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A free night in Sicily sounds amazing. Booking it is complicated.

The vacation deal from Visit Sicily requires you to book over email with an Italian travel agency

A fishing boat in the harbor in Cefalu, Sicily.
A fishing boat in the harbor in Sicily. (Aleksandar Todorovic/Shutterstock)
5 min

If you’re considering a trip to Italy — and you have deep reserves of patience — Sicily’s tourism office will pay for a chunk of your stay to include the dreamy Mediterranean island in your plans.

Under its See Sicily program, Visit Sicily offers a free night’s stay, a complimentary excursion and a discount on an airfare or ferry ticket. After the tourism office unveiled the travel promotion two years ago, it’s back for 2023.

Andiamo, right? Not so fast.

The deal is riddled with confusing details and caveats, including two blackout months in the summer. I spent days trying to arrange a test booking before making any progress.

Visit Sicily created the package to boost tourism, which withered during the coronavirus pandemic. Compared with 2019 figures, tourism in Italy fell by 61 percent in 2020 and 58 percent in 2021, according to the U.N. World Tourism Organization. In 2019, about 65 million people visited one of the world’s top tourist destinations.

The deal, which is outlined on Visit Sicily’s website, seems straightforward enough. Book two nights at any of the dozens of participating accommodations and receive a third night free. You can also double the rewards with two free nights on a six-night stay.

Additionally, you get to choose a “tourist service,” such as a guided walking tour or a diving trip. As a further incentive, the tourism office will throw in a voucher that claims to cover 50 percent of your air or ferry expenses.

But don’t start packing your Dolce & Gabbana caftan yet. You’re about to begin trading emails with travel agents working on Italian time.

The fine print for See Sicily offers

The promotion runs through Sept. 30, but July and August, two of Sicily’s most popular months, are blacked out. Some of the lodgings, which include hotels, apartment rentals, bed-and-breakfasts and campsites, are closed during the slow season covering parts of winter and spring.

One of the most notable — and burdensome — requirements is that you must book through a travel agency in Sicily.

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The math for the travel discount also does not add up. According to the website, the rebate is capped at $109 for domestic or continental flights and $217 for international airfare. That won’t cover half of most transatlantic tickets, which can cost about $900 in the offseason and $1,600 or more in the summer.

“Overall, it’s probably not worth all the effort,” said Steve Perillo, president and owner of Perillo Tours, a New Jersey-based tour operator that specializes in Italy, “and it has to be booked directly with Sicilian travel agents or hotels, and who knows what exchange rate they’ll charge your credit card.”

Of course, any travel deal, especially one for Sicily, which is known for its ancient ruins, silky beaches, caponata and Marsala wine, is worth some effort. Or at least an attempt.

“To some people this would be an attractive promotion,” said Ann Castagna Morin, an Italian American travel adviser based in Massachusetts, “[like] independent travelers who are comfortable exploring on their own.”

What happens when you try to book

The tourism office provides a long list of travel agencies affiliated with the deal; some even have “See Sicily” in their email addresses. The companies are organized by city, such as Palermo, Enna and Trapani. When I unleashed my first dozen inquiries, I received one response.

The agency reiterated the package details, including the confounding bit about the discount, and asked me about my vacation style (active, relaxed, foodie), preferred category of lodging (depending on the number of meals) and choice of outings: an “exciting” trek up Mount Etna or a city walking tour?

I immediately replied, but I never heard back from the company that signed off as the “Take it slowly Team.” (The tourism office sporadically emailed me back, but several of my questions remain unanswered, such as further clarification of the travel voucher.)

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I submitted another round of inquiries the following evening, so Sicily would welcome the new day with messages from me.

I eagerly opened an email from Ulisse Tour Operator in Palermo. Anna Maria Ulisse advised me to research flights and share my findings with her, so she could book it. But she never replied to my follow-up questions.

The next night, aware of the desperation creeping into my text, I tried again, hitting up a new batch of agents.

I scored the most success this time around. One agent replied, confirming my email address. Dimensione Sicilia in Catania sent me tantalizing videos of the island and of a self-drive tour, plus a few itinerary ideas.

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“You could spend the 3 nights in Palermo, the capital city, very [rich] in art and monuments and have a free visit of Palermo or spend the 3 nights in Catania, the second most important city and get an excursion on Mount Etna, the highest active volcano in Europe or visit the lovely Taormina,” Daisy, an employee, suggested.

With Shell Travel Agency, the fog started to lift, and I could actually see a vacation in Sicily forming on the horizon. An agent named Alessandra explained that although her agency did not offer the travel voucher, she could arrange my lodging and outing.

She recommended Taormina, the beach town near Mount Etna that appears in Season 2 of “The White Lotus,” and a few excursions, such as a visit to Alcantara Gorges or a city walking tour. She just needed my dates, then we could finalize the trip.

After the days-long pursuit, I had finally hooked a free night in Sicily.


A previous version of this article gave an incorrect name for the U.N. World Tourism Organization. This version has been corrected.