Our Greek Island vacations & tours
Our Greek Islands vacations are the perfect way to explore these lands of legend that have provided centuries of creative inspiration for writers, musicians and artists. There are thousands of Greek islands, but only a couple of hundred or so that are inhabited. Divided into clusters, east, south and west of the mainland, our trips will take you sailing in the Cyclades or Ionian islands, hiking on Crete, scuba diving off Rhodes, the largest of the Dodecanese Islands, or yoga-posing on Skyros, one of the more remote Sporades. Choose a small ship cruise with a local crew that knows the best hidden beaches and peaceful harbours, or opt to stay in a picturesque, whitewashed village with sea views and homecooked Mediterranean meals a speciality. Hellenic heaven.
Our top trips
Sailing adventure in the Cyclades, Greece
From
£930 to £1095
8 days
ex flights
Explore The Aegean Islands On a Skippered, Sailing Yacht
Small group
Greek Island gulet cruises
From
£959
8 days
ex flights
Greek Island gulet cruise to the North Dodecanese
Small group
Greek Islands tour
From
US $3030 to US $3320
14 days
ex flights
Explore the very best of Greece with stunning scenery
Small group2027: 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
Hidden Greece small group tour
From
£2755
12 days
ex flights
Go off the beaten track to discover Evia and Skyros Island.
Small group2027: 10 Apr, 24 May
Greek Islands Cycling tour, Cyclades
From
€1120
8 days
ex flights
Explore Cyclades, the unique Greek islands in the Aegean sea
Tailor made
Greece sailing vacation for families
From
£580 to £750
7 days
ex flights
Sailing trip for families/friends in Greek islands
Small group2027: 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
11 Greek Islands small ship cruise
From
£2515
8 days
ex flights
Cruise to Santorini, Mykonos and some lesser known islands
Small group2027: 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
Greek Island hopping cruise in the Aegean
From
£1899 to £2345
8 days
ex flights
Cruise the Greek Islands on board a classic small ship
Small group2027: 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
Rhodes gulet cruise in Greece
From
€1100 to €1500
8 days
ex flights
8 day Rhodes cruise around the South Dodecanessae
Small group2027: 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
See all our Greek Islands vacationsContact 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
Greek Islands map & highlights
The largest Greek island is Crete, followed by Evvia, Lesvos and Rhodes. Divided into clusters, they are better known as the Sporades to the east, Cyclades to the south east, the Dodecanese over near Turkey, the Ionian Islands west of the mainland and the Argo-Saronic, tucked in the middle of them all. Ranging from the volcanic Santorini, the ancient mountainous hiking paths of Ithaca or Lefkada to the remote artists’ retreats of Skyros, you can sail, hike, hail or bike around them. Whichever you choose, each proffers its own mythical quality and epic experiences.
Crete
1. Crete
Greece’s largest island is packed with small communities and magnificent hiking landscapes, such as the White Mountains, snow dusted until spring when they explode into a frenzy of wildflowers. The epic cleft of Samaria Gorge beckons hiking pilgrims annually. Throw in the island’s superb food, beaches and history, from the Minoan Palace of Knossos to memories of Venetian, Byzantine, Moorish and Ottoman settlers.
The Cyclades
2. The Cyclades
This seriously sensual cluster makes for many a 'ship ahoy!' as this is sailing central. However, most Cyclades Islands also offer spectacular hiking landscapes. Walk to the Cyclades’ highest peak, Zas on Naxos, or its orchard-filled Tragea Valley. Traverse the unforgettable volcanic caldera on Santorini, or ancient paths across Paros and Syros. Bring binoculars and bathing suits; coves and dolphins are omnipresent.
Ithaca
3. Ithaca
At over 100km² and with 3,000 residents, Ithaca isn’t tiny but this legendary home of Homer’s Odysseus is worth the journey. Vathi, the main town, is a traditional, waterfront treat, with summer sailors competing for moorings. The only dilemma is choosing which beach to go to. Gorgeous shingle coves such as Gidaki which, like many, is only accessible by boat. Or Filiatro, where olive trees dip down to proffer shade.
Karpathos Island
4. Karpathos Island
Karpathos is like the subtly exquisite diamond hidden between two stonking great emeralds of Crete and Rhodes. It also has the island of Saria as part of its municipality, so it’s like a beautiful ‘bogof’. Because it’s remote, it has preserved not only many of its traditions in terms of local dress, customs and dialect but also its wilderness: the mountains’ flowers and plants proffering a veritable botanical blowout in spring.
Lefkada
5. Lefkada
One of the main Ionian Islands, connected to the mainland by a causeway, this is another ‘wander and wild swimming-lust’ location. With ancient footpaths leading into traditional mountain villages perched around its highest peak, Stavrota (1,158m), it’s an Hellenic hiking haven with ancient oak Skaros forest, valleys watered by falls and natural springs as well as the Gira lagoon, home to flamingos and pelicans.
Rhodes
6. Rhodes
Part of the Dodecanese chain, and one of the largest Greek islands, Rhodes is very popular for family vacations. Look beyond its reputation of runaway resort-doms and rampaging tourists in Faliraki –mere blips on this map of historical and natural marvels. Sail away from the crowds to the likes of Afantou or Ladiko beach, hike through the Valley of the Butterflies (really) or scuba dive at St Paul bay in Lindos.
Skyros
7. Skyros
Skyros is the most remote of the Sporades Islands, and has become famous for those seeking a haven to be mindful and creative. Attracting writers, yogis and artists to drink in the healing powers of its quiet beaches, hillwalking and fine food in its idyllic island main town of Skyros. It’s beyond mindful really because you’d be out of your mind not to go there if you have half the chance.
Latest reviews
4.6
378Greek Islands vacations reviews
Katherine Gettys31 Oct 2026
This vacation is a unique itinerary and special. Just book!read more
richard Loudis30 Oct 2026
Exceptional - far exceeded my expectations.read more
Laura Harris26 Oct 2026
I had a fantastic time; we must have walked over 100km over the week, but took in some amazing views, learnt a lot about the flower/fauna and Greek culture with our wonderful guide Annie and had gorgeous beach swims.read more
