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Greek island hopping on a sailboat

Sailing holidays in Greece, enjoy the charm of the many islands
27 reviews
Climb aboard and go Greek Island hopping on a sailboat. You will get to know the many different towns and picturesque villages and be amazed by the natural beauty of the landscape. Choose the plan that is right for you and enjoy the tranquility of a holiday around the Greek Islands.
Choose from 46 experiences
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Boat holidays greece
Greece is one of the most popular destinations for those who want to enjoy a boating holiday. The coast and the hundreds of Greek islands hide some of the best sailing spots in the whole Mediterranean, which is why thousands of sailors visit its waters every year.
  • Claudia Krug
  • Alvaro G
By Álvaro García y Claudia Krug
10 January, 2023
Next plans
Experience Start Plazas Price
Share & Sail ex-Syros, 7days/6nights
From 29 Apr to 5 May
29 Apr
7 days
8 More information Reserve for 990€
Corfu Sightseeing & Relaxation Yacht Cabin Charter
From 2 May to 9 May
2 May
8 days
25 More information Reserve for 1,000€
Zakynthos Ionian Islands Sightseeing & Relaxation Cruise
From 2 May to 9 May
2 May
8 days
25 More information Reserve for 1,000€
Half Board Gulet Holiday from Rhodes
From 2 May to 9 May
2 May
8 days
24 More information Reserve for 1,200€
8-day/7-night Saronic gulet cruise!
From 2 May to 9 May
2 May
8 days
4 More information Reserve for 929€
Discover Greece on a sailing cruise in the Saronic Gulf
From 2 May to 9 May
2 May
8 days
6 More information Reserve for 630€
Share & Sail ex-Syros, 7days/6nights
From 6 May to 12 May
6 May
7 days
8 More information Reserve for 990€
Salamina Party & Relaxation Yacht Cabin Charter
From 9 May to 16 May
9 May
8 days
46 More information Reserve for 850€
Corfu Sightseeing & Relaxation Yacht Cabin Charter
From 9 May to 16 May
9 May
8 days
25 More information Reserve for 1,000€
Zakynthos Ionian Islands Sightseeing & Relaxation Cruise
From 9 May to 16 May
9 May
8 days
25 More information Reserve for 1,000€
Half Board Gulet Holiday from Rhodes
From 9 May to 16 May
9 May
8 days
24 More information Reserve for 1,200€
8-day/7-night Zante gulet cruise!
From 9 May to 16 May
9 May
8 days
4 More information Reserve for 899€
8-day/7-night Rhodes gulet cruise!
From 9 May to 16 May
9 May
8 days
2 More information Reserve for 949€
8-day/7-night Saronic gulet cruise!
From 9 May to 16 May
9 May
8 days
4 More information Reserve for 929€
Discover Greece on a sailing cruise in the Saronic Gulf
From 9 May to 16 May
9 May
8 days
6 More information Reserve for 630€
Salamina Party & Relaxation Yacht Cabin Charter
From 16 May to 23 May
16 May
8 days
46 More information Reserve for 850€
Corfu Sightseeing & Relaxation Yacht Cabin Charter
From 16 May to 23 May
16 May
8 days
25 More information Reserve for 1,000€
Zakynthos Ionian Islands Sightseeing & Relaxation Cruise
From 16 May to 23 May
16 May
8 days
25 More information Reserve for 1,000€
8-day/7-night Saronic gulet cruise!
From 16 May to 23 May
16 May
8 days
4 More information Reserve for 989€
Discover Greece on a sailing cruise in the Saronic Gulf
From 16 May to 23 May
16 May
8 days
6 More information Reserve for 630€
Sailing holidays in the Sporades Islands of Greece: relaxation and sports
From 17 May to 24 May
17 May
8 days
6 More information Reserve for 495€
Salamina Party & Relaxation Yacht Cabin Charter
From 23 May to 30 May
23 May
8 days
46 More information Reserve for 850€
Corfu Sightseeing & Relaxation Yacht Cabin Charter
From 23 May to 30 May
23 May
8 days
25 More information Reserve for 1,000€
8-day/7-night Corfu gulet cruise!
From 23 May to 30 May
23 May
8 days
4 More information Reserve for 889€
8-day/7-night Saronic gulet cruise!
From 23 May to 30 May
23 May
8 days
4 More information Reserve for 989€
Discover Greece on a sailing cruise in the Saronic Gulf
From 23 May to 30 May
23 May
8 days
5 More information Reserve for 630€
Greece Catamaran Sailing Experience — Cyclades Islands
From 23 May to 30 May
23 May
8 days
0 More information No availability
Greece Catamaran Sailing Experience — Cyclades Islands
From 23 May to 6 Jun
23 May
15 days
7 More information Reserve for 3,325€
The Saronic Islands by sail, with skipper and on-board cuisine
From 26 May to 1 Jun
26 May
7 days
5 More information Reserve for 950€
Share & Sail ex-Athens: 6days/5nights
From 28 May to 2 Jun
28 May
6 days
8 More information Reserve for 880€
