In a historic villa in a small coastal town, our Sicilian-American family fell in love with the island all over again — and finally got to relive the simple joys of traveling together.

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The lush exterior of Villa Don Arcangelo all Olmo in Sicily
Credit: Nina Ruggiero

Sicily — particularly Taormina — has become a special place for my family over the years. Although our Sicilian heritage traces back to a small town almost 200 miles away, the strikingly beautiful hilltop town, lively beaches below, and friends we've made have captured our hearts, and we can't stop going back.

The moment Italy reopened to Americans, we promptly shifted our collective energy from whining about missing Sicily to planning our imminent return. (What can I say? I come from a long line of proactive women.)

Anyone who hadn't yet been fully vaccinated made an appointment; I cross-checked calendars and COVID rules from our respective points of departure; my aunt started distributing her Delta miles; and my sister began visualizing our coordinating vacation wardrobes. 

But while we normally book rooms or an apartment at our favorite hotel in town, we knew this was our year to try something different. It would be the first international trip for most of my relatives since COVID began, and the first time we were all reuniting in months.

Of course, we had our reservations about being some of the first American tourists back in the country, tackling constantly fluctuating regulations, and traveling internationally during an ongoing pandemic in general. Although as New Yorkers our booking belief system is based upon "location, location, location," this time, we didn't want to be in the center of town — and it was more important to us than ever to have private space to ourselves where we could spread out and enjoy our time together. 

Villa Don Arcangelo all Olmo pool and gardens
Credit: Nina Ruggiero

Through my research at Travel + Leisure, I knew vacation home rentals were a popular COVID-era option, especially for family trips. I also knew that having on-the-ground professionals help with the logistics would save us hassle and keep us safe. It seemed like the perfect time to check a European villa rental site I'd been eyeing for a while. The rest, as they say, is history.

Finding the Right Villa Rental Site

For the trip we were planning, The Thinking Traveller had it all: it specialized in the sunny European destinations we were craving, from Italian and Greek islands to Corsica and Mallorca. So many of its beautiful villas came with private pools and on-site chefs, so we wouldn't have to leave to partake in some of our favorite vacation activities: swimming and eating.

Villa Don Arcangelo all Olmo dining room
Credit: Nina Ruggiero

Every booking came with a personal concierge who would help plan ahead and a local expert who would assist with on-the-ground logistics, recommendations, and coordinating experiences, from wine tastings and cooking classes to treks and bike tours.

Whether we needed to book a last-minute COVID test or make sure a certain type of wine was stocked in our kitchen, they'd make it happen. When it comes to a family vacation and appeasing a variety of preferences and personalities across generations, this kind of assistance makes a huge difference.

About Our Villa

Passing through the shaded stone entryway of Don Arcangelo all'Olmo and entering its main courtyard — lined with ivy, olive and citrus trees, and tropical flowers and palms — felt like entering an alternate universe where The Princess Diaries happened to us, and we woke up European royalty.

Villa Don Arcangelo all'Olmo Sicily ivy-covered exterior
Credit: Nina Ruggiero

We were welcomed by the exuberant owner of the villa, Marina, who greeted us so warmly it was as if she too was a member of our family reunion. The only time a smile left her face was when she realized we brought our own wine: "We have everything here!" she scolded, and by lunchtime we'd realize she was not exaggerating.

The property dates back to the early 18th century and has been in Marina's family since the days it was a working vineyard, its walls bursting with barrels of wine. Now, it's an eight-bedroom vacation dream home (with a guest house that brings the bedroom count up to 12 for even bigger groups), filled with artwork and memories from Marina's own family trips around the world.

Living room with artwork at villa Don Arcangelo all'Olmo in Sicily
Credit: Nina Ruggiero

Some bedrooms have en-suite soaking tubs, others have canopy beds or panoramic terraces. Each room has its own style and personality, and choosing one was probably the hardest decision we had to make for the entire week.

As a remote working destination, the villa had it all — a sophisticated study, multiple living areas, and Wi-Fi in almost every room.

