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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.

631

experiences

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Weekend Sailing in Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

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+3 travellers

have booked

Starting from

€300

Per person

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4.8

Weekend - L’Elba... i profumi, il mare e i suoi colori!

Duration:

2 days - 2 nights

Italy:

Tuscany

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+8 travellers

have booked

Starting from

€180

Per person

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Sailing weekend in Camogli and Portofino from Genoa

Duration:

2 days - 1 night

Italy:

Liguria

Give this experience a try!

€199

Per person

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W.E Golfo Dei Poeti-Portovenere-Rosse-Ferale

Duration:

2 days - 2 nights

Italy:

Liguria

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+44 travellers

have booked

Starting from

€190

Per person

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4.9

Sailing trip around Toulon

Duration:

1 day - 0 nights

France:

French Riviera and Porquerolles

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+2 travellers

have booked

€75

Per person

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5.0

Sailing to the 5 Terre and Portovenere - Pearls of Liguria

Duration:

2 days - 2 nights

Italy:

Liguria

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+6 travellers

have booked

Starting from

€250

Per person

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Fine Settimana in Liguria - All inclusive

Duration:

2 days - 2 nights

Italy:

Liguria

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+21 travellers

have booked

€380

Per person

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5.0

A day sailing in the fantastic Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

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+4 travellers

have booked

€99

Per person

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The sailing adventure of your summer

Duration:

6 days - 6 nights

Greece:

Dodecanese

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+2 travellers

have booked

€1,450

Per person

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Bachelorette Party

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

Starting from

€166

€175

Per person

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5.0

Sailing course for novice drivers, enthusiasts and holidaymakers

Duration:

6 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€500

Per person

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Discovering the wonderful Hvar - Vis - Korcula

Duration:

6 days - 7 nights

Croatia:

Split Archipelago

Give this experience a try!

Starting from

€518

€575

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

14275 reviews

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25 April - 4 days sailing between La Maddalena and Bonifacio

05/3/2024

Bart S.

-

Spain

Excellent sailing trip in a comfortable boat with a great captain!! Grazie per tutto Leo & Crew!!!
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Sailing, early sun and aperitif at sunset ... What else?

05/3/2024

Cristiana L.

-

Italy

Giornata stupenda! lo skipper Emanuele molto simpatico, alla mano e soprattutto molto preparato e affidabile. Abbiamo veleggiato con un bel vento, io sono interessata alla vela ed Emanuele mi ha spiegato tante cose, fatto fare delle manovre e riposto pazientemente a tutte le mie tante domande. Abbiamo anche fatto un bellissimo aperitivo all'ancora. Non posso che consigliare vivamente questa esperienza!
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May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms

05/2/2024

susanna s.

-

Italy

una splendida vacanza . Fabio e Angela gentilissimi mi hanno offerto ogni confort a bordo e insegnato i primi rudimenti della vela .
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25 April - Whale watching expedition with WWF researcher in Liguria

05/2/2024

Rossella D.

-

Italy

Esperienza complessivamente decisamente positiva, nonostante le importanti difficoltà causate dalle pessime condizioni meteorologiche. L'estrema professionalità dello skipper e delle guide di whale watching, insieme al grande affiatamento e collaborazione che si è creato con tutto l'equipaggio, hanno fatto in modo che l'intera esperienza si vivesse nel migliore dei modi, in totale armonia, portando a casa anche grandi soddisfazioni di avvistamento di delfini, balenottere e tartarughe! Un'esperienza davvero indimenticabile, grazie di cuore!

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