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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

Super!

Four days in Ponza and Palmarola

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

Per person

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4.8

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

7 departures available

June - August

Starting from

€410

€369

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

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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4.8

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

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

17744 reviews

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June 2 long weekend in the Pontine Islands

06/9/2026

Clara A.

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IT

Fabio is truly a phenomenal skipper who took us to discover the wonderful Pontine islands. Absolutely recommended experience!! Thank you very much Fabio, see you soon!

It's time for sun and sea!

06/8/2026

Benedetta D.

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IT

Climbing [hidden] is like entering Carlo's house. A hospitable, caring and attentive friend. His boat is beautiful, comfortable but above all maintained with care and with the dedication of a passionate person. Carlo managed to convey his love for the sea and gave us a wonderful weekend of relaxation and approach to the magical world of sailing. I can only recommend this experience and I hope to get back on board as soon as possible!!
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Long weekend in Sardinia

06/8/2026

Davide I.

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IT

Wonderful group, magnificent places and sea, super skipper!
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Weekend of the Pontine Islands to discover Ponza and Palmarola

06/8/2026

Ilaria A.

Unforgettable experience! Marco and Giada are fantastic, attentive to everyone's needs, flexible and ready for any experience. The boat is home to it's nice to share every space. I wish you a journey like this, a journey of the soul between the waves of the sea and the waves of the wind.

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