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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

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

8 departures available

June - August

Starting from

€410

€369

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

3 departures available

July - August

Starting from

€800

Per person

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4.9

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

2 departures available

August

Starting from

€1,060

Per person

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5.0

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

2 departures available

July - September

Starting from

€350

Per person

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5.0

Super!

Weekend between Ponza and Palmarola Comfortable - max 4 people

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€495

€446

Per person

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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

9 departures available

June - October

€650

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

6 departures available

July - October

€260

Per person

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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

9 departures available

June - August

Starting from

€250

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

5 departures available

July - August

Starting from

€900

Per person

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4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

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

17736 reviews

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Midweek special between Capraia and Northern Corsica

06/7/2026

DANIELA C.

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IT

Thank you very much, Marco! You are an attentive, kind and always available skipper. From the first moment you manage to make everyone feel welcomed and at ease, sharing your beautiful boat with great generosity. Your experience and expertise convey safety and serenity, allowing everyone to fully enjoy every moment of navigation. The boat is perfect, spotless and equipped with every comfort. You know how to choose the best routes and spectacular destinations. Thanks also to my travel companions for the pleasant company.

Midweek special between Capraia and Northern Corsica

06/7/2026

Silvia G.

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IT

Thank you Marco, you were an excellent skipper, you told us so many interesting things, you led us safely to beautiful places.,Waking up in the morning and swimming in an emerald bay, all for us, is an unforgettable experience! Thanks also to all the travel companions who helped make this trip magical.....and thanks especially to [hidden]!

Midweek special between Capraia and Northern Corsica

06/7/2026

Samantha G.

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IT

Four unforgettable days between Capraia and North Corsica with fantastic travel companions! Marco is a perfect skipper: kind, professional, prudent, always available and caring with everyone! I hope to be able to travel with him again in the future
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Midweek special between Capraia and Northern Corsica

06/7/2026

Maurizio Z.

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IT

Beautiful experience, the skipper Marco, prepared, helpful and caring. The boat is very beautiful and well cared for and above all very clean. The tour was very nice and Marco introduced us to places and legends of the Island of Capraia and Corsica. We felt pampered and above all safe throughout the trip. Definitely to be repeated in another itinerary!

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