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Day trips yacht sailing holidays & tours in Italy

Discover more than 20 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!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

4 departures available

July - August

Starting from

€420

€378

Per person

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5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

10 departures available

July - September

Starting from

€99

Per person

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5.0

Super!

AperiBarca: afternoon sunset aperitif

Italy: Tuscany

1 day - 0 nights

One departure available

July

€35

Per person

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5.0

Super!

Day trip on a sailing boat

Italy: Tuscany

1 day - 0 nights

4 departures available

July

€180

Per person

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4.9

Super!

Excursion to the Gulf of Alassio and Gallinara Island

Italy: Liguria

1 day - 0 nights

6 departures available

July - August

€100

Per person

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5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

One departure available

July

€75

Per person

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5.0

Super!

Afternoon sailing and barbecue evening

Italy: Lake Garda

1 day - 0 nights

One departure available

August

€149

Per person

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5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

13 departures available

July - September

Starting from

€79

Per person

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5.0

Super!

Sailing day in the Gulf of Poets

Italy: Liguria

1 day - 0 nights

One departure available

July

€160

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

9 departures available

July - August

€150

Per person

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5.0

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

7 departures available

July - October

Starting from

€99

€94

Per person

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Discover the Egadi Islands on a sailboat with aperitif and hostess on board!

Italy: Aegadian islands

1 day - 0 nights

68 departures available

July - September

Starting from

€130

€117

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

586 reviews

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

07/16/2025

Rodolfo R.

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Italy

Beautiful experience, found not very windy day, but we still had fun with sailing. Walked around Sirmione seeing the splendid castle and the Grottoes of Catullus from the lake; that I had never seen. Emanuele was very good at teaching the secrets of the baraca and some anecdotes of the area. Then we stopped, took a nice bath and had a tasty lunch. Everyone returned with the desire to return in their hearts.
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Day trip with aperitif at sunset!

07/6/2025

Giulia P.

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Italy

Unforgettable weekend on a boat with the legendary Andrea! From the first moment he proved to be super hospitable and easy-going, it seemed to leave for an adventure with friends. We sailed towards Arenzano, enjoyed the sea and stopped for a regenerating swim. Packed lunch with sea view, chatting, relaxation and zero stress. The return was textbook: aperitif with his Hugo (secret recipe, but a bomb!) and fresh focaccia to lick your lips — and no, I'm not exaggerating! In the evening we slept on the boat, lulled by the quiet roll of the waves... A unique and super relaxing experience that made us forget everything else. Thank you Andrea for making this weekend special, genuine and full of beautiful vibes. See you very soon!
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Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

07/6/2025

Maila L.

We were on board with Matteo and Maria Teresa last Sunday and it was a beautiful day. A serene escape and laughter that we needed. Sailing with only the sound of the sea and the laughter of new friends was the added value. The boat is beautiful and maintained with the perfect care of the hosts. A heartfelt thank you for the welcome, attention to detail and empathy. Maila and Davide
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Aperitif Trip to the Gulf of Tigullio - All inclusive!

07/6/2025

alice b.

-

Italy

Truly fabulous experience. Super recommended!

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