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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Greece sailing holiday for families

Greece sailing holiday for families

Sailing trip for families/friends in Greek islands
From 750 to 960 8 days ex flights
Small group travel: 2024: 26 May, 2 Jun, 16 Jun, 30 Jun, 7 Jul, 28 Jul, 4 Aug, 11 Aug, 25 Aug, 1 Sep, 8 Sep, 15 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 805 to 892 7 days ex flights
Small group travel: 2024: 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul, 3 Aug, 10 Aug, 17 Aug, 24 Aug, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Cyclades sailing & walking vacation in Greece

Cyclades sailing & walking vacation in Greece

Combine a sailing & hiking adventure around the Cyclades
From 785 to 872 7 days ex flights
Small group travel: 2024: 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul, 3 Aug, 10 Aug, 17 Aug, 24 Aug, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct, 2 Nov
Sailing vacation in the Aegean Sea

Sailing vacation in the Aegean Sea

Uninhabited islands in a 6 person boat
From 690 to 767 7 days ex flights
Small group travel: 2024: 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul, 3 Aug, 10 Aug, 17 Aug, 24 Aug, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct, 2 Nov
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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.
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Family yacht charter sailing vacation in Greece

Family yacht charter sailing vacation in Greece

Private sailing with fun games, reliving mythical tales
From 2,100 to 2,910 8 days ex flights
Tailor made: This holiday is chartering the whole catamaran, minimum 6, maximum 10
Greece sailing vacation in Ionian Sea

Greece sailing vacation in Ionian Sea

Sail, explore and experience the Ionian islands in Greece
From 1,100 6 days ex flights
Small group travel: 2024: 23 Jun, 14 Jul, 28 Jul, 4 Aug, 11 Aug, 25 Aug, 8 Sep
Saronic Greek Islands luxury charter cruise

Saronic Greek Islands luxury charter cruise

Luxury sailing Greek islands, while reliving mythical tales
From 2,050 to 2,890 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
Yoga and sailing retreat in Greece

Yoga and sailing retreat in Greece

-A week of relaxation and yoga while sailing the Ionian sea!
From 800 to 1,000 7 days ex flights
Small group travel: 2024: 2 Jun, 30 Jun, 14 Jul
Sailing vacation in Greece, Mykonos to Santorini

Sailing vacation in Greece, Mykonos to Santorini

The boat, the beach and inviting Greek villages
From US $1,721 to US $2,155 8 days ex flights
Small group travel: 2024: 7 May, 11 May, 21 May, 25 May, 4 Jun, 8 Jun, 22 Jun, 2 Jul, 6 Jul, 16 Jul, 20 Jul, 30 Jul, 3 Aug, 13 Aug, 17 Aug, 27 Aug, 31 Aug, 10 Sep, 14 Sep, 24 Sep, 28 Sep
Greece family sailing vacation

Greece family sailing vacation

Sailing adventure for families or friends in Greek islands
From 4,750 7 days ex flights
Small group travel: 2024: 26 May, 2 Jun, 16 Jun, 30 Jun, 7 Jul, 28 Jul, 4 Aug, 11 Aug, 25 Aug, 8 Sep, 15 Sep, 22 Sep, 29 Sep
Freediving and sailing vacation in Greece

Freediving and sailing vacation in Greece

Sail, freedive and explore the Ionian Sea
From 1,350 7 days ex flights
Small group travel: 2024: 26 May, 19 Jun, 7 Jul, 1 Sep, 8 Sep, 13 Oct
Greek Islands family sailing vacation

Greek Islands family sailing vacation

Enjoy the beauty of the Greek islands
From US $1,340 to US $1,550 8 days ex flights
Small group travel: 2024: 21 Jul, 28 Jul, 4 Aug, 18 Aug
Sailing vacation in the Ionian Sea

Sailing vacation in the Ionian Sea

An unforgettable sailing adventure
From 690 to 767 7 days ex flights
Small group travel: 2024: 4 May, 18 May, 1 Jun, 15 Jun, 29 Jun, 13 Jul, 27 Jul, 10 Aug, 24 Aug, 7 Sep, 21 Sep
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: 2024: 31 May, 7 Jun, 21 Jun, 28 Jun, 5 Jul, 12 Jul, 26 Jul, 2 Aug, 23 Aug
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.
1-866-821-6866
Call toll free
Calling from outside the USA
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: 2024: 19 Apr, 26 Apr, 3 May, 10 May, 17 May, 24 May, 14 Jun, 21 Jun, 28 Jun, 5 Jul, 12 Jul, 19 Jul, 26 Jul, 16 Aug, 30 Aug, 6 Sep, 13 Sep, 20 Sep, 27 Sep, 4 Oct, 11 Oct, 18 Oct
Sailing & conservation vacation in Greece

