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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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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

July - October

Starting from

€700

Per person

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5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

9 departures available

July - September

Starting from

€790

Per person

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4.8

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

4 departures available

July - August

Starting from

€410

€369

Per person

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4.8

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€583

€525

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

13 departures available

July - November

Starting from

€540

€513

Per person

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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - October

Starting from

€650

€585

Per person

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4.8

Super!

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

5 departures available

July - September

Starting from

€400

€360

Per person

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4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

2 departures available

August

Starting from

€800

€720

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

10 departures available

July - October

Starting from

€230

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

4 departures available

July - September

Starting from

€490

€466

Per person

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5.0

Super!

La Maddalena Archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

July - August

€750

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€800

€600

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

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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

17936 reviews

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From Mykonos to Milos

07/2/2026

Maximiliano S.

-

AR

Great experience, we traveled 2 couples and we are very grateful for all the attention provided by Andrea, we sailed through all the cyclades and she made us enjoy and share great moments and know places. Unique and incredible and having fun with our travel companions Elena, Patrick and Toni, who were very funny. A sublime experience.

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

07/2/2026

Luigi C.

-

IT

Good evening, the all-inclusive writing is misleading as it is not clear from the program that to go down to Positano and Capri there are other costs to be divided among the participants.

Mini-cruise with WWF guide in the heart of the Tuscan Archipelago

07/2/2026

Bianca Matelda C.

-

IT

Beautiful days in the middle of the sea, freedom, discovery, full nature and new friends! The WWF guide Elisa and the skipper Nico were very good, nice, professional and prepared to manage the outings and make a group. These are days that I carry in my heart. I recommend bringing little stuff, just enough to protect yourself from the sun and feel good.. but above all to a lot of curiosity and team spirit!

In the heart of the Cyclades, from Milos to Athens (Lavrio)

07/2/2026

Christine H.

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DE

This was my first sailing trip and I was able to have an exciting and valuable experience. Unfortunately, we could not follow the originally planned route due to the weather. But Andrea quickly had an alternative ready. Unfortunately, the weather conditions were sometimes challenging for me despite the changed route. But Andrea led us confidently through them and I guided myself safely at all times. Whenever possible, Andrea responded to our wishes, and he also contributed many of his own suggestions and ideas, which certainly simplified the decision-making process within our group. At the same time, I would have liked to see more proactive communication regarding the respective daily schedules. The boat has already been allowed to cover many nautical miles, which can be seen in one place or another. But everything you need is available. For me as a sailing novice, the distances covered could have been a little shorter and the rest periods more extended. But this was certainly also due to the changed, longer route. Thank you Andrea for this experience and your support! 😌

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