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Whole boat with skipper yacht sailing holidays & tours in Spain

Discover more than 2 opportunities to get on board a Whole boat with skipper adventure in Spain. A unique experience with a local skipper, starting at €350 a week.

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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 - Whole boat with skipper yacht sailing holidays & tours in Spain

85 reviews

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IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper and skipper and travel insurance

11/3/2025

Patrizia M.

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Italy

*Return to the helm* A parenthesis of the long-awaited – and missed – summer holidays, in a late October... where everything was perfectly aligned: ☀️ sun, 💨 wind up to 30 knots, unfurled sails and breathtaking destinations, among the most varied shades of sunrises and sunsets. The skipper? What can I say... An excellence in terms of safety, handling and upwind and crosswind. Even at night: impeccable navigation, always under full sail! I left alone, with the courage and the awareness that it would be an experience to be savored to the fullest. To be discovered and then left a trace. And so it was! Mouth-watering lunches and dinners, a wonderful and intense boat holiday, lived following and supporting the wave motion. I was amazed at the sight of dolphins with Es Vedrà in the background... a boat all for me and for my unexpected furry friend, **Nao**, the skipper's affectionate dog: a sweet and ever-present companion, a real **unexpected pet therapy** that made every moment even more special. And then, **back at the helm**... feel the force of the wind in your hands, the thrill of the route, the freedom that only the sea can give! Thank you, Filippo, and thanks also to Nao — it's been a long time since I sailed with the genuine enthusiasm of feeling the wind flow between jib and mainsail...
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IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper

10/25/2025

Sara C.

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Italy

A week of relaxation, laughter, new friendships, baths, good food, karaoke, and slow life marked by the movements of the sea. Filippo is an expert, sunny captain, attentive to every need, super cook and master of the grill! His dog Nao is an adorable companion for travel and adventures in sup and cycling. The natural beauty of Ibiza and Formentera in October offers breathtaking views between rocky cliffs and blue sea, white sandy beaches and crystal clear water, perfect weather for exploring Formentera by bike and visiting its lighthouses overlooking the sea and well-kept villages. [hidden] comfortable, solid and spacious boat has given us beautiful sailing crossings.
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Unspoilt Balearic Islands for max 4 guests: north Mallorca and south Menorca

10/18/2025

John D.

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Switzerland

Great skipper with excellent knowledge of the different harbours and coves in Mallorca and Menorca.. Enrico is very flexible and can adjust to changing weather.. Many thanks to our skipper and fantastic cook for making this voyage safe, smooth, and and simply unforgetable!
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IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper

10/15/2025

Cinzia R.

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Italy

Nice holiday, as described and above all the skipper Filippo is a marvel, he manages everything with the utmost naturalness, always in safety, and great surprise (sorry to spoil :D), he is a spectacular cook!! Its all-inclusive formula is really super, delicious dishes, without wasting anything! P.S. Nao is adorable :)

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