115

experiences

4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

June

€625

Per person

4.2

Discover the South of Sardinia by sailing, white beaches and tradition

Italy: Southern Sardinia

6 days - 7 nights

3 departures available

July - August

€950

€855

Per person

Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

3 departures available

March - May

Starting from

€640

Per person

4.7

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - August

Starting from

€920

€828

Per person - min 2 pax

4.6

The Saronic jewels with Hydra and Spetses exclusively for four

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

May

€1,250

€1,125

Per person

4.4

The unspoiled paradise of the BVI

Caribbean: BVI - British Virgin Islands

10 days - 10 nights

One departure available

March

€1,350

€1,147

Per person

5.0

Weekend of Sailing and Relaxation

Italy: Liguria

2 days - 1 night

20 departures available

March - August

Starting from

€290

Per person

4.2

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

France: French Riviera and Porquerolles

6 days - 7 nights

10 departures available

June - September

Starting from

€730

€657

Per person

4.8

Thailand: a dream to discover sailing with a hostess

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

4 departures available

January - December

€1,050

Per person

4.8

New Year's Eve wandering among the islands of Thailand with hostesses

Thailand: Phuket, Krabi and Phi Phi Islands

11 days - 11 nights

One departure available

December - January

€1,646

Per person

5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

20 departures available

June - October

Starting from

€1,100

Per person

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€850

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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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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