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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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4.9

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

Italy: Aeolian Islands

6 days - 7 nights

5 departures available

July - September

Starting from

€750

Per person

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4.7

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€999

€949

Per person

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4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

3 departures available

July

Starting from

€390

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

2 departures available

August

€510

€459

Per person

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5.0

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

3 departures available

June - July

Starting from

€285

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - October

Starting from

€600

€540

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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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

June - September

€280

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

4 departures available

June - August

Starting from

€700

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

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

10 departures available

June - October

Starting from

€800

€720

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

17704 reviews

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2 June: Whale watching expedition with WWF guide on an 18-meter schooner

06/3/2026

Deborak S.

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IT

Generally, when you think of participating in such a trip, you inevitably create high and beautiful expectations... well, I must say that they have all been exceeded by far, day after day! On board the Mahayana you can enjoy the dream that created it, the environmental vision that pervades it, the professionalism, kindness and ability to make everyone feel at ease in the crew. Our whale watching guide was an inexhaustible source of very interesting and detailed information and spread his passion for the sea and its inhabitants very well. A trip that I would do a thousand times again. Thank you❤️
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Four nights in the Pontine Islands - midweek

06/3/2026

Alessandro R.

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IT

Overall positive and beautiful experience. The Pontine islands are a real beauty, especially when seen from a sailboat. The skipper Antonio was a nice acquaintance, a very kind person and always with a story to tell about the places visited. The only flaw was not having had the opportunity to open the sails.
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Long weekend to discover the island of Capraia

06/3/2026

Eleonora C.

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IT

We had a great experience in [hidden]. The nice and caring skipper. The boat was perfect for sailing comfortably between coves and breathtaking views. We couldn't ask for anything better for our relaxation!

Long weekend of June 2 with WWF guide in the heart of the Tuscan Archipelago

06/3/2026

Eliana P.

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IT

Beautiful experience, fantastic skipper and guide, super travel companions, to be done again absolutely!

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