136

experiences

4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

4 departures available

September - October

€1,300

Per person

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

September - October

Starting from

€700

Per person

4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

September - November

Starting from

€585

€527

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

4 departures available

October

€570

Per person

5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

4 departures available

September - October

€370

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

4 departures available

September - October

Starting from

€570

Per person

5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

Per person

4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

€750

Per person

5.0

Super!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

Per person

4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

One departure available

September

€490

€440

Per person

4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€750

€675

Per person

4.8

Super!

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

Italy: Tuscany

2 days - 2 nights

4 departures available

September - October

Starting from

€230

Per person

Why book a holiday with Sailsquare?

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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

19159 reviews

Five days barefoot between Tuscany and Corsica

09/18/2026

daniela s.

It was an unforgettable experience, the travel companions were delightful, efficient and fun. Lorenzo, the captain was splendid in managing the crew lightly and equally splendid in managing the storm while sailing

A week sailing in the most beautiful places in the world

09/18/2026

Davide G.

Fantastic experience! We got to discover incredible places traveling with the wind. Piero is a great skipper and a person of heart, he taught us the basics of sailing. We always felt safe even in strong winds. Giusy is a super cook and as a sailor she is no different. He spoiled us for a week! Comfortable, welcoming and organized boat in every detail. Super recommended experience for those who love the sea, nature and conviviality. Ps: LET PIERO WIN AT SCOPONE ahaha

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

09/17/2026

Cecilia A.

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.

Great experience

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