header cover
sailsquare logo

All inclusive yacht sailing holidays & tours in Italy

Discover more than 17 opportunities to get on board a All inclusive adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

17

experiences

cover image
avatar image
Full board South-East Sardinia Cruise with hostess

Duration:

6 days - 6 nights

Italy:

Southern Sardinia

Give this experience a try!

€1,226

€1,290

Per person

cover image
avatar image

5.0

Super!

A day sailing in the fantastic Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

avatar image
avatar image
avatar image

24 travellers

components.thumb.crew.booked

€94

€99

Per person

cover image
avatar image
Full board South Sardinia Cruise with hostess

Duration:

6 days - 6 nights

Italy:

Southern Sardinia

Give this experience a try!

€1,226

€1,290

Per person

cover image
avatar image

4.6

Premium

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

avatar image
avatar image
avatar image

150 travellers

components.thumb.crew.booked

Starting from

€1,416

€1,490

Per person

cover image
avatar image
Sardinia Aperitif at sunset in Mari Pintau - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Southern Sardinia

Give this experience a try!

Starting from

€95

Per person

cover image
avatar image

5.0

Super!

A fantastic day on a boat in the blue sea of Tuscany

Duration:

1 day - 0 nights

Italy:

Tuscany

avatar image
avatar image
avatar image

53 travellers

components.thumb.crew.booked

Starting from

€130

Per person

cover image
avatar image

4.9

Aperitif Trip to the Gulf of Tigullio - All inclusive!

Duration:

1 day - 0 nights

Italy:

Liguria

avatar image
avatar image
avatar image

112 travellers

components.thumb.crew.booked

€89

Per person

cover image
avatar image

4.9

Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

Duration:

1 day - 0 nights

Italy:

Liguria

avatar image
avatar image
avatar image

269 travellers

components.thumb.crew.booked

€150

Per person

cover image
avatar image

4.5

Premium

Capri Dream Premium - Catamaran cruise full board

Duration:

6 days - 7 nights

Italy:

Naples & Amalfi Coast

Starting from

€1,260

Per person - min 2 pax

cover image
avatar image

5.0

Sailing, early sun and aperitif at sunset ... What else?

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar image
avatar placeholder
avatar placeholder

9 travellers

components.thumb.crew.booked

Starting from

€59

Per person

cover image
avatar image

5.0

Afternoon sailing and barbecue evening

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar image
avatar placeholder
avatar placeholder

18 travellers

components.thumb.crew.booked

Starting from

€129

Per person

cover image
avatar image

5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar image
avatar image
avatar placeholder

128 travellers

components.thumb.crew.booked

Starting from

€99

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 - All inclusive yacht sailing holidays & tours in Italy

513 reviews

avatar image

New Year's Eve 2024 on the Amalfi Coast - All inclusive

01/3/2025

Ilaria C.

-

Italy

Straordinario skipper , grande capacità di unire persone interessanti esperienza che intendo rifare proprio con questa barca questo skipper e la qualità delle sue scelte
avatar image

New Year's Eve 2024 on the Amalfi Coast - All inclusive

01/2/2025

Gabriella M.

-

Italy

È stata una piacevole vacanza in ottima compagnia. Lo skipper Fabrizio è una persona competente, simpatica e molto disponibile, oltre ad essere un ottimo cuoco
avatar image

All Inclusive Cruise to the Egadi Islands

10/8/2024

Francesca D.

-

Italy

Scrivo una sola parola: speciali. Agata e Leonardo prima di tutto. Le prelibatezze a bordo. La barca. I luoghi.
avatar image

A wonderful day on Lake Garda - ALL INCLUSIVE

09/30/2024

Alessandro B.

-

Italy

Una delle più belle esperienze in barca vela mai fatte! Lo skypper è stato eccezionale sotto tutti i punti di vista e ci ha fatto trascorrere una giornata super. Complice un meteo che ci ha permesso di vivere la vela a tutto tondo, ci portiamo a casa un bellissimo ricordo. Sicuramente ripeteremo l'esperienza.

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!

Italy: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964