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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

5 departures available

September - 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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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

10 departures available

July - November

Starting from

€500

€425

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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5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August

€650

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

8 departures available

August - October

€650

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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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

2 departures available

July - September

Starting from

€200

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

14 departures available

July - November

Starting from

€600

€540

Per person

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5.0

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

10 departures available

June - September

Starting from

€700

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

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

17818 reviews

"Nel Blu dipinto di Blu" - midweek in Ponza, Palmarola and Ventotene

06/20/2026

Fabio F.

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IT

Everything above expectations, beautiful islands, beautiful boat, exceptional captain. to be repeated absolutely.

Long weekend on a sailing boat between Capraia and Corsica

06/20/2026

Mattia V.

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IT

We were speechless, congratulations, we couldn't have ended up in better hands, great skipper, perfect welcome!' Thank you Massimo top !!!!

Midweek relaxing in the Pontine Islands

06/20/2026

MARINA C.

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IT

Thank you Mirko everything perfect!
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4 weekdays in the Pontine Islands

06/20/2026

simona s.

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IT

Stefano is an excellent captain. Admired the mooring maneuver in Nettuno, not very easy. Also always calm, kind, nice. Even with the crew it went quite well. The only regret is almost always the engine, but it's no one's fault, especially if you have a busy schedule to respect because those who signed up want to do that. I need experience to understand that in the next short period I will look for only one Ponza, so you can choose the coves where to go according to where the wind blows and really sail. Until next time, Stefano

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