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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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4.4

Sailing Excursion Alghero ( Skipper + Hostess )

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€90

Per person

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4.7

Long weekend of April 25 to discover the most beautiful Liguria from the sea

Duration:

4 days - 4 nights

Italy:

Liguria

Give this experience a try!

€590

Per person

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5.0

Mini Crociera Sail Academy

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€500

Per person

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5.0

Ischia Ventotene and Procida between sailing and nature

Duration:

4 days - 4 nights

Italy:

Gulf of Naples

Give this experience a try!

€300

Per person

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Weekend nelle Magiche Pontine

Duration:

5 days - 4 nights

Italy:

Pontine Islands

Give this experience a try!

€350

Per person

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5.0

Sailing in Cinque Terre and Portofino

Duration:

4 days - 4 nights

Italy:

Liguria

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+2 travellers

have booked

€450

Per person

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4.3

25 April sailing on the Côte d'Azur

Duration:

4 days - 4 nights

France:

French Riviera and Porquerolles

Give this experience a try!

€414

€460

Per person

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4.9

Sailing excursion to Capri / Positano

Duration:

1 day - 0 nights

Italy:

Gulf of Naples

Give this experience a try!

€160

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

Starting from

€95

Per person

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5.0

Long weekend of April 25th in the Tuscan Archipelago where the wind prunes us!

Duration:

4 days - 3 nights

Italy:

Tuscany

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+3 travellers

have booked

€470

Per person

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4.8

An unforgettable sail to discover the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

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+17 travellers

have booked

€350

Per person

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5.0

3 DAYS 2 NIGHTS Sailing the Ligurian Coast from GENOVA

Duration:

3 days - 2 nights

Italy:

Liguria

Give this experience a try!

Starting from

€324

€360

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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