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How to Plan a Glitzy Italian Getaway Fancy Enough to Impress Your Mother

My mother has always dreamed of visiting Italy, and for her first post-pandemic voyage abroad, I set out to make her Italian dream come true.

The first time that I went traipsing through Italy, I had only a backpack, a single change of clothing, and a pair of worn-in boots. I ate slices of focaccia and drank straight from three-euro bottles of wine. In my exhilarated state, I lost track of time and took a train from Cinque Terre to Florence a day earlier than I was scheduled to and was met by a confused hostel front-desk worker who informed me that I couldn’t check in until the following afternoon.

Desperation and a lack of funds led to me sharing a room that night with a fellow American who’d shacked up with an Australian backpacker she’d met on a train. All in all, it was a fantastic trip. But it was not the sort of trip I would take my mother on.

My mother has always dreamed of visiting Italy, and for her first post-pandemic voyage abroad, I set out to make her Italian dream come true—I wanted it to be the epitome of living la dolce vita—delicious drawn-out meals, hotels suited for royalty, sparkling seas, and sweeping sunset views. Here’s my guide to a luxury trip that includes Rome, Ravello, Positano, and Capri.

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Erika Hobart


We started our journey in Rome. I arrived at Fiumicino Leonardo da Vinci International Airport shortly before my mother, and upon spotting me waiting, she called out, “Ciao!” I rolled my eyes but was secretly pleased by her eagerness. On the taxi ride to our hotel, she chattered away in excitement and revealed she’d made a list of pasta dishes she wanted to try on our trip.

Where to Stay: Julia Roberts chose to live at Rome Cavalieri for a month during the filming of Eat, Pray, Love. I figured, if it’s good enough for Julia, it’s good enough for my mother. My reasoning was sound: The opulent hotel is set within a lush 15-acre park atop the highest hill in Rome, which means it boasts the most spectacular panoramic views of the entire city. “It’s like a painting,” my mother marveled more than once. We woke up to a backdrop of the Eternal City bathed in a soft pink glow, and went to sleep when the sky became a dark velvet blanket. But great views aren’t all that Rome Cavalieri has to offer: It also houses one of the world’s largest private art collections, a range of priceless works from the 16th century onward, displayed in the lobby and halls for guests to enjoy. To top it off, the hotel’s top floor is where La Pergola–the city’s first and only 3-star Michelin restaurant–is located.

Rome3_Ponte Umberto
Erika Hobart

Where to Eat: Roscioli is a tiny but mighty eatery that also operates as a bakery, deli, and wine shop. It’s as good for people-watching as it is dining: We observed as many locals dropping in to select a bottle of vino as we did tourists vying for one of its coveted tables. We headed to Roma Sparita to sample cacio e pepe, Rome’s most famous pasta dish. The late Anthony Bourdain was a huge fan of the restaurant’s take on the decadent dish, which involves serving it in a parmesan cheese bowl. My mother declared that Rome Sparita’s gnocchi with clams and zucchini flowers was the best meal she had on our entire trip. For dessert, we loved Giolitti, the oldest ice cream parlor in Rome. We both ordered the pistachio flavor, and my mother asked for whipped cream in Italian. “I’ve been studying for weeks,” she said proudly after noticing my surprised expression. I rolled my eyes again, but a smile crept across my face. It felt good to see the way that Italy brought my mother out of her shell.

What to Do: As cliche as it’s become, the Trevi Fountain is still a must-visit. We woke up at sunrise so that we could avoid too large of a crowd and truly appreciate its magnificence. After the early wakeup, we gulped down espresso at a nearby bar. Later at sunset, we strolled through Giardino degli Aranci, a splendid park with fragrant orange trees that draws everyone from dog owners to young couples in love to musicians and painters putting their talents on display.

Erika Hobart


From Rome, we took a train to Naples and then a ferry to breathtakingly beautiful Positano on the Amalfi Coast–which my mother admitted she had never heard of until our trip. As someone who puts an extensive amount of planning into my travels, I found her approach refreshing. My mother wasn’t in Italy because she wanted to visit the most popular places. She just wanted to spend time with me (well, that, and to eat pasta). The fact that she could do these things in a place as iconic as Positano was merely a bonus.

Where to Stay: Hotel Poseidon is worthy of having its own Wes Anderson film. Its story began in 1950 when Bruno and Liliana Aonzo bought a little house among lemon trees to spend their summers. The couple turned their holiday home into a hotel in 1955, and it now includes a restaurant and pool overlooking the sea. The Aonzo family live on the top floor of Hotel Poseidon, along with their two dogs, Nina and Lucas, who make frequent appearances in the lobby and on the outdoor terraces. As if all of that wasn’t endearing enough, Hotel Poseidon also has an adorable 1970s convertible Beetle that guests can rent free of charge to go for a ride through the winding roads of the Amalfi Coast.

