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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.

24

experiences

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4.9

Trekking, E-bike & Sailing Experience, 1 May adventure on Elba.

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€618

€650

Per person

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5.0

Freediving & Yoga retreat in Marsa Alam Satayah Dolphin Reef

Duration:

5 days - 5 nights

Africa:

Egypt & Red Sea

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+6 travellers

have booked

Starting from

€795

Per person

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4.5

A week with YOGA and SAILING lessons in the Tuscan Archipelago

Duration:

7 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€1,350

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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4.7

Ibiza All Inclusive on comfortable 18m ketch with skipper and skipper

Duration:

6 days - 7 nights

Spain:

The Balearic Islands

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+7 travellers

have booked

Starting from

€1,280

€1,600

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!

€699

€999

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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+5 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

Give this experience a try!

€419

€599

Per person

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4.5

A weekend of YOGA and SAILING on a boat

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€370

Per person

Why book a holiday with Sailsquare?

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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.

1278 reviews

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Wine Experience with Sommelier on the Island of Elba

10/4/2023

Davide Q.

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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.

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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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Two boats together - Sailing on the island of Elba! Between the sea, courses and new friends... you forget everything! :-)

09/29/2023

Italy B.

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Italy

Questa vacanza con Luca ha rispettato le aspettative. Luca è molto disponibile anche ad accomodare eventuali necessità. La vacanza è stata divertente e con possibilità di timonare ed apprendere nuove conoscenze riguardo la navigazione.
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Holistic Sail Aeolian in Catamaran - Sailing and Yoga for a Week of Relaxation and Energy

09/26/2023

Lorenza P.

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Italy

Esperienza fantastica! Alex capitano disponibile e attento alla sicurezza in mare! Massimiliano, insegnante yoga, ci ha accompagnato nella pratica facendoci entrare in contatto con l'energia dei luoghi, magici e stupefacenti! Vacanza indimenticabile e da fare ancora!!!

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