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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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Fine Settimana in Liguria - All inclusive

Duration:

2 days - 2 nights

Italy:

Liguria

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+21 travellers

have booked

€380

Per person

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4.9

Slovenia and Croatia - departure Sistiana (Trieste)

Duration:

2 days - 1 night

Croatia:

Istrian peninsula

Give this experience a try!

Starting from

€230

Per person

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4.9

Beautiful bays between North Sardinia and South Corsica on a catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+47 travellers

have booked

Starting from

€820

Per person

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4.8

Elba Capraia and Caorsica - Sea and Colour

Duration:

6 days - 7 nights

Italy:

Tuscany

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+8 travellers

have booked

Starting from

€480

Per person

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Sporades Islands: sailing holidays are more than just holidays!

Duration:

7 days - 7 nights

Greece:

Sporades

Give this experience a try!

Starting from

€800

Per person

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5.0

Explore Sardinia's coastline! Skipper & Hostess - All included

Duration:

6 days - 6 nights

Italy:

Northern Sardinia

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+13 travellers

have booked

Starting from

€1,390

Per person

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Discovering the wonderful Hvar - Vis - Korcula

Duration:

6 days - 7 nights

Croatia:

Split Archipelago

Give this experience a try!

Starting from

€518

€575

Per person

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5.0

Discovering the Southern Dodecanese

Duration:

6 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

€550

Per person

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4.9

In the blue between Sardinia and Corsica on a sailboat

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+116 travellers

have booked

Starting from

€650

Per person

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4.5

Sailing holiday with maximum comfort

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

Starting from

€360

Per person

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4.9

Cruise North Sardinia, Costa Smeralda, Maddalena, Caprera and Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+50 travellers

have booked

Starting from

€499

€600

Per person

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4.0

Sailing, Relaxation and Fun in the Pontine and Phlegraean Islands on a 15-meter Boat

Duration:

7 days - 7 nights

Italy:

Pontine Islands

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+7 travellers

have booked

Starting from

€600

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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