What we rate and what we don't
21 Cyclades holidays found
Sailing holiday in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From £995£932 to £1,121 8 days ex flights
Small group travel:
2019: 29 Jun, 24 Aug
2020: 16 May, 30 May, 13 Jun, 27 Jun, 11 Jul, 25 Jul, 8 Aug, 22 Aug, 5 Sep, 19 Sep, 3 Oct
2020: 16 May, 30 May, 13 Jun, 27 Jun, 11 Jul, 25 Jul, 8 Aug, 22 Aug, 5 Sep, 19 Sep, 3 Oct
Up to £60 off selected dates.
Late availability on these dates: 29 Jun, 24 Aug
Late availability on these dates: 29 Jun, 24 Aug
Greek Islands sailing holiday, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From £1,010£945 to £1,171 8 days ex flights
Small group travel:
2019: 6 Jul, 20 Jul, 3 Aug, 17 Aug, 28 Sep
2020: 9 May, 23 May, 6 Jun, 20 Jun, 4 Jul, 18 Jul, 1 Aug, 15 Aug, 29 Aug, 12 Sep
2020: 9 May, 23 May, 6 Jun, 20 Jun, 4 Jul, 18 Jul, 1 Aug, 15 Aug, 29 Aug, 12 Sep
Up to £70 off selected dates.
Late availability on these dates: 06 Jul, 20 Jul, 03 Aug, 17 Aug, 28 Sep
Late availability on these dates: 06 Jul, 20 Jul, 03 Aug, 17 Aug, 28 Sep
Cyclades walking holidays in Greece
A gently active holiday in the Cyclades
From £1,279 to £1,499 8 days inc UK flights
Small group travel:
2019: 8 Sep, 22 Sep, 13 Oct, 27 Oct
2020: 29 Mar, 5 Apr, 26 Apr, 10 May, 17 May, 24 May, 7 Jun, 21 Jun, 6 Sep, 20 Sep, 4 Oct, 11 Oct, 18 Oct, 25 Oct, 1 Nov
2020: 29 Mar, 5 Apr, 26 Apr, 10 May, 17 May, 24 May, 7 Jun, 21 Jun, 6 Sep, 20 Sep, 4 Oct, 11 Oct, 18 Oct, 25 Oct, 1 Nov
Late availability on these dates: 08 Sep, 22 Sep
Cyclades sailing & walking holiday in Greece
Combine a sailing & hiking adventure around the Cyclades
From £685 to £759 7 days ex flights
Small group travel:
2019: 21 Sep, 28 Sep, 5 Oct, 12 Oct
Travel Team
If you would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.
Family sailing holiday in the Cyclades, Greece
Enjoy the beauty of the Greek islands
From £1,150 to £1,299£1,169 8 days inc UK flights
Small group travel:
2019: 11 Aug
2020: 26 Jul, 2 Aug, 9 Aug, 16 Aug
2020: 26 Jul, 2 Aug, 9 Aug, 16 Aug
Late availability on these dates: 11 Aug
Cyclades walking & island hopping holiday, Greece
Walk and explore nature of Naxos, Small Cyclades & Santorini
From £846 to £1,280 14 days ex flights
Small group travel
Cyclades walking holiday, Greece
Walk ancient paths and enjoy stunning Cycladic sceneries
From £592 to £640 7 days ex flights
Small group travel
Naxos and Amorgos hiking holiday, Cyclades Greece
Naxos-Amorgos. Amazing memorable walking adventure holiday!
From €1,276 to €1,442 10 days ex flights
Small group travel:
2019: 4 Jul, 27 Aug, 22 Sep
Kythnos walking holiday, Greece
Activity holidays to the West Cyclades. Exploring Kythnos!
From €526 5 days ex flights
Tailor made:
Available between March – November
Sailing and cycling Cyclades holiday, Greece
Self guided or guided (upon request) tour in the Cyclades
From €1,500 8 days ex flights
Small group travel:
2019: 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
The Cyclades cycling holiday, Greece
Cycling & island hopping; Paros, Antiparos and Naxos
From €521 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Santorini walking short break, Greece
Walk and discover all Santorini has to offer in 4 days
From €410 to €520 4 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Kythnos nature walking holiday in Greece
Explore Kythnos's flora and fauna with a Greek naturalist
From €350 6 days ex flights
Small group travel
Greek Island hopping cruise in the Aegean
Cruise the Greek Islands on board a classic sail cruiser
From £1,715 to £1,935 8 days ex flights
Small group travel:
2019: 19 Jul, 26 Jul, 2 Aug, 23 Aug, 30 Aug, 13 Sep, 18 Oct
2020: 17 Apr, 24 Apr, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun
2020: 17 Apr, 24 Apr, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun
Walking holiday in the West Cyclades, Greece
Walk & explore the authentic Serifos, Sifnos & Milos islands
From £592 to £914 10 days ex flights
Small group travel:
2019: 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Cyclades Islands sailing holiday, Greece
Swim in turquoise seas & explore ancient towns
From £1,280£1,183 to £1,435£1,315 10 days ex flights
Small group travel:
2019: 10 Jul, 20 Jul, 30 Jul, 9 Aug, 19 Aug, 18 Sep, 28 Sep
2020: 9 May, 19 May, 29 May, 8 Jun, 18 Jun, 28 Jun, 8 Jul, 18 Jul, 28 Jul, 7 Aug, 17 Aug, 27 Aug, 6 Sep, 16 Sep, 26 Sep
2020: 9 May, 19 May, 29 May, 8 Jun, 18 Jun, 28 Jun, 8 Jul, 18 Jul, 28 Jul, 7 Aug, 17 Aug, 27 Aug, 6 Sep, 16 Sep, 26 Sep
Up to £120 off selected dates.
