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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

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

9 departures available

July - October

Starting from

€230

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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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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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

9 departures available

June - August

Starting from

€390

€351

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

13 departures available

July - November

Starting from

€540

€513

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€800

Per person

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4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

One departure available

August

€800

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

5 departures available

June - August

Starting from

€900

€765

Per person

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5.0

Super!

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

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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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

9 departures available

July - November

Starting from

€500

€425

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

July

€590

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

17857 reviews

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

06/23/2026

Martina B.

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IT

A wonderful holiday. Francesco in addition to being an excellent skipper, is also a fantastic cook! His deep knowledge of the islands and the locals allowed us to live an even deeper and more special experience. With his boat [hidden] he took us to discover wonderful corners, making us feel part of the life of the Aeolian Islands. Emotions that we will always carry in our hearts. Thank you for everything!

Weekend at the Pontine Islands between Ponza and Palmarola

06/23/2026

sara g.

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IT

Beautiful experience, skipper Marco super nice!!!
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Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

06/23/2026

Kim W.

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CA

An amazing experience, not simply a choice destination (nature, culture, cuisine, weather) but truly memorable from the standpoint of staffing, communication and service. From the moment you book the trip, Bledar is in contact, verifying your needs. I felt 100% certain my celiac daughter would be well-supported on the journey with an unusual sophistication of dietary understanding. Bledar is an excellent chef for celiacs and non-restricted diets alike. In addition to his captain credentials, he is a delight to talk with and the purveyor of fun. His magnetic personality gives him so many connections to the community that you will be guaranteed to enjoy the best nature, eating, shopping spots. Whatever you desire Bledar and his first mate Alesandro will make the memory possible! I would go back and sail with them in a heartbeat.

Amazing Pontine Islands on a sailboat with private bathrooms

06/23/2026

Giulia C.

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IT

Wonderful first sailing experience! Comfortable boat, adequate space. Carlo and Barbara super nice and easy-going. The swim at the Cathedrals is super recommended. Absolutely recommended experience

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