Sailing & conservation vacation in Greece

A unique wildlife & sailing adventure
From 785 to 872 7 days ex flights
Small group travel: 2024: 4 May, 11 May, 18 May, 25 May, 1 Jun, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Greek Islands sailing vacation, Santorini to Mykonos

Greek Islands sailing vacation, Santorini to Mykonos

Sapphire waters, whitewashed villages & history laden ruins
From US $1,721 to US $1,940 8 days ex flights
Small group travel: 2024: 4 May, 14 May, 18 May, 28 May, 1 Jun, 15 Jun, 25 Jun, 29 Jun, 9 Jul, 13 Jul, 23 Jul, 27 Jul, 6 Aug, 10 Aug, 20 Aug, 24 Aug, 3 Sep, 7 Sep, 17 Sep, 21 Sep, 1 Oct
Ionian Islands sailing and walking vacation

Ionian Islands sailing and walking vacation

Sail and walk around the Ionian islands, Greece
From 890 to 990 7 days ex flights
Small group travel: 2024: 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Small ship sail powered Greek Island cruise

Small ship sail powered Greek Island cruise

-Sail on a beautiful ship around the Greek Islands
From 4,402 to 4,650 8 days ex flights
Small group travel: 2024: 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul, 3 Aug, 10 Aug, 17 Aug, 24 Aug, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct
Sailing and archaeology vacation in Greece

Sailing and archaeology vacation in Greece

A unique sailing adventure through Greece's ancient history!
From 2,600 8 days ex flights
Small group travel: 2024: 11 May, 12 Oct
Luxury Greece yacht charter in the Aegean

Luxury Greece yacht charter in the Aegean

Luxury sailing the Aegean, while reliving mythical tales
From 2,100 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
Yacht charter in Ionian Greek Islands

Yacht charter in Ionian Greek Islands

Luxury sailing in the Greek islands, reliving mythical tales
From 2,100 to 2,910 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 $3,495 7 days ex flights
Small group travel: 2024: 18 May
Cyclades islands sailing vacations in Greece

Cyclades islands sailing vacations in Greece

A fantastic sailing adventure in the Cyclades islands!
From 2,300 to 2,450 8 days ex flights
Small group travel: 2024: 8 Jun, 6 Jul, 7 Sep, 21 Sep
Gastronomy and sailing vacation in Greece

Gastronomy and sailing vacation in Greece

Explore the Greek islands and their gastronomy with a chef!
From 970 7 days ex flights
Small group travel: 2024: 8 Sep, 15 Sep
Saronic Gulf sailing vacation in Greece

Saronic Gulf sailing vacation in Greece

An 8 day trip combines sailing & swimming in Greece
From 2,180 to 2,450 8 days ex flights
Small group travel: 2024: 25 May, 13 Jul, 24 Aug, 5 Oct
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 Island Cruise

Greek Island Cruise

Discover Greece on this relaxing cruise around Evia
From US $1,340 to US $1,410 8 days ex flights
Small group travel: 2024: 16 Jun, 23 Jun, 30 Jun, 7 Jul, 25 Aug, 1 Sep, 15 Sep, 22 Sep
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: 2024: 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, 23 Oct, 30 Oct
Cyclades Islands sailing vacation, Greece

Cyclades Islands sailing vacation, Greece

Swim in turquoise seas & explore ancient towns
From US $2,533 to US $2,823 10 days ex flights
Small group travel: 2024: 4 May, 14 May, 24 May, 3 Jun, 7 Jun, 13 Jun, 17 Jun, 23 Jun, 27 Jun, 3 Jul, 7 Jul, 13 Jul, 17 Jul, 23 Jul, 27 Jul, 2 Aug, 6 Aug, 12 Aug, 16 Aug, 22 Aug, 26 Aug, 1 Sep, 5 Sep, 11 Sep, 15 Sep, 21 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]