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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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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!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

2 departures available

July - September

€740

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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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

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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5.0

Holiday in the Aeolian Islands: comfort, adventure and music! - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August

€1,050

Per person

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5.0

Super!

ONE WAY Marina River - Porto Vecchio

France: Corsica

3 days - 3 nights

One departure available

August

€290

Per person

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4.4

Magnificent weekend of approach to sailing on the island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

July

€250

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

17915 reviews

Leave everything for the Island of Elba

06/29/2026

Marco D.

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IT

Really crazy experience! We were a group of 6 friends and had a blast. Impeccable organization, Joshua q super helpful and great atmosphere. It was a different experience than usual, perfect to share with friends and to remember. We absolutely recommend it to anyone who wants to spend a weekend full of fun and the sea. Definitely to be redone!

Week end Liguria Costa Azzurra

06/29/2026

salvatore r.

-

IT

It was a great experience... Olaf TOP👍
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Weekend of sea and colors between Ischia, Procida and Vivara

06/29/2026

Manuela M.

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IT

Very nice experience, comfortable and clean boat, Gennaro the skipper a person always available and kind. Highly recommended!

An exclusive weekend on Elba between aperitifs and sailing

06/29/2026

Alessandra R.

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IT

Very positive experience, Elba always enchanting. The Skipper Luca L. very kind and professional, a great connoisseur and lover of the Tuscan archipelago, with the timing and talent necessary to transform what is in the galley into very pleasant moments at the table in the cockpit, after a perfect swim and in the middle of a fabulous sunset.

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