Boat rental

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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.

experiences

5.0

Freediving & Yoga retreat in Marsa Alam Satayah Dolphin Reef

Duration:

5 days - 5 nights

Africa:

Egypt & Red Sea

+6 travellers

have booked

Starting from

€795

Per person

4.5

Weekend di vela e Trekking all'Isola d'Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

+2 travellers

have booked

€280

Per person

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

5.0

The island of Ischia between sailing and trekking

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

€200

Per person

5.0

Trekking & Sailing Experience-Weekend lungo a Capraia in compagnia

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€361

€380

Per person

4.9

Vela Trekking e Mountain Bike

Duration:

3 days - 3 nights

Italy:

Aeolian Islands

Give this experience a try!

€265

Per person

4.5

Weekend YOGA in barca a vela

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€370

Per person

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

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

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

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

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

Why book a holiday with Sailsquare?

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

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

04/30/2024

luca f.

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!

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!!

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.

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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