experiences

4.8

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

Duration:

5 days - 5 nights

Italy:

Naples & Amalfi Coast

6 travellers

Starting from

€1,059

€1,115

Per person

4.8

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

Duration:

6 days - 6 nights

Italy:

Naples & Amalfi Coast

6 travellers

€1,316

€1,385

Per person

5.0

A day sailing in the fantastic Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

30 travellers

Starting from

€94

€99

Per person

5.0

Super!

Day trip on a sailing boat

Duration:

1 day - 0 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€150

Per person

Full board South Sardinia Cruise with hostess

Duration:

6 days - 6 nights

Italy:

Southern Sardinia

Give this experience a try!

€1,290

Per person

4.8

All Inclusive - Procida, Ischia, Capri: the Pearls of the Gulf

Duration:

3 days - 2 nights

Italy:

Naples & Amalfi Coast

Give this experience a try!

€680

Per person

4.4

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

Full board South-East Sardinia Cruise with hostess

Duration:

6 days - 6 nights

Italy:

Southern Sardinia

Give this experience a try!

€1,290

Per person

5.0

Super!

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

Duration:

1 day - 0 nights

Italy:

Tuscany

53 travellers

Starting from

€125

Per person

5.0

Super!

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

Duration:

1 day - 0 nights

Italy:

Lake Garda

36 travellers

Starting from

€59

Per person

4.8

3 days - Sorrento, Capri, Positano, Amalfi - Luxury Sailing Yacht

Duration:

3 days - 2 nights

Italy:

Naples & Amalfi Coast

Give this experience a try!

Starting from

€1,325

Per person

4.6

Premium

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

244 travellers

Starting from

€980

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

512 reviews

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

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

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.

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

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 2035144220

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!