Where to Eat: Ristorante da Costantino is situated at the top of Positano and overlooks all of its colorful houses and rugged coast. It’s got charismatic servers–ours told us when he relocated us to a window view that he only provided the upgrade for “the most beautiful guests.” Costantino also has a seafood menu that varies based on what’s caught that day. Due to its remote location, the establishment offers a complimentary shuttle service for diners. My mother and I received just as warm of a welcome at Da Vincenzo, a cozy restaurant that does some of the best renditions of favorites like ricotta stuffed zucchini blossoms and scialatielli a frutti di mare.

What to Do: Pick up a pretty linen outfit at La Bottega Di Brunella and shop for pieces at Ceramica Assunta, which has been selling handmade pottery since 1948. (My mother selected a bright blue ceramic vase painted with lemons.) Book a speedboat excursion and glide across sparkling seas, so you soak up postcard-worthy views. Positano is one of the most picturesque towns in the world, so it’s worth seeing (and photographing) from every perspective.

Erika Hobart


After two nights, we traded Positano for its quieter, more sophisticated sister on the Amalfi Coast: Ravello. It’s only an hour’s drive between the two cities and between the two is the town of Amalfi, from which it’s easy to catch ferries to other nearby islands and cities. Despite being responsible for all the logistics of our trip, I found that being a tour guide for my mother was surprisingly easy. Everything delighted her. Our excursion to Ravello was no exception.

Erika Hobart

Where to Stay: Belmond Hotel Caruso is undoubtedly the best best-located hotel in Ravello, as every taxi driver will tell you as they drive to the top of the town’s layered cliffs overlooking the Amalfi Coast. It feels as though the former 11th-century palace is magically suspended between the sea and sky. Converted into a five-star hotel over four painstaking years, Caruso is still very much fit for royalty. The rooms are full of precious antiques and sumptuous furnishings. The grounds carry the scent of roses and are lined with lemon, olive, and pomegranate trees. Adding a modern-day edge to the fairytale setting is a stunning infinity pool.

Where to Eat: Belmond Hotel Caruso’s Ristorante Belvedere pays tribute to the region’s flavors, and its menu follows the seasons. The Cetara red tuna tartare and tagliatelle with porcini mushrooms (when available) are stand-outs. If you prefer a hidden gem over a crowned jewel, head to Babel Wine Bar Deli & Art. The unassuming bistro has only a handful of tables and serves homemade pasta and salads, plus a great wine list that highlights local producers.

What to Do: We wandered through Villa Cimbrone, an 11th-century manor known for its lush gardens and dramatic views of the Mediterranean–a place so gorgeous that even reclusive movie star Greta Garbo was willing to have a headline-making rendezvous there in 1938. More botanical beauty can be found at Villa Rufolo, a 13th-century palace that contains two tiers of gardens and an outstanding vista of the Gulf of Salerno.

Erika Hobart


From Ravello, we made our way to one of Italy’s most desirable destinations: Capri.

Even I’ve heard of Capri,” my mother informed me when I attempted to start a conversation about the island’s glamorous reputation.  

Where to Stay: Caesar Augustus is a yellow vision perched on a cliff overlooking Italy’s Bay of Naples. A historic Mediterranean villa transformed into a five-star hotel, it manages to exude both unpretentious charm and unapologetic luxury. Owner Paolo Signorini’s son Francesco is a dashing figure who welcomes each and every guest like a close friend. The family’s warm presence can also be felt in the beloved books and heirlooms that adorn the hotel. The breakfast spread is something that my mother is still raving about. I was thrilled by the self-serve champagne station. Meanwhile, my mother was more impressed by the fresh fruit and home-baked pastries. “Can you believe we can take as many strawberries as we want?” she asked me in awe. In addition to an abundance of berries, Caesar Augustus offers complimentary port-to-hotel transfers that make arrivals and departures a breeze.

Where to Eat: Da Paolino deserves to be as popular as it is. The glamorous establishment is nestled in a grove of lemon trees and has fabulous food. My mother and I both agreed that the lemon pasta was divine. The service is also impeccable, and you’re bound to receive star treatment like Beyoncé and Rihanna, who are among the countless celebrities who’ve dined here. For a more rustic atmosphere and freshly-grilled seafood, go to Le Grotelle, a darling restaurant nestled on a cliff with expansive sea views.

What to Do: Go for a spin in a convertible taxi, Capri’s signature form of transportation. My mother and I spent the entire ride giggling as the wind whipped through our hair and the driver navigated the island’s narrow twists and turns. It felt like all of Italy belonged to the two of us.

Erika Hobart

My mother surprised me in Italy. She was quicker than me to get out of bed each morning. She spoke to strangers in a foreign language. She devoured every plate of pasta as if it were her last meal on earth. This woman I thought I knew so well was more daring than I gave her credit for. I was determined to take her on the most lavish vacation ever, but I realized by the end of our journey that she might have actually enjoyed an afternoon spent idling over focaccia and a three-euro bottle of wine. The greatest luxury of all was the time we shared together. That and all the pasta.

crahol December 24, 2022

So what did all of this cost? In 2016 my wife and I spent 3 weeks in Italy. I rented a car and we went to many of the places that you went to; stayed at nice hotels but not nearly as expensive as the hotels in your article. I can't wait to go back.