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

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€935

€748

Per person

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Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

5 departures available

July - September

Starting from

€293

€264

Per person

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4.8

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Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

9 departures available

August - October

Starting from

€850

€808

Per person

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Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

7 departures available

July - October

Starting from

€550

Per person

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From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

4 departures available

July - September

Starting from

€660

Per person

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4.9

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Sailing dreams in the Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

August

€350

Per person

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4.9

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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

10 departures available

July - October

Starting from

€550

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

4 departures available

July - September

Starting from

€1,041

€989

Per person

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ONE WAY From the Phlegraean to the Pontine Islands

Italy: Pontine Islands

8 days - 7 nights

3 departures available

July - September

Starting from

€680

€544

Per person

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4.9

Super!

Life-changing experiences - Escape to the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

6 departures available

July - September

Starting from

€370

€352

Per person

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5.0

Super!

South Sardinia

Italy: Southern Sardinia

6 days - 7 nights

9 departures available

July - September

Starting from

€790

€751

Per person

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4.8

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

11 departures available

July - October

Starting from

€530

€504

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

16134 reviews

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Relaxing holiday on the Côte d'Azur

07/6/2025

VALENTINA D.

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Italy

Un esordio alle crociere in barca a vela importante e significativo. Gruppo coeso e simpatico. skipper attento e coinvolgente. Consiglio l' esperienza almeno una volta nella vita.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/6/2025

Dario B.

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Italy

una gran bella esperienza! non è stata la mia prima crociera in barca a vela ma sicuramente la più bella. Alessandro è giovane ma competente, conosce benissimo le zona e i fondali e, cosa non da poco, è gentile e disponibilissimo con tutti. Carlo è formidabile, disponibile, super sportivo e cucina benissimo! insieme al fratello abbiamo creato una piccola flottiglia di due imbarcazioni, e anche un bel gruppo. Con loro abbiamo visto i posti più belli della zona. ero un po’ scettico su Corfù prima di partire, ma mi sono dovuto ricredere, e dalla barca è tutta un’altra prospettiva . 5 stelle su tutto, super meritate.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/6/2025

francesco f.

Che dire.. primo viaggio in barca assolutamente indimenticabile. Grazie ad Ale, lo skipper, sempre attento e disponibile a ogno nostra esigenza o richiesta.. Grazie a Carlo, imprescindibile steward sempre con il sorriso sulle labbra , nonche' ottimo cuoco e grande "suppista". E grazie a entrambi per le chiacchierate piacevoli durante la navigazione. Esperienza che ripeteremo sicuramente con lo stesso equipaggio. Non se, ma quando.. Un saluto anche ad Eros una compagnia breve ma intensa. A presto!.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/6/2025

Claudio S.

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Italy

Settimana bellissima. Destinazioni scelte con cura. L’equipaggio ci ha fatti sentire fin da subito benvenuti. Un grazie speciale ad Alessandro e Carlo che hanno sempre avuto un sorriso per noi e sono sempre stati attenti alle nostre esigenze compatibilmente con la vita da barca. Esperienza da consigliare. Ripeteremo con lo stesso equipaggio il prima possibile.

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