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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.

675

experiences

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5.0

A fantastic day on a boat in the blue sea of Tuscany

Duration:

1 day - 0 nights

Italy:

Tuscany

Give this experience a try!

€130

Per person

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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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4.6

Tour del Peloponneso e isole Ioniche su una barca di 17 metri con Chef

Duration:

9 days - 9 nights

Greece:

Peloponnese

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+3 travellers

have booked

€980

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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+17 travellers

have booked

Starting from

€400

Per person

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4.6

Ponza and its wonders

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€400

Per person

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4.9

Long weekend sailing between Elba and Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

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+29 travellers

have booked

€320

Per person

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4.3

Elba a sea of Izola - Hostess on board (3Cab/3Bagni) - ALL INCLUSIVE

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€499

Per person

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5.0

Weekend sailing among the Pontine Islands

Duration:

3 days - 3 nights

Italy:

Pontine Islands

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+3 travellers

have booked

Starting from

€360

Per person

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4.8

Sailing on Elba

Duration:

3 days - 3 nights

Italy:

Tuscany

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+2 travellers

have booked

Starting from

€324

€360

Per person

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Sailing in Ponza and Palmarola

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€270

Per person

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4.5

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

Duration:

4 days - 3 nights

France:

French Riviera and Porquerolles

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+3 travellers

have booked

€440

Per person

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5.0

Gulf of Trieste and Istria

Duration:

4 days - 3 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€279

€310

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

14307 reviews

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Weekend of sea and colors between Ischia, Procida and Vivara

05/21/2024

Juri R.

-

Germany

Se sei ancora indeciso…PRENOTA! Visitare Procida e Ischia con Emiliano e Ida é molto di più di un semplice tour in barca a vela. Emiliano é un velista esperto che conosce bene le coste di Napoli e dintorni, con lui ti potrai sentire al sicuro sulla barca. Potrai decidere dove fermarti, se attraccare al porto per la notte o semplicemente visitare qualche isola e godere del buon cibo. Ad ogni modo non dovrai fare altro che rilassarti e goderti la magica atmosfera che si crea con i tuoi compagni di viaggio perché tanti aperitivi e risate al tramonto sono assicurati. E`stata davvero una bella esperienza, Emiliano e Ida sono fantastici e ci hanno fatti sentire come a casa. Grazie ragazzi per questo indimenticabile Weekend! Agnese e Juri.
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The fantastic Saronic Islands and the surroundings of Athens

05/21/2024

Steve T.

-

Canada

My family and I spent a week onboard with Alessandro exploring the Saronic Islands. We were taken to some amazing places that I will remember forever. Some were busy with people and tourists and some were completely ours - just the bay and our boat. This was a trip of a lifetime with a great skipper!
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Sailing course on the Côte d'Azur aboard a 15-metre sailboat

05/21/2024

Marie-Albane r.

-

France

Superbe stage sur Solal ! Grâce à Cyril et ses très nombreuses connaissances nous nous sommes tous amusés en apprenant beaucoup , nous garderons un très bon souvenir de notre escapade en mer. Un grand merci ,
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Weekend of sea and colors between Ischia, Procida and Vivara

05/21/2024

Annalisa S.

-

Italy

Disponibilità flessibilità amicizia. Emiliano uno skipper perfetto e Ida super. La barca è davvero grande comoda e pulita. Forniti di tutto lenzuola asciugamani e coperta ben lavati. Siamo stati benissimo a loro tutta la mia riconoscenza per un weekend rilassante e piacevole Raccomandatissimi!

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