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Day trips yacht sailing holidays & tours in Italy

Discover more than 22 opportunities to get on board a Day trips adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

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5.0

Super!

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

2 departures available

June - July

€99

Per person

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5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

31 departures available

June - September

Starting from

€99

Per person

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5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

26 departures available

June - September

Starting from

€79

Per person

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5.0

Super!

Day trip on a sailing boat

Italy: Tuscany

1 day - 0 nights

24 departures available

June - July

Starting from

€150

Per person

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5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

2 departures available

July

€69

Per person

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5.0

Super!

Afternoon sailing and barbecue evening

Italy: Lake Garda

1 day - 0 nights

5 departures available

June - August

Starting from

€129

Per person

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4.9

Aperitif Trip to the Gulf of Tigullio - All inclusive!

Italy: Liguria

1 day - 0 nights

6 departures available

June - August

€89

Per person

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4.9

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

Italy: Liguria

1 day - 0 nights

15 departures available

June - August

€150

Per person

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4.9

A day of sailing in the Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

One departure available

July

€100

Per person

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5.0

Sail to the Cecina lighthouse with aperitif on board

Italy: Tuscany

1 day - 0 nights

One departure available

June

€100

Per person

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4.8

A day of Sailing & Relaxation in the Gulf of Poets

Italy: Liguria

1 day - 0 nights

3 departures available

June

€150

Per person

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5.0

Daily sailing in the Tavolara Marine Park

Italy: Northern Sardinia

1 day - 0 nights

2 departures available

June

€125

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

573 reviews

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Day trip with aperitif at sunset!

06/2/2025

Maria Cristina S.

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Italy

È stato divertente ed emozionante (7 delfini avvistati!)!!!
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A day on a sailing boat to Gallinara Island or the Dianese Gulf

05/21/2025

Roberta N.

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Italy

Bellissima giornata nelle acque liguri, Matteo skipper professionale e simpatico ha insegnato a me ed alla mia amica le basi del veleggiare ottimo l’aperitivo, peccato nn aver visto i delfini sarà x la prossima uscita 😊
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A day on a sailing boat to Gallinara Island or the Dianese Gulf

05/20/2025

Sabrina L.

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Italy

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A day sailing in the fantastic Gulf of Trieste

05/20/2025

dino m.

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Italy

Giornata splendida per il tipo di esperienza, per l’ambiente e per la preparazione dello skipper che è stato ottimo anche per tutte le informazioni su quel tratto di costa che ci ha fornito. Molto preparato.. Persona gentile e cordiale, Ci siamo divertiti. Esperienza da ripetere!!

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