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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

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

2 departures available

July

€350

Per person

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4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

3 departures available

July - August

€800

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

Per person

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4.8

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September - October

€242

€218

Per person

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5.0

Super!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

3 departures available

July - September

€740

Per person

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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

5 departures available

June - July

Starting from

€490

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - August

Starting from

€900

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€410

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August

Starting from

€849

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

17803 reviews

A taste of the magnificent Island of Elba

06/17/2026

valentina t.

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IT

We with friends at the Top! The boat very clean and welcoming, Alberto always on the piece helpful and attentive.
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Gulf of Poets and Cinque Terre

06/17/2026

Nicola P.

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IT

Excellent company of Giorgio with his wife Francesca, friendly, nice, they immediately put you at ease with all the rest of the crew. The cuisine is good and plentiful. As you know, to make the edges on a sailboat you need the wind, let's hope next time to have a BETTER WIND!!

Magical Pontine: full sail to discover the archipelago

06/17/2026

Nicolò B.

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IT

Positive experience. Possibility to visit wonderful places. Experience on a boat, it is well known, requires a spirit of adaptation and flexibility. The skipper was helpful, giving all the directions. Despite the change of plans for the last day (due to strictly weather conditions), the skipper provided a refund quickly.

Week-end all'Elba - Hostess a bordo

06/16/2026

Andrea P.

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IT

We spent a beautiful holiday beyond all expectations: the comfort and spaciousness of the boat, the beauty of the places, the kindness and skill of Giulia in the kitchen, the care and professionalism of Vittorio at the helm, together with the sympathy of the other day-trippers (and the wonderful weather!) allowed us to enjoy our first sail - around Elba - in a fantastic way, celebrating my wife's birthday in an exciting way on a holiday that we hoped would not end so soon. Five well-deserved 😀 stars

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