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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!

Flottiglia Sun & Fun Marmaglia - Età 25-40 anni

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,100

€950

Per person

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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€719

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€900

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,190

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

July - September

Starting from

€650

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

August - October

Starting from

€200

Per person

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4.7

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

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€650

Per person

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4.9

Super!

Week of sea, nature and fun in the Egadi Islands!

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - September

Starting from

€690

€621

Per person

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5.0

Super!

North and south Sardinia of Corsica sailing

Italy: Northern Sardinia

7 days - 7 nights

3 departures available

July - August

Starting from

€900

€810

Per person

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4.8

Super!

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€820

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

July - October

Starting from

€751

Per person

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5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€935

€748

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

16178 reviews

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Experience the sea at 360 degrees? embark with us in Kos

07/9/2025

Davide M.

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Italy

Indeciso sulla scelta di Vacanza da affrontare Gianfranco mi ha messo subito a mio agio, tanto che è stato difficile scendere dalla sua "[hidden]" l'ultimo giorno. Vacanza pazzesca con bagni in calette incontaminate spettacolari per non parlare dei ristoranti da lui consigliati ottimi. Gianfranco trovami una location dove si balla Boogie boogie per giugno 2026 .Grazie ancora e ci rivedremo presto
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Escape from the city for a weekend of sea and relaxation

07/9/2025

Monica v.

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Italy

Sono stata con i miei due figlii sulla barca di Carlo nel weekend tra il 4 e il 6 luglio. . La barca è splendida, praticamente nuova, con spazi ampi e confortevoli. Carlo è una persona squisita, socievole ma al tempo stesso discreta, attento alle esigenze degli ospiti. e felice di condividere le sue conoscenze con noi che eravamo alla prima esperienza.. Nonostante le condizioni meteo non fossero eccezionali abbiamo goduto appieno del mare e del vento, avvistato i delfini e dormito anche in rada una notte.. Nota positiva anche per il porto in cui è ormeggiata la barca , che offre servizi eccellenti
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Weekend only four guests - Elba Island

07/9/2025

Paola F.

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Italy

Bellissima esperienza! Pierpaolo skipper super disponibile sia nell’organizzazione sia nello strutturare le varie tappe per farci godere al meglio la barca a vela. Da rifare!
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Sailing weekend in the Pontine Islands

07/9/2025

Antonio F.

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Italy

Abbiamo vissuto un'esperienza che porteremo nel cuore per molto tempo. Un weekend in barca a vela che è stato molto più di una semplice fuga dalla routine, è stato un tuffo in una dimensione fatta di silenzi, risate, salsedine e libertà. La barca era spaziosa, pulita, curata in ogni dettaglio e organizzata in modo impeccabile, si percepiva l’amore e la professionalità con cui viene gestita. Lo skipper? Straordinario. Presenza discreta ma sempre attenta, ci ha guidati con sicurezza e passione, rendendo ogni momento sereno e autentico. L’organizzazione è stata impeccabile dall’inizio alla fine, senza intoppi, con la sensazione costante di essere in ottime mani. Un’esperienza che consigliamo con il cuore.

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