experiences

5.0

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

4 departures available

August - October

Starting from

€99

€94

Per person

5.0

Fantastic BARCOLANA: Racing in safety and joy!

Italy: Venice and the Gulf of Trieste

2 days - 1 night

One departure available

October

€250

Per person

5.0

Free in the Wind... scents and wonders in the upper Adriatic

Italy: Venice and the Gulf of Trieste

2 days - 1 night

One departure available

August

€230

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 - Sailboat yacht sailing holidays & tours in Venice and the Gulf of Trieste

204 reviews

Free in the Wind... scents and wonders in the upper Adriatic

08/13/2025

Laura P.

Italy

Paolo is very affable, cultured, knows how to put people at ease, super expert in sailing, to be redone 🙂

Weekend cruise from Trieste in Slovenia

08/11/2025

Andrea T.

Italy

Super positive experience! Comfortable boat, a truly characteristic destination and skipper always on the ball and available

Weekend cruise from Trieste in Slovenia

07/28/2025

Emilia D.

Italy

It was beautiful: none of us wanted to get off the boat at the end, time flew by.... Our girls had fun diving repeatedly from the boat and we can say that Flavio easily won them over with his seafood pasta! A real goodness! Undoubtedly to be repeated and recommended

A day sailing in the fantastic Gulf of Trieste

07/23/2025

Antonella D.

Italy

An unforgettable day

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!