Sailing holidays in Greece

It doesn't matter whether you're lolling on a stylish varnished gulet or working the winches on a modern catamaran, when the breeze hits, there's nothing like a sailing holiday in Greece. This is a destination that's simply made for sailors. Hop between islands, test the tavernas, and moor in remote, rocky bays where you can smell the black pines on the hillside. Bliss.

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Luxury gulet cruise in the Aegean 2023

Luxury gulet cruise in the Aegean 2023

5 star services while cruising the Greek Islands in luxury
From 1,250 8 days ex flights
Small group travel: 2023: 27 May, 2 Sep
Liveaboard diving and sailing holiday in Greece

Liveaboard diving and sailing holiday in Greece

Combine a sailing and diving adventure in the Greek islands
From 719 to 799 7 days ex flights
Small group travel: 2022: 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Sailing holiday in Greece, Mykonos to Santorini

Sailing holiday in Greece, Mykonos to Santorini

The boat, the beach and inviting Greek villages
From 1,251 to 1,381 8 days ex flights
Small group travel: 2022: 3 Sep, 17 Sep
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: 03 Sep, 17 Sep
Cyclades sailing & walking holiday in Greece

Cyclades sailing & walking holiday in Greece

Combine a sailing & hiking adventure around the Cyclades
From 712 to 791 7 days ex flights
Small group travel: 2022: 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 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.
Yoga and sailing retreat in Greece

Yoga and sailing retreat in Greece

-A week of relaxation and yoga while sailing the Ionian sea!
From 720 to 950 7 days ex flights
Small group travel: 2022: 25 Sep
2023: 28 May, 25 Jun
Greek Islands sailing holiday, Santorini to Mykonos

Greek Islands sailing holiday, Santorini to Mykonos

Sapphire waters, whitewashed villages & history laden ruins
From 1,221 to 1,381 8 days ex flights
Small group travel: 2022: 10 Sep
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, 9 Sep, 23 Sep, 26 Sep
Late availability on these dates: 10 Sep
Family sailing holiday in Greece

Family sailing holiday in Greece

Private sailing with fun games, reliving mythical tales
From 2,300 to 2,880 8 days ex flights
Tailor made: This holiday is chartering the whole catamaran, minimum 6, maximum 10
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: 2022: 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct
Sailing holiday in the Aegean Sea

Sailing holiday in the Aegean Sea

Unique sailing adventure off the beaten track in Greece
From 502 to 613 7 days ex flights
Small group travel: 2022: 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Greek Island cruising holiday

Greek Island cruising holiday

Discover a side of Greece riddled with myth and magic.
From 2,7052,124 to 3,5802,780 9 days ex flights
Small group travel: 2022: 8 Sep
2023: 18 May, 22 Jun, 20 Jul, 3 Aug, 17 Aug, 21 Sep
Up to 910 off selected dates.
Late availability on these dates: 08 Sep
Greece sailing holiday for families

Greece sailing holiday for families

Sailing trip for families/friends in Greek islands
From 4,250 to 5,600 8 days ex flights
Small group travel: 2022: 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep
Enjoy a great offer -400 for a week trip with your family/friends 25.9-1.10! This trip was originally booked and just became available!
Small group sailing in Saronic Greek Islands

Small group sailing in Saronic Greek Islands

Luxury sailing in the Greek islands with mythical adventures
From 2,800 8 days ex flights
Small group travel: 2023: 8 Jul
Greek Aegean Island hopping holiday

Greek Aegean Island hopping holiday

Get on board and visit ten stunning Aegean islands
From 2,400 to 3,650 8 days ex flights
Small group travel: 2022: 16 Sep
Greek Cyclades island hopping cruise

Greek Cyclades island hopping cruise

Greek Island Hopping, Sandy beaches and Clear azure waters
From 2,070 to 3,450 8 days ex flights
Small group travel: 2022: 19 Aug, 26 Aug, 2 Sep, 9 Sep, 16 Sep, 23 Sep, 30 Sep, 7 Oct, 14 Oct, 21 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.
Luxury sailing holiday in the Aegean

Luxury sailing holiday in the Aegean

Luxury sailing the Aegean, while reliving mythical tales
From 2,340 to 2,940 8 days ex flights
Tailor made: This holiday is chartering the whole catamaran, minimum 6, maximum 10. Sailing Season is from May 28 to Oct 1
Late availability for departures in September.
Saronic Greek Islands luxury cruise

Saronic Greek Islands luxury cruise

Luxury sailing Greek islands, while reliving mythical tales
From 2,100 to 2,860 8 days ex flights
Tailor made: This holiday is chartering the whole catamaran, minimum 6, maximum 10. Sailing Season is from May 28 to Oct 1
Small group sailing holiday Greece

