SailSterling Yacht Charter in Italy

Yacht Charter In Italy

Sailing holidays done to perfection

SailSterling Essential Italy

Chartering a yacht in Italy through SailSterling gives you an unbeatable combination of history, culture, food and delightful sailing conditions. Not to mention the freedom to set your own pace. So, if your tour at Pompeii overruns or a two-hour lunch in your new favourite trattoria becomes a four hour one…no problem…you’re on holiday and you’re in charge.

Italy has more UNESCO World Heritage-listed sites than any other country and a SailSterling yacht charter gives you a unique perspective from which to see them. It’s the same story for vibrant coastal towns and cities not to mention enchanting islands such as Capri, Ischia and Ponza. And wherever you sail, some of the best food and wine anywhere in the world is always close. 

Fun Fact

Italians knock back 14 billion espressos a year. But at an average of 5.8kg of coffee per person per year, that only puts them 18th on the list of coffee consumers…the Finns are way ahead with a whopping 12kg per capita each year.

Food and culture highlights

It’s pretty hard to go wrong at any Italian restaurant or café: even if you don’t understand the menu, whatever comes out of the kitchen will be delicious, even if it might not quite be what you thought you were ordering!

Breakfast isn’t really the meal you might be used to at home…a coffee and a pastry (a cornetto) suffice for most people. Locals think of a cappuccino as just a morning drink, so don’t order one after lunch or dinner.

Midday and evening meals are not affairs to be rushed, especially when accompanied by a glass or three of local wine. Antipasti gives you something to nibble on and could be hot or cold. Primi are the starters, secondi the main dishes, contorni are side dishes, insalata is salad, formaggi are cheeses and dolce is the desert. Of course, you don’t have to have all of them, but when in Rome (or Naples or Palermo) as they say…

In Sardinia, you’ll often find fresh fish and local pork on the menu, while in Sicily you’ll be able to discern the Arab influences that have pervaded the island’s cuisine over the centuries. In Naples, you have to have pizza for at least one meal, in the home city of the world’s most ubiquitous snack. In Tuscany, savour a delicious steak, acquacotta (bread-based) soup garnished with grated parmesan and poached egg, as well as regional cheeses, mushrooms, chestnuts and tomatoes.

When it comes to culture, you could easily argue no other country on earth has had as much of an impact as Italy. Whether it’s architecture, the arts, music, fashion or religion, a holiday afloat gives you a unique perspective from which to see them all.

SailSterling Tip

If you treat yourself to a night at the opera, don’t wear purple as it’s associated with funerals in Italy and actors generally think of it as being an unlucky colour.

Weather and climate (when to visit)

Naples starts to warm up in May and cool off in October. Between those months you’d be unlucky if the temperature dipped below the low 20s centigrade and from June to September you can expect things to get much warmer than that, often climbing to around 30 centigrade or above. Spring and Autumn tend to be showery. For example, in April an average of 13 days could see rain. June and September are two of our favourite months for sailing when you’ll find good weather and fewer crowds.


Imagine almost impossibly-turquoise bays and beaches with sand so dazzling you might think it’s snowed. That’s Sardinia, where the exclusive Costa Smeralda gives way to a hilly, sheep-rearing hinterland with the remains of over 7,000 Bronze Age towers where life hasn’t changed much for centuries. 

There’s over 2,000km of coast here and you’re sure to find a private hideaway cove in which to moor up to swim and have lunch. The Maddelena Islands in particular are a treasure trove and many are uninhabited so you really could have one all to yourself.

Further down the east coast, the Golfo di Orosei, backed by dramatic limestone cliffs, is another gem, where you can drop anchor in translucent waters before going ashore to explore the namesake national park.

San Teodoro
San Teodoro


The dolce vita doesn’t get much sweeter than on the island of Capri, which has been attracting the rich and famous for decades. Take the funicular up to the main square, sit and have an aperol spritz while watching the world go by or wander the whitewashed lanes for some retail therapy. Then hop in an open-top taxi for a tour of the island, stopping in quieter Anacapri for a late lunch, perhaps heading back down to enjoy your afternoon in one of the exclusive beach clubs, such as La Fontelina, that hug the shoreline. In the evening, a more tranquil air envelopes the whole island and you’ll have a wide choice of chic spots at which to dine and drink.



Naples is an assault on the senses – sight, sound and smell. The waft of a freshly-baked pizza drifting from a pavement trattoria. The honking of car horns on a busy street, accompanied by some impressive hand gestures that you won’t see back in Beaconsfield. And the impossibly-chic citizen dressed up like they’re going to a wedding, but who’s probably just on the way to work. 

The city is built upon layers and layers of history. You can see them 40 metres under the historic centre when you descend on a tour to the ancient Greco-Roman aqueducts and the excavations that were used as air raid shelters in WWII. 

Above ground you can tick off monuments, museums and churches or just wander the streets and soak up the atmosphere before you choose where to eat – and what a choice! 

Hiring a local guide is a good idea, both to tell you where to go and where not to: Naples has a certain reputation that comes with any gritty port city, and, as with all places where wealth mixes with poverty, being careful without being paranoid will ensure you have an amazing time.


Elba, Tuscany

Napoleon may not have had much of a soft spot for Isola d’Elba – escaping after just a year when he was exiled there in the early 19th century – but modern visitors are never in such a hurry to get away.

And why would they be, when there are vineyards, olive groves and glorious beach-lined inlets to explore? Its main town, Portoferraio, with its web of narrow alleys, certainly hums with visitors in high season, but outside of July and August it’s a more tranquil spot in which to meander and discover.

Elba lies only around 8km from the mainland so you can use it as a base from which to explore, in particular to enjoy Tuscany’s rich and varied cuisine, from fresh fish to pasta and scrumptious deserts.


"Even now I miss Italy dearly, I dream about it every night"

-Eila Hiltunen


Stringent cleaning procedures are already in-place across all boats globally for the well-being of our crew and guests.  These will be further enhanced to meet government guidelines in the UK and Italy which are in place in July 2021 in relation to the COVID pandemic.  These will include temperature checks prior to boarding; hand-sanitising stations in public areas; additional deep cleans of public areas including decks; social distancing if required.  With each catamaran’s capacity at a maximum of 10 people including skipper and chef, if required in August, guests would remain in catamaran bubbles during visits to vineyards and other on-shore activities.