Cyclades vacations

Cyclades vacations 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 vacation, Santorini to Mykonos

Greek Islands sailing vacation, Santorini to Mykonos

Sapphire waters, whitewashed villages & history laden ruins
From US $1,640US $1,255 to US $1,837 8 days ex flights
Small group travel: 2022: 4 Jun, 18 Jun, 2 Jul, 16 Jul, 30 Jul, 13 Aug, 27 Aug
2023: 6 May, 9 May, 20 May, 1 Jun, 3 Jun, 17 Jun, 25 Jun, 1 Jul, 15 Jul, 18 Jul, 29 Jul, 10 Aug, 12 Aug, 26 Aug, 3 Sep, 9 Sep, 23 Sep, 26 Sep
Up to US $380 off selected dates.
Late availability on these dates: 04 Jun, 18 Jun, 02 Jul, 16 Jul, 30 Jul, 13 Aug, 27 Aug
Cyclades sailing & walking vacation in Greece

Cyclades sailing & walking vacation in Greece

Combine a sailing & hiking adventure around the Cyclades
From £712 to £791 7 days ex flights
Small group travel: 2022: 28 May, 4 Jun, 11 Jun, 18 Jun, 25 Jun, 2 Jul, 9 Jul, 16 Jul, 23 Jul, 30 Jul, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
Family sailing vacation in the Cyclades, Greece

Family sailing vacation in the Cyclades, Greece

Enjoy the beauty of the Greek islands
From US $1,170 to US $1,390 8 days ex flights
Small group travel: 2022: 24 Jul, 31 Jul, 14 Aug, 21 Aug
2023: 23 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug
Late availability on these dates: 24 Jul, 31 Jul, 14 Aug, 21 Aug
Cyclades walking holidays in Greece

Cyclades walking holidays in Greece

A gently active holiday in the Cyclades
From US $2,249 to US $2,399 8 days ex flights
Small group travel: 2022: 5 Jun, 4 Sep, 2 Oct, 9 Oct, 23 Oct
2023: 19 Mar, 2 Apr, 16 Apr, 7 May, 14 May, 4 Jun, 18 Jun, 3 Sep, 17 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct
Late availability on these dates: 05 Jun
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.
Cyclades walking & island hopping holiday, Greece

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: 2022: 28 May, 10 Sep, 24 Sep, 8 Oct, 22 Oct, 5 Nov
Sailing vacation in Greece, Mykonos to Santorini

Sailing vacation in Greece, Mykonos to Santorini

The boat, the beach and inviting Greek villages
From US $1,422 to US $1,837 8 days ex flights
Small group travel: 2022: 23 Jul, 6 Aug, 20 Aug, 17 Sep, 1 Oct
2023: 13 May, 16 May, 27 May, 8 Jun, 10 Jun, 24 Jun, 2 Jul, 8 Jul, 22 Jul, 25 Jul, 5 Aug, 17 Aug, 19 Aug, 2 Sep, 10 Sep, 16 Sep, 30 Sep, 3 Oct
Late availability on these dates: 23 Jul, 06 Aug, 20 Aug
Cyclades hiking vacation, Greece

Cyclades hiking vacation, Greece

Walk ancient paths and enjoy stunning Cycladic sceneries
From £592 to £640 7 days ex flights
Small group travel: 2022: 28 May, 4 Jun, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
Naxos and the small Cyclades walking vacation, Greece

Naxos and the small Cyclades walking vacation, Greece

Walk and discover Naxos and the unspoilt Small Cyclades
From £592 to £914 10 days ex flights
Small group travel: 2022: 28 May, 4 Jun, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct, 5 Nov
Greek Islands Cycling tour on the Cyclades shell

Greek Islands Cycling tour on the Cyclades shell

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
Greece Cyclades islands small group tour

Greece Cyclades islands small group tour

Explore the Cyclades on this Greek island adventure
From US $3,880US $3,079 to US $4,675 9 days ex flights
Small group travel: 2022: 29 May, 19 Jun, 26 Jun, 3 Jul, 28 Aug, 4 Sep, 11 Sep, 18 Sep
2023: 14 May, 21 May, 28 May, 18 Jun, 25 Jun, 2 Jul, 27 Aug, 3 Sep, 10 Sep, 17 Sep
Up to US $1020 off selected dates.
Late availability on these dates: 29 May, 19 Jun, 26 Jun, 03 Jul, 28 Aug
Greece tour, highlights of the Cyclades

