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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!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

12 departures available

May - October

Starting from

€230

Per person

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4.9

An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

8 departures available

June - September

Starting from

€750

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

11 departures available

May - October

Starting from

€250

Per person

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4.6

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

9 departures available

June - September

Starting from

€650

Per person

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4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

4 departures available

July - August

Starting from

€480

€432

Per person

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5.0

Super!

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

Croatia: Split Archipelago

7 days - 7 nights

13 departures available

June - October

€1,250

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

3 departures available

May

€350

Per person

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5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August

€650

Per person

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5.0

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

21 departures available

May - October

Starting from

€540

Per person

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4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

4 departures available

July - August

€800

Per person

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5.0

Super!

Weekend at the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

5 departures available

June - July

Starting from

€285

Per person

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4.6

Different flotilla in Ionian Greece: nature, new friends and fun

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

Starting from

€874

€699

Per person

Why book a holiday with Sailsquare?

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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

17637 reviews

Weekend sailing course from Bandol

05/2/2026

Nathalie R.

-

France

A beautiful sailing discovery stay, in a friendly atmosphere and perfect weather. Thank you
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4 Days Exploring the Chausey Islands from Saint-Malo

04/30/2026

Claire M.

-

France

Four days of pure happiness from Saint-Malo to the Chausey Islands! Skipper at the top: professional, reassuring and hyper attentive to safety. Comfortable, impeccable boat, you immediately feel good. And the icing on the cake: home-made, balanced and delicious meals, prepared by the skipper himself. Total disconnection, a real holiday!

Sailing cruise in the Greek islands - The Saronic Islands

04/29/2026

Marc G.

-

Canada

A week on a roller coaster too windy, no more wind. Mother Nature is in charge! However our skipper was really up to the situation, Alexandre is a good captain and a good GO (nice organizer) his knowledge of the islands and the people who live there adds a lot to the fun and experience. Regarding the boat, although old, it is a very good boat but unfortunately there were several small problems that did not affect our trip, we believe that preventive maintenance could be in order. Thank you again Alexandre for your Carbonaras and the typical Greek evening. Good winds from Quebec Hélène and Marc

April 25th: cetacean watching expedition in the Pelagos Sanctuary with WWF guide

04/28/2026

Michele B.

-

Italy

Relatively short but interesting sea outing, with an excellent skipper and WWF experts. On board a nice and multinational company. There has been no shortage of dolphin sightings.

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