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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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5.0

New

Just relaxing while sailing on the Côte d'Azur

France: French Riviera and Porquerolles

2 days - 2 nights

One departure available

September

€450

Per person

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4.9

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

Greece: Sporades

6 days - 7 nights

2 departures available

September

Starting from

€750

Per person

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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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5.0

Let's discover Portofino, Santa Margherita and Sestri Levante together

Italy: Liguria

2 days - 2 nights

6 departures available

September - November

Starting from

€380

Per person

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

€1,161

Per person

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4.4

Ocean miles Malaga-Lanzarote

Atlantic islands: Canary Islands

11 days - 11 nights

One departure available

October - November

€1,490

Per person

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€350

Per person

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4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€890

Per person

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4.5

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€845

€676

Per person - min 2 pax

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

€325

€309

Per person

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4.9

Weekend sailing course from Bandol

France: French Riviera and Porquerolles

2 days - 1 night

6 departures available

September - November

€301

Per person

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5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

4 departures available

September - October

Starting from

€1,100

Per person

Why book a holiday with Sailsquare?

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

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

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

19051 reviews

Egadi mon amour: seven days to fall in love, be amazed and relax.

09/7/2026

Monica Sofia S.

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IT

Giuseppe is a very prepared and competent skipper, as well as nice.
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A sailing story between Favignana, Levanzo and Marettimo

09/7/2026

DANIELA L.

-

IT

... Fantastic week thanks both to the company but above all to the engaging sympathy and the undisputed professionalism of the skipper Stefano ... always available and attentive to everyone's needs ... highly recommended... I thank everyone for the wonderful experience

Unforgettable adventure in the Aeolian Islands

09/7/2026

Elisabetta M.

First of all, for our choice as a group too much navigation from Palermo to the islands (2 days lost) the boat needs maintenance and accessories inside (from the 4th day we no longer sailed). Elizabeth
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Sailing in the magical Sardinia of the South

09/7/2026

Elisa C.

-

IT

A truly unforgettable first experience on a sailing boat, which far exceeded my expectations. A week lived between the sea, beautiful landscapes and a pleasant and relaxed atmosphere, which made me discover how fascinating it can be to experience the sea in this way. A special thanks to Gianluca, our captain, for his professionalism and, above all, for the great passion he puts into his work. An authentic passion, which he manages to convey naturally to guests, making the experience even more interesting and engaging. Thanks also to Valeria and Francesco, always available, kind and attentive, who together with Gianluca helped to create a pleasant and well-organized environment. It was an experience that gave me emotions, lightness and beautiful memories. A week that flew by too quickly, but that left me wanting to come back soon!

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