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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!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€370

Per person

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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

6 departures available

July - October

€260

Per person

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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

8 departures available

June - August

Starting from

€250

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

15 departures available

June - November

Starting from

€600

€540

Per person

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4.9

Super!

Leave everything for the Island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

July

€320

Per person

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New

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

4 departures available

June - July

Starting from

€300

€270

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

4 departures available

July - August

Starting from

€900

Per person

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

3 departures available

June - September

€280

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

5 departures available

July - September

Starting from

€400

€360

Per person

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5.0

Super!

Sail in Menorca with a cook on board!

Spain: The Balearic Islands

5 days - 5 nights

3 departures available

June - August

Starting from

€950

€808

Per person

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4.9

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

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

17779 reviews

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Midweek relaxing in the Pontine Islands

06/15/2026

Andrea G.

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IT

Experience to frame! Mirko is a very prepared and helpful skipper, as well as a wonderful person and an excellent cook. The boat is large and equipped with every comfort and convenience. The scenery of the Pontine made everything superlative and unforgettable. SUPER RECOMMENDED!!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/15/2026

Kamil J.

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GB

Our yacht trip with Alessandro was absolutely incredible. The weekly itinerary was perfectly planned, and every place we stayed was beautiful, with just the right amount of time spent at each destination. Carlo, our host, is the sweetest person on earth. He looked after us the entire time and made us feel truly welcome. The boat was very comfortable, and we never felt like there wasn’t enough space. Alessandro is extremely patient and such a genuinely nice person—it’s impossible not to like him. This has been one of the best experiences we’ve ever had, and we would highly recommend it to anyone considering this trip.

Midweek relaxing in the Pontine Islands

06/15/2026

Emanuele S.

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IT

I would say everything perfect! Starting with the boat which is almost new, clean and efficient! Then special mention for the skipper Mirko who, in addition to being an excellent captain, is at the same time a cook, tour guide, entertainer, barman ... etc etc . super recommended holiday ! Fair winds to all !!

Dream weekend in the Pontine Islands

06/15/2026

Federico F.

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IT

Beautiful experience! Breathtaking landscapes and crystal clear sea. Stefano, an expert commander, cheered us up during the day allowing us to sail and collaborate in maneuvers, and in the evening with guitar and songs in the moonlight; Francesca, the perfect hostess, pampered us by cooking delicacies and never letting us miss anything. When we spoke to her for the first time, she immediately made us feel welcomed, and so it was. The boat is comfortable and well maintained. In addition, the luck of having met sociable and expansive people on board made everything perfect. Highly recommended

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