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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

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

4 departures available

June - September

Starting from

€950

€855

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

€689

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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5.0

Super!

Weekend at the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€350

Per person

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4.6

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

35 departures available

January - December

Starting from

€300

€270

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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4.8

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

6 departures available

June - September

Starting from

€490

€466

Per person

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4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

3 departures available

July - August

Starting from

€1,052

Per person

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5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

10 departures available

June - September

Starting from

€790

Per person

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4.4

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

12 departures available

June - September

Starting from

€730

€657

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

17808 reviews

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Weekend between Ponza and Palmarola Comfortable - max 4 people

06/18/2026

Cecilia M.

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IT

I loved this trip, I would do it again right away. I hope to find something similar in my area. both David and Antonella and Danila were welcoming, nice and competent people, there was not a single problem in all 3 days, thank you and see you soon, Palmarola amazed me with how wild it is.
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Discovering the Tuamotu Islands and the Leeward Islands - 21 Days

06/18/2026

Jean-christophe S.

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FR

The trip of a lifetime: A cruise on a high-performance sailboat, Angela and Hervé taking care of you, and the discovery of many islands of Polynesia between each crossing. 3 weeks that went by too quickly
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Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Domenico T.

This was my first boat adventure and what an adventure, starting from the boat which is much more spacious than I expected, passing to Emiliano, the skipper, who with his professionalism and sympathy explained the rudiments of navigation and finally the location, Ischia and Procida, which are a spectacle of Campania.

Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Domenico R.

Beautiful sailing experience between Naples, Ischia and Procida. Emiliano is a kind and helpful skipper who manages to make the experience special, actively involving those who want to feel part of the crew. Highly recommended!

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