26 Cyclades holidays found
Naxos and the small Cyclades walking holiday, Greece
Walk and discover Naxos and the unspoilt Small Cyclades
From £744 to £1,097 10 days ex flights
Small group travel:
2026: 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
£100 off Sept & Oct departures
Greek Island hopping cruise in the Aegean
Cruise the Greek Islands on board a classic small ship
From £1,899 to £2,345 8 days ex flights
Small group travel:
2026: 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct
2027: 16 Apr, 23 Apr, 30 Apr, 7 May, 14 May, 21 May, 28 May, 4 Jun, 11 Jun, 18 Jun, 25 Jun, 2 Jul, 9 Jul, 16 Jul, 23 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct
2027: 16 Apr, 23 Apr, 30 Apr, 7 May, 14 May, 21 May, 28 May, 4 Jun, 11 Jun, 18 Jun, 25 Jun, 2 Jul, 9 Jul, 16 Jul, 23 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct
Island hopping cruise in Greece
Hidden Greece: Unexplored Greek Islands Cruise
From £2,732 8 days ex flights
Small group travel:
2026: 4 Sep
Greek Islands Cycling tour, Cyclades
Explore Cyclades, the unique Greek islands in the Aegean sea
From 1,120 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Contact Us
Call us for a chat about our holidays. We are happy to discuss your holiday and help in any way we can. No bots, queues or awful hold music.
01273 823 700
Call us tomorrow after 9am
Calling from outside the UK
rosy@responsibletravel.com
Cyclades sailing & walking holiday in Greece
Combine a sailing & hiking adventure around the Cyclades
From £788 to £1,045 7 days ex flights
Small group travel:
2026: 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
£100 off Sept & Oct departures
Naxos & the Small Cyclades holiday in Greece
Walk & island hop Naxos, Iraklia & Amorgos, Small Cyclades
From £674 to £858 10 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
£100 off Sept & Oct departures
Greece guided walking holidays, Tinos and Andros
Walkers paradise in the northern Cyclades
From £2,529 to £2,959 15 days inc UK flights
Small group travel:
2026: 10 Sep, 24 Sep
Sailing & conservation holiday in Greece
A unique wildlife & sailing adventure
From £785 to £872 7 days ex flights
Small group travel:
2026: 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Athens and Paros holiday, tailor made
Paros the popular Cycladic island of the Aegean Sea & Athens
From 1,870 9 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Private sailing and cycling island hopping, Greece
Self guided or guided (upon request) tour in the Cyclades
From 1,500 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 £352 to £447 4 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Cyclades walking & island hopping holiday, Greece
Walk and explore nature of Naxos, Small Cyclades & Santorini
From £987 to £1,538 14 days ex flights
Small group travel:
2026: 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
£100 off Sept & Oct departures
Walking holiday in the West Cyclades, Greece
Walk & explore the authentic Serifos, Sifnos & Milos islands
From £744 to £1,098 10 days ex flights
Small group travel:
2026: 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
£100 off Sept & Oct departures
Greek Islands sailing holiday, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From £1,160£994 to £1,460£1,448 8 days ex flights
Small group travel:
2026: 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, 17 Aug, 21 Aug, 31 Aug, 4 Sep, 14 Sep, 28 Sep, 2 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, 17 Aug, 21 Aug, 31 Aug, 4 Sep, 14 Sep, 28 Sep, 2 Oct
Up to £300 off selected dates.
Late availability on these dates: 18 Aug, 22 Aug, 01 Sep, 05 Sep, 15 Sep, 19 Sep, 29 Sep, 03 Oct
Late availability on these dates: 18 Aug, 22 Aug, 01 Sep, 05 Sep, 15 Sep, 19 Sep, 29 Sep, 03 Oct
Contact Us
Call us for a chat about our holidays. We are happy to discuss your holiday and help in any way we can. No bots, queues or awful hold music.
01273 823 700
Call us tomorrow after 9am
Calling from outside the UK
rosy@responsibletravel.com
Cyclades Islands sailing holiday, Greece
Swim in turquoise seas & explore ancient towns
From £1,570£1,431 to £1,951 10 days ex flights
Small group travel:
2026: 20 Aug, 24 Aug, 30 Aug, 3 Sep, 9 Sep, 13 Sep, 19 Sep, 23 Sep, 29 Sep
2027: 1 May, 11 May, 21 May, 25 May, 31 May, 4 Jun, 10 Jun, 14 Jun, 20 Jun, 24 Jun, 30 Jun, 4 Jul, 10 Jul, 14 Jul, 20 Jul, 24 Jul, 30 Jul, 3 Aug, 9 Aug, 13 Aug, 19 Aug, 23 Aug, 29 Aug, 2 Sep, 8 Sep, 12 Sep, 18 Sep, 22 Sep, 28 Sep
2027: 1 May, 11 May, 21 May, 25 May, 31 May, 4 Jun, 10 Jun, 14 Jun, 20 Jun, 24 Jun, 30 Jun, 4 Jul, 10 Jul, 14 Jul, 20 Jul, 24 Jul, 30 Jul, 3 Aug, 9 Aug, 13 Aug, 19 Aug, 23 Aug, 29 Aug, 2 Sep, 8 Sep, 12 Sep, 18 Sep, 22 Sep, 28 Sep
Up to £190 off selected dates.
