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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!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

17 departures available

July - November

Starting from

€540

€513

Per person

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4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€420

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - October

Starting from

€600

€540

Per person

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4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

3 departures available

July - August

€800

Per person

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5.0

Super!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

4 departures available

June - September

€740

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

3 departures available

July - August

Starting from

€800

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

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

2 departures available

August

Starting from

€849

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!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

2 departures available

August

Starting from

€1,060

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

17765 reviews

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Three-Day Sailing Tour to the Pontine Islands

06/13/2026

Giorgio T.

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IT

the trip to palmarola is wonderful, and the skipper Antonio was very professional, we had a great time,

Magical Bridge to the Pontine Islands

06/12/2026

Federica G.

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IT

Fantastic experience! Amazing group and fabulous skippers. Special mention for the Super Costy who spoiled and pampered us for all 4 days!
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Summer is made for the Aeolian Islands! Weekly cruise

06/11/2026

Patrizia R.

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IT

Very comfortable boat. For the first time I found a skipper who lent himself to the purchase of a galley without waste and in any case complete and integrated by specific requests of the crew. The skipper also prepared tasty meals on board, including typical dishes of the Aeolian culinary tradition. On board we enjoyed a relaxed and very pleasant atmosphere and the stops took place, weather permitting, in the most iconic places of the Aeolian archipelago. It is an experience that I certainly recommend. Patricia

June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide

06/10/2026

Guido F.

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IT

Beautiful experience. The enthusiasm and ability to involve biologists is remarkable. The only pity we never sailed.

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