Our Cyclades holidays & tours
Our Cyclades holidays offer a feast for the senses, as they roam one of the most beautiful and varied island groups in Greece. Walking and cycling tours create plenty of opportunities to taste regional cuisine from family-run tavernas, soak your feet in warm sea, and enjoy fragrant groves of citrus fruit, pomegranates and olives. If you join one of our escorted small group trips then low-impact slow travel like this is a fantastic way to get to know our local guides and about the culture of the communities they hail from. We help you to explore beautiful islands like Santorini, Mykonos, Paros and Naxos, escaping the most crowded areas for quieter corners, and spreading the economic benefits of tourism far and wide.
Our top Cyclades holidays
Naxos and the small Cyclades walking holiday, Greece
From
£744 to £1097
10 days
ex flights
Walk and discover Naxos and the unspoilt Small Cyclades
Small group2026: 4 Apr, 11 Apr, 18 Apr, 25 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Island hopping cruise in Greece
From
£2584
8 days
ex flights
Classic small ship cruise to Greek Islands & Ephesus
Small group2026: 15 May, 22 May, 29 May, 5 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 4 Sep
Cyclades sailing & walking holiday in Greece
From
£788 to £1045
7 days
ex flights
Combine a sailing & hiking adventure around the Cyclades
Small group2026: 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 13 Jun, 20 Jun, 27 Jun, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Cyclades walking holidays in Greece
From
£1279 to £1899
8 days
ex flights
A gently active holiday in the Cyclades
Small group2026: 22 Mar, 12 Apr, 4 May, 17 May, 24 May, 27 Sep, 11 Oct, 25 Oct, 2027: 21 Mar, 28 Mar, 11 Apr, 18 Apr, 3 May, 16 May, 23 May, 26 Sep, 10 Oct, 24 Oct
Cyclades walking holiday, Greece
From
£744 to £1097
7 days
ex flights
Walk ancient paths and enjoy stunning Cycladic sceneries
Small group2026: 4 Apr, 18 Apr, 2 May, 16 May, 12 Sep, 26 Sep, 10 Oct, 24 Oct
Cyclades walking & island hopping holiday, Greece
From
£987 to £1538
14 days
ex flights
Walk and explore nature of Naxos, Small Cyclades & Santorini
Small group2026: 4 Apr, 11 Apr, 18 Apr, 25 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Sailing holiday in Greece, Mykonos to Santorini
From
£1336 to £1516
8 days
ex flights
The boat, the beach and inviting Greek villages
Small group2026: 5 May, 9 May, 19 May, 23 May, 2 Jun, 6 Jun, 16 Jun, 20 Jun, 30 Jun, 4 Jul, 14 Jul, 18 Jul, 28 Jul, 1 Aug, 11 Aug, 15 Aug, 25 Aug, 29 Aug, 8 Sep, 22 Sep, 6 Oct, 2027: 4 May, 8 May, 18 May, 22 May, 1 Jun, 5 Jun, 15 Jun, 19 Jun, 29 Jun, 3 Jul, 13 Jul, 17 Jul, 27 Jul, 31 Jul, 10 Aug, 14 Aug, 24 Aug, 28 Aug, 7 Sep, 11 Sep, 21 Sep, 25 Sep, 5 Oct
Greek Islands sailing holiday, Santorini to Mykonos
From
£1306 to £1556
8 days
ex flights
Sapphire waters, whitewashed villages & history laden ruins
Small group2026: 2 May, 12 May, 16 May, 26 May, 30 May, 9 Jun, 13 Jun, 23 Jun, 27 Jun, 7 Jul, 11 Jul, 21 Jul, 4 Aug, 8 Aug, 18 Aug, 22 Aug, 1 Sep, 5 Sep, 15 Sep, 19 Sep, 29 Sep, 3 Oct, 2027: 1 May, 11 May, 15 May, 25 May, 29 May, 8 Jun, 12 Jun, 22 Jun, 26 Jun, 6 Jul, 10 Jul, 24 Jul, 3 Aug, 7 Aug, 17 Aug, 21 Aug, 31 Aug, 4 Sep, 14 Sep, 28 Sep, 2 Oct
Greek Islands Cycling tour, Cyclades
From
€1120
8 days
ex flights
Explore Cyclades, the unique Greek islands in the Aegean sea
Tailor made
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Cyclades map & highlights
You feel like you’ve fallen into the lap of the gods in the Cyclades. The highest mountain of the chain is Zas, on Naxos, and is named after the daddy of the gods, Zeus, who is said to have grown up here. Amorgos was home to Aphrodite’s temple and Thera, or Santorini, was created as a hiding place for the love child of a sea nymph, out of harm’s from the nymph’s father, the sea god Triton. And Delos, the Cycladic centrepiece, was said to be the birthplace of Apollo and Artemis. The former is said to be god of many things, including music, healing, sun, light and poetry. All of which you will find in the Cyclades.
