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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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4.9

Trekking, E-bike & Sailing Experience, 1 May adventure on Elba.

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€618

€650

Per person

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4.6

May Day Long Bridge between Tuscany and Corsica

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€380

Per person

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5.0

May Day: I love you Capraia! Only for 4 guests

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€490

Per person

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5.0

May 1st in the waters between the Tuscan coast and the Island of Elba

Duration:

1 day - 1 night

Italy:

Tuscany

Give this experience a try!

€90

€95

Per person

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5.0

May 1st long weekend on the Côte d'Azur

Duration:

5 days - 5 nights

France:

French Riviera and Porquerolles

Give this experience a try!

€625

Per person

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4.8

Cruise in the Gulf of Baratti

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€216

€240

Per person

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4.3

Mini-cruise on the French Riviera

Duration:

5 days - 5 nights

France:

French Riviera and Porquerolles

Give this experience a try!

€513

€570

Per person

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4.4

Sailing course on the Côte d'Azur aboard a 15-metre sailboat

Duration:

5 days - 4 nights

France:

French Riviera and Porquerolles

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+5 travellers

have booked

€520

Per person

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4.9

Long live May Day!

Duration:

5 days - 4 nights

Italy:

Aeolian Islands

Give this experience a try!

€382

Per person

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5.0

May 1st long weekend between sailing, islands and wineries

Duration:

5 days - 5 nights

Italy:

Gulf of Naples

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+2 travellers

have booked

€550

Per person

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5.0

Orthodox Easter in Greece in the Saronic Islands

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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+6 travellers

have booked

€500

Per person

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Weekend in the Magical Pontine

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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Elena S.

has booked

€350

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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