header cover
sailsquare logo

Yacht sailing holidays & skippered tours in Italy

Discover more than 181 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

cover image
avatar image

4.8

Super!

Lampedusa, Lampione e Linosa fra colori magici

Italy: Pantelleria and Lampedusa

7 days - 7 nights

One departure available

July

€700

€595

Per person

cover image
avatar image

4.7

Two boats walking on the island of Elba: the magic of the roadstead!

Italy: Tuscany

6 days - 5 nights

2 departures available

July

Starting from

€750

€638

Per person

cover image
avatar image

4.6

Cruise to the Maddalena Archipelago and South Corsica

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

July - August

Starting from

€785

€667

Per person

cover image
avatar image

5.0

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

July

Starting from

€200

€170

Per person

cover image
avatar image
Two boats walking on the island of Elba: the magic of the roadstead!

Italy: Tuscany

6 days - 5 nights

One departure available

July

Starting from

€1,000

€850

Per person

cover image
avatar image

4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

3 departures available

July

Starting from

€380

€342

Per person

cover image
avatar image

4.3

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

Italy: Northern Sardinia

6 days - 7 nights

One departure available

July

Starting from

€800

€720

Per person

cover image
avatar image
Eco Mini-Cruise on the West Coast of Sicily

Italy: Sicily

2 days - 2 nights

One departure available

July

Starting from

€500

€450

Per person

cover image
avatar image

5.0

Weekend in Ogliastra, super Sardinia with skipper and hostess

Italy: Southern Sardinia

3 days - 2 nights

2 departures available

July

€680

€612

Per person

cover image
avatar image

4.9

Super!

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

2 departures available

July

Starting from

€395

€356

Per person

cover image
avatar image

4.3

Sailing in the natural parks of Sardinia, from La Maddalena to Asinara

Italy: Northern Sardinia

6 days - 7 nights

One departure available

July - August

€900

€810

Per person

cover image
avatar image
Sailing Cruise - The Odyssey - Egadi Islands - Sicily

Italy: Aegadian islands

6 days - 6 nights

One departure available

July

Starting from

€950

€855

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

avatar placeholder

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.
avatar placeholder

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
avatar image

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.
avatar placeholder

1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

05/8/2025

Maria Pia D.

-

Italy

TOP

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964