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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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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

6 departures available

September - October

Starting from

€1,300

€1,040

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

September - October

Starting from

€700

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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5.0

Super!

Weekend of the Pontine Islands to discover Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

€490

€441

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

3 departures available

September

Starting from

€441

€419

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€750

€675

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€570

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€550

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

18933 reviews

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.

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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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Let's discover the Aeolian Islands together by sailing

08/30/2026

Gaudenzia B.

-

IT

Mario was able to make us feel all the magic of these extraordinary islands and give us a lot of laughs! [hidden] forever in our hearts!

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