How Hollywood Does Italy: Where to Stay, What to Do and How to Get Around

Matteo Carassale
The Rosewood at Castiglion del Bosco in Tuscany, with its 17th and 18th century farmhouse villas and a rare 18-hole private course, is where Paul McCartney marked his 70th birthday.

Europe without the terrorism and beaches without the hurricanes, the Boot now boasts everything from Quentin Tarantino's seafood spot in Rome to George Clooney's top hotel in Venice and more.

With Google hosting its summer camp for billionaires in Sicily (Prince Harry attended, and Elton John and Lenny Kravitz performed) and David Geffen entertaining Bob Iger, Oprah Winfrey and Barry Diller aboard his Portofino-bound yacht, Italy is proving to be an unparalleled draw for Hollywood heavies and tech moguls. Indeed, Italia may seem like one of the few safe options as the State Department issues travel warnings highlighting other parts of Europe due to terrorism and hurricanes continue to slam the Caribbean. This fall, as tourists thinned and truffles came in season, Julia Roberts headed to Italy, The Rolling Stones played in Lucca, and Sting and Trudie Styler hosted a cocktail block party at their villa in Tuscany. "Italy is my favorite country," says Terry George, who directed Oscar-nominated Hotel Rwanda. "We did music for the film there and found a wonderful combination of great food, style, culture and eccentric, fun people." Producer Mark Canton agrees: "Dennis Hopper first brought me to Italy — the filmmakers are legendary, food is the best, people are better and the fashion great." Adds Judy Stein of Ovation Travel: “The new styles come to Milan first, so you can buy bags and clothing from Fendi, Gucci and Prada that nobody has yet." (All room rates fluctuate and are approximate, but the exchange rate is excellent.)


Will Arnett calls Blade's Bounce helicopter service — which takes travelers from New York City to JFK or Newark in five minutes, or from DTLA, Santa Monica or Malibu to LAX in 10 — a "game changer." Patrick Whitesell's wife, Laura Sanchez, prefers it to Uber, which "could take two hours in traffic."

Instead of Alitalia, many opt for Air France (flights stop in Paris en route to Italy from LAX; from $9,402, first-class round trip), with new, fully mattressed suites, complimentary black pajamas, a 24-inch HD screen, cocktails from the head bartender at Paris' Ritz and meals like tarragon shrimp and squid in lobster sauce from chefs Daniel Boulud and Michel Roth. Emirates, which offers deals, has a direct flight from JFK to Milan, with a shower in first class and car service to and from the airport as well as from the airport to your hotel.


High-speed trains are remarkably comfortable, and getting from Florence to Rome, for example, takes less than an hour and a half. "Italo is the newer, more stylish private train company, offering better service and internet than the state-run company," says luxury tour operator Dino Triantafillou, who arranged part of Katy Perry's July visit.

Helicopter service Hoverfly provides speedy travel in Italy, and in Venice, Triantafillou books the Moa luxury limo boat, with "free-flowing champagne for VIPs."

Jet owners, take note: Ampu­gna­no, a private airport in Tuscany, "opened this year and is closer than Grosetto — fantastic service,'' says Sienna Charles travel expert Jaclyn Sienna India.


VENICE George Clooney is such a frequent visitor to Cipriani (Giudecca, 10; from $902), which has one of the City of Water's few pools, canal views and private docks, that he created two drinks with the bartender; Steven Spielberg, Harrison Ford and Uma Thurman have been guests. "Everyone in Hollywood loves the Cipriani — I stayed there when we shot Contagion," says Activision Blizzard Studios' Stacey Sher. "Gwyneth Paltrow liked their tomato sauce so much, she got the recipe. She had just started Goop, and she posted it." Clooney threw his wedding reception, attended by Matt Damon, Bill Murray and Emily Blunt, at onetime palazzo Aman Venice (Calle Tiepolo Baiamonte, 1364; from $1,120), which features ornate fireplaces and soaring frescoed ceilings amid sleek design. Former owners "the count and countess" still live on the top floor, says Destination Happiness travel guru Melissa Schwartz (201-314-3633), who adds that the hotel, which was built in the 16th century, has a secret entrance with "access to the Rialto Bridge and its fabulous market.'' The hotel's new restaurant with garden is "very private, and each room has a different mood," says India.

