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Holidays and cruises on sailboats with organized activities.

Do you love to relax but also need to stay active or pursue your greatest passions? On a sailboat, you can enjoy a week or weekend of sailing and sea, combining activities such as trekking, yoga, snorkeling, and even gastronomic tastings.

12

experiences

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4.5

Weekend YOGA in barca a vela

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€370

Per person

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Sardinia and Costa Smeralda in Comfort - with Hostess - All Inclusive

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

Starting from

€1,690

Per person

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4.8

Week in Southern Sardinia - Science of Happiness on board

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€711

€790

Per person

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5.0

Sailing BenEssere in Ionian Greece

Duration:

6 days - 6 nights

Greece:

Ionian Islands

Give this experience a try!

Starting from

€1,125

€1,250

Per person

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5.0

Sail & Climb in Trieste

Duration:

3 days - 2 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€420

Per person

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Salt, Earth and Sun: yoga retreat on a catamaran with hostess (Full Board) 

Duration:

7 days - 7 nights

Greece:

North Egean Islands

Starting from

€1,855

Per person

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South Corsica Comfort with Hostess and Yoga Teacher - All Inclusive

Duration:

7 days - 7 nights

France:

Corsica

Give this experience a try!

€2,240

Per person

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4.9

Flotilla fitness experience with personal trainer

Duration:

7 days - 7 nights

Croatia:

Split Archipelago

Give this experience a try!

€799

€999

Per person

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5.0

Sailing, Reiki Wellness and Meditation in the magic of Corsica

Duration:

6 days - 7 nights

France:

Corsica

Give this experience a try!

€1,000

Per person

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5.0

Selvaggio Blu: sailing and trekking in Sardinia

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

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+8 travellers

have booked

€1,100

Per person

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4.9

Wine Experience with Sommelier on the Island of Elba

Duration:

4 days - 3 nights

Italy:

Tuscany

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+2 travellers

have booked

€419

€599

Per person

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5.0

Sailing and books in the sea of Trieste for those who love reading and sailing

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€94

€99

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 - Holidays and cruises on sailboats with organized activities.

1280 reviews

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Trekking & Sailing Experience 25 Aprile tra Elba e Capraia - 2 barche

04/30/2024

luca f.

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Italy

Esperienza bellissima, nonostante il meteo non abbia consentito di raggiungere Capraia, lo skipper Edoardo ha organizzato con Francesco, la guida trekking, un itinerario molto divertente ed esaustivo dell'isola d'Elba. Edoardo bravo, competente e molto comunicativo, davvero una bella persona!
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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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Wine Experience with Sommelier on the Island of Elba

10/4/2023

Davide Q.

-

Italy

Una splendida esperienza, una crew affiatata e divertente che ha scoperto alcuni angoli suggestivi dell'Isola d'Elba e che ha potuto vivere una vera Wine-experience, tra visita in cantina, trekking in vigna, degustazioni e cena con abbinamenti. Il tutto guidato da esperti sommelier.
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All Inclusive Mallorca - Ibiza on large 18m Ketch with Insurance and Steward

10/1/2023

Stefano G.

-

Italy

Purtroppo le condizioni meteo ed il mare grosso hanno un po' stravolto il programma della vacanza. Filippo e' simpatico e paziente e sa quel che fa, ponendo attenzione alla sicurezza. E' stato anche molto gentile prestandomi un suo vecchio telefono perche' avevo avuto un problema con il mio e non potevo usarlo. Ottimo il BBQ a bordo ed in generale tutto il cibo servito era molto buono.

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