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Sailboat yacht sailing holidays & tours in Italy

Discover more than 296 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - September

Starting from

€719

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

July - September

Starting from

€650

Per person

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5.0

Super!

North and south Sardinia of Corsica sailing

Italy: Northern Sardinia

7 days - 7 nights

3 departures available

July - August

Starting from

€900

€810

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,190

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

August - October

Starting from

€200

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

2 departures available

August - September

Starting from

€793

€714

Per person

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4.7

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

Italy: Northern Sardinia

6 days - 7 nights

9 departures available

July - September

Starting from

€650

Per person

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4.9

Super!

Week of sea, nature and fun in the Egadi Islands!

Italy: Aegadian islands

7 days - 7 nights

7 departures available

July - September

Starting from

€690

€621

Per person

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4.8

Super!

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

July - August

Starting from

€780

Per person

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5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€935

€748

Per person

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4.8

Super!

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

4 departures available

July - September

Starting from

€660

Per person

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4.9

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

9 departures available

August - November

Starting from

€530

€477

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

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

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.

Find out before you book who's waiting for you on board

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

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 yacht sailing holidays & tours in Italy

11459 reviews

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Short sailing cruise in the Gulf of Naples

07/5/2025

francesca s.

-

Italy

Esperienza gratificante un ottimo inizio estate, luoghi incantevoli e compagnia piacevolissima
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Un giorno intero in barca a vela nel golfo di ALASSIO

07/5/2025

Aaron C.

-

Italy

Piacevolissimo pomeriggio in compagnia di Daniele e della sua Famiglia. Relax, tuffi e nuotate.
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All Inclusive Tour: Capri, Amalfi, Cetara, and Sorrento

07/5/2025

MANJA B.

-

Slovenia

The whole trip was great in every way. Alessandro spoiled us by cooking lunches, preparing snacks and making coffee whenever we felt like it! We saw all the planned places/towns and enjoyed every moment on deck and in the sea:)
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Life-changing experiences: Four days in the Pontine Islands

07/5/2025

Massimo M.

-

Italy

Esperienza davvero positiva. Organizzazione ottima, barca confortevole e itinerario unico! Un ringraziamento speciale allo skipper, che è stato professionale, competente e sempre disponibile. Ha gestito tutto con tranquillità e attenzione, creando un bel clima a bordo e facendoci sentire sempre al sicuro. Consiglio questa esperienza a chi vuole avvicinarsi alla vela in modo sereno e ben organizzato.

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