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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.

384

experiences

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4.2

Easter in Portofino - sailing between the Gulf of Poets and the Tiguillio

Duration:

3 days - 3 nights

Italy:

Liguria

Give this experience a try!

€332

€390

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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56 travellers

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Starting from

€675

€750

Per person

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Ionian Islands: An Epic Week in the Kingdom of Odysseus

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€729

€810

Per person

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5.0

Island of Capraia sailing and wild nature

Duration:

4 days - 4 nights

Italy:

Tuscany

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4 travellers

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€405

€450

Per person

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4.9

Super!

Easter sailing between the islands: Elba and Capraia

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€356

€395

Per person

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4.9

Super!

Midweek on Elba, from Monday to Thursday

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€324

€360

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€630

€700

Per person

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4.9

Super!

Long weekend between Elba and Capraia, from Thursday to Sunday

Duration:

3 days - 3 nights

Italy:

Tuscany

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2 travellers

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Starting from

€369

€410

Per person

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Spring in the Cinque Terre

Duration:

2 days - 2 nights

Italy:

Liguria

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4 travellers

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€189

€210

Per person

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5.0

Easter Sailing: Explore the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€495

€550

Per person

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5.0

April 25th and May 1st: sailing to the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€504

€560

Per person

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5.0

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

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

15780 reviews

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New Year's Eve under the Caribbean sun

01/14/2025

Gaetano F.

Era da tempo che volevo fare un veleggiata fino alle Grenadine. Sono complessivamente alquanti soddisfatto della vacanza, nonostante un po' di tensione tra un membro dell'equipaggio ed il capitano
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New Year's Eve Flotilla: Relaxation and Fun in Guadeloupe - FIXED PRICE FLIGHT FROM PARIS

01/7/2025

Laura B.

-

France

let yourself go… in every adventure and fun ☀️🥂⛵️🪩👯 always perfect with marmaglia ♥️
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New Year's Eve Flotilla: Relaxation and Fun in Guadeloupe - FIXED PRICE FLIGHT FROM PARIS

01/7/2025

Valentina C.

-

Italy

Vacanza organizzata alla perfezione! Giro molto bello, gruppo di persone bilanciato molto bene, c'erano molti dei partecipanti che già si conoscevano perchè avevano già partecipato ad altre vacanze con Marmaglia e si erano trovati benissimo, e hanno dato un'ottimo feedback. Nel complesso stra consiglio, adatto a chi ha voglia di una vacanza attiva e divertente!
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New Year's Eve Flotilla: Relaxation and Fun in Guadeloupe - FIXED PRICE FLIGHT FROM PARIS

01/6/2025

Massimo C.

-

Italy

Condizioni climatiche velisticamente eccellenti, anche se purtroppo le abbiamo sfruttate poco, ma a vantaggio del relax e di attività a terra comunque meritevoli, Ottima organizzazione e cortesia dello staff Marmaglia. Tutti i partecipanti hanno dato il loro contributo, come necessario perchè una vacanza di questo tipo riesca bene.

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