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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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4.9

Super!

Sailing Sporades: A Green Paradise in the Heart of the Aegean

Greece: Sporades

6 days - 7 nights

One departure available

June

€890

Per person

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4.9

Super!

Kavala Thassos Samothraki Limnos on a magnificent 15-meter boat

Greece: North Egean Islands

7 days - 7 nights

One departure available

May - June

€800

Per person - min 2 pax

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4.9

Super!

Dodecanese: Fast Sailing, Crystal Clear Seas and Gourmet Cuisine

Greece: Dodecanese

6 days - 7 nights

One departure available

July

€950

Per person

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5.0

Super!

One way from Neptune to the paradise of Sardinia

Italy: Northern Sardinia

6 days - 6 nights

One departure available

July

€1,250

Per person

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4.9

Super!

The North Dodecanese from Samos on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

2 departures available

June - July

€1,000

Per person - min 2 pax

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4.9

Super!

From Milos to Zakynthos: the Peloponnese on a magnificent 15-meter boat

Greece: Peloponnese

10 days - 10 nights

One departure available

September

€900

Per person - min 2 pax

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4.8

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

July - August

€900

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€890

Per person

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4.8

Super!

From Kalamata to Milos: the fantastic and wild South Peloponnese

Greece: Cyclades

7 days - 7 nights

One departure available

July

€900

Per person

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4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

€903

Per person

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4.9

Super!

Chios, Oinoussa, Fournoi and Samos on a magnificent 15-meter boat

Greece: North Egean Islands

7 days - 7 nights

One departure available

June

€800

Per person - min 2 pax

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4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

6 departures available

June - August

Starting from

€1,052

€999

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

17628 reviews

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Easter in Capraia and Corsica

04/14/2026

Giunio M.

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Italy

Wonderful days in the company of quiet people and lovers of the sea and sailing
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Offshore and night navigation course on cabin cruisers

04/13/2026

Marco B.

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Italy

Sailing course... but also a holiday. Navigation to Giglio and back via Elba with departure at night. Despite the little wind that blew in those days, Paolo was able to convey notions and make the students practice, all with the utmost sympathy ... Be prepared to be made fun of, especially if you're an engineer.
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Easter on the Island of Elba

04/9/2026

Miriam C.

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Italy

Very pleasant sailing experience. The boat was in good condition. Everything went according to expectations and the navigation was safe and relaxing. The only negative note concerns the owner, Enrico. During communications he was often grumpy, with a rather rigid attitude and not inclined to confrontation. This made the interaction less pleasant, especially at times when more availability and friendliness would have been useful. Overall, I recommend the experience for the quality of the boat and the service at sea, but I suggest the owner to improve the approach with customers to make everything really impeccable.
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Easter in Capraia and Corsica

04/9/2026

Monica L.

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Italy

Weekend absolutely up to expectations. Marco is a trained skipper, with great experience, very helpful, kind and caring towards his crew. His boat is hospitable and excellently cared for by him. All positive!!

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