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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!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

3 departures available

September - October

Starting from

€59

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

2 departures available

September - October

€279

Per person

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4.8

Super!

3 days - Sorrento, Capri, Positano, Amalfi - Luxury Sailing Yacht

Italy: Naples & Amalfi Coast

3 days - 2 nights

9 departures available

September - October

Starting from

€1,325

Per person

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4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,400

Per person

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5.0

Super!

Island of Vulcano (Aeolian Islands) in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

2 days - 1 night

4 departures available

September - October

€265

€239

Per person

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5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

4 departures available

September - October

Starting from

€69

Per person

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4.9

Super!

Life-changing experiences: Four days in the Pontine Islands with photographer on board

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€420

€399

Per person

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5.0

5-day sailing course: discovery and learning

France: French Riviera and Porquerolles

5 days - 4 nights

5 departures available

September - October

€680

Per person

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4.9

Super!

A weekend of sailing in Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

October

€220

Per person

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4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

7 departures available

October - December

€190

Per person

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4.9

Super!

Trekking & Sailing Experience-Weekend lungo a Capraia in compagnia

Italy: Tuscany

4 days - 3 nights

One departure available

September

€440

Per person

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5.0

Super!

South Sardinia

Italy: Southern Sardinia

6 days - 7 nights

One departure available

September

€790

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17478 reviews

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Relaxing weekend between Portovenere and the 5 Terre

09/18/2025

Silvia I.

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Italy

First experience on a sailing boat and it was very nice. Pleasant company and comfortable boat. Too bad for the weather that did not allow us to visit the Cinque Terre, we could certainly have been luckier! I recommend it.
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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

09/17/2025

Mauro Z.

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Italy

Very nice cruise, despite the weather was not favorable, the skipper managed to let us enjoy the beauties of the Costa Smeralda
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Weekend at the Pontine aboard a splendid 16-meter sailboat

09/17/2025

Giulia E.

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Italy

It was my first time on a sailing boat but the skipper Leonardo and his wife Elena were immediately very professional and attentive to everyone's needs. The boat is very nice, functional and clean; perfect for enjoying the sea in total relaxation. The excellent company, the favorable weather and the crystal clear water of the Pontine islands then made the experience perfect!
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Egadi paradise for sailing and snorkeling

09/17/2025

Vicky H.

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Belgium

Mario is a competent and friendly skipper. The Egadi islands are beautiful and the boat is in good shape. It is a pity that 2 French-speaking fellow passengers had a lot of criticism, made little effort to involve the skipper in the conversations and were very present during the trip, to the displeasure of the other passengers.

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