620

experiences

4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

4.4

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

13 departures available

June - September

Starting from

€730

€657

Per person

5.0

Super!

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

13 departures available

June - October

€1,250

Per person

5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

June - July

Starting from

€350

Per person

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

12 departures available

May - September

Starting from

€600

€540

Per person

4.9

An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

6 departures available

June - September

Starting from

€750

Per person

4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

3 departures available

July

Starting from

€390

Per person

5.0

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

3 departures available

June - July

Starting from

€285

Per person

4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

4 departures available

July - August

€800

Per person

5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

7 departures available

June - August

Starting from

€850

Per person

5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August

€650

Per person

4.7

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€999

€949

Per person

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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

17683 reviews

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

05/26/2026

Roberto L.

A great weekend! Beautiful places visited, particular attention was paid to organizing the tour in maximum safety in navigation and in maximum comfort. The skipper Gennaro is very prepared, a well-equipped boat, very comfortable and externally clean. Highly recommended

Weekend Elba o Capraia

05/26/2026

Sabrina S.

Fantastic holiday with the guidance of Francesco who involved us a lot in managing the destination and the boat, taught us how the sea can create bonds.

Weekend among the most beautiful coves of Elba

05/26/2026

Samantha G.

We were literally welcomed by Marco and Carmen, it seemed to have known them for a lifetime. Evidently they attract beautiful people because the rest of the crew was also wonderful. Beautiful sailings (you can move as little as possible), but managed in full comfort. Finally, an excellent knowledge of the places that does not hurt and makes you enjoy unforgettable coves

Tuscan archipelago between nature and relaxation

05/26/2026

Francesco D.

Riccardo is a true professional, a reliable person and also an excellent travel companion. He was able to perfectly interpret our requests with availability and empathy, becoming in a few minutes a friend, an accomplice in adventures, a trusted person, as if we had always known each other ... Not just a skipper! Thanks to Riccardo and "[hidden]" for this wonderful experience!

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