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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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4.8

Super!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

7 days - 7 nights

8 departures available

January - December

€850

Per person

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4.8

Super!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

6 days - 6 nights

4 departures available

February - December

€730

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

18 departures available

May - October

Starting from

€689

Per person

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4.8

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

10 departures available

May - July

Starting from

€650

€585

Per person

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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

26 departures available

March - September

Starting from

€650

€618

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€625

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

31 departures available

March - October

Starting from

€460

Per person

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4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

24 departures available

May - October

Starting from

€600

Per person

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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

19 departures available

May - October

Starting from

€600

€540

Per person

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4.9

Super!

Traveling and Dreaming in the Gulf of Poets - All inclusive

Italy: Liguria

2 days - 2 nights

One departure available

May

€360

Per person

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4.9

Super!

"Nel blu dipinto di blu" - Sailing cruise in Northern Corsica

Italy: Tuscany

7 days - 7 nights

10 departures available

June - September

Starting from

€680

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

June

€360

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 - Sailboat holidays & skippered tours

17615 reviews

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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/5/2025

Marco F.

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Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.
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LET'S GO TO TOTANI - Festival in Capria

11/5/2025

Marco D.

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Italy

Unforgettable and fun experience, very prepared skipper who tamed a sea that was not exactly docile. The fishing competition is beautiful and suggestive.
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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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End of season weekend in the Aeolian Islands

11/3/2025

Collwyn Y.

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Italy

I come from the North Sea but I now live the Italian Alps and I’ve been really missing the ocean. So, after much thinking, I decided to treat myself to a little sailing holiday in October. [hidden] (the boat) is cozy yet has every comfort and the hosts really make you feel like you’re being treated to an Italian family gateway. Giacomo and Laura go above and beyond to fit everyone's need and requests. They exceeded my expectations! Great company, great food and insane landscapes! Nothing quite like sleeping under the stars, lulled by the gentle rocking of the boat. Thank you, I hope next time I can bring my family from Scotland!

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