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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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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

6 departures available

May - October

Starting from

€320

€272

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

5 departures available

June - September

Starting from

€999

€949

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

8 departures available

June - September

Starting from

€650

€585

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

14 departures available

May - October

Starting from

€230

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

3 departures available

July - September

Starting from

€390

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

June - October

Starting from

€650

Per person

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4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

21 departures available

May - November

Starting from

€650

€618

Per person

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4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

8 departures available

June - October

Starting from

€420

€399

Per person

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5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€790

Per person

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4.6

Different flotilla in Ionian Greece: nature, new friends and fun

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

Starting from

€874

€699

Per person

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4.8

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

6 days - 7 nights

7 departures available

June - September

Starting from

€583

€525

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

11 departures available

May - September

Starting from

€400

€380

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.

-

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.

-

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.

-

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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