113 Greek Islands vacations found
Rhodes gulet cruise in Greece
8 day Rhodes cruise around the South Dodecanessae
From 1,100 to 1,500 8 days ex flights
Small group travel:
2027: 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct
Greek Island gulet cruises
Greek Island gulet cruise to the North Dodecanese
From £959 to £1,135 8 days ex flights
Small group travel:
2026: 15 Aug, 22 Aug, 29 Aug, 26 Sep, 3 Oct, 10 Oct, 17 Oct
11 Greek Islands small ship cruise
Cruise to Santorini, Mykonos and some lesser known islands
From £2,485 to £2,515 8 days ex flights
Small group travel:
2026: 14 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct
2027: 23 Apr, 30 Apr, 7 May, 14 May, 21 May, 28 May, 4 Jun, 11 Jun, 18 Jun, 25 Jun, 2 Jul, 9 Jul, 6 Aug, 13 Aug, 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct
2027: 23 Apr, 30 Apr, 7 May, 14 May, 21 May, 28 May, 4 Jun, 11 Jun, 18 Jun, 25 Jun, 2 Jul, 9 Jul, 6 Aug, 13 Aug, 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct
Hidden Greece small group tour
Go off the beaten track to discover Evia and Skyros Island.
From £2,555 to £2,755 12 days ex flights
Small group travel:
2026: 15 Sep, 20 Oct
2027: 10 Apr, 24 May
2027: 10 Apr, 24 May
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
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
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
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
Greek Island activity vacation
Year round Greek island adventure holiday
From £895 8 days ex flights
Small group travel:
2026: 15 Aug, 29 Aug, 3 Oct, 10 Oct
Greece sailing holiday for families
Sailing trip for families/friends in Greek islands
From £580 to £750 7 days ex flights
Small group travel:
2026: 30 Aug, 20 Sep
2027: 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
2027: 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
£400 off a whole boat charter Sun 30 August to Sat 5 September for your family or friends (up to 6 people). Now available due to a last minute cancellation. Discount refers to whole charter booking and not per person.
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
Greek Islands tour
Explore the very best of Greece with stunning scenery
From US $3,040US $2,810 to US $3,430 14 days ex flights
Small group travel:
2026: 6 Sep, 13 Sep, 27 Sep, 11 Oct
2027: 18 Apr, 2 May, 9 May, 16 May, 23 May, 6 Jun, 13 Jun, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct
2027: 18 Apr, 2 May, 9 May, 16 May, 23 May, 6 Jun, 13 Jun, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct
Up to US $280 off selected dates.
Late availability on these dates: 06 Sep, 13 Sep, 27 Sep, 11 Oct
Late availability on these dates: 06 Sep, 13 Sep, 27 Sep, 11 Oct
Greece hiking vacation, Kythnos
Hiking vacation on Kythnos, a beautiful Greek island in the Cyclades group
From 635 6 days ex flights
Small group travel:
2026: 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Walking tours resume on Kythnos in September after our pause for the hot weather. Prices stay the same for the remainder of the year. Enjoy still warm weather and sea water, ideal for walking and swimming, Best taverna open until of October.
Luxury Greek Island vacation
Organic country estate by the sea on Greek island of Ithaca
From 2,995 to 5,575 per villa per week
Accommodation
Ionian Islands small ship cruise, Greece
Cruise around the emerald green Islands of the Ionian
From £2,165 to £3,261 8 days ex flights
Small group travel:
2026: 14 Aug, 21 Aug
2027: 6 Jun, 11 Jun, 18 Jun, 25 Jun, 2 Jul, 16 Jul, 23 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug
2027: 6 Jun, 11 Jun, 18 Jun, 25 Jun, 2 Jul, 16 Jul, 23 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug
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
Saronic Greek Islands luxury charter cruise
Private sailing through Greeces romantic Saronic islands
From 1,450 to 1,600 7 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 4 people. Season runs from end of May to beginning of October.
Walking vacation in Crete
Hike the Samaria Gorge and enjoy the beaches and simple life
From US $1,810US $1,550 to US $1,880 8 days ex flights
Small group travel:
2026: 12 Sep, 26 Sep, 3 Oct
2027: 8 May, 22 May, 11 Sep, 25 Sep, 2 Oct
2027: 8 May, 22 May, 11 Sep, 25 Sep, 2 Oct
Up to US $280 off selected dates.
Late availability on these dates: 12 Sep, 26 Sep, 03 Oct
Late availability on these dates: 12 Sep, 26 Sep, 03 Oct
Corfu self catering cottages, Greece
Lovely old olive press converted into selfcatering cottages
From 65 to 140 per accommodation per night
Accommodation
Evia walking vacation, Greece
Walk well worn stone pathways & visit sleepy villages
From US $2,055 to US $2,400 8 days ex flights
Small group travel:
2026: 18 Oct, 22 Nov, 20 Dec, 27 Dec
2027: 14 Mar, 4 Apr, 25 Apr, 9 May, 30 May, 26 Sep, 3 Oct, 17 Oct, 31 Oct, 21 Nov, 19 Dec, 26 Dec
2027: 14 Mar, 4 Apr, 25 Apr, 9 May, 30 May, 26 Sep, 3 Oct, 17 Oct, 31 Oct, 21 Nov, 19 Dec, 26 Dec
Up to US $140 off selected dates.
Late availability on these dates: 18 Oct
Late availability on these dates: 18 Oct
Liveaboard diving and sailing vacation in Greece
Combine a sailing and diving adventure in the Greek islands
From £807 to £1,074 7 days ex flights
Small group travel:
2026: 15 Aug, 22 Aug, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Historical Greece with Santorini tour
Discover Athens the Peloponnese, Meteora, Crete
& Santorini
From £2,845 to £3,225 10 days ex flights
Small group travel:
2026: 21 Sep, 27 Oct
2027: 10 Apr, 23 May
2027: 10 Apr, 23 May
Greek Islands cruise holiday, Antiquity to Byzantium
Cruising in the beautiful Greek Islands
From £2,436 to £3,148 8 days ex flights
Small group travel:
2026: 23 Oct, 30 Oct, 6 Nov, 13 Nov
Crete self-guided walking holiday, Greece
Selfguided trekking in Samaria Natural Park & South coasts
From 655 to 720 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
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
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
Sailing vacation in the Aegean Sea
Uninhabited islands in a 6 person boat
From £690 to £870 7 days ex flights
Small group travel:
2026: 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
£100 off Sept & Oct departures
Kefalonia, Lefkada & Ithaki hiking vacation
Walk with us and explore the lush, green Ionian islands
From £779 to £1,197 10 days ex flights
Small group travel:
2026: 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Ionian Islands small group sailing vacation
8-day Greek odyssey exploring Zante & nearby islands
From £739 to £1,099£979 8 days ex flights
Small group travel:
2026: 17 Oct
2027: 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct
2027: 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct
Late availability on these dates: 17 Oct
Sifnos hiking holiday in Greece
Guided walking on clean trails to historic sites, beaches
From 615 5 days ex flights
Small group travel:
2026: 2 Sep, 9 Sep, 16 Sep, 23 Sep, 30 Sep, 7 Oct, 14 Oct, 21 Oct, 28 Oct
Walking tours resume on Sifnos in September after our pause for the hot weather. Prices stay the same for the remainder of the year. Enjoy still warm weather and sea water, ideal for walking and swimming, Best taverna open until of October.
