Sailing holidays in Italy: discover the rich beauty of the Mediterranean.

Boating holidays in Italy. Explore Sicily, Sorrento, Capri, and the Amalfi coast.

World-renowned for its rich culture and cuisine, cities such as Rome, Florence, Venice, and Milan are adored for their ancient architecture, iconic art collections, striking canal systems, and influence on fashion respectively. But what do you know of Italy's slightly more secretly kept stunning costal regions?

Italy has over 7,500km of Mediterranean coastline, playing host to a great number of secluded islands, rock formations, and bays - and is recognised by sailors as having particularly smooth conditions and a pleasant climate. Partnering such locations and conditions is of course a unique and proud plethora of food and wine - try the famous seafood dish sscialatielli ai frutti di mare with a glass of Sicilian Nero d’Avola as you cruise the warm waters of the Mediterranean? On a sailing holiday around Italy, you'll never be short of things to do.

On Sailsquare you can find experiences around popular Italian sailing destinations, including: Sicily, Sorrento, Capri, and the Amalfi coast.

Best time to travel: Sailing conditions around Italy are ideal between May and October.

Costs: A sailing weekend from €150 per person, a week sailing from €450 per person.

Sailing in Italy:
When cruising past the coast of Sicily remember to keep an eye on Stromboli, as with a bit of luck you may witness one of the famously mild, yet striking Strombolian volcano eruptions.

The crystal-clear waters of La Maddalena Archipelago in Sardinia, are a speechless taste of paradise.

Or, immerse yourself in some of most fun and engaged sailing tradition with the Barcolana in Trieste - a famous regatta, that in 2018 set a new record with 2689 boats coming together in celebration!

Visiting Florence or Pisa? Then we implore you to account some extra time to your travels and sail to Elba Island and the other striking gems of the Tuscan Archipelago.

These are the last people to have explored Italy.