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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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4.8

LONG WEEKEND 25 April barefoot: 4 days between Capraia and the island of Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

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+4 travellers

have booked

€349

Per person

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4.2

Ponte del 25 Aprile in navigazione con rotta per la Capraia.

Duration:

4 days - 4 nights

Italy:

Tuscany

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+4 travellers

have booked

€435

Per person

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5.0

Long weekend in Capraia and North Corsica

Duration:

4 days - 4 nights

Italy:

Tuscany

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+6 travellers

have booked

€375

Per person

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4.8

Long weekend in Corfu

Duration:

3 days - 3 nights

Greece:

Ionian Islands

Give this experience a try!

€390

Per person

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5.0

First dives in the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

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+11 travellers

have booked

Starting from

€360

Per person

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4.9

25 April - 4 days sailing between La Maddalena and Bonifacio

Duration:

4 days - 5 nights

Italy:

Northern Sardinia

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+5 travellers

have booked

€390

Per person

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4.9

Long weekend of April 25 in Elba, Corsica and Capraia

Duration:

4 days - 4 nights

Italy:

Tuscany

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+7 travellers

have booked

€405

Per person

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5.0

Long weekend of April 25th between sea, land and good food for only 4 guests

Duration:

4 days - 4 nights

Italy:

Tuscany

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+2 travellers

have booked

€420

Per person

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5.0

Capraia and Corsica: 2 islands in 4 days!

Duration:

4 days - 3 nights

Italy:

Tuscany

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+2 travellers

have booked

€395

Per person

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4.9

25 April between Liguria and Côte d'Azur from Imperia - Stewardess on board

Duration:

4 days - 4 nights

Italy:

Liguria

Give this experience a try!

€500

Per person

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4.5

Sailing in the Gulf of Tigullio

Duration:

4 days - 3 nights

Italy:

Liguria

Give this experience a try!

Starting from

€450

Per person

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4.8

DISCOVERING THE EGADI ISLANDS on the Routes of the Florio Family

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+2 travellers

have booked

Starting from

€550

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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