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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!

Sailing & Trekking to discover the Island of Elba

Italy: Tuscany

4 days - 3 nights

One departure available

September

€530

€477

Per person

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4.8

Super!

Week in the north of Corsica, via Capraia - in company

Italy: Tuscany

7 days - 6 nights

One departure available

August

€890

Per person

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4.7

Kornati: the pearl of Croatia

Croatia: Kornati Islands

6 days - 7 nights

2 departures available

August

Starting from

€800

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

4 departures available

August - October

€650

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€200

Per person

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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

5 departures available

August - September

Starting from

€700

Per person

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5.0

Super!

Sailing Holiday with a Hostess Among the Wonders of Northern Sardinia

Italy: Northern Sardinia

6 days - 6 nights

4 departures available

August - September

Starting from

€1,450

Per person

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5.0

Super!

Vento di Sicilia: from the Aeolian Islands to Trapani

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€920

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

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4.9

Super!

Quattro giorni all'Elba - Hostess a bordo

Italy: Tuscany

4 days - 5 nights

One departure available

August

€800

Per person

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4.7

Whale watching mini-cruise in the Pelagos Sanctuary with WWF guide

Italy: Liguria

4 days - 4 nights

One departure available

September

€609

€579

Per person

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4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

2 departures available

August - September

Starting from

€1,010

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.

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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 - Sailboat holidays & skippered tours

18244 reviews

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Week end in Costa Azzurra

07/28/2026

Roberta R.

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IT

Sufficient
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Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

07/28/2026

Sara D.

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IT

Wonderful week among endless shades of blue! Beautiful islands and wonderful sea. Thank you Alessandro, for making this experience unique, for transmitting your love for the sea and sailing! A trip I will not forget!
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Gulf of Poets and Cinque Terre

07/28/2026

Valentina P.

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IT

From the description I was very excited to get on board. I couldn't wait to sleep in the roadstead with the sound of the sea, sail and discover a part of Liguria that I didn't know and that everyone talks about. but I quote what was written in the experience "We will sail along a coast rich in history and beauty, between spectacular cliffs, villages overlooking the blue and dreamy coves. It will be possible to relax in the sun, swim in crystal clear waters and listen only to the wind in the sails and the sound of the waves." Here.. let's say that it didn't go quite like that!! We slept both nights in the port of La Spezia, without the owners sleeping at home (what to the as absurd and not specified in the proposal) and arrived in the morning.. by 9 o'clock, so time to have breakfast and go out was not before 10.30. Definitely strange hours, waking up at 7 with the light. We sailed very little, there was also wind and the sail was opened only once and we stopped in the bay of I bring Venus both days. Together with two hundred boats, jet skis and kiters arrows. Not exactly what I honestly expected. Among other things, on Saturday there was an event on Radio 105 so loud music and half of Liguria landed, there was very little crystal clear water, I did the bathroom only for the heat. (The tender was out of order.) With the fact that on Sunday the weather was not favorable (then in the end it was not so), we expected a more planned tour with several stops in the various coves that the area offers, in order to take advantage of the better the only two days at the beach. Alas we simply sailed next to the coast without stopping and returning for lunch to Porto Venere and remained there in the the same point both Saturday and Sunday. Let's say that, after a night of rain, lightning and wind, spent in port, among us guests (and fortunately nothing happened), finding ourselves in the same place as the day before was quite disappointing. To do a few hours soaking in the same place, I would have rented a dinghy and slept in the hotel halfway through the price!. Managed and organized like this sorry but I don't recommend it!!
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Long weekend among the wonders of Elba and Capraia

07/28/2026

Luca C.

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IT

Very pleasant experience indeed! I spent a wonderful sailing holiday on the Island of Elba with skipper Marco. Right from the start he proved to be competent, helpful and always attentive to the needs of the crew. The atmosphere on board was relaxed and fun, and we visited beautiful places. It was an experience

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