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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!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€410

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

One departure available

June

€312

Per person

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4.4

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

13 departures available

June - September

Starting from

€730

€657

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

6 departures available

June - August

Starting from

€900

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

3 departures available

July - September

Starting from

€750

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

3 departures available

July - August

Starting from

€850

€765

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

€999

Per person

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5.0

Super!

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

11 departures available

June - October

Starting from

€1,200

Per person

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New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

8 departures available

June - September

Starting from

€650

€585

Per person

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4.7

Whale watching cruise with WWF guide in the Corfu archipelago

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,052

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

17 departures available

June - November

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

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.

-

IT

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

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