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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

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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4.6

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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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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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August

Starting from

€849

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!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

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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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

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

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

17763 reviews

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Summer is made for the Aeolian Islands! Weekly cruise

06/11/2026

Patrizia R.

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IT

Very comfortable boat. For the first time I found a skipper who lent himself to the purchase of a galley without waste and in any case complete and integrated by specific requests of the crew. The skipper also prepared tasty meals on board, including typical dishes of the Aeolian culinary tradition. On board we enjoyed a relaxed and very pleasant atmosphere and the stops took place, weather permitting, in the most iconic places of the Aeolian archipelago. It is an experience that I certainly recommend. Patricia

June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide

06/10/2026

Guido F.

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IT

Beautiful experience. The enthusiasm and ability to involve biologists is remarkable. The only pity we never sailed.

Weekend in Ischia and Ventotene: History and Nature

06/10/2026

Michele F.

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IT

Wonderful holiday! The boat was very comfortable, spacious and always spotlessly clean. A special thanks to Umberto, skipper par excellence: excellent sailor, profound connoisseur of the places visited and always ready to share curiosities and advice. Always available, professional and super nice, he made the experience even more enjoyable. Highly recommended for those who want to experience a relaxing and fun boat holiday with an excellent selection of music!

June 2nd long weekend between Ponza, Palmarola, Zannone and Ventotene

06/10/2026

Donatella L.

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IT

Extraordinary, welcoming skippers and also creative cooks! Highly recommended!

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