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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.

647

experiences

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5.0

Smart working by boat in Santa Margherita Ligure and Sestri Levante

Duration:

1 day - 1 night

Italy:

Liguria

Give this experience a try!

€125

Per person

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5.0

Spring on Lake Garda

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+23 travellers

have booked

€99

Per person

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5.0

Weekend in Capraia, the island with timeless sunsets

Duration:

2 days - 2 nights

Italy:

Tuscany

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+6 travellers

have booked

Starting from

€200

Per person

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4.8

Weekend in Corfu

Duration:

2 days - 2 nights

Greece:

Ionian Islands

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+5 travellers

have booked

€290

Per person

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4.9

Vela Trekking e Mountain Bike

Duration:

3 days - 3 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€223

Per person

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4.8

Capri LightBlue e Positano BluSKy

Duration:

2 days - 2 nights

Italy:

Amalfi Coast

Give this experience a try!

€298

Per person

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5.0

Educational Cruise

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€380

Per person

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4.5

Weekend di vela e Trekking all'Isola d'Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+2 travellers

have booked

€280

Per person

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4.9

Veleggiate e aperitivi all'Elba e isole vicine

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€217

Per person

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5.0

Long weekend between Amalfi, Positano and Capri

Duration:

3 days - 2 nights

Italy:

Amalfi Coast

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+10 travellers

have booked

Starting from

€350

Per person

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5.0

Sailing, early sun and aperitif at sunset ... What else?

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+6 travellers

have booked

€59

Per person

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Weekend in Tuscany between Argentario and Giglio Island

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€300

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

14261 reviews

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Luxury sailing in the Gulf of Poets

04/15/2024

Antonio C.

-

Italy

Giornata splendida, mare e barca perfetti, altissimo valore aggiunto l’equipaggio, simpatico gentile preparato ma soprattutto disponibile, e Costanza ottima cuoca, esperienza fantastica, da ripetere!!
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Sailing Cyclades

04/15/2024

yannis b.

-

France

Séjour incroyable avec Yann ! Très attentif, drôle et chill dans toutes les situations, dans un bateau très confortable !
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Thailand and the Andaman Sea

04/13/2024

Paola S.

-

Italy

Esperienza ottima, paesaggi magnifici e luoghi stupefacenti. Gianluca è un vero lupo di mare, esperto conoscitore dei luoghi e sempre attento alle esigenze delle persone con lui a bordo, con la sua simpatia ed energia è travolgente. Vacanza ideale per staccare la spina ed immergersi in differenti realtà culturali, divertendosi e sempre veleggiando!
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Veleggiata verso il farò di Cecina con Aperitivo a bordo

04/11/2024

maurizio r.

-

Italy

Grazie per la bella domenica di relax in barca Maurizio e Giuliana

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