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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!

South Sardinia

Italy: Southern Sardinia

6 days - 7 nights

One departure available

September

€790

Per person

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5.0

Super!

Sailing weekend in Liguria

Italy: Liguria

2 days - 1 night

One departure available

September

€225

Per person

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5.0

Super!

Southern Sardinia on a beautiful 16m boat with a Professional Skipper

Italy: Southern Sardinia

7 days - 7 nights

4 departures available

September - October

€990

Per person

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4.8

Super!

LET'S GO TO TOTANI - Festival in Capria

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€420

Per person

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4.7

Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

September

€452

Per person

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4.3

European Mile Builder - Leg 6: Malta to Gibraltar

Spain: Andalusia

9 days - 9 nights

One departure available

October - November

€470

Per person

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5.0

North-East Sardinia and South Corsica on a sailing boat with gourmet cuisine

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September

€900

Per person

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4.8

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€300

Per person

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5.0

Two days on a sailing boat in Elba: zero stress!

Italy: Tuscany

3 days - 2 nights

2 departures available

September

Starting from

€300

€270

Per person

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4.8

Cous cous Festival in San Vito lo Capo and the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€600

€570

Per person

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4.7

IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper

Spain: The Balearic Islands

6 days - 7 nights

3 departures available

September - October

Starting from

€600

Per person

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Autumn Gems of Cyclades away from the crowds on 51 ft yacht

Greece: Cyclades

7 days - 7 nights

One departure available

October

€580

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17477 reviews

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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

09/17/2025

Mauro Z.

-

Italy

Very nice cruise, despite the weather was not favorable, the skipper managed to let us enjoy the beauties of the Costa Smeralda
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Weekend at the Pontine aboard a splendid 16-meter sailboat

09/17/2025

Giulia E.

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Italy

It was my first time on a sailing boat but the skipper Leonardo and his wife Elena were immediately very professional and attentive to everyone's needs. The boat is very nice, functional and clean; perfect for enjoying the sea in total relaxation. The excellent company, the favorable weather and the crystal clear water of the Pontine islands then made the experience perfect!
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Egadi paradise for sailing and snorkeling

09/17/2025

Vicky H.

-

Belgium

Mario is a competent and friendly skipper. The Egadi islands are beautiful and the boat is in good shape. It is a pity that 2 French-speaking fellow passengers had a lot of criticism, made little effort to involve the skipper in the conversations and were very present during the trip, to the displeasure of the other passengers.
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A week in the Aeolian Islands - 6 islands in seven days

09/17/2025

Giuseppe I.

-

Italy

The sailing trip with Nicola was an experience that enriched me a lot, unique emotions and sensations. The navigation, the wind, the sun and the sea created a perfect mix of adventure and relaxation. I recommend everyone to try this experience at least once in their life: it is an opportunity to discover the beauty of the sea, the Aeolian Islands and the feeling of freedom. Thanks to all the crew, who made all this possible.

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