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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

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

Greece: Sporades

6 days - 7 nights

2 departures available

May - June

Starting from

€850

Per person

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5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

April - May

€450

Per person

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4.9

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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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5.0

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The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

7 departures available

July - September

Starting from

€650

Per person

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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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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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4.8

Super!

Paros Serifos Kytnos the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€950

€855

Per person

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5.0

Super!

Short cruise to Milos, Kimolos and Poliegios

Greece: Cyclades

3 days - 3 nights

One departure available

June

€420

Per person

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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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4.8

Super!

Discovering the wild Peloponnese

Greece: Peloponnese

7 days - 7 nights

One departure available

July

€880

€792

Per person

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4.8

Super!

From Cagliari to Cannigione.. exploring the east coast of Sardinia

Italy: Southern Sardinia

6 days - 7 nights

One departure available

May

€550

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

17617 reviews

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Thailand: a dream to discover while sailing

02/2/2026

Giovanna C.

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France

Giovanni and Raffaela are two skippers with their hearts in their hands. In addition to being excellent sailors, they are extremely hospitable people, helpful and attentive to every need of guests. professionalism in managing all aspects of navigation, always calmly and safely, and care for the well-being of everyone on board. It was our first trip to Thailand - short but we will be back An experience that we absolutely recommend! Joan and Mary
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Cape Horn and Patagonia Glaciers Expedition 15 days/14 nights

01/31/2026

Francesco C.

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Italy

A dream that has become reality! Passing Cape Horn under sail cannot be described. The expedition both from a sailing and naturalistic point of view was fantastic. Laurent is a very good skipper from all points of view, the emotions in crossing certain landscapes are incredible. The on-board company is just as pleasant. However, the difference is made by Laurent: prepared, reliable, calm, helpful and much more. An experience that I recommend to all sailors! Thank you Laurent !!
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Midweek special on the island of Elba, 2 nights

01/24/2026

Sara M.

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Italy

I left with my brother: there were 7 of us, plus Marco. It was our first boat experience and we couldn't ask for anything better! Marco was extremely kind, helpful and attentive to every detail. The combination of the boat excursion and the trekking on the island was simply fantastic, everything impeccably organized. In addition, there was also the opportunity to enjoy free time in total relaxation. I absolutely recommend this experience with Marco!
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Wellness Adventure Retreat

01/14/2026

Donna S.

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Canada

We had an amazing time on board. Great food. Lots of activities. We got to see sharks, dolphins, and many types of tropical fish. Luca was a great host. The boat was beautiful and very clean. The location was absolutely stunning!

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