Francesca Bortolotto Possati, owner of the 19th century Bauer Palazzo with its arched lancet windows and gothic facade that sits on the Grand Canal (S. Marco, 1459; from $295), remembers: “Angelina and Brad were so in love with the view of San Marco from the balcony. Donald Sutherland and Jeremy Irons always stay at the Bauer and both love to go antiquing, shop in unknown areas of Venice and see the beautiful old glass and textile houses like Rubelli. Jeremy once went windsurfing along the canals.’’

Natalie Portman, Salma Hayek and Yoko Ono managed to find off-the-beaten-track Antiche Carampane (Rio Tera de le Carampane, 1911), one of Venice's oldest family-run trattorias whose grilled octopus and pasta with spider crab stand out. At Centrale (Calle Piscina de Frezzaria, 1659/B), a supper club in a 15th century palazzo, the menu comes on an iPad; Spike Lee has been spotted here. Be sure to stroll through the Peggy Guggenheim Museum (Dorsoduro, 701-704), says producer and manager Jane Rose, currently in Italy with The Rolling Stones: "I'm in love with the collection."

ROME Jay McInerney recommends the intimate La Posta Vecchia (Palo Laziale, Ladispoli; from $386). "It's just outside Rome, on the sea and close to the airport, so it's perfect if you are leaving on a cruise or flight," he says. Hotel Eden (Via Ludovisi, 49) has been freshly renovated to include walk-in rain showers in its suites. "We put top Hollywood producers" in the Bellavista Suite ($1,600), which has spectacular city views, says India (she also recommends Hotel de Ricci, Via della Barchetta, 14; from $446), because "our Hollywood clients can take over the hotel"). In April, director George stayed at contemporary classic De Russie (Via del Babuino, 9; from $857). "It’s got great energy. They even helped me find a butcher," he says. "The first time I was there, the Ocean's Twelve crew had taken the whole roof and top floor." Former family home Palazzo Dama (Lungotevere Arnaldo da Brescia, 2; from $415) is popular with Oscar-nominated scribe Richard LaGravenese: "It has a courtyard bar with magnificent architecture, a perfect place to meet friends for cocktails.''

The Americans producer Joel Fields reports that his family starts the day at Tazza d'Oro cafe: "You get your daily shot of espresso in a cloud of shaved ice and whipped cream." A new branch of the London restaurant Zuma opened last spring, (Via della Fontanella di Borghese, 48), says concierge company Quintessentially's Benjamin Le Hay, who adds, "restaurants in Rome can feel stodgy, but this modern place has taken off with our clientele." Quentin Tarantino and Jamie Foxx are patrons of longtime treasure Pierluigi (Piazza de'Ricci, 144), which specializes in seafood straight from the ports. LaGravenese says about L'Antico Porto (Via Federico Cesi, 36): "You feel like you are walking into someone's home; it has the most incredible fresh fish and spaghetti vongole. We had a raw fish antipasto that was insane."

For culture, "Il Kino (Via Perugia, 34) boasts an outdoor cinema showing classic and experimental movies and half a dozen truly great food stands,'' says Paul Haggis. "If you want to drink wine with young Italian filmmakers, you will find them [here]." He adds that Jerry Thomas Speakeasy (Vicolo Cellini, 30) "is my favorite bar, where the cocktails are made from ridiculously fresh ingredients. You can try using my name to get in, but it probably won't work.'' Fields loves the Pantheon, which "looks like another old Roman building, but inside is one of the most awe-inspiring rooms in the world. The fact that this vast, geometrically perfect space was built so many years ago without the aid of modern technology is mind-blowing."

TUSCANY During the shooting of 2016's Inferno, Dan Brown and Tom Hanks rented the extremely private Villa Mangiacane (Via Faltignano 4; from $222), built in the 15th century with views of Florence and an indoor pool for rainy days. Once the historic castle of director Luchino Visconti, the 4,200-foot Castello di Casole (Localita Querceto, Casole D'Elsa; from $650) has been transformed into an oasis complete with a breathtaking pool on a hill overlooking a valley of vineyards, a spa and three restaurants (farms with spectacular homes are available for purchase starting at $6.5 million). According to India, top producers book the master suite deluxe with private pool at Hotel Il Pellicano (Localita Sbarcatello; from $503), perched on a coastal cliff: "During the day, they take a boat out to Isla di Giglio for lunch and swimming." Canton says he and Amanda Seyfried stayed at Hotel Adler Thermae (Str. Di Bagno Vignoni, 1; from $317) on a shoot: "It's in the middle of nowhere and a very serious spa with thermal baths.'' James Cameron, Justin Bieber and Pink are all fans of Michelin-starred Castello del Nero Hotel & Spa (Str. Spicciano, 7; from $529), which uses indigenous ingredients in its therapies.

