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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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5.0

Let's discover Portofino, Santa Margherita and Sestri Levante together

Italy: Liguria

2 days - 2 nights

4 departures available

October - November

Starting from

€380

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September - October

€680

Per person

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

Starting from

€325

€309

Per person

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4.8

Sailing and Trekking in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€730

Per person

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New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

September - October

Starting from

€585

€527

Per person

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4.7

Feast of Santa Candida alle Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€390

Per person

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4.6

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€700

€490

Per person

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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

Per person

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€350

Per person

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4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€890

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 holidays & skippered tours

19150 reviews

Wellness, sun, sea and adventure: a weekend full of sailing!

09/15/2026

rosanna n.

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IT

We had a beautiful we on a sailing boat. Daniele and Maria Pia are wonderful in putting everyone at ease. Excellent company, the itinerary and the food prepared by Pia who is a wonderful cook, able to find any variation she is asked for. Daniele gladly lent himself to a change of cove for an unforgettable swim, due to the headwind compared to the established itinerary. Everything perfect.
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Sailing weekend in Istria

09/15/2026

Simona G.

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IT

Mirco top as captain 😊 you will only find out why by sailing with him 😝 boat in perfect conditions, cozy and equipped with all comforts. I will definitely be back at sea with Mirco. Thank you for everything !!

Week end in Costa Azzurra

09/15/2026

Massimiliano M.

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CH

Really beautiful experience! Alessandro was an extremely professional, competent and attentive commander, but above all kind and helpful. We were with three children under 4 years old, including a 10-month-old girl, and she was able to meet our needs with great patience and naturalness, making us experience and appreciate the boat (first time)! She took care of every organizational / logistical aspect to perfection, but her way of relating to the children was really an added value, fundamental to make the weekend serene and pleasant for everyone. An exquisite person and a captain of great professionalism. An experience that made us want to do it again soon! Thank you very much. Stefania + Massimiliano + Lori
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Week between the Tuscan Islands and Northern Corsica

09/15/2026

Silvia M.

-

IT

Beautiful experience, beautiful places, close-knit group and Francesco.. a real sea dog!

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