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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

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

Starting from

€325

€309

Per person

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4.4

Atlantic crossing by sailboat from Tenerife to the Caribbean

Caribbean: Grenadines & Martinique

20 days - 20 nights

One departure available

November - December

€3,900

Per person

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4.8

Sailing and Trekking in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€730

Per person

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New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

September - October

Starting from

€585

€527

Per person

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4.7

Feast of Santa Candida alle Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€390

Per person

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4.6

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€700

Per person

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4.4

New Year's Eve in the Caribbean: Martinique and the Grenadines OneWay

Caribbean: Grenadines & Martinique

10 days - 11 nights

One departure available

December - January

€1,590

Per person

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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

Per person

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€350

Per person

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4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€890

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

19155 reviews

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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

09/16/2026

Olivia C.

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US

We had the best week with Capitano! He took us to the most beautiful places! The trip was a 10/10! No notes! You will not be disappointed if you book with him! Hope to sail with him again someday! :)

Weekend Elba or Capraia

09/16/2026

Mauro G.

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IT

Fun boat in sailing. Too bad for the weather conditions of the previous days that made the sea not optimal. Still pleasant experience throughout. I recommend, for the optimal training of the guest crew, to plan the mood of the experience in advance. Thanks again to skipper Nicola who made us experience the thrill of upwind ⛵😊👍🏻

Week between the Tuscan Islands and Northern Corsica

09/16/2026

Rosanna B.

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IT

Fantastic experience!! Splendid and very comfortable boat, wonderful itinerary!! Francesco is a very prepared, kind skipper, always present and attentive to any problem that may arise. He also knows the places on the itinerary very well and also provides very useful information on how to get around on land... I can only thank him!!
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L'Île de Beauté: sailing in Corsica with night return

09/16/2026

Marco F.

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IT

If you are looking for a skipper you can trust 100% while sailing, Sandro is definitely the person for you. Be aware, however, that the price to pay is to accept his abrupt, gruff and not always properly polite ways. Its ability to interpret the sea is inversely proportional to its ability to make you feel at ease on board. For him, passengers are basically a nuisance. If, like me, you are at your first experience on a boat, ask questions that seem obvious to him or you make mistakes simply dictated by lack of experience, everything becomes even more complicated... for him and for you! Added to this is practically non-existent communication and explanations reduced to a minimum. But, on the other hand, every coin has its downside and, in this wonderful boat experience, I got to know both sides of the coin. On the one hand, an extremely competent skipper, able to read the sea and convey confidence. On the other, a man with decidedly unaccommodating manners. In the end, it's up to you to decide which of the two weighs more.

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