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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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4.4

From Martinique to Guadeloupe riding the trade winds

Caribbean: Guadeloupe

10 days - 10 nights

One departure available

February

€1,250

€1,125

Per person

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5.0

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

Spain: The Balearic Islands

6 days - 6 nights

One departure available

October

€950

Per person

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5.0

New

Cruise to the Golden Islands via the capes and bay of St Tropez

France: French Riviera and Porquerolles

5 days - 4 nights

27 departures available

February - October

Starting from

€595

Per person

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4.1

Totano's cup 2027 weekend of sailing and party on the island

Italy: Tuscany

3 days - 2 nights

One departure available

October

€350

Per person

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New

Sailing Week Sardinia and Corsica

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

October

€600

Per person

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4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

June

€625

Per person

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5.0

New

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

€590

Per person

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Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

€890

Per person

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4.8

Let's sail in relaxation on Lake Garda - All Inclusive

Italy: Lake Garda

1 day - 0 nights

5 departures available

October

€150

Per person

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4.4

The unspoiled paradise of the BVI

Caribbean: BVI - British Virgin Islands

10 days - 10 nights

One departure available

March

€1,350

€1,147

Per person

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5.0

New

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€250

Per person

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4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

3 departures available

October

€320

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

19255 reviews

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

10/5/2026

Aldo B.

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AT

My partner and I had an amazing week at sea, and a big part of that was our crew. Alessandro, our skipper, was highly professional and made us feel safe and well looked after at every moment. Carlo, our steward, was warm, attentive and always ready with a smile. The route between Corfu, Paxos and Antipaxos was stunning, with crystal-clear water and charming harbours. The crew went out of their way to make the trip special. We explored sea caves by dinghy, played an unforgettable volleyball match in the middle of the sea, and got great restaurant recommendations for our evenings ashore. Carlo's lunches on board were delicious, fresh and beautifully prepared. Alessandro and Carlo truly made this trip. We would happily sail with them again and recommend them to anyone looking for a relaxed, fun and well-organized holiday on the water. Thank you both!
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Maddalena Archipelago, southern Corsica: wonderful Sardinia

10/5/2026

Michelle B.

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US

Mossimo and Valentina were superb! Incredible sailing, delicious food, taking us to stunning locations it far exceeded my expectations! I highly recommend sailing with them. Cheers! Michelle

Egadi paradise for sailing and snorkeling

10/4/2026

Luzia K.

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DE

Unfortunately, a wonderful week has come to an end. Mario is a great skipper and host. I can't even list all the bays where we swam in the crystal clear water. Gaia took very good care of us. Nice people, sun, absolutely relaxed.

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

10/4/2026

Livia R.

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IT

Everything perfect.. Very well organized. Very nice and engaging experience.

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