522

experiences

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

4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

5 departures available

July - September

Starting from

€400

€360

Per person

5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

Per person

5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

July - August

Starting from

€950

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

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

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

3 departures available

July - August

Starting from

€900

Per person

5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

8 departures available

July - September

€1,600

Per person

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

5.0

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€350

Per person

5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€410

Per person

5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

One departure available

August

€849

Per person

Why book a holiday with Sailsquare?

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Reviews - Sailboat holidays & skippered tours

17914 reviews

Week end Liguria Costa Azzurra

06/29/2026

salvatore r.

It was a great experience... Olaf TOP👍

Weekend of sea and colors between Ischia, Procida and Vivara

06/29/2026

Manuela M.

Very nice experience, comfortable and clean boat, Gennaro the skipper a person always available and kind. Highly recommended!

An exclusive weekend on Elba between aperitifs and sailing

06/29/2026

Alessandra R.

Very positive experience, Elba always enchanting. The Skipper Luca L. very kind and professional, a great connoisseur and lover of the Tuscan archipelago, with the timing and talent necessary to transform what is in the galley into very pleasant moments at the table in the cockpit, after a perfect swim and in the middle of a fabulous sunset.

Midweek among the wonders of the island of Elba

06/29/2026

Jonathan K.

Luca, Claudia are very nice and sympathetic hosts and their boat [hidden] is absolutely amazing. I had a wonderful experience on the boat and can only recommend to go sailing with them in Tuscany! I look forward to sailing with them again

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