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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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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

June - September

Starting from

€750

€675

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

2 departures available

August

€1,290

€1,190

Per person

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4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,180

€1,080

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - October

Starting from

€590

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

11 departures available

July - October

Starting from

€1,300

€1,170

Per person

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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,260

€1,134

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

10 departures available

June - September

Starting from

€620

€558

Per person

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4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

2 departures available

June - July

Starting from

€390

€351

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€795

€716

Per person

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4.7

Marmaglia mini-flotilla: discovering the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,140

€1,040

Per person

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4.6

Long weekend between Ponza and Palmarola: adventure at the Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

Per person

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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

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

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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

17800 reviews

Week-end all'Elba - Hostess a bordo

06/16/2026

Andrea P.

-

IT

We spent a beautiful holiday beyond all expectations: the comfort and spaciousness of the boat, the beauty of the places, the kindness and skill of Giulia in the kitchen, the care and professionalism of Vittorio at the helm, together with the sympathy of the other day-trippers (and the wonderful weather!) allowed us to enjoy our first sail - around Elba - in a fantastic way, celebrating my wife's birthday in an exciting way on a holiday that we hoped would not end so soon. Five well-deserved 😀 stars

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

06/16/2026

Liubov S.

A wonderful experience! Highly recommended!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/16/2026

Tomas F.

-

GB

No No No !!!! :(. I want more. This 7 days with Allesandro ( Skipper) and Carlo (Host) was Amazing. They will take you to the best places around Corfu. Paxos and Antipaxos are paradise. Fantastic food during sailing, healthy and everyday different. We even catch big fish during sailing, and next day bee served for lunch by Fantastic Carlo. I could write review for 100 pages, but you have to explore this wonderful trip. Greetings also for Chiara, Catarina and Luca.
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A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

06/16/2026

Alessandro L.

-

IT

Enrico the skipper is a real sea dog and like all sea dogs he must be caressed by the way he furs. Nice experience..

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