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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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4.1

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

35 departures available

January - December

Starting from

€275

€248

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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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

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4.7

Tuscany and Liguria, we sail between the Apuan Alps and the Gulf of Poets

Italy: Liguria

2 days - 2 nights

One departure available

April - May

€300

Per person

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Balearic Cruise: Alicante-Ibiza-Formentera-Mallorca

Spain: The Balearic Islands

7 days - 7 nights

One departure available

April

€1,950

€1,755

Per person

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4.8

South Sardinia - A Marine Paradise to Explore!

Italy: Southern Sardinia

7 days - 7 nights

5 departures available

August - September

Starting from

€830

Per person

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5.0

Tuscany & Corsica Energy Program between food, sea, sun and adventure

Italy: Tuscany

6 days - 6 nights

6 departures available

July - August

Starting from

€801

Per person

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New

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

June - July

€400

€360

Per person

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4.5

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

9 departures available

July - September

Starting from

€688

Per person

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5.0

Sailing excursion from Naples to Procida or Sorrento

Italy: Naples & Amalfi Coast

1 day - 0 nights

19 departures available

November - December

€100

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

19290 reviews

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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.

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IT

Great!
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Squid Festival 2026! - Capraia Isola

11/3/2026

Andrea C.

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IT

Good experience, too bad for the weather conditions not ideal.
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The fantastic Saronic Islands and the surroundings of Athens

10/20/2026

Francesca A.

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IT

We spent a beautiful week together with Alessandro.Even if the weather was not the most clement, we were able to visit beautiful and characteristic places that we could never have discovered in any other way. In addition to the fantastic experience itself, it was Alessandro who made the difference: an experienced captain, a true master of life, with a wealth of stories to write a book about. We spent days between the sea, the wind and its stories, eating and drinking together as old friends. Thank you Ale, we will always carry you in our hearts with the hope of meeting again soon. Francesca and Davide

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