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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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4.8

New Year's Eve wandering among the islands of Thailand with hostesses

Thailand: Phuket, Krabi and Phi Phi Islands

11 days - 11 nights

One departure available

December - January

€1,646

Per person

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4.8

Tenerife and La Gomera aboard an 18 m ketch - ALL-INCLUSIVE

Atlantic islands: Canary Islands

6 days - 7 nights

10 departures available

January - December

Starting from

€900

Per person

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4.1

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

31 departures available

January - December

Starting from

€275

€248

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

13 departures available

January - December

€1,400

Per person

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4.4

Caribbean by boat, the Grenadines and Tobago Cays

Caribbean: Grenadines & Martinique

7 days - 7 nights

2 departures available

January

€950

€855

Per person

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5.0

Thailand and the Andaman Sea

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

11 departures available

February - December

Starting from

€1,500

€1,425

Per person

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4.9

Day in the Gulf of Tigullio on a Sailing Boat

Italy: Liguria

1 day - 0 nights

9 departures available

July - August

€130

Per person

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4.5

Wild Corsica: The Magic of a Boat Trip

France: Corsica

7 days - 7 nights

4 departures available

July - August

Starting from

€1,000

Per person

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4.8

Thailand: a dream to discover while sailing

Thailand: Phuket, Krabi and Phi Phi Islands

14 days - 14 nights

One departure available

January

€2,100

Per person

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New

San Blas Paradise: Island Hopping by Sailboat

Caribbean: San Blas Islands - Panama

9 days - 9 nights

One departure available

December

€1,670

Per person

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4.9

Skiathos, Skopelos, Alonissos: The Sporades as you've never seen them before.

Greece: Sporades

6 days - 6 nights

19 departures available

May - September

Starting from

€700

Per person

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4.8

Share & Sail 5 days ex-Lavrio: Exploring the Greek islands

Greece: Cyclades

4 days - 4 nights

One departure available

April

€1,080

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

19291 reviews

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Feast of Santa Candida in Ventotene

11/9/2026

Gennaro A.

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IT

Pleasant holiday in an always suggestive setting. The feast of Santa Candida in Ventotene is a pleasant discovery and every year I gladly go back ...

It's time for sun and sea!

11/5/2026

francesca t.

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IT

All very nice !! and Carlo... A very good sailor and a very kind and hospitable person !! Francesca
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Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

11/3/2026

Paolo P.

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IT

Excellent experience, boat up to expectations, skipper attentive to the safety of the crew and always available to evaluate every request of the people on board. To repeat the adventure for other destinations.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

11/3/2026

Alvise V.

-

IT

Great!

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