Cyclades holidays

Cyclades holidays offer a meze of Greek charms. On Naxos, walk the orchard-filled Tragea Valley and scale the chain's highest peak, flanked by tiny hamlets. Traverse the unforgettable volcanic caldera on Santorini, or ancient paths across Paros and Syros from virgin cove to virgin cove. Nature abounds - from Natura 2000 havens like Amorgos and Koufonisia to dolphins, seals and turtles accompanying inter-island sailing.

Filters

Greek Islands sailing holiday, Santorini to Mykonos

Greek Islands sailing holiday, Santorini to Mykonos

Sapphire waters, whitewashed villages & history laden ruins
From £1,281 to £1,376 8 days ex flights
Small group travel: 2024: 4 May, 14 May, 18 May, 28 May, 1 Jun, 11 Jun, 15 Jun, 25 Jun, 29 Jun, 9 Jul, 13 Jul, 23 Jul, 27 Jul, 6 Aug, 10 Aug, 20 Aug, 24 Aug, 3 Sep, 7 Sep, 17 Sep, 21 Sep, 1 Oct
Cyclades walking holidays in Greece

Cyclades walking holidays in Greece

A gently active holiday in the Cyclades
From £1,795 to £2,045 8 days inc UK flights
Small group travel: 2023: 8 Oct, 15 Oct
2024: 17 Mar, 31 Mar, 14 Apr, 5 May, 2 Jun, 29 Sep, 6 Oct, 13 Oct, 20 Oct
Late availability on these dates: 08 Oct, 15 Oct
Cyclades sailing & walking holiday in Greece

Cyclades sailing & walking holiday in Greece

Combine a sailing & hiking adventure around the Cyclades
From £726 to £797 7 days ex flights
Small group travel: 2023: 30 Sep, 7 Oct, 14 Oct, 21 Oct, 28 Oct, 4 Nov
We are currently offering £100 off Oct 2023 departures, book now!
Naxos and the small Cyclades walking holiday, Greece

Naxos and the small Cyclades walking holiday, Greece

Walk and discover Naxos and the unspoilt Small Cyclades
From £896 to £996 10 days ex flights
Small group travel: 2023: 7 Oct, 21 Oct, 4 Nov
We are currently offering £100 off Oct 2023 departures, book now!
Responsible Travel, Travel Team

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.
01273 823 700
Call us after 9am
Calling from outside the UK
Cyclades walking & island hopping holiday, Greece

Cyclades walking & island hopping holiday, Greece

Walk and explore nature of Naxos, Small Cyclades & Santorini
From £894 to £1,394 14 days ex flights
Small group travel: 2023: 7 Oct, 21 Oct
We are currently offering £100 off Oct 2023 departures, book now!
Sailing holiday in Greece, Mykonos to Santorini

Sailing holiday in Greece, Mykonos to Santorini

The boat, the beach and inviting Greek villages
From £1,281 to £1,441 8 days ex flights
Small group travel: 2024: 7 May, 11 May, 21 May, 25 May, 4 Jun, 8 Jun, 22 Jun, 2 Jul, 6 Jul, 16 Jul, 20 Jul, 30 Jul, 3 Aug, 13 Aug, 17 Aug, 27 Aug, 31 Aug, 10 Sep, 14 Sep, 24 Sep, 28 Sep
Cyclades walking holiday, Greece

Cyclades walking holiday, Greece

Walk ancient paths and enjoy stunning Cycladic sceneries
From £647 to £720 7 days ex flights
Small group travel: 2023: 30 Sep, 14 Oct, 28 Oct
Sailing & conservation holiday in Greece

Sailing & conservation holiday in Greece

A unique wildlife & sailing adventure
From £729 to £820 7 days ex flights
Small group travel: 2023: 30 Sep, 7 Oct, 14 Oct, 21 Oct, 28 Oct
Greek Islands bike and boat holiday

Greek Islands bike and boat holiday

Cycle and sail around the Cyclades Greek Islands
From £2,650 8 days ex flights
Small group travel: 2024: 19 Apr, 26 Apr, 3 May, 10 May, 17 May, 31 May, 7 Jun, 14 Jun, 30 Aug, 13 Sep, 20 Sep
The Cyclades guided walking holiday

The Cyclades guided walking holiday

Discover Serifos, Sifnos & Milos on this 10-day trip!
From €2,795 10 days ex flights
Small group travel: 2024: 2 Jun, 1 Sep
Greece in 2 weeks holiday

Greece in 2 weeks holiday

Visit Athens, Delphi, Olympia, Mycenae and Nafplion
From £2,795£2,755 to £3,259 14 days ex flights
Small group travel: 2023: 1 Oct, 8 Oct
2024: 12 May, 26 May, 9 Jun, 23 Jun, 7 Jul, 1 Sep, 15 Sep, 29 Sep, 6 Oct
Up to £120 off selected dates.
Late availability on these dates: 01 Oct, 08 Oct
Greek Islands Cycling tour, Cyclades

Greek Islands Cycling tour, Cyclades

Explore Cyclades, the unique Greek islands in the Aegean sea
From €890 8 days ex flights
Tailor made: This trip can be tailor made throughout the year to suit your requirements
Cyclades islands tour

