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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

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

9 departures available

July - October

Starting from

€230

Per person

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4.8

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

One departure available

June

€750

€675

Per person

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4.4

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

13 departures available

June - September

Starting from

€730

€657

Per person

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New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

9 departures available

June - September

Starting from

€650

€585

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

2 departures available

July - September

Starting from

€750

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - August

Starting from

€850

€765

Per person

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4.7

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

€999

Per person

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4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

5 departures available

July - September

Starting from

€650

€585

Per person

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4.9

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

4 departures available

July - August

Starting from

€410

€369

Per person

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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

5 departures available

June - September

Starting from

€312

Per person

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4.7

Whale watching cruise with WWF guide in the Corfu archipelago

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,052

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

19 departures available

June - November

Starting from

€420

€399

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

17724 reviews

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2 June long weekend - discovering the Gulf of Poets and Portofino

06/5/2026

Annalisa P.

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IT

Skipper very kind and responsive even pre departure, boat a bit spartan. Destination with very beautiful landscapes, but necessarily a bit "uncomfortable", as there are not many shelters/ports for stops

2 June long weekend on a sailing boat in the beautiful Ligurian setting

06/5/2026

Franco P.

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IT

We spent four fun and pleasant days even with wind and sea conditions that were not optimal for sailing

2 June long weekend - Capraia and Cap Corse

06/5/2026

claudio p.

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IT

First experience on a sailing boat decidedly positive! Enrico has great experience and is an excellent captain (and cook!), helpful and pleasant company. Thanks to the wonderful weather and the right crew found on board, the long weekend to Corsica was perfect. The boat has all the necessary amenities, with bathrooms in each cabin and spaces suitable for relaxing in the waves. Till the next one!

Long weekend of June 2nd on the Costa Smeralda

06/5/2026

Anna O.

-

IT

All top :) Francesco serious and reliable, an excellent cook. 4 days of relaxation in Costa Smeralda, to be done again, beautiful experience.

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