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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.

616

experiences

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4.7

Ibiza All Inclusive on an 18m ketch with skipper and skipper

Duration:

6 days - 7 nights

Spain:

The Balearic Islands

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35 travellers

Starting from

€960

€1,200

Per person

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5.0

Oslofjord - East Coast Norway - Round trip

Duration:

6 days - 5 nights

North Sea:

Norway

Give this experience a try!

€480

€600

Per person

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5.0

Oslofjord - West Coast of Sweeden - Round trip

Duration:

6 days - 5 nights

North Sea:

Norway

Give this experience a try!

€480

€600

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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62 travellers

€990

€1,190

Per person

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5.0

Super!

Settimana in barca a vela tra Toscana e Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€1,275

€1,500

Per person

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5.0

Super!

Unspoilt Balearic Islands for max 4 guests: north Mallorca and south Menorca

Duration:

6 days - 6 nights

Spain:

The Balearic Islands

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12 travellers

Starting from

€765

€900

Per person

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Escape to the Magical Blue of the Pontine Islands

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€353

€415

Per person

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From Paros to Milos, the hidden gems of Cyclades

Duration:

5 days - 5 nights

Greece:

Cyclades

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2 travellers

Starting from

€765

€900

Per person

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4.8

Super!

Lampedusa, Lampione e Linosa fra colori magici

Duration:

7 days - 7 nights

Italy:

Pantelleria and Lampedusa

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34 travellers

€595

€700

Per person

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4.6

Cruise to the Maddalena Archipelago and South Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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28 travellers

Starting from

€667

€785

Per person

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5.0

Super!

To the Tremiti for the spring long weekends

Duration:

4 days - 3 nights

Italy:

Tremiti Islands

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4 travellers

€319

€375

Per person

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5.0

Super!

Sailing cruise on the French Riviera between the Lerins Islands

Duration:

6 days - 7 nights

France:

French Riviera and Porquerolles

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19 travellers

Starting from

€765

€900

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

15802 reviews

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12 day Cruising/Sailing Experience around St. Martin and St. Barth's

04/17/2025

Basiel B.

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United States

We had a fantastic trip sailing around St. Martin, St. Barth and St. Kitts & Nevis with Rob and Jackie, who were super relaxed and made us feel 200% welcome. The boat is beautiful and very well taken care of, a perfect intro to real-deal sailing. Rob is an excellent skipper mindful of safety (& comfort), and Jackie spoils you with her cooking. Snorkeling gear an paddle board available for aquatic leisure. Cannot recommend them more for a relaxing trip around the Caribbean!
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Spring in the Cinque Terre

04/15/2025

Monica L.

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Italy

E' stata un'esperienza fantastica! Chiara e Andrea ci hanno viziati e coccolati! E Silla è bellissima e superconfortevole! Consigliatissimo!
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Capri LightBlue and Positano BluSKy

04/14/2025

Stella A.

-

Argentina

Muy gentil Genaro
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Day trip with aperitif at sunset!

04/14/2025

Sandrine P.

-

Italy

Salve Sarebbe utile: - segnalare per chi si sposta con i trasporti pubblici e deve organizzare la trasferta, l'indirizzo preciso dell'ormeggio, In questo caso da Genova Prà e non Genova in modo generico, Non é stato molto carino iscriversi e scoprire DOPO che l'ormeggio non era proprio dove se lo eravamo immaginato. - aprire il gruppo WhatsApp un pò prima per magari dare l'opportunità a tutti di sentirsi ed eventualmente organizzarsi tra di noi se lo skipper non è particolarmente loquace. Barca ed equipaggio ok Per una prima esperienza con SailsSquare, ad aprile, in Liguria, meteo cosi cosi. Magari era ancora un pò prestino ma non dipende da nessuno.

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