Golfers will appreciate the rare 18-hole private course on the Castiglion del Bosco estate (Localita Castiglion del Bosco; from $880) where Paul McCartney celebrated his 70th birthday. The Rosewood property has suites in the main house and unique private villas with heated pools, created from 17th and 18th century farmhouses. “Villa Agresto just opened there. It is the largest one with five bedrooms, has the best view, a private pool and technology so you can control everything from your iPhone,’’ says India.

In bordering Umbria, new multimillion-dollar villas have just been unveiled to buy or rent out from Castello di Recchio (Fattoria di Reschio, Lisciano Niccone; $5,900). "They are incredibly well designed," says India. "Umbria is picturesque like Tuscany but wilder and less manicured." Cashmere devotees can tour the nearby Brunello Cucinelli headquarters (Piazza Carlo Alberto dalla Chiesa 6). 

ISCHIA Canton, who has chaired the Ischia Film Festival for the last decade, says of Regina Isabella (1 Lacco Ameno; from $232): "This is the single most extraordinary hotel; I've brought so many friends and colleagues here. We watch movies in an amphitheater on the sea. One night, Sting, Andrea Bocelli and Zucchero started singing impromptu." The on-site restaurant, Indaco, is Michelin starred, and the island's 2,500-year-old spa offers medical checkups and Botox treatments along with hot springs and mud wraps. "The actors come by speedboat, yacht or helicopter,'' says Pascal Vicedomini, who runs the fest. "This summer, everyone went to St. Tropez for Leonardo DiCaprio's party but came right back till the Venice Festival.'' 

CAPRI Jennifer Aniston is among those who love the easy-in-and-out harbor location of wellness beachfront hotel JK Place (Via Tragara, 8; from $658), which provides a Mercedes or golf cart to zip guests into town and a 24/7 concierge. At no-kids-allowed Scalianatella (Via Tragara, 8; from $411), Tony Bennett sits by the pool and sketches. Says Le Hay of the Hotel Caesar Augustus (Via Giuseppe Orlandi, 4; from $423): "Most starlets and members of Egypt's royal family flock to this exceedingly refined hotel,'' which is set 2,000 feet above the sea with extraordinary views of the Bay of Naples and Amalfi Coast. The hotel has added a new culinary program that includes four private chef’s tables, cooking classes utilizing the two-acre organic kitchen garden and wine tastings each Monday.   

A trip to Capri's famous blue grotto can be moving, as one guide confides: "When Mariah Carey got to the grotto, she started to cry and we saw her human side." Aurora restaurant (Fuorlovado, 18) is known for its thin-crust pizza and sightings of Beyonce. "On Aug. 30, Giorgio Armani was at the next table celebrating his birthday,'' says Schwartz, adding that she saw Valentino at the Terrace at Grand Hotel Quisisana (Via Camerelle, 2). Christie Brinkley loves Da Paolino (Via Palazzo a Mare, 11) for the "best mozzarella, and you sit under fragrant lemon trees."

POSITANO/AMALFI COAST The former home of Franco Zeffirelli was transformed in 2016 into Villa Tre Ville (Via Arienzo, 30; from $872). Have the hotel arrange for a boat to take you to the privately owned islands of Li Galli for secluded swimming, suggests Andrew Saffir, founder of NYC's Cinema Society; the "scenery is so idyllic, you'll want to pinch yourself." Hollywood favorite Le Sirenuse (Via Cristoforo Colombo, 30; from $825), frequented by Reese Witherspoon and CAA's Jim Toth, has added an open-air bar called Franco's and "a beautiful shop last year that sells great sweaters and scarves," says India. "It looks like it’s hanging off the hill and it's very happening,'' says Schwartz. Geffen, Winfrey, Diller and Diane von Furstenberg pulled up to Lo Scoglio restaurant just west of Positano (Piazza delle Sirene, 15); a menu highlight is sea urchin and clams. Design aficionados love the Ceramiche Cosmolena store in Ravello: "One of Hollywood's leading ladies made a special trip to this ultimate ceramic store,'' reports Ovation Travel's Judy Stein.

