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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!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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5.0

Super!

Squid Festival in Capraia with a professional skipper and chef

Italy: Tuscany

2 days - 2 nights

One departure available

October

€250

Per person

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4.5

New

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September - October

€890

Per person

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5.0

Let's discover Portofino, Santa Margherita and Sestri Levante together

Italy: Liguria

2 days - 2 nights

4 departures available

October - November

Starting from

€380

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

€4,200

Per person

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5.0

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

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

€690

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

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

One departure available

September

€345

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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4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€890

Per person

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5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

3 departures available

September - October

€1,100

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

19162 reviews

North Corsica & Tuscan Archipelago: we love to travel a lot

09/19/2026

francesca vera p.

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IT

Beautiful holiday, lovely places. Thanks to Marco and his travel companions!
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Five days barefoot between Tuscany and Corsica

09/19/2026

Mariella D.

-

IT

The holiday went well. Matteo was helpful. For 4 nights, arriving in Corsica becomes very long the navigation and inevitably the possibilities of swimming are reduced. Then the cost of fuel can affect a lot
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A sailing story between Favignana, Levanzo and Marettimo

09/19/2026

Alessandro P.

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IT

First experience of a week on a sailing boat: I can only be enthusiastic! To the itinerary with a "right" navigation for a baptism was added a skipper who was not only technically capable, but also attentive to everything (even to my being a vegetarian) and to everyone's well-being, through a valid program, taking time in the first person also to go and buy the necessary on land and pamper ourselves with the right music playlist. To be added then the reassuring assistance from his team, both before departure and during navigation. The group was varied but in each one there was respect and desire to feel good alone and with others, so much so that no one ever backed down in the daily routine of preparing meals and tidying up the necessary. The boat, [hidden], also proved to be a friend: adequate spaces, functional bathrooms, practical kitchen: a great boat kept to perfection and with care. Finally, the sea of the Egadi Islands is magnificent and even the islands have treasures made up of people to chat with, but also paths to explore. To conclude: the organizational part was excellent but we must not forget that the favor of temperatures, sea and wind - which are an exclusive matter of Jupiter, Neptune and Aeolus - made everything more beautiful and enjoyable.

Five days barefoot between Tuscany and Corsica

09/18/2026

daniela s.

-

IT

It was an unforgettable experience, the travel companions were delightful, efficient and fun. Lorenzo, the captain was splendid in managing the crew lightly and equally splendid in managing the storm while sailing

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