Late availability on these dates: 20 Aug, 24 Aug, 30 Aug, 03 Sep, 09 Sep, 13 Sep, 19 Sep, 23 Sep, 29 Sep
Late availability on these dates: 20 Aug, 24 Aug, 30 Aug, 03 Sep, 09 Sep, 13 Sep, 19 Sep, 23 Sep, 29 Sep
Sailing holiday in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From £1,260£1,051 to £1,488 8 days ex flights
Small group travel:
2026: 15 Aug, 25 Aug, 29 Aug, 8 Sep, 12 Sep, 22 Sep, 26 Sep, 6 Oct
2027: 4 May, 8 May, 18 May, 22 May, 1 Jun, 5 Jun, 15 Jun, 19 Jun, 29 Jun, 3 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
2027: 4 May, 8 May, 18 May, 22 May, 1 Jun, 5 Jun, 15 Jun, 19 Jun, 29 Jun, 3 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
Up to £190 off selected dates.
Late availability on these dates: 15 Aug, 25 Aug, 29 Aug, 08 Sep, 12 Sep, 22 Sep, 26 Sep, 06 Oct
Late availability on these dates: 15 Aug, 25 Aug, 29 Aug, 08 Sep, 12 Sep, 22 Sep, 26 Sep, 06 Oct
Cyclades walking holiday, Greece
Walk ancient paths and enjoy stunning Cycladic sceneries
From £744 to £1,097 7 days ex flights
Small group travel:
2026: 12 Sep, 26 Sep, 10 Oct, 24 Oct
Cyclades walking holidays in Greece
A gently active holiday in the Cyclades
From £1,669 to £1,799 8 days ex flights
Small group travel:
2026: 27 Sep, 11 Oct
2027: 21 Mar, 11 Apr, 3 May, 16 May, 26 Sep, 10 Oct, 24 Oct
2027: 21 Mar, 11 Apr, 3 May, 16 May, 26 Sep, 10 Oct, 24 Oct
Late availability on these dates: 27 Sep, 11 Oct
Cyclades islands tailor made tour
An unforgettable holiday to Paros, Tinos, Santorini, Mykonos
From 2,600 14 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Cyclades Islands holiday, off the beaten track in Greece
Tailor-made trip to wonderful Sifnos, Milos & Amorgos
From 2,040 to 2,265 16 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
The Cyclades guided walking holiday
Discover the Cyclades islands of Sifnos, Milos & Kimolos!
From 3,680 to 3,945 10 days ex flights
Small group travel:
2026: 5 Sep, 3 Oct
Cyclades islands tour with added comfort
Explore the Cyclades on this Greek island adventure
From £3,995£3,384 to £4,960 9 days ex flights
Small group travel:
2026: 23 Aug, 6 Sep, 13 Sep, 15 Sep, 22 Sep, 27 Sep
2027: 9 May, 23 May, 30 May, 13 Jun, 27 Jun, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 17 Oct
2028: 7 May, 21 May, 28 May, 11 Jun, 25 Jun, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 15 Oct
2027: 9 May, 23 May, 30 May, 13 Jun, 27 Jun, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 17 Oct
2028: 7 May, 21 May, 28 May, 11 Jun, 25 Jun, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 15 Oct
Up to £870 off selected dates.
Late availability on these dates: 23 Aug, 06 Sep, 13 Sep, 15 Sep, 22 Sep, 27 Sep
Late availability on these dates: 23 Aug, 06 Sep, 13 Sep, 15 Sep, 22 Sep, 27 Sep
Cyclades islands sailing holidays in Greece
A fantastic sailing adventure in the Cyclades islands!
From 2,480 to 2,620 8 days ex flights
Small group travel:
2026: 5 Sep
2027: 12 Jun, 10 Jul, 4 Sep, 25 Sep
2027: 12 Jun, 10 Jul, 4 Sep, 25 Sep
Cyclades multi activity holiday in Greece
Explore the Cyclades islands beyond the beaten path
From 1,690 to 1,850 7 days ex flights
Small group travel:
2026: 20 Sep, 11 Oct
2027: 21 Mar, 18 Apr, 9 May, 19 Sep, 10 Oct
2027: 21 Mar, 18 Apr, 9 May, 19 Sep, 10 Oct
Cyclades sailing honeymoon, Greece
Enjoy a romantic honeymoon sailing in the Cyclades islands
From £3,800 to £5,209 7 days ex flights
Tailor made
Greek Islands bike and boat holiday
Cycle and sail around the Cyclades Greek Islands
From £3,560 to £3,800 8 days ex flights
Small group travel:
2026: 21 Aug, 28 Aug, 11 Sep, 25 Sep
Late availability on these dates: 21 Aug, 28 Aug, 11 Sep, 25 Sep
