109

experiences

4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

13 departures available

June - September

Starting from

€641

Per person

4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,300

Per person

4.8

Super!

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

11 departures available

July - September

Starting from

€700

Per person

5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

33 departures available

March - October

Starting from

€490

Per person

5.0

Super!

Relaxing holiday on the Côte d'Azur

France: French Riviera and Porquerolles

7 days - 7 nights

9 departures available

April - August

Starting from

€540

€486

Per person

5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€850

€765

Per person

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

33 departures available

March - October

Starting from

€490

Per person

4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

3 departures available

August

Starting from

€1,040

Per person

5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

16 departures available

June - October

Starting from

€778

€700

Per person

4.9

Super!

Week on the Côte d'Azur between Porquerolles and Calanques

France: French Riviera and Porquerolles

6 days - 7 nights

7 departures available

July - August

Starting from

€800

Per person

New

Sailing for a day in the Tuscan Archipelago

Italy: Tuscany

1 day - 0 nights

14 departures available

November - December

€125

Per person

4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€990

Per person

Why book a holiday with Sailsquare?

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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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

It's time for sun and sea!

11/5/2026

francesca t.

All very nice !! and Carlo... A very good sailor and a very kind and hospitable person !! Francesca

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

11/3/2026

Paolo P.

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.

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

11/3/2026

Alvise V.

Great!

Squid Festival 2026! - Capraia Isola

11/3/2026

Andrea C.

Good experience, too bad for the weather conditions not ideal.

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