120

experiences

4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

18 departures available

May - October

Starting from

€680

Per person

4.8

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€962

€866

Per person

5.0

New

Cruise to the Golden Islands via the capes and bay of St Tropez

France: French Riviera and Porquerolles

5 days - 4 nights

27 departures available

February - October

Starting from

€595

Per person

5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

18 departures available

June - October

Starting from

€690

Per person

4.1

Totano's cup 2027 weekend of sailing and party on the island

Italy: Tuscany

3 days - 2 nights

One departure available

October

€350

Per person

New

Sailing Week Sardinia and Corsica

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

October

€600

Per person

4.4

L'Île de Beauté: sailing in Corsica with night return

France: Corsica

6 days - 7 nights

5 departures available

July - August

Starting from

€750

Per person

4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

June

€625

Per person

5.0

New

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

€590

Per person

4.2

Discover the South of Sardinia by sailing, white beaches and tradition

Italy: Southern Sardinia

6 days - 7 nights

2 departures available

August

Starting from

€896

€806

Per person

Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

€890

Per person

4.8

Let's sail in relaxation on Lake Garda - All Inclusive

Italy: Lake Garda

1 day - 0 nights

3 departures available

October

€150

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.

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

19271 reviews

The fantastic Saronic Islands and the surroundings of Athens

10/13/2026

Alexander S.

We had an exciting and memorable week on board with Alessandro. We were lucky to enjoy boat trips every day and especially loved sharing his delicious pasta meals. We quickly embraced his Italian spontaneity, with new destinations and ideas along the way, making the experience all the more adventurous and unique. A wonderful week for those who enjoy a relaxed, authentic Italian sailing experience!

Sailing and Trekking in the Aeolian Islands

10/12/2026

Filippo D.

I was lucky enough to have a "sailing + trekking" experience aboard Mario's beautiful boat. He is a true expert in sailing and the Aeolian Islands! He is also very willing to teach and explain all the technicalities related to this fascinating world. The boat is maniacally maintained and is very comfortable I recommend it

Adventure weekend in the Egadi Islands

10/12/2026

Alessandro B.

Route, stops and perfect overnight stays, skipper very helpful.

Barcolana 58: a day at the most famous regatta in the world

10/12/2026

Sara B.

5-star skipper: his experience and love for sailing can be seen in the naturalness with which he leads [hidden] and the serenity he transmits makes you want to continue sailing and never get off again! A 5-star destination: you have to experience the Barcolana to understand its extraordinariness... It is a regatta (where the competitive spirit comes out in a genuine way) and a party at the same time. 5-star boat: [hidden] performed very well... A true lady of the sea!

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