Late availability on these dates: 10 Jul, 20 Jul, 30 Jul, 09 Aug, 19 Aug, 18 Sep, 28 Sep
Late availability on these dates: 10 Jul, 20 Jul, 30 Jul, 09 Aug, 19 Aug, 18 Sep, 28 Sep
Cyclades sailing honeymoon, Greece
Enjoy a romantic honeymoon sailing in the Cyclades islands
From £3,440 to £5,209 7 days ex flights
Tailor made
Greek Islands cycling and sailing holiday
Cycle and sail around the Cyclades Greek Islands
From £1,390 8 days ex flights
Small group travel
Sailing & conservation holiday in Greece
A unique wildlife & sailing adventure
From £683 to £759 7 days ex flights
Small group travel:
2019: 29 Jun
Travel Team
If you would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.
Naxos and the small Cyclades walking holiday, Greece
Walk and discover Naxos and the unspoilt Small Cyclades
From £592 to £914 10 days ex flights
Small group travel:
2019: 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Santorini villa holiday in a converted Windmill, Greece
Unique private Windmill Villa's with pool in Santorini
From €200 to €800 per house per night
Accommodation
From
£945
excluding flights
Memorable parts?
Weather conditions were ideal for most days of our week of sailing, from fair to rough, but always safe and secure in the hands of our master mariner, Antonio
Tips?
Be prepared for slight changes in your sailing itinerary - the wind blows where it wants to. You'll pack too many clothes - think sun - casual - a woolly for the wind. With time on your hands on board think of what you might do - read, write, converse. You're part of a crew/team not just an individual... (more)Bill McKenzie
From
£1,279
including UK flights
The area is very beautiful and fascinating to explore. The whole thing was the best bit! I would go again.
(more)Sarah Day
We thoroughly enjoyed all aspects and thought everything well thought out and organised. Loved the ferry journeys. So nice it was all taken care of. 10 out if 10. Wished we could experience it all again. Onwards and upwards maybe try out some more walking hols! (more)Annette Scott
The highlight was the walks in the countryside surrounded by spring flowers and wild herbs. The three islands were very different, but each were magical in their own way. It was a very good group with a very enthusiastic leader and it gave me a taste of what the Greek islands can offer. (more)Rosemary Chinchen
From
£846
excluding flights
We loved seeing the fields of wildflowers and walking through light rain, swollen streams and windy mountain sides. (more)Nancy Schmidt
The visit to Kastro was very enjoyable. The walk it was good, the town was beautiful at dusk and our dinner was very enjoyable with live local musicians. (more)Leanne Nicholson
The hikes were thoughtfully selected as they were scenic, exposed us to local culture/lifestyle and mileage covered was sufficiently challenging. Excellent trip. (more)Sze Mei Lim
From
£592
excluding flights
Great walking, great food, great guide (Annie) and great hotel in Sifnos (more)Joanne burke
The most memorable parts were the wonderful people, mountains, flowers, and beautiful bodies of water in Greece. (more)Jennifer Pappa
Hard to pick one the most memorable moment, maybe climbing up to monastery on highest point on Sifnos. Fantastic views from the B&B whatever the time of day. Both islands were really interesting. (more)Cherry Shelton
From
£685
excluding flights
Excellent. Annie and Sotiris were excellent hosts and ensured that the trip ran smoothly. On the one day that the wind was too strong for sailing, we had a
busy sightseeing day instead. (more)Lyndsay Gough
The first 2 days of the trip were glorious! Beautiful less visited islands & fishing villages. Our walking guide Yannis & Captain Soteris made sure we visited
areas & restaurants off the beaten path, making for an authentic experience. (more)Jennifer Simon
Fantastic! Very memorable. Something I'd want to repeat. (more)Jane Cousins
From
£932
excluding flights
From
€521
excluding flights
From
£1,183
excluding flights
Memorable parts?
Sailing and learn a bit on how to do it
Tips?
Try to build a nice team spirit with your co-travellers
Local benefits?
We tried to do so
Overall rating?
I would give it an 8 or 9 over 10 (I am very demanding) ;) (more)Ana Granadero
From
£592
excluding flights
Excellent (more)rena alekperova
Excellent and well organised and choosing walks bearing in mind everyone's walking ability (more)Victoria Taylor
Superb....Everything was exciting: the weather, scenery, local food and drinks were marvellous (well, I don't think there's an appropriate adjective to describe the kind of emotions the environment provokes). (more)Alexander Kartashov
From
£592
excluding flights
The most memorable part was sharing the delicious meals with new friends after a days walking... It was wonderful thanks to Anna's local knowledge of geology, places to stay & eat. (more)Rosie Champness
The holiday was excellent It was wonderful to spend our days exploring the varied landscape, villages and beaches of the small lesser known islands of Milos
and Sifnos. (more)Lorne beiles
The highlight was reaching some amazing views by walking and then having a delicious dinner at a small Taverna serving local specialities. This was a lovely holiday and our guide Annie was very well organised and friendly whilst being flexible and relaxed which made the trip very enjoyable. (more)Anne-Marie Mayer
From
£683
excluding flights
The whole experience was wonderful. Sotiris, our skipper was fantastic , very professional, kind and fun. This holiday was wonderful...it could not have been better...we should have stayed longer. It really was a very unique experience, very special to me. (more)Joanne David
Excellent! Every aspect was amazing. My partner and I are both deeply grateful to everyone who works for the operator for making such a special and memorable experience. We will almost certainly be booking up again! (more)Alison Crawford
A fabulous holiday. Sotiri and Melita were delightful and knowledgeable hosts. Annie who did the reservations was efficient and friendly. The boat was well equipped, safe and comfortable and the fellow guests good company. (more)Susan Sargeant
From
£1,390
excluding flights
From
£1,715
excluding flights
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