experiences

5.0

Super!

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

5 departures available

September - October

Starting from

€99

Per person

5.0

Super!

AperiBarca: afternoon sunset aperitif

Italy: Tuscany

1 day - 0 nights

One departure available

August

€65

Per person

5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

One departure available

October

€69

Per person

5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

11 departures available

August - October

Starting from

€69

Per person

4.8

Super!

Day trip with aperitif at sunset!

Italy: Liguria

1 day - 0 nights

One departure available

August

€65

Per person

Daily Sailing Adventure to the Tremiti Islands

Italy: Tremiti Islands

1 day - 0 nights

38 departures available

August - October

Starting from

€130

Per person

Bachelorette Party

Italy: Liguria

1 day - 0 nights

2 departures available

August

Starting from

€290

Per person

Daily sailing trip off the coast of beautiful Pisa

Italy: Tuscany

1 day - 0 nights

45 departures available

August - November

Starting from

€115

Per person

5.0

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

2 departures available

August - October

€99

Per person

Sailing tour in the Gulf of Orosei with gourmet lunch - All inclusive

Italy: Southern Sardinia

1 day - 0 nights

10 departures available

August - September

€160

Per person

Sardinia Aperitif at sunset in Mari Pintau - ALL INCLUSIVE

Italy: Southern Sardinia

1 day - 0 nights

One departure available

August

€115

Per person

4.2

A roundabout by the sea

Italy: Liguria

1 day - 0 nights

10 departures available

August - September

Starting from

€75

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 - Day trips yacht sailing holidays & tours in Italy

611 reviews

A full day on a sailing boat in the Gulf of ALASSIO

08/24/2025

Claudia B.

Italy

Simply fantastic day. Daniele in a short time was able to make us feel among friends. Sun, sea and wind gave a special day leaving a great desire to repeat the experience. The assistant skipper Edo a show

Discover the Egadi Islands on a sailboat with aperitif and hostess on board!

08/24/2025

Marta F.

Italy

We were unable to make the boat tour due to bad weather twice but we were not 100% refunded and we were only offered a voucher for the next few years by the skipper. Sailsquare has so far been of no help to solve the problem.

A full day on a sailing boat in the Gulf of ALASSIO

08/20/2025

Patrizia F.

Italy

It was a perfect day. Daniele was very kind, he is a really competent skipper and put all of us at ease at all times, making us feel "at home" on his boat. The boat is very comfortable and clean and it was beautiful both sailing and motoring. We had a wonderful day.

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

08/18/2025

Lucia A.

Italy

Beautiful experience!! … I was lucky enough to meet extraordinary people!!.. The skipper very professional and nice!! … the boat very beautiful and well-kept!! Great food!.. Thank you for everything and see you soon! Hello!.. Lucia

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 (730)Whole boat with skipper (575)Cooking service onboard (120)Catamaran (85)Family sailing cruises (80)All inclusive (80)Day trips (70)Courses & regatta (35)Sport & wellness (30)WWF Sailing Cruises (15)

Other travel ideas

Sailboat (253)Whole boat with skipper (203)Cooking service onboard (72)All inclusive (49)Catamaran (49)Exotic destinations (36)Family sailing cruises (21)Courses & regatta (20)Day trips (17)Offshore (14)