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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

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

2 departures available

May

€350

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

4 departures available

May - July

Starting from

€350

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

12 departures available

May - September

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

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

21 departures available

May - November

Starting from

€600

€540

Per person

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5.0

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

20 departures available

May - October

Starting from

€550

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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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!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

5 departures available

June - July

Starting from

€285

Per person

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4.9

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

3 departures available

July - August

Starting from

€410

€369

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!

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

Italy: Aeolian Islands

6 days - 7 nights

13 departures available

May - 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

17663 reviews

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Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola

05/12/2026

Paola A.

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Italy

We immediately felt comfortable with everything and everyone. We left as strangers and came back as a group of friends. The treatment was higher than expected. WELL DONE WELL DONE !

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

05/11/2026

Lucia K.

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Switzerland

Our sailing holidays around Corfu were simply exceptional. The combination of crystal-clear waters, stunning islands, and peaceful hidden bays made every single day unforgettable. The crew Andrea, Marta & Mattias was incredibly friendly, professional, and always made us feel welcome and relaxed on board. The itinerary was perfectly balanced between discovering beautiful Greek islands, enjoying time at sea, and experiencing authentic local culture. The food was another highlight — fresh, delicious, and healthy, with plenty of local specialties prepared with care. It was truly a unique and unforgettable experience that we would highly recommend to anyone looking for the perfect mix of adventure, relaxation, and comfort.

May Day between Elba and Capraia

05/11/2026

Valeria C.

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Italy

The weather helped us enjoy a fantastic navigation also thanks to the experience of the skipper Enrico and the comfort of the boat. Mixed crew sea... It could have gone very badly or very well and it went very well!
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Relaxing weekend in the Pontine Islands

05/11/2026

Flavia F.

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Italy

Great experience! Stefano and Adriano welcomed us as great hosts in their beautiful "family boat". This made our holiday serene, pleasant and constructive p.s. with a group that we did not know before! All together they supported us in making the first sailing experience of our children aged 8 and 11 unforgettable... they would already like to come back! 😊 Thank you Antonietta and Remo, thank you Daniela and Paolo. Fair winds Commander!

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