experiences

4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

4 departures available

June - August

Starting from

€1,150

Per person

5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

2 departures available

October

€215

Per person

4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

26 departures available

May - October

Starting from

€1,320

€1,056

Per person - min 2 pax

5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

2 departures available

October - November

€723

Per person

5.0

3 days sailing among the hidden gems of Palermo - All inclusive & flexible dates

Italy: Sicily

3 days - 2 nights

One departure available

October

€315

Per person

5.0

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

One departure available

October

€69

Per person

4.4

Premium

SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

23 departures available

May - October

Starting from

€1,525

€1,373

Per person - min 2 pax

Why book a holiday with Sailsquare?

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

581 reviews

Sailing, swimming and aperitif at sunset ... What else?

10/3/2026

Victoire D.

Perfect afternoon with Emanuele! Wonderful host, generous food and drink and the boat is beautiful and welcoming Many thanks!!

All-Inclusive Sailing: Capri, Positano, Amalfi

09/28/2026

Nathalie P.

Very nice cruise with our skipper Alessandro who was very knowledgeable and very attentive. Highly recommend.

Let's sail in relaxation on Lake Garda - All Inclusive

09/1/2026

Henry d.

Fabio and his wife adorable and welcoming. Drinks and cold cuts/cheeses for a picnic. Fabio speaks perfect French and English.

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

08/19/2026

Carlotta C.

Experience in wonderful places, Alessandro's kindness and shrewdness are certainly the plus of the holiday

Customer Support

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!

Call us at

+44 20 3514 4220

Read our

Contact & Support

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

Sailboat (305)Whole boat with skipper (270)Cooking service onboard (100)Catamaran (65)All inclusive (35)Day trips (25)Family sailing cruises (20)Courses & regatta (15)Sport & wellness (10)Gulet and sailing ship (5)

Other travel ideas

Sailboat (123)Whole boat with skipper (111)Cooking service onboard (54)Catamaran (42)Exotic destinations (31)All inclusive (28)Courses & regatta (10)Offshore (9)Family sailing cruises (5)Day trips (5)