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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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4.6

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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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

11 departures available

June - October

Starting from

€690

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

13 departures available

June - October

Starting from

€570

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August

€890

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

Starting from

€874

€699

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€1,041

Per person

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4.6

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

36 departures available

January - December

Starting from

€300

€270

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

6 departures available

June - September

Starting from

€650

€585

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

8 departures available

June - September

Starting from

€490

€466

Per person

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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

13 departures available

June - October

Starting from

€650

€585

Per person

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5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

11 departures available

June - September

Starting from

€790

Per person

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5.0

Weekend at the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

2 departures available

July

€350

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

17762 reviews

June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide

06/10/2026

Guido F.

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IT

Beautiful experience. The enthusiasm and ability to involve biologists is remarkable. The only pity we never sailed.

Weekend in Ischia and Ventotene: History and Nature

06/10/2026

Michele F.

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IT

Wonderful holiday! The boat was very comfortable, spacious and always spotlessly clean. A special thanks to Umberto, skipper par excellence: excellent sailor, profound connoisseur of the places visited and always ready to share curiosities and advice. Always available, professional and super nice, he made the experience even more enjoyable. Highly recommended for those who want to experience a relaxing and fun boat holiday with an excellent selection of music!

June 2nd long weekend between Ponza, Palmarola, Zannone and Ventotene

06/10/2026

Donatella L.

-

IT

Extraordinary, welcoming skippers and also creative cooks! Highly recommended!

In the blue of Capri and the infinity of the Amalfi Coast

06/10/2026

Antonio D.

-

IT

We stayed on GEM for the weekend in Capri. Hospitality and Top Professionalism! The skipper is a prepared and kind person, the boat is very well maintained and with all the necessary comforts. Experience to be redone, congratulations to Spasso a Vela.

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