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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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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

3 departures available

September

€700

Per person

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4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

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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

5 departures available

September - October

Starting from

€230

Per person

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4.9

Super!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

One departure available

September

€400

Per person

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4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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4.9

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

Italy: Tuscany

7 days - 6 nights

2 departures available

August - September

Starting from

€650

Per person

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

Per person

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4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, e Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

September

€1,150

Per person

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5.0

Super!

Pula and the enchanting Kvarner islands: special price private cruise

Croatia: Kornati Islands

6 days - 6 nights

One departure available

August

€780

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

6 departures available

September - October

Starting from

€370

Per person

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4.8

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

One departure available

September

€380

€361

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

18677 reviews

Gargano National Park and Marine Protected Area of the Tremiti Islands

08/22/2026

Antonella B.

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IT

This 5-day sailing experience with Marco was a pleasant discovery and I would recommend it to anyone. Not only do you visit beautiful places in themselves, the Tremiti islands and the Gargano, but they are experienced in an authentic way: full but relaxed, far from the usual experiences. Spending a night in the roadstead, observing the starry sky together, surrounded by a splendid white cove dominated by the forest of the Gargano park, where the wind and the sea determined the destination: this is for me the essence of this trip. Marco is a multifaceted person, who has filled our hearts and heads with experiences, knowledge and emotions, making us feel at ease and always safe; It was a pleasure to share this holiday with him and the rest of the crew! ☺️

Vento di Sicilia: from the Aeolian Islands to Trapani

08/22/2026

Laura G.

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IT

A beautiful week at sea! Many thanks to Stefano, Adriano and Rosa who with their professionalism, kindness and helpfulness have made this experience truly unique. It was a real pleasure to share this adventure with you and all the other guests!!
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Island of Elba and South Corsica fantastic week

08/22/2026

Myriam C.

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IT

I would have liked to go a little sailing instead of always motoring! For the rest wonderful places, fun and nice people, captain a little too rigid with the crew!
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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

08/22/2026

Emanuele P.

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IT

Beautiful experience, supercompetent skipper (Luca and Tommaso) who ensured most of the sailing even when many boats remained in port or roadstead. Program respected greatly. Beautiful crew and level kitchen and assistance. Absolutely to recommend

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