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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

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€850

Per person

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4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

11 departures available

June - September

Starting from

€736

Per person

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5.0

Raja Ampat: a Christmas at the end of the world

Indian Ocean: Indonesia

8 days - 8 nights

One departure available

December

€1,428

Per person

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4.4

Guadalupe to St. Martin via Antigua, Barbuda, St. Barth, and Anguilla

Caribbean: Saint Martin

14 days - 14 nights

One departure available

February

€1,490

€1,341

Per person

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4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

30 departures available

April - November

Starting from

€650

€618

Per person

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4.2

Easter sailing on the Côte d'Azur: enchanting roadsteads and Provençal villages

France: French Riviera and Porquerolles

3 days - 3 nights

One departure available

March

€380

€342

Per person

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4.9

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

17 departures available

May - September

Starting from

€600

€540

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

12 departures available

July - September

Starting from

€750

€675

Per person

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4.8

Sailing excursion to Capri / Positano

Italy: Naples & Amalfi Coast

1 day - 0 nights

90 departures available

July - September

€150

Per person

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New

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

May

€400

Per person

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4.8

From Funchal to Lanzarote: adventure and unforgettable emotions

Atlantic islands: Canary Islands

6 days - 7 nights

One departure available

December

€900

Per person

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4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

12 departures available

July - September

Starting from

€745

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 - Sailboat holidays & skippered tours

19291 reviews

It's time for sun and sea!

11/5/2026

francesca t.

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IT

All very nice !! and Carlo... A very good sailor and a very kind and hospitable person !! Francesca
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Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

11/3/2026

Paolo P.

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IT

Excellent experience, boat up to expectations, skipper attentive to the safety of the crew and always available to evaluate every request of the people on board. To repeat the adventure for other destinations.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

11/3/2026

Alvise V.

-

IT

Great!
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Squid Festival 2026! - Capraia Isola

11/3/2026

Andrea C.

-

IT

Good experience, too bad for the weather conditions not ideal.

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