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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!

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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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,260

€1,134

Per person

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4.8

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

2 departures available

June - August

Starting from

€1,150

Per person

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4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

41 departures available

January - December

Starting from

€300

€270

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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4.9

Super!

Life Changing Experiences - Arcipelago La Maddalena

Italy: Northern Sardinia

6 days - 6 nights

3 departures available

August

€1,100

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

6 departures available

July - August

Starting from

€850

€765

Per person

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5.0

Super!

Zakynthos and the Strofades Islands: a unique route in Ionian Greece

Greece: Ionian Islands

6 days - 6 nights

3 departures available

June - July

Starting from

€850

Per person

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4.9

Super!

Weekend at the Pontine. Travel with photographer-Life changing experiences

Italy: Pontine Islands

3 days - 2 nights

10 departures available

June - September

Starting from

€370

€352

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

2 departures available

August

Starting from

€977

€879

Per person

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5.0

Super!

From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

June

€1,000

Per person

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5.0

Super!

Sailing in the Aegean, the sea of the Gods!

Greece: Cyclades

7 days - 7 nights

One departure available

May

€500

Per person

Why book a holiday with Sailsquare?

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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

17662 reviews

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!

Unspoilt Balearic Islands for max 4 guests: Mallorca and/or Menorca

05/10/2026

Charlotte W.

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France

A great experience aboard Enrico's sailboat! We loved sailing, discovering coves, sleeping at anchor... all with a great atmosphere, Enrico knows how to put people at ease and he is an excellent skipper! Special mention to his pasta recipes:) we will be back!

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