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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!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

4 departures available

August - October

€650

Per person

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5.0

Super!

Cruise for Singles from Sanremo to Saint-Tropez

France: French Riviera and Porquerolles

8 days - 7 nights

One departure available

August

€750

Per person

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5.0

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

One departure available

July - August

€400

€360

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

3 departures available

September

€200

Per person

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5.0

Super!

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€690

€613

Per person

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4.7

Whale watching cruise with WWF guide between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

One departure available

July - August

€946

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

One departure available

July - August

€890

€680

Per person

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4.8

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

August - October

Starting from

€750

€675

Per person

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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!

Week in the north of Corsica, via Capraia - in company

Italy: Tuscany

7 days - 6 nights

One departure available

August

€890

Per person

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4.7

Kornati: the pearl of Croatia

Croatia: Kornati Islands

6 days - 7 nights

3 departures available

August

Starting from

€800

Per person

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5.0

Super!

Vento di Sicilia: from the Aeolian Islands to Trapani

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€920

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

18170 reviews

Long weekend among the queens of the archipelago - Elba and Capraia

07/24/2026

Eleonora F.

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IT

We couldn't have wished for a better skipper! Very professional but easy-going, prepared, always kind and available for any need. The boat is very well equipped and well organized. He made us experience the real thrill of sailing by explaining all the details of sailing. Highly recommended, we will definitely return to the sea with him! We saw beautiful places, a variety of coves and a super blue sea! THANK YOU EDO!
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Emerald Flotilla: La Maddalena Archipelago with Velasquez

07/24/2026

Donato F.

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IT

Claudio was an attentive and caring skipper but at the same time nice and fun! It was a pleasure to sail with him in the Maddalena archipelago and through the Strait of Bonifacio, with an eye always attentive to the weather conditions to do everything safely! Super recommended!
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Emerald Flotilla: La Maddalena Archipelago with Velasquez

07/24/2026

Stefano Carlo V.

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IT

Fantastic holiday Wonderful boat and prepared and engaging skipper ... holiday 🔝

The Island of Elba, to make you live a special experience!

07/24/2026

Filippo C.

Livio is an attentive and scrupulous skipper, a connoisseur of Elba, but also a nice and jovial person with whom to spend quality time. Highly recommended as a first experience.

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