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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.

657

experiences

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5.0

Itinerant Coastal Cruise Training Course

Duration:

6 days - 5 nights

France:

Atlantic Coast

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+6 travellers

have booked

Starting from

€700

Per person

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5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+86 travellers

have booked

Starting from

€99

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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+6 travellers

have booked

Starting from

€700

Per person

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4.8

All in the Family: 5 days sailing on Elba on a comfortable 17m boat

Duration:

4 days - 4 nights

Italy:

Tuscany

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+7 travellers

have booked

€490

Per person

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4.8

Little sailors grow up: 5 days sailing on the island of Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

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+5 travellers

have booked

€490

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

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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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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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5.0

3 DAYS 2 NIGHTS Sailing the Ligurian Coast from GENOVA

Duration:

3 days - 2 nights

Italy:

Liguria

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+7 travellers

have booked

Starting from

€324

€360

Per person

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5.0

Sailing, swimming and aperitif at sunset ... What else?

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+10 travellers

have booked

Starting from

€69

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

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

14300 reviews

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Let's discover the Aeolian Islands together by sailing

05/18/2024

Eros Giorgio M.

-

Italy

Bellissime le Eolie, bella la combinazione vela ed escursioni, piacevole il gruppo e Mario un esperto ed affidabile velista.
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Weekend at the Pontine Islands: Ponza and Palmarola

05/18/2024

Giulio S.

-

Italy

Una tre giorni davvero bella. Tempo splendido, Ponza ancora con pochi turisti. Marco, oltre che uno skipper esperto, è una persona incredibile, generosa, amichevole e a Ponza conosce tanti luoghi e persone. Ci ha fatto passare momenti di relax, tra buon cibo, buona musica, belle foto scattate e tanti aneddoti. Pur essendo una persona che non fa amicizia velocemente mi sono trovato subito bene con lui e gli altri viaggiatori. Mi piacerebbe vedere le Eolie con lui. Lo consiglio!
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In the blue of Capri and the infinity of the Amalfi Coast

05/15/2024

simona b.

Esperienza stupenda! Grazie per la disponibilità e la simpatia ! A presto!
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An unforgettable sail to discover the Egadi Islands

05/14/2024

Marco B.

-

Switzerland

Bel giro, bella compagnia e ottimo equipaggio

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