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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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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

7 departures available

August - November

Starting from

€500

€348

Per person

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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€600

Per person

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5.0

Super!

Cruise for Singles from Sanremo to Saint-Tropez

France: French Riviera and Porquerolles

8 days - 7 nights

One departure available

August

€650

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

5 departures available

September - October

Starting from

€275

Per person

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5.0

Super!

Wandering between Tigullio and Cinque Terre

Italy: Liguria

7 days - 7 nights

One departure available

September

€700

Per person

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4.6

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

7 departures available

July - September

Starting from

€700

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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4.5

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August

Starting from

€850

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

5 departures available

August - October

€650

Per person

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5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

4 departures available

August - September

€649

Per person

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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

4 departures available

July - August

Starting from

€250

Per person

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4.8

Super!

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

6 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

18084 reviews

Cast off for a week at sea, a thousand ways to experience it!

07/15/2026

Michael J.

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DE

Our one-week sailing trip through the Saronic Gulf deserved a definitive 5-star rating for its perfect blend of adventure and incredible food. We explored the car-free streets of Hydra and swam in the crystal-clear, secluded bays of Dokos. Captain Alexandre amazed us, especially with a rich, authentic Bolognese that tasted like it simmered for hours. Our stops in Spetses and Poros offered beautiful views, but the true highlight was dining right on deck. Captain Alexandre's perfectly creamy risotto easily rivaled any high-end restaurant we found onshore. Each night ended with stargazing and the gentle rocking of the yacht under the Greek sky. This five-star combination of spectacular island views and gourmet sailing cuisine made for an unforgettable journey.

Corfu between bays, taverns and myths.

07/15/2026

Chrystel O.

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FR

Wonderful experience ! Nice and friendly people on board. Beautiful landscapes. Would definitely book again with this crew anywhere :)
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The Sporades Islands: A Hidden Paradise of Greece

07/15/2026

Valerio R.

-

IT

Fantastic experience

Weekend in the Pontine Islands

07/15/2026

Sara F.

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IT

Dream experience! Thank you Dario, skipper attentive to his guests and their needs, very prepared and a great connoisseur of the Ponza/Palmarola area. I definitely recommend a weekend to enjoy this adventure

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