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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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4.0

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

4 departures available

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

2 departures 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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4.5

Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€290

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

2 departures 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

6 departures available

October

€150

Per person

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5.0

Capraia and Elba Island - Sun, Sea and Fun!

Italy: Tuscany

4 days - 3 nights

One departure available

October

€400

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

19235 reviews

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From Milos to Athens: the fantastic Western Cyclades

09/29/2026

Jonas D.

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BE

Good times … meandering from island to island !

All-Inclusive Sailing: Capri, Positano, Amalfi

09/28/2026

Nathalie P.

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FR

Very nice cruise with our skipper Alessandro who was very knowledgeable and very attentive. Highly recommend.

Let's discover Portofino, Santa Margherita and Sestri Levante together

09/28/2026

Cristina A.

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IT

Beautiful ride, professionalism and friendliness at the top
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A week sailing in the most beautiful places in the world

09/28/2026

sara s.

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IT

A wonderful experience!! We stayed a week with Piero and Giuseppina booking the whole boat. Despite the adverse weather forecast, the weather was always good. But we have always relied on the wise course decisions of Piero, who in addition to always being attentive and scrupulous, is a very good skipper in all aspects: his daily lessons will not be forgotten! A special mention goes to Giuseppina, with whom I immediately found myself in tune even with just a smile. His cuisine is spatial, better than that of many restaurants in the area! But Piero in the kitchen is not bad either, his spaghetti are excellent! Thank you for this trip and for the company!

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