Homepage cover
logo

Log in

All inclusive yacht sailing holidays & tours in Italy

Discover more than 14 opportunities to get on board a All inclusive adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

cover image
avatar image

4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September

€790

Per person

cover image
avatar image

4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, e Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

September

€1,150

Per person

cover image
avatar image

4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

4 departures available

October

Starting from

€1,320

€1,188

Per person - min 2 pax

cover image
avatar image

4.8

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

Italy: Lake Garda

1 day - 0 nights

19 departures available

August - October

€150

Per person

cover image
avatar image

4.9

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

Italy: Liguria

1 day - 0 nights

3 departures available

August

Starting from

€150

Per person

cover image
avatar image

5.0

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

Italy: Sicily

2 days - 1 night

4 departures available

August - September

Starting from

€215

€194

Per person

cover image
avatar image

5.0

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

Italy: Aeolian Islands

2 days - 2 nights

5 departures available

August - September

Starting from

€723

€650

Per person

cover image
avatar image

4.9

Sailing in Tigullio: Half-Day Experience from Rapallo

Italy: Liguria

1 day - 0 nights

2 departures available

August

€91

Per person

cover image
avatar image

5.0

From the sun to the moon - Afternoon All inclusive on Lake Garda

Italy: Lake Garda

1 day - 0 nights

One departure available

August

€149

Per person

cover image
avatar image

5.0

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

Italy: Sicily

3 days - 2 nights

5 departures available

August - September

Starting from

€315

€284

Per person

cover image
avatar image

5.0

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

Italy: Lake Garda

1 day - 0 nights

16 departures available

August - October

Starting from

€59

Per person

cover image
avatar image

4.4

Premium

SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

September - October

Starting from

€1,345

€1,143

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

571 reviews

avatar image

Sailing in Tigullio: Half-Day Experience from Rapallo

08/5/2026

Maurizio P.

-

IT

Fantastic experience, very kind staff who made us feel at home. Highly recommend.

Sailing in Tigullio: Half-Day Experience from Rapallo

08/4/2026

LUCA ADRIANO B.

-

IT

Well organized sailing excursion. We bathed, without haste, in two beautiful places.. Captain and crew treated us well with lots of focaccia and pizza for a snack!

Sailing in Tigullio: Half-Day Experience from Rapallo

08/4/2026

Barbara P.

-

IT

Pleasant outing

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

08/4/2026

Assunta D.

-

AU

Our sailing cruise with Alessandro was truly unforgettable! From exploring charming island villages and mooring in picturesque ports to diving straight into the warm, glorious sea, every moment was a highlight. Alessandro’s friendliness and cooking of local dishes made the experience even more special. Beyond being a fantastic host, he is an exceptionally skilled sailor with deep local knowledge of the Naples and Amalfi coast—and plenty of great stories to share. Experiencing these islands from the water offers a whole new perspective that you just can't get by land. We will definitely do this again.

Customer Support

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!

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

MastercardVisaGoogle PayApple Pay

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