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5 breathtaking sailing routes in Italy every skipper should experience at least once

2026.09.08.

Italy is best discovered by boat: turquoise bays, dramatic coastlines and charming harbours await. Here are 5 sailing routes every skipper should experience at least once.

Italy by boat

1. Amalfi Coast and Capri

Starting from Salerno, you can easily combine Amalfi, Positano, Capri and Sorrento into a 5–7 day sailing itinerary. It is worth docking in Amalfi and walking into the old town, while simply seeing Positano from the sea is an experience in itself.

Sailing past the Faraglioni rocks in Capri is almost a must, while Anacapri and the Blue Grotto are great options for a trip ashore. In the evening, enjoy fresh seafood at one of the restaurants near the harbour.

Boat traffic along this coastline can be heavy in summer, so it is worth planning your berths and alternative stops in advance.

2. Sardinia and La Maddalena

Starting around Porto Cervo, Caprera, La Maddalena, Spargi and Budelli can comfortably be explored within a few days. Here, sightseeing takes a back seat to anchoring, secluded coves and incredibly clear water.

It is still worth spending an evening in La Maddalena town, sitting down at a restaurant near the harbour and trying a local fish dish or fregola.

The archipelago is a protected natural area, so always check the latest navigation and anchoring regulations before departure.

3. Aeolian Islands and Stromboli

Lipari, Vulcano, Salina, Panarea and Stromboli can easily be combined into a one-week sailing trip. Thanks to the volcanic origins of the islands, the scenery is completely different from what you may be used to in the Adriatic.

In Lipari, take a walk through the old town. In Salina, try the local capers and seafood, and near Stromboli, plan to sail past the island around sunset.

This is already slightly more demanding sailing territory, with several open-water passages, so weather, wind and route planning are especially important.

4. Elba and the Tuscan Islands

If you are looking for calmer Mediterranean sailing, Elba and the Tuscan Islands are a great choice. Portoferraio is an excellent starting point, with Giglio and Giannutri also within reach.

On Elba, it is worth visiting Napoleon’s former residence. After docking in Giglio Porto, head up to Giglio Castello for the panoramic views. In the evening, a simple fresh fish dinner by the harbour is hard to beat.

May, June and September are particularly good months to visit, with pleasant weather and fewer summer crowds.

5. Tremiti Islands

If you are looking for new waters on the Italian side of the Adriatic after sailing in Croatia, the Tremiti Islands are a great destination. Starting from Vieste, San Domino and San Nicola can easily be explored by boat.

San Domino is perfect for swimming and snorkelling thanks to its caves, rocky coves and clear water. On San Nicola, it is worth going ashore for a few hours to explore the historic fortifications.

A fresh fish dinner at a local trattoria is the perfect way to end the day. However, because the crossing between Vieste and the islands takes you across open water, choosing the right weather window is particularly important.

Which route is right for you?

If you are looking for dramatic coastlines and classic Italian atmosphere, Amalfi and Capri are hard to beat. For turquoise bays and peaceful anchorages, head to La Maddalena. Choose the Aeolian Islands for a more adventurous sailing experience, Elba for a calmer cruise, and the Tremiti Islands if you love the Adriatic.

Whichever route you choose, arriving somewhere new as a skipper feels completely different when you decide the route, the stops and the next harbour yourself.

Get on the Water with Us!

At Sidro Nautika, we teach you safe boating so that you know what to do in every situation. Although stories of ghost ships are exciting, the best experience is when you return to the harbor as a confident captain. Whether it is a boating course, sailing training, or a motorboat course, with us you can build on solid foundations.

If sea adventures attract you, you can apply for the Skipper C course, which we hold directly in Rijeka and Split, in a real maritime environment. This is the training that allows you to legally navigate on any ocean and sea in the world.

Our offer also includes Yachtmaster A and Yachtmaster B, full maritime navigation training, as well as the opportunity to complete practical-focused sailing maneuvering training and obtain a motorboat license. In addition, our boating license prices and motorboat training prices are transparent, so you know exactly what to expect.

If you already have a boating license and are looking for a boat for your next holiday, check out our sea boat rental options and choose from several thousand available boats! 

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