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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

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

10 departures available

July - November

Starting from

€500

€425

Per person

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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

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5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August

€650

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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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

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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5.0

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

10 departures available

June - September

Starting from

€700

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

Per person

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5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

10 departures available

July - September

Starting from

€550

€495

Per person

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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

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

17811 reviews

Long weekend of June 2 in the archipelago of La Maddalena and south of Corsica

06/19/2026

Marco R.

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IT

It was a wonderful experience, from all points of view. The boat is kept in perfect condition and is very comfortable (availability of space, a bathroom for each cabin, for example). The care and attention of skipper Fabrizio in making guests feel at home are of a high level (towel and sheet kit, beautiful and quality, just to give an example). The destinations are beautiful, also thanks to the skipper's advice in finding the most beautiful, less crowded bays. An experience to be recommended and redone. Thank you Fabrizio.! Versione Italiana It was a truly wonderful experience in every respect. The boat, kept in perfect condition, is very comfortable (for example, thanks to the availability of space and a private bathroom for each cabin). The care and attention of the skipper, Fabrizio, in making guests feel at home are of a very high standard (just to give one example, the towel and linen kit provided is beautiful and of excellent quality). The destinations are stunning, also thanks to the skipper's advice in finding the most beautiful and less crowded bays. An experience highly recommended and definitely worth repeating. Thank you, Fabrizio!

Weekend of sea and colors between Ischia, Procida and Vivara

06/19/2026

FEDERICA L.

Really great sailing weekend! In addition to the beauty of the experience and the places visited, I had the opportunity to learn many things about the world of sailing. A special thanks to Emiliano, who with great competence and passion explained the operation of the boat, actively involving us and letting us try out different activities on board. It was a beautiful way to experience the sea not only as a passenger. Experience that I absolutely recommend to those who want to combine fun, adventure and learning!

Cruise to the Golden Islands via the capes and bay of St Tropez

06/19/2026

Keiko Y.

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JP

It’s a wonderful experience to cruise one of the most beautiful seas in summer. It’s also an opportunity to learn how to sail for beginners+ with very experienced and knowledgeable skipper Stephane.
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Weekend between Ponza and Palmarola Comfortable - max 4 people

06/18/2026

Cecilia M.

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IT

I loved this trip, I would do it again right away. I hope to find something similar in my area. both David and Antonella and Danila were welcoming, nice and competent people, there was not a single problem in all 3 days, thank you and see you soon, Palmarola amazed me with how wild it is.

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