experiences

4.9

Super!

Sailing dreams in the Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

August

€350

Per person

4.8

Super!

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

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

August

€1,115

Per person

5.0

Super!

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

Italy: Tuscany

1 day - 0 nights

27 departures available

August

€145

Per person

4.8

Super!

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

Italy: Naples & Amalfi Coast

6 days - 6 nights

3 departures available

July - September

Starting from

€1,385

€1,316

Per person

4.9

Super!

Traveling and dreaming in the Gulf of Poets - All Inclusive

Italy: Liguria

2 days - 1 night

One departure available

September

€260

Per person

5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

12 departures available

August - September

Starting from

€79

Per person

4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

September

€360

Per person

5.0

Super!

Day trip on a sailing boat

Italy: Tuscany

1 day - 0 nights

7 departures available

July

€180

Per person

5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

One departure available

July

€75

Per person

4.8

Super!

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

Italy: Naples & Amalfi Coast

3 days - 2 nights

26 departures available

July - October

Starting from

€1,325

Per person

5.0

Super!

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

12 departures available

July

€99

Per person

4.8

Super!

Capri and Amalfi Coast by catamaran - ALL INCLUSIVE

Italy: Naples & Amalfi Coast

3 days - 2 nights

5 departures available

July - October

Starting from

€1,800

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

529 reviews

Traveling and dreaming in the Gulf of Poets - All Inclusive

07/7/2025

Michele T.

Italy

Weekend fantastico, all’insegna del relax, mare, ottima compagnia e divertimento. Francesca e Giorgio sono stati accoglienti, professionale e ci hanno coccolati preparandoci prelibatezze e aperitivi super. Da rifare sicuramente!!

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

07/6/2025

Sasa G.

Slovenia

We were a group of five women and Alessandro took us to all the beautiful places we had hoped to see. From the start, we felt completely safe and well looked after. He was kind, discreet, and attentive, always making sure we were comfortable and enjoying ourselves. Thanks to Alessandro, we experienced some truly magical moments and places.

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

07/6/2025

Maila L.

Siamo stati a bordo con Matteo e Maria Teresa domenica scorsa ed è stata una giornata bellissima. Una fuga serena e di risate che ci serviva. Veleggiare con il solo rumore del mare e delle risate di nuovi amici è stato il valore aggiunto. La barca è bellissima e tenuta con la cura perfetta dei padroni di casa. Un grazie di cuore per l’accoglienza, l’attenzione ai dettagli e l’empatia. Maila e Davide

Aperitif Trip to the Gulf of Tigullio - All inclusive!

07/6/2025

alice b.

Italy

Esperienza veramente favolosa. Super consigliata!

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!

Italy: the best travel ideas

Sailboat (1430)Whole boat with skipper (1115)Cooking service onboard (175)Catamaran (140)Family sailing cruises (130)All inclusive (110)Day trips (110)Courses & regatta (45)WWF Sailing Cruises (40)Sport & wellness (35)

Other travel ideas

Sailboat (499)Whole boat with skipper (389)Cooking service onboard (96)Catamaran (69)All inclusive (57)Family sailing cruises (33)Courses & regatta (27)Day trips (26)Offshore (20)Sport & wellness (17)