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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!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

One departure available

September

€300

Per person

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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

Starting from

€312

Per person

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4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€600

Per person

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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

September - October

Starting from

€370

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

3 departures available

September - October

€650

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

One departure available

September

€260

Per person

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4.8

Super!

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€280

Per person

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4.9

Super!

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

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,300

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

Starting from

€1,000

€750

Per person

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4.9

Super!

Sail to the edge of the world among the wonders of the North (cottage + sailboat)

North Sea: Norway

7 days - 7 nights

One departure available

October

€1,200

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

19107 reviews

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Midweek getaway between Elba and Capraia

09/12/2026

Nikhita R.

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IT

Unforgettable experience and even better to have made a friend discover this reality. We both fell in love with it. Thanks to Edoardo who had the patience and the right spirit of adaptation in managing several generations of women! We can't wait to set sail again.
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Midweek relaxing in the Pontine Islands

09/12/2026

Giovanni F.

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IT

The boat is large, new and equipped with all comforts, but the highlight is certainly Mirko who in addition to being an excellent skipper also managed to make us feel comfortable and safe when we encountered a lucky man on the return trip. The islands are very beautiful and being able to enjoy them from the sea makes the experience top!
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Summer 2026 - Catamaran week in the Pontine Islands

09/12/2026

Maverick R.

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IT

It took me a week to decide what to write and how to describe this wonderful holiday spent on board with a formidable captain like Marco and a splendid Giulia who pampered us for a week. It is also difficult to express the sensations felt in seeing those wonderful places that Marco himself, with great will and I imagine also effort, has led us to see, and experience. A real merit also to his professionalism in managing every situation, in wanting to be the right detached but with a chat that is never denied. I feel I want to recommend this experience to those who will read this review of mine, as I will also recommend to those I know and ask me where to go, to take a holiday by the sea, to try this experience. Really, really good and both good! A heartfelt thank you ☺️

Midweek getaway between Elba and Capraia

09/11/2026

Samanta B.

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IT

Fantastic experience on board! Edoardo is a competent skipper, a real sea dog who knows how to create a cozy atmosphere on the boat and patiently explained to us how to sail. He also recommended excellent trekking routes in Elba, an extra touch that made the cruise even more special, and the boat was very clean and well cared for

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