Corfu Sightseeing & Relaxation Yacht Cabin Charter
From 30 May to 6 Jun
30 May
8 days
25 More information Reserve for 1,000€
Greece Catamaran Sailing Experience — Cyclades Islands
From 30 May to 6 Jun
30 May
8 days
0 More information No availability
Half Board Gulet Holiday from Rhodes
From 30 May to 6 Jun
30 May
8 days
24 More information Reserve for 1,200€
Sailing holidays in the Sporades Islands of Greece: relaxation and sports
From 31 May to 7 Jun
31 May
8 days
8 More information Reserve for 630€
Discover Greece on a sailing cruise in the Saronic Gulf
From 31 May to 6 Jun
31 May
7 days
6 More information Reserve for 855€
The Saronic Islands by sail, with skipper and on-board cuisine
From 2 Jun to 8 Jun
2 Jun
7 days
4 More information Reserve for 950€
Share & Sail ex-Athens: 6days/5nights
From 3 Jun to 8 Jun
3 Jun
6 days
8 More information Reserve for 880€
Corfu Sightseeing & Relaxation Yacht Cabin Charter
From 6 Jun to 13 Jun
6 Jun
8 days
25 More information Reserve for 1,000€
A Week's Sailing in the Ionian Islands: The Ultimate Experience in Greece
From 6 Jun to 12 Jun
6 Jun
7 days
4 More information Reserve for 4,500€
8-day/7-night Saronic gulet cruise!
From 6 Jun to 13 Jun
6 Jun
8 days
4 More information Reserve for 989€
Discover Greece on a sailing cruise in the Saronic Gulf
From 6 Jun to 13 Jun
6 Jun
8 days
6 More information Reserve for 765€
Zakynthos Ionian Islands Sightseeing & Relaxation Cruise
From 6 Jun to 13 Jun
6 Jun
8 days
25 More information Reserve for 1,000€
Sailing holidays in the Sporades Islands of Greece: relaxation and sports
From 7 Jun to 14 Jun
7 Jun
8 days
8 More information Reserve for 630€
From Mykonos to Kos: sailing with hostess on board
From 7 Jun to 14 Jun
7 Jun
8 days
4 More information Reserve for 669€
The Saronic Islands by sail, with skipper and on-board cuisine
From 9 Jun to 15 Jun
9 Jun
7 days
5 More information Reserve for 950€
Corfu Sightseeing & Relaxation Yacht Cabin Charter
From 13 Jun to 20 Jun
13 Jun
8 days
25 More information Reserve for 1,000€
A Week's Sailing in the Ionian Islands: The Ultimate Experience in Greece
From 13 Jun to 19 Jun
13 Jun
7 days
4 More information Reserve for 4,500€
8-day/7-night Rhodes gulet cruise!
From 13 Jun to 20 Jun
13 Jun
8 days
2 More information Reserve for 1,009€
8-day/7-night Saronic gulet cruise!
From 13 Jun to 20 Jun
13 Jun
8 days
4 More information Reserve for 989€
Discover Greece on a sailing cruise in the Saronic Gulf
From 13 Jun to 20 Jun
13 Jun
8 days
6 More information Reserve for 765€
Half Board Gulet Holiday from Rhodes
From 13 Jun to 20 Jun
13 Jun
8 days
24 More information Reserve for 1,200€
Sailing holidays in the Sporades Islands of Greece: relaxation and sports
From 14 Jun to 21 Jun
14 Jun
8 days
8 More information Reserve for 630€
From Attica to Mykonos by sail, with skipper and on-board cuisine
From 16 Jun to 22 Jun
16 Jun
7 days
5 More information Reserve for 1,000€
Corfu Sightseeing & Relaxation Yacht Cabin Charter
From 20 Jun to 27 Jun
20 Jun
8 days
25 More information Reserve for 1,000€
Zakynthos Ionian Islands Sightseeing & Relaxation Cruise
From 20 Jun to 27 Jun
20 Jun
8 days
25 More information Reserve for 1,000€
Half Board Gulet Holiday from Rhodes
From 20 Jun to 27 Jun
20 Jun
8 days
24 More information Reserve for 1,200€
A Week's Sailing in the Ionian Islands: The Ultimate Experience in Greece
From 20 Jun to 26 Jun
20 Jun
7 days
4 More information Reserve for 4,500€
8-day/7-night Saronic gulet cruise!
From 20 Jun to 27 Jun
20 Jun
8 days
4 More information Reserve for 989€
Discover Greece on a sailing cruise in the Saronic Gulf
From 20 Jun to 27 Jun
20 Jun
8 days
6 More information Reserve for 765€
Sailing holidays in the Sporades Islands of Greece: relaxation and sports
From 21 Jun to 28 Jun
21 Jun
8 days
0 More information No availability
Mykonos and the Cyclades Islands by sailboat, with skipper and on-board cuisine
From 23 Jun to 29 Jun
23 Jun
7 days
0 More information No availability
Zakynthos Ionian Islands Sightseeing & Relaxation Cruise
From 27 Jun to 4 Jul
27 Jun
8 days
25 More information Reserve for 1,000€
A Week's Sailing in the Ionian Islands: The Ultimate Experience in Greece
From 27 Jun to 3 Jul
27 Jun
7 days
4 More information Reserve for 4,500€
8-day/7-night Saronic gulet cruise!
From 27 Jun to 4 Jul
27 Jun
8 days
4 More information Reserve for 989€
Among the mythical Cyclades, from Thira to Milos on my catamaran
From 27 Jun to 4 Jul
27 Jun
8 days
4 More information Reserve for 783€
Among the mythical Cyclades, from Thira to Milos on my catamaran
