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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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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,070

Per person

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4.7

Flotilla Martello Sun & Fun - Croatia - WOMEN'S PLACES ONLY

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,180

€980

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,290

€1,190

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€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

3 departures available

August

Starting from

€920

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

August - September

Starting from

€600

€570

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

8 departures available

August - October

Starting from

€590

Per person

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4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

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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4.6

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,110

€799

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

2 departures available

August - September

Starting from

€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

18249 reviews

Discover the Egadi Paradise by sailboat from San Vito Lo Capo

07/29/2026

Marta P.

-

IT

The skippers were very good, professional, fun and company. Egadi is a paradise on earth, an ideal destination to make peace with the world. Super comfortable and spotless boat... If the wind decides to participate, it sails which is a fairy tale. thanks Jo! thanks Andre!

Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/29/2026

Maria Z.

Very nice experience, skipper super helpful to make us appreciate wonderful bays and beaches of the Pontine islands,
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Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

07/29/2026

Claudio A.

-

IT

A sailing holiday simply fantastic! An unforgettable experience, between sea, relaxation and adventure. The skippers were very good: professional, prepared, helpful and always attentive to everyone's needs. (Very comfortable boat). They gave us beautiful moments, showing great attention to us, creating a very special atmosphere on board. Highly recommended, I can't wait to leave!
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Island of Elba and South Corsica fantastic week

07/29/2026

Alessandra G.

-

IT

Francesco was an excellent "host"! We had to revise the itinerary due to the weather conditions (little wind) but he was able to identify beautiful places without making us absolutely regret the tour that was planned! It was a fantastic experience to repeat

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