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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

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September - October

€242

€218

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

6 departures available

July - October

€260

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

15 departures available

June - November

Starting from

€600

€540

Per person

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4.9

Super!

Leave everything for the Island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

July

€320

Per person

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5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

9 departures available

July - September

Starting from

€550

€495

Per person

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New

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

4 departures available

June - July

Starting from

€300

€270

Per person

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

3 departures available

June - September

€280

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

5 departures available

July - September

Starting from

€400

€360

Per person

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5.0

Super!

Sail in Menorca with a cook on board!

Spain: The Balearic Islands

5 days - 5 nights

3 departures available

June - August

Starting from

€950

€808

Per person

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4.9

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

Per person

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4.9

Super!

Fast Sailing Experience between Authentic Islands and Good Food

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.8

Super!

From Milos to Athens: the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

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

17796 reviews

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Four days in Ponza and Palmarola

06/16/2026

Daniela A.

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IT

I have been sailing since the age of 8 and have crossed many seas in different conditions and I can say that such an experienced skipper as Fabio is difficult and rare to meet. Reliable, professional and precise in maneuvering... Nothing left to chance..... We sailed night and day without any worries due to his experience. Together with his unquestionable skill as a skipper, I discovered a great personality: nice, patient and polite. Excellent travel companions. Thank you for the wonderful experience.
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Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

06/16/2026

Stefano S.

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IT

Pleasant week on a comfortable boat with a skipper who loves to sail even with little wind in a beautiful area.
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Giglio or Elba the pearls of the Tuscan archipelago

06/16/2026

Moira C.

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IT

I spent 2 fantastic days, together with wonderful people, I couldn't ask for anything better. Cleanliness, kindness and safety assured! I have traveled a lot by sailboat and have always felt safe. I will definitely be back on the boat with Simone, an attentive, kind and polite skipper. Thank you!

Four days in Ponza and Palmarola

06/16/2026

laura B.

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IT

The days spent on the boat with skipper Fabio and all the other companions were a breath of serenity and lightness for me and my daughter. Exceptional skipper and unforgettable travel companions. Thank you for the wonderful experience.

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