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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!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

6 departures available

July - October

Starting from

€230

Per person

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4.8

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

July

€410

Per person

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5.0

Super!

"Born to Sail" - One Way from Tuscany to Sardinia

Italy: Northern Sardinia

6 days - 6 nights

One departure available

July - August

€900

Per person

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4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

2 departures available

July - August

Starting from

€1,150

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

One departure available

July - August

€890

€680

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

One departure available

August

€900

Per person

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5.0

Super!

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€780

€693

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€1,020

Per person

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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€750

€675

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

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

4 departures available

August

€990

Per person

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5.0

Super!

Educational cruise between Tuscany and Corsica

Italy: Tuscany

14 days - 14 nights

One departure available

August

€1,700

Per person

Why book a holiday with Sailsquare?

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

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

18079 reviews

Weekend at the Pontine Islands between Ponza and Palmarola

07/14/2026

Luca T.

-

IT

Beautiful weekend! Marco, a true professional, and his travel companions, an explosion of sympathy, who made the experience at the Pontine Islands unforgettable. Thank you all sincerely.

Long weekend among the queens of the archipelago - Elba and Capraia

07/14/2026

CHIARA A.

-

IT

Edoardo was a perfect skipper, professional, very kind and helpful. Super recommended 😉 experience we will definitely ☺️ be back
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Long weekend among the queens of the archipelago - Elba and Capraia

07/14/2026

Alessia B.

-

IT

Beautiful experience, thanks also to Edoardo who welcomed us on board his boat with kindness and sympathy. 4 days flown between wonderful bays, aperitifs and laughter. The experience with Edoardo is absolutely recommended
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Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

07/14/2026

Luca S.

-

IT

Full marks for Matteo and Alessio!! Perfect itinerary, impeccable boat, seriousness and organization! I hope I can plan a weekend again and get back on board!! FANTASTIC!

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