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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

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€600

Per person

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5.0

Super!

Cruise for Singles from Sanremo to Saint-Tropez

France: French Riviera and Porquerolles

8 days - 7 nights

One departure available

August

€650

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

5 departures available

September - October

Starting from

€275

Per person

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5.0

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

5 departures available

July - August

Starting from

€425

€383

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

5 departures available

August - October

€650

Per person

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5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

4 departures available

August - September

€649

Per person

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4.8

Super!

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

6 departures available

July - September

Starting from

€900

€855

Per person

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5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€550

€495

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€900

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

4 departures available

July - September

Starting from

€200

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

18043 reviews

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Sailing cruise between the Maddalena archipelago and Corsica

07/13/2026

Ilaria B.

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IT

Always beautiful places, a prepared, serious and very helpful skipper, I would even say a perfect cook! Definitely a positive and quality experience to be repeated as soon as possible. Spacious, welcoming boat, very well cared for in detail. Excellent cleanliness
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Egadi Islands, Zingaro Reserve and San Vito Lo Capo

07/13/2026

Federica N.

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IT

Carmen and Mario are two special people! Attentive to everyone's needs and super available to please guests without losing sight of safety at sea. Carmen is a sweet, welcoming woman and she really does her best to keep the boat very clean; We will never forget the great meals he prepared for us. Mario is a gentleman and a skipper also available to change itineraries; He did it so that we wouldn't lose a minute of the sea and for this we thank him so much. We spent unforgettable days and evenings. It couldn't have gone better than this. Thank you and a big hug. Federica, Cristiana and Emma
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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

07/13/2026

Loredana R.

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IT

Perfect holiday ! Luca is a very good skipper, a great connoisseur of the area to sail safely and, ready to hoist the sails at any time to fully enjoy the pleasure of the wind with the precious help of Tommaso, an expert sailor and great cook. He delighted us with lunches, aperitifs and dinners of the highest level always seasoned with kindness and smiles. . Galley made with mastery with exquisite local products, from fish to cheeses, fruit and vegetables. Very comfortable boat, spaces for everyone and a not insignificant plus: air conditioning. Thank you guys, you are an example of how to do quality tourism! P.s I have rarely seen moored with such mastery!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/13/2026

Sara E.

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IT

I thought I had given myself a gift by booking a boat holiday with unknown people but the real gift was having Alessandro and Carlo as skipper and host. They were wonderful, they made me feel immediately welcomed not to mention the WONDERFUL places where they took us (and I say this as a Sardinian!) with maximum flexibility and availability for every need. A special mention for Eros, Alessandro's dog, who has remained in my heart. In short, give yourselves a great gift and set sail with them!! Fair winds :)

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