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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

IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper

Spain: The Balearic Islands

6 days - 7 nights

One departure available

October

€900

Per person

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4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

4 departures available

September - October

Starting from

€690

Per person

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New

Weekends immersed in the blue of the sea and the green of the island of Elba

Italy: Tuscany

3 days - 2 nights

2 departures available

September - October

€275

Per person

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5.0

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

October

€295

Per person

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4.5

Relaxing weekend and sailing school

Italy: Tuscany

2 days - 1 night

4 departures available

September - October

€220

Per person

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4.0

Outdoor and lifestyle exploration

Greece: Peloponnese

6 days - 6 nights

One departure available

September

€815

Per person

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4.0

European Mile Builder - Leg 2: Gibraltar to Las Palmas

Atlantic islands: Canary Islands

6 days - 6 nights

One departure available

November

€660

Per person

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5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

5 departures available

September - October

Starting from

€215

€194

Per person

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4.0

European Offshore Mile Builder - Leg 5: St Tropez to Malta

France: French Riviera and Porquerolles

6 days - 6 nights

One departure available

October

€550

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

4 departures available

September - October

Starting from

€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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New

Sailing Week Sardinia and Corsica

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

October

€600

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

19157 reviews

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Whale watching mini-cruise in the Pelagos Sanctuary with WWF guide

09/17/2026

Cecilia A.

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PT

Beautiful, I absolutely recommend! Flavia and Gianni were top! Beautiful experience and we spotted Bottlenose Dolphins :)

Just relaxing while sailing on the Côte d'Azur

09/17/2026

Marco V.

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IT

Great experience
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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

09/16/2026

Olivia C.

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US

We had the best week with Capitano! He took us to the most beautiful places! The trip was a 10/10! No notes! You will not be disappointed if you book with him! Hope to sail with him again someday! :)

Weekend Elba or Capraia

09/16/2026

Mauro G.

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IT

Fun boat in sailing. Too bad for the weather conditions of the previous days that made the sea not optimal. Still pleasant experience throughout. I recommend, for the optimal training of the guest crew, to plan the mood of the experience in advance. Thanks again to skipper Nicola who made us experience the thrill of upwind ⛵😊👍🏻

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