How to Vacation Like Olivia Pope in Italy

In this second installment in our imaginary celebrity travel itineraries we take on Scandal’s Olivia Pope and envision her dream vacation in Florence and beyond in Tuscany.

Italy expert Andrea Grisdale, CEO of the travel agency IC Bellagio, is back to carefully craft the perfect Italian getaway for the one and only Ms. Pope. Now the only question is, who will she take? Fitz? Jake? Or will she take a mysterious solo trip to escape the drama in Washington D.C.?

Here’s some inspiration for fellow red wine loving, ultra-private gladiators:

DAY 1

Arrival and Check-In at JK Florence

After being greeted at the airport and swiftly escorted through immigration, Pope will arrive—by private car of course—at the understated yet elegant boutique JK Florence hotel on the Piazza di Santa Maria Novella.

Afternoon Walking Tour

Grisdale has arranged an introductory Florence Walking Tour during which Pope will explore the city’s most famous landmarks—Piazza del Duomo, the “old bridge” over the Arno River, and Palazzo Vecchio to name a few. No tour would be complete without stopping at the Accademia to see Michelangelo’s David and a backstreets tour of ancient tower houses. To cap off the night, Ms. Pope has a reservation at Enoteca Pinchiorri, which boasts one of the best wine cellars in all of Europe. Of course.

RELATED: 10 Tips for Visiting European Museums

DAY 2

Morning Tour of Uffizi Gallery and Vasari Corridor

Grisdale has arranged an exclusive viewing at the Uffizi Gallery, where, in true Olivia Pope fashion, Ms. Pope can slip away into a Medici secret passageway to explore the Vasari Corridor. After the tour she will enjoy lunch at the brand-new Savoy Hotel in the Piazza della Repubblica and dine among visiting celebs.

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Meet With One of Florence’s Best Designers

Grisdale will send the fashionable Pope to the luxurious Renaissance Palazzos for an unforgettable look at Italian fashion. She will tour the showroom and workshop with a personal shopping assistant and a well-known designer before a private fashion show. After, she will travel by car to Fiesole, and enjoy views of the city from La Loggia’s rooftop at Hotel Villa San Michele.

DAY 3

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Tour of the Fattoria Monteriggioni Estate

Grisdale now will send Ms. Pope to Tuscany to visit the vineyards and wine cellars of the Chianti Hills. On this private tour with the estate owners, the Bindi Sergardi family, Pope will learn their stories first hand and enjoy a Tuscan lunch with the family.

Check in to Castello del Nero

Nestled in the Tuscan countryside, Ms. Pope will sleep in a deluxe suite in a 12th century castle. Fit for a modern queen, the hotel has a spa, indoor and outdoor pools, a terrace with panoramic views, and an authentic Tuscan restaurant, La Taverna, where Ms. Pope will dine fireside.

RELATED: 7 Luxe Hotels Where You Can Sleep Like Royalty

DAY 4

Tour of Tuscan Towns

Grisdale has arranged a full-day private tour through Montepulciano, Pienza, and Montalcino with a local driver. The focus on local foods and experiences includes sampling Pecorino cheese in Pienza and red wine (Pope’s favorite) tastings in Montepulciano and Montalcino. After the full day tour, Pope will have time to enjoy the hotel and dinner at a local restaurant.

RELATED: 10 Truly Unique City Tours Around the World

DAY 5

Tour of Siena

After enjoying a spa treatment at the Castello del Nero, Ms. Pope will travel by car to Siena for another full day in a Tuscan town. The tour includes stops at the old financial area, “Il Campo,” the Duomo, and an exclusive visit to a local “Contrada”, or district, a part of Siena’s oldest traditions. Grisdale explains: “Originally, there were about fifty-nine ‘Contrade;’ now only seventeen remain, ten of which take part in the historical pageant and in the race at each ‘Palio’ (the famous horserace around ‘Il Campo’).”

RELATED: Siena: Italy’s Medieval Heart and Soul

Final Dinner at Badia a Passignano Vineyard

For Ms. Pope’s final night, Grisdale has arranged a private visit to one of Tuscany’s most distinguished vineyards. Ms. Pope will visit the vineyards and cellars, then enjoy an olive-oil tasting and take an introductory lesson on wine decanting before enjoying dinner with extensive wine pairings.

More from SmarterTravel:

• How to Vacation Like George Clooney in Italy
• Five Things You Can Do to Improve Your Stay in Florence
• 10 Secret Places in Italy

(Photo: Bernd Thaller via flickr/CC Attribution)