experiences

5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

35 departures available

April - August

Starting from

€59

Per person

5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

11 departures available

June - August

Starting from

€390

€351

Per person

5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

5 departures available

June - August

Starting from

€135

Per person

4.9

Super!

A day of sailing in the Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

2 departures available

May - June

€99

Per person

4.9

Super!

Sailing day from Savona

Italy: Liguria

1 day - 0 nights

2 departures available

May

€125

Per person

5.0

Super!

Sailing day in the beautiful Marine Protected Area of Capo Milazzo

Italy: Sicily

1 day - 0 nights

One departure available

June

€98

Per person

4.9

Super!

Sailing day in the Gulf of Follonica

Italy: Tuscany

1 day - 0 nights

One departure available

June

€100

Per person

5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

5 departures available

June - August

Starting from

€69

Per person

5.0

Super!

Spring on Lake Garda

Italy: Lake Garda

1 day - 0 nights

One departure available

May

€99

Per person

5.0

Super!

A wonderful day.... sul Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

35 departures available

April - August

Starting from

€99

Per person

5.0

Sailing day between the Apuan coast and the Gulf of Poets

Italy: Tuscany

1 day - 0 nights

One departure available

June

€77

Per person

4.9

Aperitif Trip to the Gulf of Tigullio - All inclusive!

Italy: Liguria

1 day - 0 nights

11 departures available

June - August

Starting from

€85

Per person

Why book a holiday with Sailsquare?

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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

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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

624 reviews

A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

Italy

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

A day sailing in the fantastic Gulf of Trieste

10/20/2025

Monica C.

Italy

The skipper Paolo simply fabulous. The super cozy and high-performance boat. We had a beautiful, immersive experience and learned even a minimum basis of sailing concepts

A wonderful day.... sul Garda - ALL INCLUSIVE

09/30/2025

MARIA GRAZIA P.

Italy

A wonderful sailing experience! 🚤⛵️ We spent Sunday in the company of nice people, with impeccable organization. Emanuele proved to be an exemplary professional: availability, kindness and attention to detail made us feel immediately at ease. Great food, stunning views and a relaxing atmosphere that made the experience truly unforgettable. Everything perfect: absolutely to try and recommend!

Day trip with aperitif at sunset!

09/16/2025

Loredana R.

Italy

Super positive experience, GREAT ADVICE!

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