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Yacht sailing holidays & skippered tours in Italy

Discover the beauty of Italy and treat yourself to a sailing holiday of relaxation, fun, and unique landscapes. Sail around the beautiful islands of Sicily and Sardinia, discover the Lipari, Pontine and Aegadian Islands by boat or anchor in the romantic bays of Tuscany or Cinque Terres.

391

experiences

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5.0

Free in the Wind... scents and wonders in the upper Adriatic

Duration:

2 days - 1 night

Italy:

Venice and the Gulf of Trieste

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12 travellers

€179

€199

Per person

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Capri, Sorrento, Positano and Amalfi by Catamaran

Duration:

5 days - 4 nights

Italy:

Naples & Amalfi Coast

Give this experience a try!

€477

€530

Per person

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4.5

In the blue of Capri and the infinity of the Amalfi Coast

Duration:

2 days - 2 nights

Italy:

Naples & Amalfi Coast

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76 travellers

Starting from

€248

€275

Per person

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Aeolian Slab in La Maddalena

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€810

€900

Per person

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4.9

Summer Camps on a Sailing Boat for girls aged 14 to 18

Duration:

7 days - 6 nights

Italy:

Pontine Islands

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5 travellers

Starting from

€675

€750

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Duration:

6 days - 7 nights

Italy:

Tuscany

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115 travellers

Starting from

€714

€793

Per person

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Women's sailing

Duration:

2 days - 1 night

Italy:

Tuscany

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5 travellers

Starting from

€177

€197

Per person

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4.7

Mini Cruise in Western Liguria, boarding from Genoa

Duration:

3 days - 2 nights

Italy:

Liguria

Give this experience a try!

€252

€280

Per person

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5.0

Super!

Weekend SS. Peter and Paul at the Pontine

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€441

€490

Per person

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Experience in the Egadi Islands: A Dream on a Sailing Boat

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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16 travellers

Starting from

€360

€400

Per person

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4.9

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

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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6 travellers

Starting from

€621

€690

Per person

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4.7

The Egadi Islands as you've never seen them before on a 16-meter boat with a professional hostess

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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87 travellers

€1,332

€1,460

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 - Yacht sailing holidays & skippered tours in Italy

12220 reviews

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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.
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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
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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.
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1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

05/8/2025

Maria Pia D.

-

Italy

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Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

Aeolian Islands

Stromboli, Vulcano and Lipari are just some of the best destinations for a sailing or catamaran vacation in Sardinia.
Guide to the Aeolian Islands on a sailing boat

Sardinia

Costa Smeralda, Maddalena Archipelago and San Pietro Island are just some of the best destinations for a sailing or catamaran holiday in Sardinia.
Guide to the Sardinia on a sailing boat

Capri, Ischia and Procida

Enchanted landscapes and elegant haunts, thermal springs and seabeds full of surprises, simplicity and glamour: there is more than one reason to choose these timeless islands as a destination for a yachting holiday in stages.
Guide to Capri, Ischia and Procida on a sailing boat

Amalfi Coast

Positano, Amalfi and Cetara are just some of the best destinations for a sailing or catamaran holiday in the Gulf of Naples.
Guide to the Amalfi Coast on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
Guide to sailing vacations with children

Italy: the most beautiful places to sail

Italy: departures by month

Other travel ideas

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