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Sport & Wellness sailing holidays & skippered tours

Do you like to relax but at the same time need to stay active? active? You can enjoy a week or a weekend of Sport & Wellness. Choose from dozens of activities such as sailing, hiking, yoga, snorkelling and, of course, sailing and, of course, sailing.

23

experiences

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5.0

E-bike & Sailing Experience with a visit to the mines on the island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

€314

€330

Per person

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4.9

Trekking & Sailing Experience 25 Apr Elba Island and Capraia - 2 boats

Duration:

4 days - 4 nights

Italy:

Tuscany

Be the first one to book!

€494

€520

Per person

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5.0

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

Duration:

4 days - 4 nights

Italy:

Tuscany

Be the first one to book!

€494

€520

Per person

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4.8

Yoga and catamaran sailing with chef on board

Duration:

4 days - 4 nights

Italy:

Aegadian islands

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+6 travellers

Have booked

€490

Per person

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4.9

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

Duration:

5 days - 5 nights

Italy:

Tuscany

Be the first one to book!

€618

€650

Per person

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5.0

Trekking, E-bike & Sailing Experience, 1 Maggio avventura all'Elba

Duration:

5 days - 5 nights

Italy:

Tuscany

Be the first one to book!

€618

€650

Per person

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4.9

June 2nd in Capraia with possible Trekking Excursion

Duration:

3 days - 3 nights

Italy:

Tuscany

Be the first one to book!

€379

€399

Per person

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5.0

Sailing BenEssere in Ionian Greece

Duration:

6 days - 6 nights

Greece:

Ionian Islands

Be the first one to book!

€1,125

€1,250

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

Be the first one to book!

€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

Be the first one to book!

€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

Be the first one to book!

€1,100

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 - Sport & Wellness sailing holidays & skippered tours

1279 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.

-

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.

-

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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