The Greek islands are among the most iconic of all summer holiday destinations. There are some 6,000 in total, all deliciously different, so the skill is in choosing the best for you. That’s where we come in. Rule One: don’t be tempted to visit more than two islands in one week or three in a fortnight - the moving around may well spoil the inherent pleasure of staying put and appreciating a different pace of life. With some 30 inhabited islands among 2,000 in total, the Cyclades Islands are worth serious consideration. Santorini, Mykonos, Sifnos, Naxos, Paros, Amorgos and Delos are islands with particularly evocative names, and all Cyclades holidays will feature villages of white houses and Byzantine churches set against an azure sky as standard.

Cyclades Islands holiday ideas

A few suggestions to get the holiday planning process started

  • One Country Greece – Santorini

    Santorini Minimoon - Romance on the Aegean

    Celebrate your other half with this dreamy four-day minimoon to Santorini, complete with sea views, slow mornings and just-us time

    4 days, from £2300 to £3700

  • One Country Greece – Cyclades Islands – Paros – Naxos

    Cyclades Islands Adventure - Exploring the Coast, Cuisine and Villages of Paros and Naxos

    Set sail for a nine-day Cyclades adventure from Paros to Naxos, discovering the islands’ coasts, culture and charm

    8 days, from £2550 to £4100

  • One Country Greece – Cyclades – Sifnos – Milos

    Secrets of the Cyclades - Island Hopping from Sifnos to Milos

    Dive into the idyllic landscapes of two postcard-perfect Greek islands on this 12-day Aegean adventure from Sifnos to Milos

    12 days, from £2700 to £4200

  • One Country Greece – Cyclades Islands – Tinos – Andros – Athens

    Secret Cyclades - Sun, Sea and Sailing in Tinos and Andros

    Discover the delights of two of the Cyclades' lesser-known islands, Tinos and Andros, on a nine-day Grecian escape

    9 days, from £2950 to £4100

  • One Country Greece – Cyclades – Kea – Kythnos – Syros

    Kea, Kythnos and Syros - The Secret Cyclades

    Discover a more authentic side to the famous Cyclades islands, exploring Kea, Kythnos and Syros over ten days

    10 days, from £3400 to £4600

  • One Country Greece – Athens – Naxos – Amorgos

    The Charm of Amorgos and Naxos - From the Ocean to the Land

    Savour a taste of the quiet life on this 11-day escape to the Cyclades, pairing Amorgos with Paxos after a brief sojourn in Athens

    11 days, from £3500 to £5050

  • One Country Greece – Serifos – Folegandros – Athens

    History & Hidden Gems - Athens and the Cyclades

    Explore iconic Athens alongside the serenity of the Cyclades on this eight-day adventure, pairing city buzz with secluded calm

    8 days, from £3650 to £5900

  • One Country Greece – Cyclades Islands – Mykonos – Paros – Santorini

    Mykonos, Paros and Santorini - Living the High Life in the Cyclades

    Soak up the Grecian sun on this ten-day escape in the Cyclades, hopping between three of the region’s most idyllic islands

    10 days, from £3800 to £6250

  • One Country Greece – Cyclades – Sifnos – Santorini

    Cycladic Luxury in Sifnos and Santorini - A Romantic Grecian Getaway

    Nestle into the amorous ambience of the Cyclades on this nine-day retreat in secluded Sifnos and stunning Santorini

    9 days, from £4750 to £6950

Greece testimonials

10 reviews
4.9 / 5
"Aggie and Ana were very helpful and efficient. The accommodation in Aristi was fantastic, and we loved visiting Zagori and seeing the Meteora monasteries. Please thank Aggie for organising a wonderful holiday and Ana for the follow up information."
A - UK
Published on 29th September 2025
"Our Concierge was very responsive and anticipated well. Excellent booking and recommendation of restaurants. "
Fiona - Bath
Published on 28th October 2024
"From start to finish the care and attention from the Original Travel team was excellent. Kate was brilliant - she really cared about making sure she tailored everything to give us the best possible experience. I usually research, book and organise all our trips myself but this trip has completely converted me to the Original Travel way! Thank you so much for a brilliant, much needed break!"
Lindsay - London
Published on 7th October 2024

What can you find during a Cyclades Islands holiday that you won't find anywhere else?

Cyclades Islands holidays offer the dreamiest version of a Greek break – think whitewashed houses perched on a mountainside that’s speckled with blue domes and windmills that look like they’re about to slide into the azure Aegean Sea below. Imagine petite fishing villages that kiss the ocean, narrow donkey tracks that wind through the breathtaking verdant landscape and heavenly beaches complete with smugglers coves and crystal clear rockpools. Cyclades Islands holidays are anything but under the radar, and places like Mykonos and Santorini attract legions of visitors, and rightly so. But there are many quieter moments to be found amongst lesser-visited islands. The beauty of a holiday in this part of the world is the ability to enjoy it all – hop from bustling clubbing hotspots to deserted beach coves in the space of a few hours and create a Greek getaway that speaks to every part of you.


What is there to do during a Cyclades Islands holiday?

Some of the world’s best beaches nestle on the sun-drenched shores of the Aegean Sea and Cyclades Islands holidays are dominated by the region’s glorious coast. Glamorous promenades studded with restaurants, sparkling stretches of wild shoreline or hidden white sandy coves all await your exploration (or your utter relaxation, depending on your taste). Beaches also mean watersports, and there’s plenty to get your pulse racing if you’re after an active trip, with kayaking, canoeing, sailing, paddle boarding and windsurfing being some of the most popular activities. Back on dry land, things are just as exhilarating, and the mountainous terrain lends itself perfectly to hiking and biking. Eating the catch of the day in local tavernas, stumbling across historic relics and soaking in the easy Greek culture are also all part of the deal here.


Need to know about the Cyclades Islands

The islands of Santorini, Mykonos, Delos, Milos and Paros are undoubtedly the stars of the Cyclades Islands show, all of which draw the majority of crowds from far and wide. But for those in the know, there’s an authentic magic to be found in the islands that have lived the same pace of life for the last 100 years, protected from hordes of visitors. Two such islands – Serifos and Folegandros – offer the perfect ingredients for a Greek holiday like no other. Tiptoe around 13th century church ruins, hike to empty beaches only accessible by foot and eat traditional honey pie in quaint cafes only frequented by locals.