experiences

5.0

Poetic Gulf of Poets

Duration:

3 days - 2 nights

Italy:

Liguria

18 travellers

Starting from

€170

€200

Per person

4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Duration:

3 days - 3 nights

Italy:

Tuscany

18 travellers

Starting from

€342

€380

Per person

4.3

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

4 travellers

Starting from

€720

€800

Per person

4.9

Super!

Sunny weekend on Elba from Friday to Sunday

Duration:

3 days - 2 nights

Italy:

Tuscany

32 travellers

Starting from

€275

€305

Per person

4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

37 travellers

Starting from

€477

€530

Per person

5.0

Super!

Weekend Elba o Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

34 travellers

Starting from

€264

€293

Per person

4.8

Super!

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

60 travellers

Starting from

€671

€745

Per person

5.0

Aeolian Islands: between sea and authentic flavours

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

123 travellers

Starting from

€585

€650

Per person

L'Estate è fatta per le Eolie! Crociera settimanale

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

32 travellers

Starting from

€630

€700

Per person

4.7

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

91 travellers

Starting from

€585

€650

Per person

4.5

Weekend of sea and colors between Ischia, Procida and Vivara

Duration:

2 days - 2 nights

Italy:

Naples & Amalfi Coast

20 travellers

Starting from

€248

€275

Per person

Women's sailing

Duration:

2 days - 1 night

Italy:

Tuscany

5 travellers

Starting from

€177

€197

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.

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.

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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 - Yacht sailing holidays & skippered tours in Italy

12220 reviews

Weekend catamaran in Portovenere and Cinque Terre

05/12/2025

Davide S.

Italy

Antonio ed il suo catamarano "Cassiopea" sono il perfetto mix tra compentenza, professionalità, freschezza, passione e disponibilità nel far sentire gli ospiti a loro agio durante tutta la permanenza in barca. Semplicemente quello che serve per staccare la spina dalla frenesia quotidiana e trascorrere dei bei momenti in mare in ottima compagnia. Super consigliato.

Weekend in Capraia, the island with timeless sunsets

05/12/2025

Stefano F.

Italy

Marco è un vero appassionato di barche e, per questo, ti fa assaporare ogni momento che si trascorre a bordo

Stuffed anchovies: magical weekend from Genoa

05/12/2025

Maurizio S.

4 stelle perché c’è sempre la possibilità di migliorare, Bella esperienza che va senz’altro rifatta in luoghi diversi.

1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

05/8/2025

Maria Pia D.

Italy

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