experiences

5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

3 departures available

September - October

€99

Per person

5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

3 departures available

September - October

Starting from

€59

Per person

5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

4 departures available

September - October

Starting from

€69

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

September - October

€99

Per person

4.7

Day trip with aperitif at sunset!

Italy: Liguria

1 day - 0 nights

One departure available

September

€65

Per person

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

Italy: Naples & Amalfi Coast

1 day - 0 nights

37 departures available

September - October

Starting from

€110

€88

Per person

Daily Sailing Adventure to the Tremiti Islands

Italy: Tremiti Islands

1 day - 0 nights

13 departures available

September - October

€130

Per person

Daily sailing trip off the coast of beautiful Pisa

Italy: Tuscany

1 day - 0 nights

29 departures available

September - November

Starting from

€115

Per person

5.0

Daily trip on a sailing boat

Italy: Liguria

1 day - 0 nights

18 departures available

September - October

Starting from

€100

Per person

5.0

Approach to sailing: day on a boat with sailing lesson

Italy: Tuscany

1 day - 0 nights

2 departures available

October

Starting from

€97

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

621 reviews

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.

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

09/12/2025

Giulia C.

Italy

Wonderful day, perfect organization, Emanuele was fantastic! Super recommended!!

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 (455)Whole boat with skipper (335)Catamaran (60)Day trips (55)All inclusive (50)Cooking service onboard (40)Sport & wellness (40)Family sailing cruises (30)Courses & regatta (25)

Other travel ideas

Sailboat (165)Whole boat with skipper (128)Cooking service onboard (46)All inclusive (40)Catamaran (39)Exotic destinations (36)Courses & regatta (13)Day trips (12)Sport & wellness (12)Offshore (10)