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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.

633

experiences

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5.0

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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+17 travellers

have booked

Starting from

€550

Per person

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4.9

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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+34 travellers

have booked

Starting from

€550

Per person

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4.6

Sicily on a Sailing Boat in the Egadi Islands

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+4 travellers

have booked

Starting from

€499

Per person

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5.0

From Corfù to Lefkas

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€500

Per person

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4.9

The Channel Islands by sailboat from Saint-Malo

Duration:

6 days - 5 nights

France:

Channel Islands

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+18 travellers

have booked

Starting from

€745

Per person

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Intro sail Liguria

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€125

Per person

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4.9

The fantastic Saronic Islands and the surroundings of Athens

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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+7 travellers

have booked

Starting from

€618

€650

Per person

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5.0

Sailing Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

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+91 travellers

have booked

Starting from

€920

Per person

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5.0

Ibiza & Formentera All inclusive week with Cook

Duration:

5 days - 6 nights

Spain:

The Balearic Islands

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+27 travellers

have booked

Starting from

€570

€600

Per person

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4.8

Gone with the Wind, Corfu and the Poseidon Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€570

Per person

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The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+4 travellers

have booked

Starting from

€650

Per person

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5.0

5-day sailing course: discovery and learning

Duration:

5 days - 4 nights

France:

French Riviera and Porquerolles

Give this experience a try!

Starting from

€630

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

14285 reviews

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Weekend with wine tasting between Santa Margherita Ligure and Portofino

05/7/2024

Valentina B.

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Italy

Siamo stati fortunati ad avere Giorgio come skipper durante il nostro weekend in barca a vela. La sua gentilezza e professionalità hanno reso l'intero viaggio un’esperienza straordinaria. Giorgio ha mostrato una grande attenzione per la sicurezza e il comfort a bordo. La sua personalità amichevole e la sua capacità di mettere a proprio agio le persone hanno reso il viaggio ancora più piacevole. Giorgio è stato un ottimo skipper ma anche un provetto chef: grazie alla conoscenza dei vini e alla passione per la cucina ha creato un aperitivo stuzzicante e una cena, a base di pesce, davvero deliziosa. La barca è molto bella, confortevole e pulita. Consiglio vivamente Giorgio a chiunque cerchi un'esperienza di vela emozionante, in un contesto amichevole.
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Week End Basic and Advanced Sailing Course

05/7/2024

Antonio R.

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Italy

Bellissima esperienza!!assolutamente da ripetere!!
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Weekend in Capraia, the island with timeless sunsets

05/7/2024

enrico g.

-

Italy

ottimi compagni di viaggio , marco m disponibilissimo e molto preparato grazie a tutti
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Weekend in Capraia, the island with timeless sunsets

05/7/2024

Irene T.

-

Italy

Marco è un gran marinaio, super esperienza!

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