Greece tour, highlights of the Cyclades

An 8 day tour of Greece's most picturesque sights
From £1,439 8 days ex flights
Small group travel: 2022: 1 Jun, 2 Jun, 3 Jun, 4 Jun, 5 Jun, 6 Jun, 7 Jun, 8 Jun, 9 Jun, 10 Jun, 11 Jun, 12 Jun, 13 Jun, 14 Jun, 15 Jun, 16 Jun, 17 Jun, 18 Jun, 19 Jun, 20 Jun, 21 Jun, 22 Jun, 23 Jun, 24 Jun, 25 Jun, 26 Jun, 27 Jun, 28 Jun, 29 Jun, 30 Jun, 1 Jul, 2 Jul, 3 Jul, 4 Jul, 5 Jul, 6 Jul, 7 Jul, 8 Jul, 9 Jul, 10 Jul, 11 Jul, 12 Jul, 13 Jul, 14 Jul, 15 Jul, 16 Jul, 17 Jul, 18 Jul, 19 Jul, 20 Jul, 21 Jul, 22 Jul, 23 Jul, 24 Jul, 25 Jul, 26 Jul ...
Naxos & the Small Cyclades vacation in Greece

Naxos & the Small Cyclades vacation 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
Kythnos nature tours in greece

Kythnos nature tours in greece

Rare flowers, migratory birds in tour aimed at naturalists
From €790 6 days ex flights
Small group travel: 2023: 27 Mar
Greece guided walking vacations, Tinos and Andros

Greece guided walking vacations, Tinos and Andros

Walkers’ paradise in the northern Cyclades
From £1,820 to £1,840 15 days inc UK flights
Small group travel: 2022: 14 Sep, 28 Sep
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.
Cyclades hopping and photography vacation

Cyclades hopping and photography vacation

A photography adventure in the stunning Cyclades islands
From £834 to £1,150 10 days ex flights
Small group travel: 2022: 28 May
Cyclades islands sailing vacations in Greece

Cyclades islands sailing vacations in Greece

A fantastic sailing adventure in the Cyclades islands!
From €1,380 to €1,480 8 days ex flights
Small group travel: 2022: 18 Jun, 2 Jul, 3 Sep, 24 Sep, 8 Oct
Sailing & conservation vacation in Greece

Sailing & conservation vacation in Greece

A unique wildlife & sailing adventure
From £633 to £731 7 days ex flights
Small group travel: 2022: 28 May, 4 Jun, 11 Jun, 18 Jun, 25 Jun
Cyclades multi activity vacation in Greece

Cyclades multi activity vacation in Greece

Explore the Cyclades islands beyond the beaten path
From €1,380 to €1,490 7 days ex flights
Small group travel: 2022: 17 Sep, 8 Oct
Naxos and Amorgos hiking vacation, Cyclades greece

Naxos and Amorgos hiking vacation, Cyclades greece

Naxos-Amorgos. Amazing memorable walking adventure holiday!
From €582 to €816 10 days ex flights
Tailor made: This trip can be tailor made throughout the year to suit your requirements
Sailing and biking Cyclades vacation, Greece

Sailing and biking Cyclades vacation, Greece

Self guided or guided (upon request) tour in the Cyclades
From €1,500 8 days ex flights
Small group travel: 2022: 28 May, 4 Jun, 11 Jun, 18 Jun, 25 Jun, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct
The Cyclades biking vacation, Greece

The Cyclades biking vacation, Greece

Fantastic Greek Islands biking experience. The Cyclades
From €638 to €831 8 days ex flights
Tailor made: This trip can be tailor made throughout the year to suit your requirements
Santorini walking holiday, Greece

Santorini walking holiday, 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
Hiking vacation in the West Cyclades, Greece

Hiking vacation in the West Cyclades, Greece

Walk & explore the authentic Serifos, Sifnos & Milos islands
From £592 to £914 10 days ex flights
Small group travel: 2022: 28 May, 4 Jun, 11 Jun, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
Cyclades Islands sailing vacation, Greece

Cyclades Islands sailing vacation, Greece

Swim in turquoise seas & explore ancient towns
From US $1,852 to US $2,347 10 days ex flights
Small group travel: 2022: 6 Jun, 16 Jun, 26 Jun, 16 Jul, 26 Jul, 5 Aug, 15 Aug, 25 Aug, 4 Sep, 14 Sep, 24 Sep
2023: 6 May, 16 May, 23 May, 26 May, 5 Jun, 15 Jun, 16 Jun, 25 Jun, 5 Jul, 9 Jul, 15 Jul, 25 Jul, 1 Aug, 4 Aug, 14 Aug, 24 Aug, 25 Aug, 3 Sep, 13 Sep, 17 Sep, 23 Sep
Late availability on these dates: 06 Jun, 16 Jun, 26 Jun, 16 Jul, 26 Jul, 05 Aug, 15 Aug, 25 Aug
Cyclades sailing honeymoon, Greece

Cyclades sailing honeymoon, Greece

Enjoy a romantic honeymoon sailing in the Cyclades islands
From £3,490 to £5,209 7 days ex flights
Tailor made
Greek Islands bike and boat vacation

Greek Islands bike and boat vacation

Bicycle and sail around the Cyclades Greek Islands
From US $2,650 8 days ex flights
Small group travel
    Photo credits: [Page banner: Klearchos Kapoutsis]