From 27 Jun to 4 Jul
27 Jun
8 days
4 More information Reserve for 783€
Discover Greece on a sailing cruise in the Saronic Gulf
From 27 Jun to 4 Jul
27 Jun
8 days
6 More information Reserve for 990€
Salamina Party & Relaxation Yacht Cabin Charter
From 27 Jun to 4 Jul
27 Jun
8 days
46 More information Reserve for 850€
Sailing holidays in the Sporades Islands of Greece: relaxation and sports
From 28 Jun to 5 Jul
28 Jun
8 days
0 More information No availability
Mykonos and the Cyclades Islands by sailboat, with skipper and on-board cuisine
From 30 Jun to 6 Jul
30 Jun
7 days
0 More information No availability
Salamina Party & Relaxation Yacht Cabin Charter
From 4 Jul to 11 Jul
4 Jul
8 days
46 More information Reserve for 1,000€
Corfu Sightseeing & Relaxation Yacht Cabin Charter
From 4 Jul to 11 Jul
4 Jul
8 days
25 More information Reserve for 1,200€
Zakynthos Ionian Islands Sightseeing & Relaxation Cruise
From 4 Jul to 11 Jul
4 Jul
8 days
25 More information Reserve for 1,200€
Half Board Gulet Holiday from Rhodes
From 4 Jul to 11 Jul
4 Jul
8 days
24 More information Reserve for 1,400€
A Week's Sailing in the Ionian Islands: The Ultimate Experience in Greece
From 4 Jul to 10 Jul
4 Jul
7 days
4 More information Reserve for 4,500€
8-day/7-night Corfu gulet cruise!
From 4 Jul to 11 Jul
4 Jul
8 days
4 More information Reserve for 1,079€
8-day/7-night Zante gulet cruise!
From 4 Jul to 11 Jul
4 Jul
8 days
4 More information Reserve for 1,079€
8-day/7-night Rhodes gulet cruise!
From 4 Jul to 11 Jul
4 Jul
8 days
2 More information Reserve for 1,129€
8-day/7-night Saronic gulet cruise!
From 4 Jul to 11 Jul
4 Jul
8 days
4 More information Reserve for 1,109€
Gone with the wind, in the sea of Ulysses between the Greek islands
From 4 Jul to 11 Jul
4 Jul
8 days
6 More information Reserve for 655€
Sailing holiday in Greece: Ionian Islands with hostess
From 4 Jul to 11 Jul
4 Jul
8 days
8 More information Reserve for 750€
Discover Greece on a sailing cruise in the Saronic Gulf
From 4 Jul to 11 Jul
4 Jul
8 days
6 More information Reserve for 990€
Sailing holidays in the Sporades Islands of Greece: relaxation and sports
From 5 Jul to 12 Jul
5 Jul
8 days
0 More information No availability
Mykonos and the Cyclades Islands by sailboat, with skipper and on-board cuisine
From 7 Jul to 13 Jul
7 Jul
7 days
1 More information Reserve for 1,000€
Corfu Sightseeing & Relaxation Yacht Cabin Charter
From 11 Jul to 18 Jul
11 Jul
8 days
25 More information Reserve for 1,200€
Zakynthos Ionian Islands Sightseeing & Relaxation Cruise
From 11 Jul to 18 Jul
11 Jul
8 days
25 More information Reserve for 1,200€
Half Board Gulet Holiday from Rhodes
From 11 Jul to 18 Jul
11 Jul
8 days
24 More information Reserve for 1,400€
A Week's Sailing in the Ionian Islands: The Ultimate Experience in Greece
From 11 Jul to 17 Jul
11 Jul
7 days
4 More information Reserve for 4,500€
8-day/7-night Corfu gulet cruise!
From 11 Jul to 18 Jul
11 Jul
8 days
4 More information Reserve for 1,079€
8-day/7-night Zante gulet cruise!
From 11 Jul to 18 Jul
11 Jul
8 days
4 More information Reserve for 1,079€
8-day/7-night Rhodes gulet cruise!
From 11 Jul to 18 Jul
11 Jul
8 days
2 More information Reserve for 1,129€
8-day/7-night Saronic gulet cruise!
From 11 Jul to 18 Jul
11 Jul
8 days
4 More information Reserve for 1,109€
Gone with the wind, in the sea of Ulysses between the Greek islands
From 11 Jul to 18 Jul
11 Jul
8 days
6 More information Reserve for 655€
Sailing holiday in Greece: Ionian Islands with hostess
From 11 Jul to 18 Jul
11 Jul
8 days
7 More information Reserve for 750€
Discover Greece on a sailing cruise in the Saronic Gulf
From 11 Jul to 18 Jul
11 Jul
8 days
6 More information Reserve for 990€
Sailing holidays in the Sporades Islands of Greece: relaxation and sports
From 12 Jul to 19 Jul
12 Jul
8 days
0 More information No availability
Dodecanese Sailing: Mediterranean Itinerary with a Hostess on Board
From 12 Jul to 19 Jul
12 Jul
8 days
2 More information Reserve for 836€
From Mykonos to Milos, sailing in the Cyclades with a skipper and onboard cuisine
From 14 Jul to 20 Jul
14 Jul
7 days
6 More information Reserve for 1,050€
Corfu Sightseeing & Relaxation Yacht Cabin Charter
From 18 Jul to 25 Jul
18 Jul
8 days
25 More information Reserve for 1,200€
Zakynthos Ionian Islands Sightseeing & Relaxation Cruise
From 18 Jul to 25 Jul
18 Jul
8 days
25 More information Reserve for 1,200€
Show all dates
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  • Why do a sailboat cruise in Greece with Sailwiz?

