header cover
sailsquare logo

Yacht sailing holidays & skippered tours in Italy

Discover more than 88 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

88

experiences

cover image
avatar image

5.0

Poetic Gulf of Poets

Duration:

3 days - 2 nights

Italy:

Liguria

avatar image
avatar image
avatar image

18 travellers

Starting from

€170

€200

Per person

cover image
avatar image

4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Duration:

3 days - 3 nights

Italy:

Tuscany

avatar placeholder
avatar placeholder
avatar placeholder

18 travellers

Starting from

€342

€380

Per person

cover image
avatar image

4.3

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

avatar placeholder
avatar placeholder
avatar placeholder

4 travellers

Starting from

€720

€800

Per person

cover image
avatar image

4.9

Super!

Sunny weekend on Elba from Friday to Sunday

Duration:

3 days - 2 nights

Italy:

Tuscany

avatar placeholder
avatar placeholder
avatar placeholder

32 travellers

Starting from

€275

€305

Per person

cover image
avatar image

4.9

Super!

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

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

avatar image
avatar image
avatar image

37 travellers

Starting from

€477

€530

Per person

cover image
avatar image

5.0

Super!

Weekend Elba o Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

avatar image
avatar image
avatar placeholder

34 travellers

Starting from

€264

€293

Per person

cover image
avatar image

4.8

Super!

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

avatar image
avatar image
avatar image

60 travellers

Starting from

€671

€745

Per person

cover image
avatar image

5.0

Aeolian Islands: between sea and authentic flavours

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

avatar image
avatar image
avatar image

123 travellers

Starting from

€585

€650

Per person

cover image
avatar image
L'Estate è fatta per le Eolie! Crociera settimanale

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

avatar image
avatar placeholder
avatar placeholder

32 travellers

Starting from

€630

€700

Per person

cover image
avatar image

4.7

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

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

avatar image
avatar image
avatar image

91 travellers

Starting from

€585

€650

Per person

cover image
avatar image

4.5

Weekend of sea and colors between Ischia, Procida and Vivara

Duration:

2 days - 2 nights

Italy:

Naples & Amalfi Coast

avatar image
avatar image
avatar image

20 travellers

Starting from

€248

€275

Per person

cover image
avatar image
Women's sailing

Duration:

2 days - 1 night

Italy:

Tuscany

avatar placeholder
avatar placeholder
avatar placeholder

5 travellers

Starting from

€177

€197

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