24 Cyclades holidays found
Sailing holiday in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From £1,172 to £1,222 8 days ex flights
Small group travel:
2020: 27 Jun, 11 Jul, 25 Jul, 22 Aug, 19 Sep
Late availability on these dates: 27 Jun
Greek Islands sailing holiday, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From £1,162 to £1,236 8 days ex flights
Small group travel:
2020: 20 Jun, 4 Jul, 18 Jul, 1 Aug, 15 Aug, 26 Sep
Late availability on these dates: 20 Jun, 04 Jul
Cyclades walking holidays in Greece
A gently active holiday in the Cyclades
From £1,299 to £1,599 8 days inc UK flights
Small group travel:
2020: 24 May, 7 Jun, 21 Jun, 6 Sep, 20 Sep, 4 Oct, 11 Oct, 18 Oct, 25 Oct, 1 Nov
2021: 21 Mar, 4 Apr, 18 Apr, 9 May, 16 May, 23 May, 6 Jun, 20 Jun, 5 Sep, 19 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct
2021: 21 Mar, 4 Apr, 18 Apr, 9 May, 16 May, 23 May, 6 Jun, 20 Jun, 5 Sep, 19 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct
Late availability on these dates: 24 May, 07 Jun, 21 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:
2020: 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 13 Jun, 27 Jun, 4 Jul, 11 Jul, 18 Jul, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 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 £1,151 to £1,321 8 days inc UK flights
Small group travel:
2020: 26 Jul, 9 Aug, 16 Aug
2021: 25 Jul, 1 Aug, 8 Aug, 15 Aug
2021: 25 Jul, 1 Aug, 8 Aug, 15 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:
2020: 4 Apr, 11 Apr, 18 Apr, 25 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Cyclades walking holiday, Greece
Walk ancient paths and enjoy stunning Cycladic sceneries
From £592 to £640 7 days ex flights
Small group travel:
2020: 4 Apr, 11 Apr, 18 Apr, 25 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Greek easter offer, 100 Eur off 11-20 April
Naxos & the Small Cyclades holiday in Greece
Walk & island hop Naxos, Iraklia & Amorgos, Small Cyclades
From £606 to £762 10 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Greece guided walking holidays, Tinos and Andros
Walkers paradise in the northern Cyclades
From £1,499 to £1,535 15 days inc UK flights
Small group travel:
2020: 6 May, 20 May, 2 Sep, 16 Sep
Cyclades hopping and photography holiday
A photography adventure in the stunning Cyclades islands
From £834 to £1,150 10 days ex flights
Small group travel:
2020: 25 Apr
100 off if you book by 31 December
Cyclades islands sailing holidays in Greece
A fantastic sailing adventure in the Cyclades islands!
From 1,120 to 1,250 8 days ex flights
Small group travel:
2020: 30 May, 13 Jun, 11 Jul, 22 Aug, 12 Sep
2021: 5 Jun, 10 Jul, 17 Jul, 4 Sep, 25 Sep
2021: 5 Jun, 10 Jul, 17 Jul, 4 Sep, 25 Sep
Sailing & conservation holiday in Greece
A unique wildlife & sailing adventure
From £683 to £759 7 days ex flights
Small group travel:
2020: 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 13 Jun, 27 Jun, 4 Jul, 11 Jul, 18 Jul, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Cyclades multi activity holiday in Greece
Explore the Aegean islands beyond the beaten path
From 1,180 to 1,250 7 days ex flights
Small group travel:
2020: 5 Apr, 2 May, 7 Jun, 27 Sep
2021: 1 Apr, 29 May, 19 Sep, 17 Oct
2021: 1 Apr, 29 May, 19 Sep, 17 Oct
Naxos and Amorgos hiking holiday, Cyclades Greece
Naxos-Amorgos. Amazing memorable walking adventure holiday!
From 1,099 to 1,555 10 days ex flights
Small group travel:
2020: 24 May, 16 Jun, 12 Jul, 2 Aug, 30 Aug, 20 Sep, 11 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.
