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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

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

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€700

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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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,070

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

7 departures available

July - September

Starting from

€600

€570

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

10 departures available

August - 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

€1,200

€1,080

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

€950

Per person

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4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€390

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

Per person

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4.6

Different flotilla in Ionian Greece: nature, new friends and fun

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,110

€999

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

10 departures available

July - October

Starting from

€570

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

17949 reviews

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

07/5/2026

Aymeric D.

-

FR

We had a wonderful week on Andrea's boat! Andrea is a very kind, professional and attentive skipper. He drove us to fabulous places and made many suggestions, he knows the area perfectly. The breakfasts and meals prepared by the hostess Carol were very good and fresh. Thank you to her for her kindness and availability. We highly recommend this experience! And a little word for Mathias, Andrea's dog, who made us laugh ❤️ a lot
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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

07/5/2026

Susanna F.

-

IT

Nice holiday, fantastic places, a beautiful sea! Stefano, the very scrupulous commander. Nice group! I wish I was still there!
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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

07/5/2026

Maurizio Z.

-

IT

Very good Skipper Stefano expert and prudent, he showed us the most evocative beaches of the Costa Smeralda, The boat was comfortable and spacious, we recommend it to those who want to live a suggestive experience in Sardinia.

A full day on a sailing boat in the Gulf of ALASSIO

07/5/2026

Raffaella F.

-

IT

Relaxing day!! Thank you Daniele and Edoardo

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