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Day trips yacht sailing holidays & tours in Italy

Discover more than 23 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

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

6 departures available

July - August

Starting from

€390

€351

Per person

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4.7

Sailing day between the Apuan coast and the Gulf of Poets

Italy: Tuscany

1 day - 0 nights

3 departures available

July - August

Starting from

€90

Per person

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5.0

From the sun to the moon - Afternoon All inclusive on Lake Garda

Italy: Lake Garda

1 day - 0 nights

3 departures available

July - August

€149

Per person

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4.9

Sailing excursion to Capri / Positano

Italy: Naples & Amalfi Coast

1 day - 0 nights

29 departures available

August

€150

Per person

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4.9

Sailing in Tigullio: Half-Day Experience from Rapallo

Italy: Liguria

1 day - 0 nights

4 departures available

July - August

€91

Per person

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4.9

Aperitif Trip to the Gulf of Tigullio - All inclusive!

Italy: Liguria

1 day - 0 nights

8 departures available

July - August

Starting from

€85

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

7 departures available

July - August

Starting from

€150

Per person

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Daily sailing excursion in La Spezia

Italy: Liguria

1 day - 0 nights

4 departures available

July

€175

Per person

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Aperitif at sunset

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

7 departures available

July

€110

Per person

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4.5

New

Afternoon, aperitif and sunset on Verbano - Lake Maggiore

Italy: Lake Maggiore

1 day - 0 nights

4 departures available

July - August

€100

Per person

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New

Between the Ionian and the Adriatic where the seas meet

Italy: Puglia

1 day - 0 nights

53 departures available

July - August

€130

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

July

€120

Per person

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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.

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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

627 reviews

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

07/5/2026

Raffaella F.

-

IT

Relaxing day!! Thank you Daniele and Edoardo

Afternoon, aperitif and sunset on Verbano - Lake Maggiore

06/22/2026

daniela m.

-

IT

I gave this experience to my husband who had dreamed of steering a sailboat for years and was satisfied! Stefano was super kind and helpful in advising me in the best possible way when and how to book and the experience itself was very nice
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Afternoon, aperitif and sunset on Verbano - Lake Maggiore

06/14/2026

Enrico C.

-

IT

We had a wonderful day on board Stefano's sailboat, a very kind and helpful person. We visited the three major islands and even managed to swim. Finally, we had a pleasant aperitif at sunset in front of the Hermitage of Santa Caterina. It was a wonderful experience, which I recommend to anyone who wants to spend a relaxing day.

A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

-

IT

Everything worked out great, Paolo was super helpful!!!! Advice 100%

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