Our Cyclades vacations & tours
Our Cyclades vacations 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 trips
Naxos and the small Cyclades walking vacation, Greece
From
£744 to £1097
10 days
ex flights
Walk and discover Naxos and the unspoilt Small Cyclades
Small group2027: 3 Apr, 10 Apr, 17 Apr, 24 Apr, 1 May, 8 May, 15 May, 22 May, 29 May, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct
Island hopping cruise in Greece
From
US $3750
8 days
ex flights
Hidden Greece: Unexplored Greek Islands Cruise
Small group2027: 7 May, 21 May, 28 May, 18 Jun, 25 Jun, 9 Jul, 16 Jul, 23 Jul, 6 Aug, 13 Aug, 20 Aug, 3 Sep, 17 Sep, 24 Sep
Cyclades walking vacations in Greece
From
US $2905
8 days
ex flights
A gently active vacation in the Cyclades
Small group2027: 28 Mar, 11 Apr, 3 May, 16 May, 26 Sep, 10 Oct, 24 Oct
Cyclades walking & island hopping vacation, Greece
From
£987 to £1538
14 days
ex flights
Walk and explore nature of Naxos, Small Cyclades & Santorini
Small group2027: 3 Apr, 10 Apr, 17 Apr, 24 Apr, 1 May, 8 May, 15 May, 22 May, 29 May, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
Hiking vacation in the West Cyclades, Greece
From
£744 to £1098
10 days
ex flights
Walk & explore the authentic Serifos, Sifnos & Milos islands
Small group2027: 3 Apr, 10 Apr, 17 Apr, 24 Apr, 1 May, 15 May, 22 May, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
Santorini walking vacation, Greece
From
£352 to £447
4 days
ex flights
Walk and discover all Santorini has to offer in 4 days
Tailor made
Greece guided walking vacations, Tinos and Andros
From
£2699
15 days
inc UK flights
Walkers’ paradise in the northern Cyclades
Small group2027: 13 May, 17 Sep
Greek Islands sailing vacation, Santorini to Mykonos
From
US $2112 to US $2272
8 days
ex flights
Sapphire waters, whitewashed villages & history laden ruins
Small group2027: 1 May, 11 May, 15 May, 25 May, 29 May, 8 Jun, 12 Jun, 22 Jun, 26 Jun, 6 Jul, 10 Jul, 20 Jul, 24 Jul, 3 Aug, 17 Aug, 21 Aug, 31 Aug, 4 Sep, 14 Sep, 18 Sep, 28 Sep, 2 Oct, 2028: 29 Apr, 9 May, 13 May, 23 May, 27 May, 6 Jun, 10 Jun, 20 Jun, 24 Jun, 4 Jul, 8 Jul, 18 Jul, 22 Jul, 1 Aug, 5 Aug, 15 Aug, 19 Aug, 29 Aug, 2 Sep, 12 Sep, 16 Sep, 26 Sep
Naxos & the Small Cyclades vacation in Greece
From
£674 to £858
10 days
ex flights
Walk & island hop Naxos, Iraklia & Amorgos, Small Cyclades
Tailor made
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
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 centerpiece, 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.
Latest reviews
4.6
137Cyclades vacations reviews
Katherine Gettys31 Oct 2026
This vacation is a unique itinerary and special. Just book!read more
Laura Harris26 Oct 2026
I had a fantastic time; we must have walked over 100km over the week, but took in some amazing views, learnt a lot about the flower/fauna and Greek culture with our wonderful guide Annie and had gorgeous beach swims.read more
Adrienne Fullerton20 Oct 2026
Wonderful! Looking forward to another trip with them. All the walks were through wonderful landscapes with stunning views.read more
Michele Sami22 Sep 2026
A 10! Annie our guide was Amazing! Accommodations were great!read more
.jpg){kind=link}