Cyclades islands tour

Explore the Cyclades on this Greek island adventure
From £3,985 to £4,775 9 days ex flights
Small group travel: 2024: 12 May, 14 May, 19 May, 21 May, 26 May, 28 May, 2 Jun, 9 Jun, 16 Jun, 23 Jun, 14 Jul, 28 Jul, 18 Aug, 25 Aug, 1 Sep, 8 Sep, 15 Sep, 17 Sep, 22 Sep, 29 Sep, 1 Oct
Greece tour, highlights of the Cyclades

Greece tour, highlights of the Cyclades

An 8 day tour of Greece's most picturesque sights
From £1,579 8 days ex flights
Small group travel: 2023: 3 Oct, 4 Oct, 5 Oct, 6 Oct, 7 Oct, 8 Oct, 9 Oct, 10 Oct, 11 Oct, 12 Oct, 13 Oct, 14 Oct, 15 Oct, 16 Oct, 17 Oct, 18 Oct, 19 Oct, 20 Oct, 21 Oct, 22 Oct, 23 Oct, 24 Oct, 25 Oct, 26 Oct, 27 Oct, 28 Oct, 29 Oct, 30 Oct, 31 Oct
Responsible Travel, Travel Team

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.
01273 823 700
Call us after 9am
Calling from outside the UK
Naxos & the Small Cyclades holiday in Greece

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
We are currently offering £100 off Oct 2023 departures, book now!
Kythnos nature tours in greece

Kythnos nature tours in greece

Rare flowers, migratory birds in tour aimed at naturalists
From €740 6 days ex flights
Small group travel: 2024: 26 Mar
Greece guided walking holidays, Tinos and Andros

Greece guided walking holidays, Tinos and Andros

Walkers’ paradise in the northern Cyclades
From £1,865 15 days inc UK flights
Small group travel
Cyclades islands sailing holidays in Greece

Cyclades islands sailing holidays in Greece

A fantastic sailing adventure in the Cyclades islands!
From €1,950 to €2,050 8 days ex flights
Small group travel: 2024: 8 Jun, 6 Jul, 7 Sep, 21 Sep
Cyclades multi activity holiday in Greece

Cyclades multi activity holiday in Greece

Explore the Cyclades islands beyond the beaten path
From €1,480 to €1,840 7 days ex flights
Small group travel: 2023: 8 Oct
2024: 26 Mar, 14 Apr, 12 May, 22 Sep, 13 Oct
Naxos and Amorgos hiking holiday, Cyclades Greece

Naxos and Amorgos hiking holiday, Cyclades Greece

Naxos-Amorgos. Amazing memorable walking adventure holiday!
From €682 10 days ex flights
Tailor made: This trip can be tailor made throughout the year to suit your requirements
Sailing and cycling Cyclades holiday, Greece

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
The Cyclades cycling holiday, Greece

The Cyclades cycling holiday, Greece

Fantastic Greek Islands biking experience. The Cyclades
From €702 8 days ex flights
Tailor made: This trip can be tailor made throughout the year to suit your requirements
Santorini walking short break, Greece

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

Greek Island hopping cruise in the Aegean

Cruise the Greek Islands on board a classic small ship
From £2,074 to £2,305 8 days ex flights
Small group travel: 2023: 6 Oct, 13 Oct, 20 Oct
2024: 3 Mar, 19 Apr, 26 Apr, 10 May, 17 May, 24 May, 31 May, 4 Jun, 14 Jun, 21 Jun, 28 Jun, 5 Jul, 12 Jul, 19 Jul, 26 Jul, 2 Aug, 9 Aug, 16 Aug, 23 Aug, 30 Aug, 6 Sep, 13 Sep, 20 Sep, 27 Sep, 4 Oct, 11 Oct, 18 Oct
Walking holiday in the West Cyclades, Greece

Walking holiday in the West Cyclades, Greece

Walk & explore the authentic Serifos, Sifnos & Milos islands
From £895 to £1,029 10 days ex flights
Small group travel: 2023: 30 Sep, 7 Oct, 14 Oct, 21 Oct, 28 Oct
Cyclades Islands sailing holiday, Greece

Cyclades Islands sailing holiday, Greece

Swim in turquoise seas & explore ancient towns
From £1,805 to £2,015 10 days ex flights
Small group travel: 2024: 4 May, 14 May, 24 May, 3 Jun, 7 Jun, 13 Jun, 17 Jun, 23 Jun, 27 Jun, 3 Jul, 7 Jul, 13 Jul, 17 Jul, 23 Jul, 27 Jul, 2 Aug, 6 Aug, 12 Aug, 16 Aug, 22 Aug, 26 Aug, 1 Sep, 5 Sep, 11 Sep, 15 Sep, 21 Sep
Cyclades sailing honeymoon, Greece

Cyclades sailing honeymoon, Greece

Enjoy a romantic honeymoon sailing in the Cyclades islands
From £3,778 to £5,209 7 days ex flights
Tailor made
    Photo credits: [Page banner: Klearchos Kapoutsis]