    You will enjoy a vacation to remember forever, aboard a sailboat. You will arrive sailing to cities and towns that you will fall in love with at first sight. In several days you can visit several islands and meet new people.
  • Sailboat cruises in Greece

    The Greek Islands are composed of several archipelagos, each with its own charms. The advantage of sailing on a sailboat is that you will not have to make large displacements to travel several of these islands.
  • What to see on the Greece cruise?

    Depending on the route we choose, you can visit more or fewer islands.

    Mykonos is one of the islands that we can highlight, its capital Chora, an authentic maze of white buildings and narrow alleyways. A true paradise both from far and near.

    One of the most photographed places is Santorini, an island formed on the caldera of an ancient volcano, hence its impressive cliffs. When you are in Fira (Thira) on the sailboat you can take some amazing photos where you will see the blue vaults of the church and the white buildings. Fira is a more touristy population while Oia is a quieter and more evocative place.

    Rhodes, an island near Turkey has a totally different landscape than the previous islands. This flirtatious "medieval" city has abundant vegetation and mountainous orography.

    Crete is the largest island in Greece, stands out for its mountainous orography. An island of idyllic beaches, lost corners, dream villages and nature worthy of admiration; An island of contrasts full of color and joy.

    Corfu has a bright beauty, with immense beaches and coves. We can find of all kinds some more cosmopolitan, other deserted, where to enjoy the nature of Greece.
  • What is the price of a sailboat cruise in Greece?
    The price range varies mainly depending on the duration of the holidays, the type of boat, the places to be visited.

    The Saronic Golfo is one of the prettiest destinations to visit while sailing. Given its meteorological conditions, for its beautiful mountainous landscapes, completely flat beaches, beautiful blue waters to sail around Greece by sailboat ...

    The distances between islands from a sailboat are very short, where you can make many stops on the most wonderful beaches you can imagine. You will also visit its picturesque villages that have a lot of charm.

    Are you going to miss going on a sailboat cruise in Greece?
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