618

experiences

5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

23 departures available

June - August

Starting from

€79

Per person

4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - August

Starting from

€900

Per person

4.9

Super!

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

Italy: Tuscany

2 days - 2 nights

4 departures available

June - September

€280

Per person

4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

Per person

5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

2 departures available

September

€900

Per person

4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,180

€1,080

Per person

5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

4 departures available

August

Starting from

€849

Per person

5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

2 departures available

September

€750

€675

Per person

4.7

Whale watching mini-cruise in the Pelagos Sanctuary with WWF guide

Italy: Liguria

4 days - 4 nights

One departure available

September

€609

€579

Per person

5.0

Super!

Long weekend of June 2 in the archipelago of La Maddalena and south of Corsica

Italy: Northern Sardinia

5 days - 4 nights

One departure available

May - June

€500

Per person

5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August

€650

Per person

4.8

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

3 departures available

June - August

Starting from

€1,150

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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