experiences

Blu Pontino - Evasione infrasettimanale

Duration:

4 days - 3 nights

Italy:

Pontine Islands

13 travellers

Starting from

€190

Per person

4.3

Weekend of theoretical and practical course

Duration:

2 days - 1 night

Italy:

Liguria

6 travellers

€250

Per person

4.8

3 days - Sorrento, Capri, Positano, Amalfi - Luxury Sailing Yacht

Duration:

3 days - 2 nights

Italy:

Naples & Amalfi Coast

Give this experience a try!

Starting from

€300

Per person

4.8

Capri and Amalfi Coast by CATAMARAN BALI 4.3 ALL INCLUSIVE

Duration:

3 days - 2 nights

Italy:

Naples & Amalfi Coast

2 travellers

Starting from

€1,200

Per person

5.0

Le Eolie da Vulcano in una Barca Esclusiva

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

4 travellers

Starting from

€500

Per person

5.0

Super!

We have known the Aeolian Islands for 20 years. - Live them with us.

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

5 travellers

€583

Per person

4.9

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

22 travellers

€299

Per person

5.0

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€650

Per person

Approach to sailing: day on a boat with sailing lesson

Duration:

1 day - 0 nights

Italy:

Tuscany

2 travellers

Starting from

€87

Per person

4.0

East Coast of Sicily From Taormina to Portopalo. Cook on board

Duration:

6 days - 7 nights

Italy:

Sicily

Give this experience a try!

Starting from

€625

Per person

4.8

Super!

Let's discover the Aeolian Islands together in Vela

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

37 travellers

Starting from

€590

Per person

4.9

Super!

LET'S GO TO TOTANI - Festival in Capria

Duration:

3 days - 3 nights

Italy:

Tuscany

8 travellers

€420

Per person

Why book a holiday with Sailsquare?

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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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