Amorgos
1. Amorgos
Famous as the location for the iconic Luc Besson film, The Big Blue (if it was before your day, it’s a must see), you can’t fail to fall in love with Amorgos. The easternmost of the Cyclades, this is another mountainous walking heaven, with ancient paths up to the likes of St. Theologos church. Aegiali Bay is the place to swim and sup, and the main village of Chora is a traditional treat.
Lesser Cyclades
2. Lesser Cyclades
The four pretty gems in the bracelet that you can only see with a magnifying glass. Aka the Lesser Cyclades, less is definitely more for some people as they anchor up at Iraklia, Schinousa, Koufonisia or Donousa. There are others, but these are the only inhabited ones. Go hiking on Iraklia to see the Cyclades’ largest cave, or dine at the taverna of the only resident family’s on Koufonisia, overlooking the Bay of Nero.
Naxos
3. Naxos
The largest island and often the start of sailing odysseys around the chain, it is Grand Central Station for ferries in peak season. It is also home to the Cyclades’ highest peak, Zas (1,004m), which you can hike up to from the fishing village of Filoti. A green and fertile island, there are plenty of hiking trails through hills covered in wild herbs, ancient villages or up to other peaks such as Fanari.
Paros
4. Paros
Some islands attract snorkellers, but this one is a hive for hikers, with a network of Byzantine footpaths or ‘strátes’ connecting beautiful traditional villages. The main one is Parikia, the island capital, with 13th century whitewashed houses, a Venetian castle and a stunning 6th century church. One of the most popular routes is Lefkes to Prodromos, taking in the coastal beauties of Marpissa and Pisso Livadhi.
Santorini (aka Thera)
5. Santorini (aka Thera)
Santorini is a stunner, where people come to walk and wallow in natural beauty for several days. You are spoiled for choice when it comes to sumptuous corners, as this is actually a small volcanic archipelago in its own right, enclosing a ridiculously blue, submerged caldera. Trek to the main caldera, or to the highest point Mt Profitis Ilias (567m). Or visit Venetian settlements and ancient castles en route.
Western Cyclades
6. Western Cyclades
Less visited than many others, they are Serifos, Sifnos and Milos, Kythnos. Hike and hop these islands to experience something special on each one. Milos is volcanic and fascinating geologically, although with more than 40 beaches, there is plenty of time out of school. Sifnos has 100km of walking trails through its protected Natura 2000 landscapes, and Serifos has archaeological beauties alongside natural ones.
Our Cyclades holidays reviews
4.6
127Cyclades holidays reviews
Susan Sargeant03 Nov 2025
An excellent way of exploring three of the most iconic Cyclades islands.. fabulous locations and culture plus great Greek hospitality.read more
Carol Baines28 Oct 2025
Really enjoyed the trip. Our guide, Daphne, was super - well organised, kind, great at reading the group, knowledgeable and fun too.read more
Margaret Lamb25 Oct 2025
An excellent holiday, every bit as good as the website suggested. Brilliant organisation by Annie and outstanding guide in Yannis. He really adapted to suit our groups needs and ensure we all had a good time. read more
Laurie Dunn18 Oct 2025
Fantastic - by far the highlight of our trip to Greece.read more
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