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:
2020: 4 Apr, 11 Apr, 18 Apr, 25 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 13 Jun, 20 Jun, 27 Jun, 4 Jul, 11 Jul, 18 Jul, 25 Jul, 1 Aug, 8 Aug, 15 Aug, 22 Aug, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
We offer 10% off for the bookings of March 2020
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
Greek Island hopping cruise in the Aegean
Cruise the Greek Islands on board a classic sail cruiser
From £1,935 8 days ex flights
Small group travel:
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:
2020: 4 Apr, 11 Apr, 18 Apr, 25 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Cyclades Islands sailing holiday, Greece
Swim in turquoise seas & explore ancient towns
From £1,465 to £1,645 10 days ex flights
Small group travel:
2020: 8 Jun, 18 Jun, 28 Jun, 8 Jul, 18 Jul, 28 Jul, 7 Aug, 27 Aug, 6 Sep, 16 Sep, 26 Sep
Late availability on these dates: 08 Jun, 18 Jun, 28 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 bike and boat holiday
Cycle and sail around the Cyclades Greek Islands
From £1,720 8 days ex flights
Small group travel:
2020: 19 Sep
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:
2020: 4 Apr, 11 Apr, 18 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 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
£1,162
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
£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
£685
excluding flights
Excellent! I would strongly recommend this to anyone who enjoys moderate walking in great landscapes, with opportunities to swim most days, the company of like-minded folk and with supportive and fun local guides.
(more)Caroline Pack
Fantastic guides Annie & Dimitria who showed so much care, thoughtfulness & took us on fantastic walks. (more)Catherine Pedersen
While hiking, we were thrilled with the landscape and felt very privileged to be in it, rather than just driving by. Each hike on the six islands we visited was different from the one before. (more)Jennifer Duschenes
From
£1,299
including UK flights
A M A Z I N G! It was very well organised, nothing was too much trouble for our guide. We were able to go at our own pace when walking, which was good, as there were so many scenes to stop and photograph. (more)Lisa Payne
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
From
£1,172
excluding flights
The most exciting part of the holiday was staying in a different island each night and our tour guide and skipper Rita with her expert knowledge of every location. (more)Robert Carr
Greek weather, good food in resturants. (more)Owen Monie
The highlight was being with family, making new friends and seeing the beautiful islands. (more)Debra Klein
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
£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
From
£1,465
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
521
excluding flights
The most memorable and exciting part of the holiday was finding remote, quiet and unspoiled bays, and beaches with local bars/tavernas. (more)Stephanie Dougan
The weather, food and scenery were memorable. (more)Peter Hegarty
The day we bicycled around Antiparos was the most memorable part of our holiday. It was fun to bicycle from Paros to catch the small ferry that took us to Antiparos. (more)Diane Doser
From
£592
excluding flights
I cant think of a particular part of the holiday that was better than the rest. It was all so good. Very well organised without being too restrictive and everybody catered for. (more)Caroline Macdonald
All of it was memorable! Our guide Annie Antonatou was absolutely wonderful in every respect, a real professional and delightful company (more)Philippa Hull
My holiday with has to be one of the most memorable holidays I have ever had (more)Ann Tector
From
£1,720
excluding flights
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
£1,935
excluding flights
The islands were beautiful, the guide informative, food was good.
(more)Margaret Dunne
Crew and the food were excellent. (more)John Gibbard
The most memorable was the terrific atmosphere on the boat. All the passengers got on really well (British, Australian, Italian and German) and the crew were excellent, they couldn't do enough for us. (more)Heather Williams
From
£3,440
excluding flights
Memorable parts?
All the different islands and experiencing their uniqueness and authenticity. Seeing dolphins while under sail!
Tips?
Be prepared to be flexible and easy going.
Local benefits?
Yes, we ate in family run taverns, tried local food and supported local economies. However it is still tourism and the hope is that somehow this can sustain communities throughout the year too somehow
Overall rating?
It was a once in a lifetime experience. (more)Katherine Bussy
From
£1,151
including UK flights
Memorable parts?
Jumping off the boat! Also the food was great.
Tips?
Be prepared for the small cabin - pack just what you need
Local benefits?
It did benefit the local resturants. I don't think it really supported conservation.
Overall rating?
Great (more)Nicholas Kirkham
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