spots. You’ll get iconic sunsets, quiet moments, and a mix of slow and social energy. For couples who want to explore at their own pace, with taste guiding the way.

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Loupr is a trading name of The JLT Group, which is ATOL protected (12564). Some of the flights and flight-inclusive holidays on this website are financially protected by the ATOL scheme. But ATOL protection does not apply to all holiday and travel services listed. Please ask us to confirm what protection may apply to your booking. If you do not receive an ATOL Certificate, then the booking will not be ATOL protected. If you do receive an ATOL Certificate but all the parts of your trip are not listed on it, those parts will not be ATOL protected. Please see our booking conditions for information or for more information about financial protection and the ATOL Certificate, go to .