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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!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

5 departures available

July - October

Starting from

€600

€540

Per person

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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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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€950

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

5 departures available

July - September

Starting from

€750

€675

Per person

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4.7

Whale watching cruise with researcher between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

2 departures available

July - August

Starting from

€946

Per person

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4.5

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August

Starting from

€850

Per person

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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

5 departures available

August - October

€650

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

2 departures available

September

€441

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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4.8

Super!

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€900

€855

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

8 departures available

July - September

Starting from

€700

Per person

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4.9

Super!

Weekend at the Pontine. Travel with photographer-Life changing experiences

Italy: Pontine Islands

3 days - 2 nights

3 departures available

September

Starting from

€370

€352

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

17939 reviews

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Weekend of emotions in Ponza and Palmarola!

07/3/2026

Francesco T.

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IT

The experience on board the [hidden] was truly splendid: well-kept boat, relaxed atmosphere and impeccable organization. Captain Valter proved to be professional, helpful and always attentive to make us experience the best of navigation in total safety. The coves of Ponza and Palmarola are wonderful, but what made everything even more special was the passion with which Valter accompanied us in this weekend of emotions. I recommend this experience to those looking for relaxation, beautiful sea and an authentic sail.

Sail in Menorca with a cook on board!

07/3/2026

Véronique S.

Everything was perfect! Very neat and very clean boat! Delicious Maussi's food and Alex the skipper very attentive and professional. You feel like part of a family. I recommend 100%.
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Four days in the Pontine Islands, just a stone's throw from Rome

07/3/2026

Simone G.

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IT

I spent fantastic days with Antonio: a true lover of the sea who knows what he is doing. Take it easy with him: he steers the boat safely and stress-free, always with a steady hand and a lot of experience. He knows perfectly the best places to anchor, the most hidden coves and the tricks of the weather, so every stop becomes a small treasure. Antonio is nice, helpful and knows how to put everyone at ease, even those who are at their first experience on a boat and, very importantly, he turned out to be an excellent cook!
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From Mykonos to Milos

07/2/2026

Maximiliano S.

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AR

Great experience, we traveled 2 couples and we are very grateful for all the attention provided by Andrea, we sailed through all the cyclades and she made us enjoy and share great moments and know places. Unique and incredible and having fun with our travel companions Elena, Patrick and Toni, who were very funny. A sublime experience.

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