Small group sailing holiday Greece

Luxury sailing in the Greek islands with mythical adventures
From 2,740 8 days ex flights
Small group travel: 2023: 1 Jul
Greek Islands sailing holiday

Greek Islands sailing holiday

Luxury sailing in the Greek islands, reliving mythical tales
From 2,300 to 2,880 8 days ex flights
Tailor made: This holiday is chartering the whole catamaran, minimum 6, maximum 10. Sailing Season is from 28th May to 1st Oct
Late availability for departures in Sept
Saronic Islands sailing holiday in Greece

Saronic Islands sailing holiday in Greece

Sail among the beautiful islands & ports of the Saronic Gulf
From US $2,995 7 days ex flights
Small group travel
Saronic Gulf small group sailing holiday in Greece

Saronic Gulf small group sailing holiday in Greece

Spend a week navigating the idyllic waters of the Saronic Gulf
From 1,899 to 1,999 8 days ex flights
Small group travel: 2023: 6 May, 27 May, 9 Sep, 16 Sep
Sailing and walking holiday in Greek Islands

Sailing and walking holiday in Greek Islands

Explore mainland hikes and secret Greek Ionian beaches
From 1,170 7 days ex flights
Small group travel: 2022: 8 Oct
Greece family sailing holiday

Greece family sailing holiday

Sailing adventure for families or friends in Greek islands
From 3,850 to 5,250 7 days ex flights
Small group travel: 2022: 25 Sep, 16 Oct
2023: 30 Jul, 6 Aug, 13 Aug, 20 Aug, 27 Aug
Enjoy a great offer -400 for a week trip with your family/friends 25.9-1.10! This trip was originally booked and just became available!
Cyclades islands sailing holidays in Greece

Cyclades islands sailing holidays in Greece

A fantastic sailing adventure in the Cyclades islands!
From 1,380 to 1,950 8 days ex flights
Small group travel: 2022: 3 Sep, 24 Sep, 8 Oct
2023: 27 May, 17 Jun, 1 Jul, 2 Sep, 23 Sep
Special last minute offer! 100 off on our Cyclades islands sailing adventure departing Sept. 3rd & Sept. 24th. Join us on board and let us show you the hidden gems of the Cyclades islands!
Gastronomy and sailing holiday in Greece

Gastronomy and sailing holiday in Greece

Explore the Greek islands and their gastronomy with a chef!
From 900 to 970 7 days ex flights
Small group travel: 2022: 2 Oct
2023: 4 Jun
Freediving and sailing holiday in Greece

Freediving and sailing holiday in Greece

-sail, freedive and explore the Ionian Sea
From 1,250 7 days ex flights
Small group travel: 2022: 25 Sep, 2 Oct
Greece sailing holiday in Ionian Sea

Greece sailing holiday in Ionian Sea

Sail, explore and experience the Ionian islands in Greece
From 600 7 days ex flights
Small group travel: 2022: 9 Oct
Enjoy a great offer -400 for a week trip with your family/friends 25.9-1.10! This trip was originally booked and just became available!
Saronic Gulf sailing holiday in Greece

Saronic Gulf sailing holiday in Greece

An 8 day trip combines sailing & swimming in Greece
From 1,330 to 1,990 8 days ex flights
Small group travel: 2022: 27 Aug, 1 Oct
2023: 20 May, 24 Jun, 26 Aug, 30 Sep
Special offer 100 off on our Saronic islands sailing adventure, departing on Oct. 1st! October is one of the best months to visit Greece and what's best than exploring the Greek islands on a sailing yacht?
Rhodes sailing holiday in Greece

Rhodes sailing holiday in Greece

Aegean sea island hopping and sailing school
From 2,000 8 days ex flights
Tailor made: Sailing during Greek summer in the Aegean Sea
Greek Islands family sailing holiday

Greek Islands family sailing holiday

Enjoy the beauty of the Greek islands
From 1,332 to 1,473 8 days inc UK flights
Small group travel: 2022: 21 Aug
2023: 23 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug
Late availability on these dates: 21 Aug
Cyclades Islands sailing holiday, Greece

Cyclades Islands sailing holiday, Greece

Swim in turquoise seas & explore ancient towns
From 1,590 to 1,800 10 days ex flights
Small group travel: 2022: 25 Aug, 4 Sep
2023: 6 May, 16 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: 25 Aug, 04 Sep
Photo credits: [Page banner: Alex Antoniadis] [Cultural holidays : A.Savin] [Activities : Patrick Hendry] [On the water : pxhere] [Family holidays : Explore] [Where to go in Greece : momo]