Homepage cover
logo

Log in

All inclusive yacht sailing holidays & tours in Italy

Discover more than 13 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

4.5

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

One departure available

October

Starting from

€1,320

€1,056

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

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

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

4 departures available

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

15 departures available

August - October

Starting from

€59

Per person

cover image
avatar image

4.5

Premium

SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

September - October

Starting from

€1,445

Per person - min 2 pax

cover image
avatar image

4.9

Aperitif Trip to the Gulf of Tigullio - All inclusive!

Italy: Liguria

1 day - 0 nights

2 departures available

August

€85

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

2 departures available

August

€150

Per person

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

577 reviews

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

08/17/2026

Prash S.

-

FR

We had one of our most memorable weeks exploring the Amalfi Coast with Alessandro and a group of wonderful strangers (now friends). Alessandro was very thoughtful and produced a great and varied programme and social experience. The whole experience felt special and authentic. I wish all weeks were as enjoyable as this ! The worst part was when it ended ! Highly recommended !
avatar image

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

08/17/2026

MANUELA B.

-

IT

A wonderful week to discover the Amalfi Coast, experienced from a very special perspective: the sea. ⛵️💙 The sailboat is comfortable, functional and welcoming, and allowed us to fully enjoy every moment of the holiday. The Amalfi Coast is simply spectacular, a beautiful sea, unique landscapes and cities full of charm, all to be discovered. A special thanks goes to the captain, Alessandro, always kind, helpful and attentive to our needs. In addition to being an excellent captain, competent and able to handle any event during navigation with tranquility, he also turned out to be a very good cook! 😊 He made us feel at ease and accompanied us in this experience with sympathy and professionalism. And then Naples... It is impossible not to fall in love with its atmosphere and especially with its food, really delicious! ❤️ It was a beautiful holiday, made up of sea, wonderful places, good food and beautiful people. An experience that I will remember with great affection. Thank you so much for this wonderful week! ⛵️☀️🌊

An all-inclusive day on a sailing boat

08/16/2026

Pierre C.

-

FR

We spent a delighted day on the boat with Federica, Luidgi and their family. Such authentic moments and love shared together. Thanks so much !!!

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

08/10/2026

Paola P.

Excellent organization! Very nice skipper and prepared. Experience to be redone!!

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