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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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5.0

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

2 departures available

August

Starting from

€390

Per person

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5.0

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

Italy: Tuscany

6 days - 6 nights

3 departures available

July - August

Starting from

€950

Per person

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5.0

Super!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August

€990

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - September

Starting from

€716

Per person

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New

Corsica Sailing Experience for only 4 people

France: Corsica

7 days - 6 nights

One departure available

August

€900

Per person

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5.0

Super!

ONE WAY Marina River - Porto Vecchio

France: Corsica

3 days - 3 nights

One departure available

August

€290

Per person

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4.4

L'Île de Beauté: sailing in Corsica with night return

France: Corsica

6 days - 7 nights

One departure available

August

€749

Per person

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5.0

Super!

Sail in Menorca with a cook on board!

Spain: The Balearic Islands

5 days - 5 nights

One departure available

August

€950

€855

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

September

€790

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

4 departures available

September - October

Starting from

€600

€540

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

18177 reviews

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Midweek getaway between Elba and Capraia

07/25/2026

Maria V.

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IT

Edoardo made me make peace with the sea! I was lucky enough to board his wonderful boat with my mom and I hope it will become an annual event :)
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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

07/25/2026

Cristian P.

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IT

Luca and Tommy super!! 😊

Aeolian Islands in the name of sailing, fishing and relaxation

07/25/2026

IRIS K.

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AT

Antonio was a very accommodating and competent captain. He fulfilled all requests and was able to give us a lot of information about the Isole Eolie. Thank you!
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Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

07/25/2026

Michele G.

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IT

Amazing holiday with a fantastic itinerary. A precise, prepared skipper who is very engaging in sailing manoeuvres. The boat is perfect.

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