21 Cyclades holidays found
Sailing holiday in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From £1,069 to £1,184 8 days ex flights
Small group travel:
2019: 18 May, 1 Jun, 29 Jun, 13 Jul, 10 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
Late availability on these dates: 18 May, 01 Jun, 29 Jun
Greek Islands sailing holiday, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From £1,104 to £1,159 8 days ex flights
Small group travel:
2019: 11 May, 25 May, 8 Jun, 22 Jun, 6 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
Late availability on these dates: 11 May, 25 May, 08 Jun, 22 Jun
Cyclades walking holidays in Greece
A gently active holiday in the Cyclades
From £1,229 to £1,399 8 days inc UK flights
Small group travel:
2019: 14 Apr, 28 Apr, 26 May, 9 Jun, 8 Sep, 22 Sep, 6 Oct, 13 Oct, 20 Oct, 27 Oct, 3 Nov
Late availability on these dates: 14 Apr, 28 Apr, 26 May, 09 Jun
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: 6 Apr, 13 Apr, 20 Apr, 27 Apr, 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 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£1,220 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
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:
2019: 30 Mar, 6 Apr, 13 Apr, 20 Apr, 27 Apr, 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun
Cyclades walking holiday, Greece
Walk ancient paths and enjoy stunning Cycladic sceneries
From £592 to £640 7 days ex flights
Small group travel:
2019: 30 Mar, 6 Apr, 13 Apr, 20 Apr, 27 Apr, 4 May, 11 May, 18 May, 25 May, 1 Jun
Greek Island hopping cruise in the Aegean
Cruise the Greek Islands on board a classic sail cruiser
From £1,715 8 days ex flights
Small group travel:
2019: 26 Apr, 24 May, 31 May, 14 Jun, 21 Jun, 19 Jul, 26 Jul, 2 Aug, 23 Aug, 30 Aug, 13 Sep, 18 Oct
Naxos and Amorgos hiking holiday, Cyclades Greece
Naxos-Amorgos. Amazing memorable walking adventure holiday!
From €1,687 to €2,008 10 days ex flights
Small group travel:
2019: 12 May, 9 Jun, 7 Jul, 15 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: 30 Mar, 6 Apr, 13 Apr, 20 Apr, 27 Apr, 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 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:
2019: 15 Apr
Each guest on the 15 April nature-themed walking holiday will receive a free copy of David Koutsogiannopoulos's 36-page Kythnos Island - a Nature Guide packed with month-by-month calendars for bird, plant, butterfly and other species appearances
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.
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: 30 Mar, 6 Apr, 13 Apr, 20 Apr, 27 Apr, 4 May, 11 May, 18 May, 25 May, 1 Jun, 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 £1,384 to £1,564 10 days ex flights
Small group travel:
2019: 11 May, 31 May, 20 Jun, 30 Jun, 20 Jul, 30 Jul, 9 Aug, 19 Aug, 8 Sep, 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
Late availability on these dates: 11 May, 31 May, 20 Jun
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:
2019: 31 Aug
Sailing & conservation holiday in Greece
A unique wildlife & sailing adventure
From £683 to £759 7 days ex flights
Small group travel:
2019: 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun
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: 23 Mar, 30 Mar, 6 Apr, 13 Apr, 20 Apr, 27 Apr, 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 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
£1,069
excluding flights
Memorable parts?
Being with family, making new friends and seeing the beautiful islands.
Tips?
It's a very slow relaxing trip.
Local benefits?
Helped local people
Overall rating?
The holiday was amazing, trust your skipper was great at sailing the boat but not very good with information about the islands. We would ask him a question
and 90% of the time it was i hate that island, just sit and have a coffee. We had a lot of wasted time waiting. (more)Debra Klein
From
£1,104
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
£1,229
including UK flights
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
Thanos, the extremely knowledgeable guide. And the unexpected interesting-ness of Naxos! Less tourists yet much more to see. (more)Janis Edgar
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
£846
excluding flights
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
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
The most memorable was climbing the peak to San Simeon on Sifnos. (more)Caroline Shuffrey
This holiday fulfilled my expectations in providing amazing walks off the beaten track and the opportunity to see rural places not visited by most tourists. (more)Hannah Wilson
From
£1,715
excluding flights
From
£1,384
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
£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
£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
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