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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

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€795

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€920

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

9 departures available

August - October

Starting from

€1,300

€1,040

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - October

Starting from

€700

Per person

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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

4 departures available

October

Starting from

€275

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

One departure available

August

€1,100

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

6 departures available

September - October

Starting from

€570

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

Per person

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5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - October

€690

Per person

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5.0

Super!

Corsica Sailing Experience for only 4 people

France: Corsica

7 days - 6 nights

One departure available

August

€900

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

18439 reviews

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

08/10/2026

Irene R.

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IT

Beautiful experience, super prepared and very kind WWF guide. The week was wonderful to repeat!!
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Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

08/10/2026

renzo b.

-

IT

When passion goes hand in hand with competence and sympathy, the result is excellent. A week spent between navigation, fun and fantastic places.
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/10/2026

Sabrina M.

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IT

Flotilla holiday in the Aeolian Islands simply incredible! ⛵️🌊 Davide and Anto, super skipper and co-skipper! Always professional but also ready to entertain us at all times. Crystal clear sea, breathtaking landscapes, super parties and above all many new friends with whom to share this unique experience. Waking up in the middle of the sea is really priceless... and seeing the sciara of the fire of Stromboli is something that stays with you forever. An unforgettable emotion! See you soon💙
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/10/2026

Mario A.

I wanted to do this trip for a while, apparently difficult to organize but they think of everything, from the airport shuttle to the galley, to every single detail. I had the pleasure of spending that week with Simone (the flotilla leader) who loves what he does! Potto and Andrea followed us in every single moment, from reorganizing the shopping, to the management of life on the boat, the various trips in the tender and the sailor's shower. You don't need big suitcases, bring the essentials!

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