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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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4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

4 departures available

June - September

Starting from

€950

€855

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

12 departures available

June - October

Starting from

€689

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

13 departures available

June - October

Starting from

€570

Per person

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5.0

Super!

Weekend at the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€350

Per person

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4.6

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

35 departures available

January - December

Starting from

€300

€270

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€1,041

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

6 departures available

June - September

Starting from

€650

€585

Per person

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4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

3 departures available

July - August

Starting from

€1,052

Per person

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5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

10 departures available

June - September

Starting from

€790

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

7 departures available

June - September

Starting from

€490

€466

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

10 departures available

June - October

Starting from

€650

€585

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

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

17805 reviews

Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Domenico R.

Beautiful sailing experience between Naples, Ischia and Procida. Emiliano is a kind and helpful skipper who manages to make the experience special, actively involving those who want to feel part of the crew. Highly recommended!

Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Sabrina C.

I left for a weekend with "Spasso a vela" and it was an unforgettable experience. The boat is very comfortable, equipped with all possible amenities, it is very spacious, the cabins are comfortable and the 3 bathrooms on board are more than enough to feel comfortable. During our weekend we encountered slightly rough seas and a bit of wind but despite this thanks to the skipper's navigation experience, both in managing the navigation and in finding strategic points to dock, the weather conditions that were not entirely favorable did not weigh on us at all, so we fully enjoyed the beautiful landscapes and the sea. It was also super interesting to participate actively in life on board, the skipper taught us a lot of notions and involved us in the maneuvers. It is an experience that I recommend and that I will definitely return to do with "Spasso a vela".

A taste of the magnificent Island of Elba

06/17/2026

valentina t.

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IT

We with friends at the Top! The boat very clean and welcoming, Alberto always on the piece helpful and attentive.
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Gulf of Poets and Cinque Terre

06/17/2026

Nicola P.

-

IT

Excellent company of Giorgio with his wife Francesca, friendly, nice, they immediately put you at ease with all the rest of the crew. The cuisine is good and plentiful. As you know, to make the edges on a sailboat you need the wind, let's hope next time to have a BETTER WIND!!

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