PUGLIA Last month, Madonna rode a white horse into her birthday party at Borgo Egnazia (Strada Comunale Egnazia, Savelletri Fasano; from $529), and both Hugh Jackman and Emily Ratajkowski vacationed at the property where Justin Timberlake and Jessica Biel were married. All guests receive a local advisor for immersion in local culture, including a visit to a mamma’s home to make fresh pasta. “We had a corner suite that we got lost in, not kidding,” says Saffir. “There were three separate rooftop terraces with amazing sunset views, plus a level below our suite, with a private plunge pool and an outdoor shower you could swim up to, off another terrace with its own private entrance, if you wanted to be extra discreet.”

Genuine Access travel specialist Gen Hershey says that more adventurous insiders might wish to take a side trip to Sicily from Puglia to hike Mount Etna. Says Sher: “What I didn’t realize is that the lava breaks down, so it’s like going uphill on gravel. It was like being on another planet, amazing and beautiful.’’ While you’re there, she advises hitting Laboratorio Pasticceria Roberto (Via Calapitrulli, 9, Taormina ME): “After visiting this place, you know there is a reason they said [in The Godfather], ‘leave the gun, take the cannoli.’”

SARDINIA Regarding Cala di Volpe (Costa Smeralda, Porto Cervo; from $412), "Michael Jordan was there Aug. 24 doing photos with everyone," but stars "who want to hide away go to their sister property, Patrizza" (Costa Smeralda; from $397), says Schwartz about the hotel with private pools, villas carved into the mountainside and a helipad. For unique dining, Ristorante Giagoni in Piazza San Pantaleo (Piazza Della Chiesa, 6) is "a five-star restaurant on the mountain, a hidden gem," says Schwartz. "It’s on one side of Costa Esmerelda in an artisan town in the hills, and you have to know about it."

MILAN "We just sent a major actress from L.A. to this newly upgraded hotel, and she was extremely happy," says Le Hay of Hotel Townhouse Galleria Milano (Via Silvio Pellico; from $845). "It’s very close to shopping, but there is a private back entrance for VIPs, and if someone wants special lychees in a drink at 2 a.m., they will come up with them.'' Insiders seek out the upscale power dining of Ristorante Cracco (Via Victor Hugo, 4). "The chef is a rock star; it's a moment in Milanese culinary history," notes Le Hay. He adds that the Ralph Lauren store may have closed, but last year the space opened as a private shopping club (Via San Barnaba, 27). “The personal attention and space is fabulous; you feel as if you are in Ralph’s personal home,” says Le Hay, who advises that a stylist or another member call in advance and set your appointment.   

FLORENCE At the family-friendly Four Seasons (Borgo Pinto, 99), insiders "favor the private garden suite with floor-to-ceiling windows in the heart of the city's park, with an exclusive view of the Duomo" (from $986), says Genuine Access travel specialist Gen Hershey. Its Michelin-starred restaurant, Il Palagio, can prepare a picnic on the property. And the just-refurbished, low-key Hotel Lungarno (Borgo S. Jacopo, 14; from $320) contains Picasso and Cocteau artwork and two floors privatized for VIPs. Eat at Enoteca Pinchiorri (Via Ghibellina, 87), suggests Le Hay, but reserve a table in advance: "People fly in to have a meal at this gastronomic temple, but getting them in can be a challenge.''


“Hollywood’s leading ladies love to head to the Palace Hotel Merano, with a stay at the world-renowned Espace Henri Chenot Health and Wellness center’’ (Via Camillo Benso Cavour, 2, Merano; from $300), says Stein. “This is where they go to decompress, recharge their batteries, get pampered and lose a few pounds.’’


A floating swimming pool on the lake is the signature feature of Villa d’Este, with new private villas (Via Regina, 40, Cernobbio Co; from $542). “They are beautiful, with great technology and privacy, and you can have a butler take care of you the whole time,” says Hershey. A new over-the top spa has helped push Grand Hotel Tremezzo (Via Regina, 8, Tremezzo; from $465) to the top of insiders’ lists. “It’s been renovated and upgraded to the luxury spot on the lake,” says luxury tour operator Triantafillou, who adds that the “new, hip hotel” is award-winning boutique Il Sereno Lago (Via Torrazza 10, Torno; from $766).

For a change of culinary pace from pasta and wine, try gastropub Casa Aqua Dulza (Via Giuseppe Mazzini, 3, Tremezzina), which is just months old and has a craft brewery. Says Stein: “It’s contemporary and creative, which makes a nice contrast to the more traditional and predictable spots on the lake.”

A version of this story first appeared in the Oct. 4 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.