experiences

4.9

Super!

A day of sailing in the Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

One departure available

October

€100

Per person

5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

One departure available

October

€59

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!

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

Italy: Lake Garda

1 day - 0 nights

2 departures available

October

€99

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

October - November

€99

Per person

A terrace overlooking the sea: a day to discover the Gulf of Naples

Italy: Naples & Amalfi Coast

1 day - 0 nights

21 departures available

October

Starting from

€110

€88

Per person

Daily sailing trip off the coast of beautiful Pisa

Italy: Tuscany

1 day - 0 nights

21 departures available

October - November

Starting from

€115

Per person

5.0

Daily trip on a sailing boat

Italy: Liguria

1 day - 0 nights

4 departures available

October

€100

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

622 reviews

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

09/30/2025

MARIA GRAZIA P.

Italy

A wonderful sailing experience! 🚤⛵️ We spent Sunday in the company of nice people, with impeccable organization. Emanuele proved to be an exemplary professional: availability, kindness and attention to detail made us feel immediately at ease. Great food, stunning views and a relaxing atmosphere that made the experience truly unforgettable. Everything perfect: absolutely to try and recommend!

Day trip with aperitif at sunset!

09/16/2025

Loredana R.

Italy

Super positive experience, GREAT ADVICE!

Day trip with aperitif at sunset!

09/15/2025

Michela C.

Italy

For me and my daughter first experience on a sailing boat. Unfortunately the weather and the sea were not the best but thanks to Andrea, an experienced and professional skipper, it was a wonderful experience!

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

09/14/2025

Marco A.

Italy

Daniele a really nice person, caring and welcoming. These are the basic characteristics with which we spent a wonderful day in his company and aboard his really beautiful and well-maintained boat. I hope to repeat another experience together as soon as possible.

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 (400)Whole boat with skipper (325)Catamaran (55)Cooking service onboard (50)Family sailing cruises (45)Sport & wellness (45)Day trips (40)All inclusive (35)Courses & regatta (15)

Other travel ideas

Sailboat (145)Whole boat with skipper (118)Cooking service onboard (39)Catamaran (37)All inclusive (37)Exotic destinations (35)Family sailing cruises (13)Courses & regatta (12)Sport & wellness (12)Day trips (9)