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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.

630

experiences

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4.8

Capri LightBlue e Positano BluSKy

Duration:

2 days - 2 nights

Italy:

Amalfi Coast

Give this experience a try!

€298

Per person

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4.9

Vela Trekking e Mountain Bike

Duration:

3 days - 3 nights

Italy:

Aeolian Islands

Give this experience a try!

€265

Per person

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4.8

Weekend between Amalfi, Positano and Capri

Duration:

3 days - 2 nights

Italy:

Amalfi Coast

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+18 travellers

have booked

€450

Per person

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4.6

Educational weekends: manoeuvres and mooring in Tuscany 

Duration:

2 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€200

Per person

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4.9

Sailing weekend in Ponza and Palmarola!

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+30 travellers

have booked

Starting from

€248

€275

Per person

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4.5

In the blue of Capri and the infinity of the Amalfi Coast

Duration:

2 days - 2 nights

Italy:

Amalfi Coast

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+12 travellers

have booked

Starting from

€261

€275

Per person

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5.0

Fantastic Weekend on Elba and Tuscan Archipelago

Duration:

2 days - 2 nights

Italy:

Tuscany

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+7 travellers

have booked

€200

Per person

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5.0

Weekend of Relaxation in the Argentario - Giglio - Uccellina

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€300

Per person

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5.0

Weekend of relaxation and fun

Duration:

2 days - 2 nights

Italy:

Liguria

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+18 travellers

have booked

Starting from

€261

€275

Per person

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5.0

Offshore sailing course to gain boating experience

Duration:

6 days - 7 nights

Greece:

Cyclades

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+4 travellers

have booked

€500

Per person

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7 Day Greek Sailing Adventure - Dodecanese Islands

Duration:

7 days - 6 nights

Greece:

Dodecanese

Give this experience a try!

€1,653

Per person

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5.0

Weekend getaway in Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

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+2 travellers

have booked

Starting from

€290

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

14264 reviews

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A weekend of sailing between Capraia and the island of Elba

04/24/2024

Angelo C.

-

Italy

Bellissima esperienza, bella gente con uno skipper top!
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Easter on the Island of Elba

04/22/2024

Antonios S.

-

Italy

Anche se il tempo non ha aiutato, è stata una bellissima esperienza
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Trekking and sailing weekend on the island of Elba

04/22/2024

Sara C.

-

Italy

Bellissima esperienza,grazie alla cordialità e professionalità di Marco e i compagni di avventura. Ho apprezzato molto anche la possibilità di fare trekking. Consigliatissimo!!
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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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