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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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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

€430

Per person

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4.7

Palma de Mallorca All Inclusive on 18m Ketch

Spain: The Balearic Islands

6 days - 7 nights

2 departures available

September

€1,290

Per person

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5.0

Midweek Tuscan archipelago

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€500

Per person

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5.0

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€295

Per person

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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August - September

€850

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

October

Starting from

€950

Per person

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4.8

COUS COUS FEST: Un Week End di Mare, Vela, Cous Cous e Musica!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

7 departures available

September - October

€320

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

30 departures available

January - December

Starting from

€300

€270

Per person

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5.0

A sailing story between Favignana, Levanzo and Marettimo

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€620

Per person

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4.4

Atlantic crossing by sailboat from Tenerife to the Caribbean

Caribbean: Grenadines & Martinique

20 days - 20 nights

One departure available

November - December

€3,900

Per person

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4.8

Egadi paradise for sailing and snorkeling

Italy: Aegadian islands

6 days - 7 nights

3 departures available

September - October

Starting from

€600

Per person

Why book a holiday with Sailsquare?

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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

18934 reviews

Sailing among the Islands of Ulysses. Stewardess on board

08/30/2026

Giovanna Paola C.

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IT

Nice experience

Southern Corsica & Maddalena - embarkation and disembarkation from Tuscany

08/30/2026

DEBORAH F.

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IT

It was a great week! ⛵️ We sailed between Elba, Northern Corsica and Capraia. Unfortunately, due to weather conditions, it was not possible to follow exactly the planned itinerary, but this did not detract from the beauty of the holiday. In fact, most of the time we were able to open the sails and fully enjoy the thrill of sailing. Francesco, the Captain, was able to involve the whole crew, transmitting his passion for sailing and making everyone part of the experience. He is a person who is very attentive to everyone's needs, competent and with great experience, but above all capable of instilling safety and harmony on board. The boat is comfortable and spacious. We spent a week between wine, laughter and sea . And there was no shortage of good food either, thanks to the luck of having missed chefs on board! A truly top crew. My experience was super positive; unlike what I read in some reviews, I highly recommend the week aboard [hidden] with Francesco.

Sailing among the Islands of Ulysses. Stewardess on board

08/30/2026

Laura C.

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IT

A great week! Thanks to the skipper Lionor always attentive and professional and to Ansel best sailor and an excellent cook, they made this boat holiday an unforgettable experience. Highly recommended!

North Corsica & Tuscan Archipelago: we love to travel a lot

08/30/2026

Fiorella F.

-

IT

Lucky experience for time, boat and company, as well as for the competence shown by Marco, an experienced and far-sighted captain who was able to foresee and manage every situation well. Highly recommend to try!!

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