26 Cyclades vacations found
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 US $3,690 8 days ex flights
Small group travel:
2026: 4 Sep
Naxos and the small Cyclades walking vacation, 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
Cyclades walking holidays in Greece
A gently active holiday in the Cyclades
From US $2,505 to US $2,700 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
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
rosy@responsibletravel.com
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
Greek Islands sailing vacation, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From US $1,780US $1,507 to US $2,250US $2,212 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 US $470 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
Sailing vacation in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From US $1,970US $1,621 to US $2,315US $2,307 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 US $330 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 hiking vacation, 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
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
Naxos & the Small Cyclades vacation 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 vacations, 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 vacation 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 vacation, 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
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
rosy@responsibletravel.com
Santorini walking holiday, 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
Hiking vacation 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
Cyclades Islands sailing vacation, Greece
Swim in turquoise seas & explore ancient towns
From US $2,435US $2,199 to US $3,019 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 US $330 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
Cyclades sailing & walking vacation 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
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 vacation, 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 hiking vacation
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 US $5,360US $4,504 to US $6,590 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 US $1150 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 vacations 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 vacation 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 vacation
Bicycle and sail around the Cyclades Greek Islands
From US $5,630 to US $5,980 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