Villa Don Arcangelo all'Olmo study lined with books and mahogany desk
Credit: Nina Ruggiero

The grounds include multiple outdoor eating and sitting areas, an expansive swimming pool with sea views, a hot tub, a giant trampoline, and a gym. Gorgeous gardens show off the best of Sicilian horticulture between it all.

The pool at Villa Don Arcangelo all'Olmo Sicily
Credit: Nina Ruggiero

Dining and Experiences

June temperatures in Sicily are toasty, and there were days when we hardly left the pool. Those were the days that, more than any trip we've taken in the past decade, brought me back to our beloved summer family vacations growing up — the source of all my favorite childhood memories.

From jumping around the trampoline to choreographing synchronized swimming routines and singing along to our favorite Italian tunes, being at the villa together brought out the kids in us again. As much as I love a hotel stay, the same, um, creative freedom just doesn't exist in spaces shared with strangers.

Our days at the villa also included home-cooked meals, served inside or out, depending on the weather and activity of mighty Mount Etna — which erupted most nights we were in town, its red lava putting on a fireworks show in the distance. From eggplant parmigiana and risotto to fresh fish and pork dishes followed by homemade gelato, every multi-course dinner left us simultaneously stuffed and excited for breakfast in the morning.

Other days, we took an excursion into central Taormina, hung out at a beach club, or went to a winery. At Cottanera, a winery in the nearby Etna region, we learned about the generations of local mothers and daughters who have harvested their grapes together. We feasted on antipasti and homemade arancini while sampling some of our new favorite wines — and picked plenty of bottles to send back to the family members missing out on the fun.

Cottanera vineyard Sicily vines
Credit: Nina Ruggiero

We'd meet up with old friends at some of our favorite spots around Taormina — browsing the shops along Corso Umberto, sharing pizzas at Osteria Le Tre Vie, dining on the rooftop at Hotel Villa Carlotta, kayaking and snorkeling at Lido la Caravella — and then return "home" to our new friends, the kind staff members of Don Arcangelo all'Olmo.

central Taormina's main street, Corso Umberto, in June 2021
Credit: Nina Ruggiero

We had the option to rent a car or call on a local transportation company for rides. We chose the latter, but also enjoyed taking walks into the nearest small town, seafront Torre Archirafi. Although we'd been to this northeastern region of Sicily so many times, we found ourselves discovering spots we'd never seen before.

COVID Safety and Travel Tips

Staying at the villa with all of its on-site amenities kept us largely protected and isolated while we were away — but we weren't shielded from the realities of international travel during COVID entirely.

It started when my aunt tested positive right before her flight and was unable to join us. She's healthy, most importantly, but not being able to see her was a huge let-down for all of us. It ended with drama at Catania Airport, when our lab-tested PCR tests were rejected for reasons we still don't understand and we had to take a taxi to a nearby testing center and rush back for our flight.

As COVID rules are ever-changing, it's so important to do research (using government websites in both your destination and point of departure) up to the very day you leave, and while you're there. Booking with a company that comes with a concierge or built-in travel agent helps take the stress out if you have any questions, and you will.

Now, fully vaccinated Americans are able to enter Italy without pre-arrival testing, but that is always subject to change. At the same time, some Italian museums, restaurants, attractions, and even trains or buses may start requiring a green pass for entry, proving you are vaccinated or have received a negative COVID test within a certain span of time.

We found that no matter how prepared you think you are, it's important to get to the airport much earlier than you normally would, just in case issues do arise. The truth is, it's still not the easiest time to go to Europe. But if you're lucky enough to be in good health, have been vaccinated, and are a flexible traveler, it's an incredible time to avoid crowds, spend much-needed time with those you love, and maybe even discover a new experience in an old favorite place.

Years from now, we'll forget the details of decoding PCR tests with airport employees — but the memories we made inside our own Italian villa will stick with us forever.

Nina Ruggiero is Travel + Leisure's deputy digital editor. A New Yorker living in Los Angeles, she's happiest on a beach, a cobblestone street, or in a hotel bathtub with a view. Find her on Instagram @ninamarienyc.