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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!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

6 departures available

July - November

€250

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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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

6 departures available

July - October

€260

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

15 departures available

June - November

Starting from

€600

€540

Per person

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5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

9 departures available

July - September

Starting from

€550

€495

Per person

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New

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

4 departures available

June - July

Starting from

€300

€270

Per person

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

3 departures available

June - September

€280

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

6 departures available

July - September

Starting from

€400

€360

Per person

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5.0

Super!

Sail in Menorca with a cook on board!

Spain: The Balearic Islands

5 days - 5 nights

3 departures available

June - August

Starting from

€950

€808

Per person

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4.9

Super!

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

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

Per person

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4.9

Super!

Fast Sailing Experience between Authentic Islands and Good Food

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

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

17803 reviews

A taste of the magnificent Island of Elba

06/17/2026

valentina t.

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IT

We with friends at the Top! The boat very clean and welcoming, Alberto always on the piece helpful and attentive.
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Gulf of Poets and Cinque Terre

06/17/2026

Nicola P.

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IT

Excellent company of Giorgio with his wife Francesca, friendly, nice, they immediately put you at ease with all the rest of the crew. The cuisine is good and plentiful. As you know, to make the edges on a sailboat you need the wind, let's hope next time to have a BETTER WIND!!

Magical Pontine: full sail to discover the archipelago

06/17/2026

Nicolò B.

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IT

Positive experience. Possibility to visit wonderful places. Experience on a boat, it is well known, requires a spirit of adaptation and flexibility. The skipper was helpful, giving all the directions. Despite the change of plans for the last day (due to strictly weather conditions), the skipper provided a refund quickly.

Week-end all'Elba - Hostess a bordo

06/16/2026

Andrea P.

-

IT

We spent a beautiful holiday beyond all expectations: the comfort and spaciousness of the boat, the beauty of the places, the kindness and skill of Giulia in the kitchen, the care and professionalism of Vittorio at the helm, together with the sympathy of the other day-trippers (and the wonderful weather!) allowed us to enjoy our first sail - around Elba - in a fantastic way, celebrating my wife's birthday in an exciting way on a holiday that we hoped would not end so soon. Five well-deserved 😀 stars

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