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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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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

12 departures available

August - November

Starting from

€540

€513

Per person

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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

6 departures available

July - October

Starting from

€650

€585

Per person

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4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

6 departures available

July - October

Starting from

€420

€399

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

7 departures available

July - October

Starting from

€230

Per person

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4.8

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

July - August

Starting from

€440

€396

Per person

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5.0

Super!

"Born to Sail" - One Way from Tuscany to Sardinia

Italy: Northern Sardinia

6 days - 6 nights

One departure available

July - August

€900

Per person

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4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

2 departures available

July - August

Starting from

€1,150

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

4 departures available

July - September

Starting from

€490

€466

Per person

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5.0

Super!

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€900

€750

Per person

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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

July - October

Starting from

€750

€675

Per person

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5.0

Super!

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

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

17999 reviews

Four days in the Pontine Islands, just a stone's throw from Rome

07/8/2026

Francesco O.

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IT

A 360° experience: from the location to the skipper and his cuisine, from the beautiful group to the sailing between Palmarola and Ponza.
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Corfu between bays, taverns and myths.

07/8/2026

Farida B.

-

IT

Fantastic experience! Traveling on a sailing boat is always a wonderful experience, if you do it with two captains like Léonore and Hansel, always professional, kind, helpful, attentive to safety and excellent cooks... becomes super awesome! They took us to discover wonderful bays and hidden corners, making us feel safe at all times. A journey dedicated to the sea, relaxation and good company that I will carry in my heart. Highly recommended!
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Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

07/8/2026

Fabio C.

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IT

Weekend on a sailing boat on the Island of Elba simply fantastic! Much of the credit goes to the skipper, an extremely professional, prepared and competent person, capable of transmitting safety and passion for the sea from the very first moment. In addition to his excellent sailing skills, he was always available, attentive to everyone's needs and good at creating a relaxed and pleasant atmosphere on board. Thanks to his knowledge of the island he took us to wonderful and uncrowded coves, making us experience places that we would hardly have discovered on our own. The boat was in perfect condition, well cared for and comfortable. It was a weekend of relaxation, fun and good company. An experience that I recommend without hesitation to anyone who wants to experience the sea in an authentic way. I would definitely do it again!
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Long weekend between Ponza and Palmarola: adventure at the Pontine!

07/8/2026

ELISABETTA P.

-

IT

boat not adequate as it is given and lacking in comfort, as well as sup, too high price for the one used. the fearful and unengaging skipper

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