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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

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - November

Starting from

€650

€585

Per person

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5.0

Super!

South Sardinia

Italy: Southern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€790

€751

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

July - October

Starting from

€615

Per person

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4.8

Magical Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€640

Per person

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4.7

Whale watching cruise with WWF guide between Tuscany and Northern Corse

Italy: Tuscany

6 days - 7 nights

7 departures available

July - September

Starting from

€1,041

€989

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

2 departures available

August

€950

Per person

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5.0

Super!

Experience in the Egadi Islands: A Dream on a Sailing Boat

Italy: Aegadian islands

7 days - 7 nights

13 departures available

July - October

Starting from

€400

€360

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

€550

Per person

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4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

5 departures available

July - October

Starting from

€240

€228

Per person

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4.8

Super!

ONE WAY From the Phlegraean to the Pontine Islands

Italy: Pontine Islands

8 days - 7 nights

2 departures available

August - September

Starting from

€660

Per person

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4.9

Super!

A week Sailing in Tuscany and Corsica

Italy: Tuscany

7 days - 7 nights

2 departures available

July - August

Starting from

€870

Per person

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4.8

Super!

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€1,080

€918

Per person - min 2 pax

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

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

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 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

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

16246 reviews

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

07/15/2025

Arianna O.

Pasquale made this holiday even more memorable and wonderful!
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Life-changing experiences - Escape to the Pontine Islands

07/15/2025

Anna R.

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Italy

Francesco super! Ponza and palmarola spendid. I celebrated a memorable birthday.
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Weekend on Elba Island

07/15/2025

Dalgisa B.

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Italy

We had a wonderful experience with a really good, competent and nice skipper, definitely to be repeated.
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Long weekend among the queens of the archipelago - Elba and Capraia

07/15/2025

Laurence B.

-

Belgium

My partner had a terrific time on this trip - Edoardo is a knowledgeable, patient, and welcoming skipper. We also loved the beautiful scenery and the crew. The boat was perfect for a group of eight. We highly recommend a long weekend trip with Edoardo and Sailsquare.

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