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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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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

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

3 departures available

July - August

Starting from

€900

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

4 departures available

July - September

Starting from

€200

Per person

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5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

7 departures available

July - September

Starting from

€1,450

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

One departure available

August

€949

Per person

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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

9 departures available

July - September

Starting from

€980

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€950

Per person

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4.7

Whale watching cruise with WWF guide between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

2 departures available

July - August

Starting from

€946

Per person

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4.8

Super!

Sea, scents and colors on Elba

Italy: Tuscany

3 days - 3 nights

One departure available

September

€300

Per person

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4.8

Super!

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€900

€855

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

17995 reviews

Sailing in the magical Sardinia of the South

07/8/2026

Cristina B.

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US

This sailing trip was everything I dreamed it would be. Gianluca is an incredibly experienced Captain, who made us feel totally safe, and comfortable and he was so generous with his energy, to sail whenever possible and to create the most memorable experience for his guests. Every stop on our trip was beautiful and unique. I feel very lucky that my first sailboat experience was with this captain!
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In the blue of Capri and the infinity of the Amalfi Coast

07/7/2026

Giuseppe I.

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GB

It was a fantastic weekend: super comfortable boat and skipper always attentive to the needs of the group, which allowed us to live a wonderful experience,

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

07/7/2026

Giorgio R.

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FR

Beautiful week in the company of Alessandro. The Greek islands of the Ionian Sea are beautiful with breathtaking small bays. Alessandro in addition to being an excellent skipper, is also a very good cook. He established a relaxed and fun atmosphere that made the holiday special. With him you will be sure to try the local delicacies in suggestive taverns and have fun aperitifs on the boat at sunset, He has such a big heart that he even saved a baby bat that had crashed on the awning boat. Thank you Alessandro !

Weekend at the Marine Protected Area of the Tremiti Islands

07/7/2026

Giovanna N.

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IT

It was our first experience on a sailing boat and, in addition to a nice and close-knit group of friends, we were lucky enough to meet an experienced and competent skipper. The outward crossing was completely under sail and, although the sea was a bit rough, he spent the best of his experience to make the navigation as stressful as possible for those of us who were at his first experience. Marco turned out to be a person attentive to our needs and every need and very pleasant entertaining us with his fascinating stories of the sea, the history of the Tremiti islands over the centuries and night observation of the constellations. A wonderful experience that we hope to repeat. See you soon and thank you again for everything Joan and Evelin

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