Sailing vacations 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 vacation 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 vacation in Greece

Liveaboard diving and sailing vacation in Greece

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

Sailing vacation in Greece, Mykonos to Santorini

The boat, the beach and inviting Greek villages
From US $1,775 to US $2,200 8 days ex flights
Small group travel: 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
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: 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 850 to 950 7 days ex flights
Small group travel: 2023: 28 May, 25 Jun
Family sailing vacation in Greece

Family sailing vacation 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 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: 1 Oct, 8 Oct, 15 Oct
Greek Island cruising vacation

Greek Island cruising vacation

Discover a side of Greece riddled with myth and magic.
From US $4,085 to US $5,410US $4,200 9 days ex flights
Small group travel: 2023: 18 May, 22 Jun, 20 Jul, 3 Aug, 17 Aug, 21 Sep
Greek Islands sailing vacation, Santorini to Mykonos

Greek Islands sailing vacation, Santorini to Mykonos

Sapphire waters, whitewashed villages & history laden ruins
From US $1,775 to US $2,135 8 days ex flights
Small group travel: 2023: 6 May, 9 May, 20 May, 1 Jun, 3 Jun, 25 Jun, 1 Jul, 15 Jul, 18 Jul, 29 Jul, 10 Aug, 12 Aug, 26 Aug, 9 Sep, 23 Sep, 26 Sep
Sailing vacation in the Aegean Sea

Sailing vacation in the Aegean Sea

Uninhabited islands in a 6 person boat
From 502 to 613 7 days ex flights
Small group travel: 2022: 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Greece sailing holiday for families

Greece sailing holiday for families

Sailing trip for families/friends in Greek islands
From 4,250 8 days ex flights
Small group travel
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 vacation

Greek Aegean Island hopping vacation

Get on board and visit ten stunning Aegean islands
From US $2,890 to US $4,390 8 days ex flights
Small group travel
10% off cruise fare for honeymoon couples, free cabin upgrade upon availability, Candle-lit dinner on board, free massage for two at the Jade Spas (selected ships) & A Bubbly Welcome Honeymoon treatment in your cabin
Greek Cyclades island hopping cruise

Greek Cyclades island hopping cruise

Greek Island Hopping, Sandy beaches and Clear azure waters
From US $2,790 to US $4,190 8 days ex flights
Small group travel: 2022: 30 Sep, 7 Oct, 14 Oct, 21 Oct
10% off cruise fare for honeymoon couples, free cabin upgrade upon availability, Candle-lit dinner on board, free massage for two at the Jade Spas (selected ships) & A Bubbly Welcome Honeymoon treatment in your cabin
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 vacation in the Aegean

Luxury sailing vacation 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
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 vacation Greece

Small group sailing vacation 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 vacation

Greek Islands sailing vacation

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
Saronic Islands sailing vacation in Greece

Saronic Islands sailing vacation 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 US $3,049 to US $3,199 8 days ex flights
Small group travel: 2023: 6 May, 27 May, 9 Sep, 16 Sep
Sailing and walking vacation in Greek Islands

Sailing and walking vacation 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 vacation

Greece family sailing vacation

Sailing adventure for families or friends in Greek islands
From 3,850 to 5,250 7 days ex flights
Small group travel: 2022: 16 Oct
2023: 30 Jul, 6 Aug, 13 Aug, 20 Aug, 27 Aug
Cyclades islands sailing vacations in Greece

Cyclades islands sailing vacations in Greece

A fantastic sailing adventure in the Cyclades islands!
From 1,380 to 1,950 8 days ex flights
Small group travel: 2022: 8 Oct
2023: 27 May, 17 Jun, 1 Jul, 2 Sep, 23 Sep
Gastronomy and sailing vacation in Greece

Gastronomy and sailing vacation 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 vacation in Greece

Freediving and sailing vacation in Greece

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

Greece sailing vacation in Ionian Sea

Sail, explore and experience the Ionian islands in Greece
From 600 7 days ex flights
Small group travel: 2022: 9 Oct
Saronic Gulf sailing vacation in Greece

Saronic Gulf sailing vacation 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: 1 Oct
2023: 20 May, 24 Jun, 26 Aug, 30 Sep
Special offer $120 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 vacation in Greece

Rhodes sailing vacation in Greece

Aegean sea island hopping and sailing school
From 2,100 to 4,350 8 days ex flights
Tailor made: Sailing during Greek summer in the Aegean Sea
Greek Islands family sailing vacation

Greek Islands family sailing vacation

Enjoy the beauty of the Greek islands
From US $1,350 8 days ex flights
Small group travel: 2023: 23 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug
Cyclades Islands sailing vacation, Greece

Cyclades Islands sailing vacation, Greece

Swim in turquoise seas & explore ancient towns
From US $2,317 to US $2,852 10 days ex flights
Small group travel: 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
Photo credits: [Page banner: Alex Antoniadis] [Cultural vacations : A.Savin] [Activities : Patrick Hendry] [On the water : pxhere] [Family vacations : Explore] [Where to go in Greece : momo]