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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.

652

experiences

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Sailing and relaxation on the Silver Coast, Tuscan Archipelago and Maremma Coast.

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€396

€440

Per person

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4.9

4 days as free as the wind, between Capraia and Corsica

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€300

Per person

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4.5

April 25 long weekend between Ischia, Procida and Ventotene from Naples

Duration:

4 days - 3 nights

Italy:

Pontine Islands

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Gennaro A.

has booked

€328

€345

Per person

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5.0

APRIL 25TH LONG WEEKEND - PROCIDA-ISCHIA AND VENTOTENE

Duration:

4 days - 3 nights

Italy:

Gulf of Naples

Give this experience a try!

€380

Per person

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4.7

Get rid! 25 April on a sailing boat Procida, Ischia and Ventotene

Duration:

3 days - 3 nights

Italy:

Gulf of Naples

Give this experience a try!

€320

Per person

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5.0

Ponza Palmarola and Ventotene by sailboat

Duration:

6 days - 5 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€580

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

Sailing weekend in Istria

Duration:

2 days - 2 nights

Croatia:

Istrian peninsula

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Alberto B.

has booked

Starting from

€190

Per person

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5.0

Weekend to discover the Pink Granite Coast

Duration:

2 days - 1 night

France:

Brittany and Normandy

Give this experience a try!

€250

Per person

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5.0

Weekend sailing course from Bandol

Duration:

2 days - 1 night

France:

French Riviera and Porquerolles

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+4 travellers

have booked

Starting from

€287

Per person

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5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+38 travellers

have booked

Starting from

€99

Per person

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The sailing adventure of your summer

Duration:

6 days - 6 nights

Greece:

Dodecanese

Give this experience a try!

€1,450

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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