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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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4.5

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 Marmaglia Sun & Fun - Croatia

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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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August

Starting from

€920

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!

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

10 departures available

August - October

Starting from

€1,400

€1,120

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

10 departures available

August - October

Starting from

€590

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

3 departures available

August - September

Starting from

€600

€570

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

5 departures available

July - September

Starting from

€900

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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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

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

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

18152 reviews

Long weekend in the Pontine Islands between Ponza and Palmarola

07/21/2026

Valeria T.

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IT

Vincenzo very helpful and professional person, we had a really good time! Highly recommended

Weekend on a Sailing Boat in the Magical Gulf of Poets

07/21/2026

Novella C.

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IT

A nice experience with fantastic skipper and crew!

Leave everything for the Island of Elba

07/21/2026

Corrado F.

-

IT

Excellent experience, Joshua proved to be super helpful in accommodating any of our requests and giving us a lot of information regarding both the trip and the management of the boat. He also proved to be an excellent cook, delighting us with simple dishes but prepared with care and dedication.
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Ibiza and Formentera between coves and fun

07/21/2026

Silvia C.

-

IT

I agree with the one Chantal wrote last year. A lot of tension. Never again...... Experience not to be repeated

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