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The Italian Job

A Peninsula firm is making it easier for travelers to live their own version of la dolce vita.

Travel Guides
Brandy Stroh and Laura Kavanaugh share an entrepreneurial spirit as well as an affinity for Tuscany.


Although Brandy Stroh and Laura Kavanaugh met in Portola Valley, where their kids were in the same kindergarten class, it was a locale more than 6,000 miles away that truly bonded the two. In 2012, both were looking for a second act—Stroh previously worked in marketing, and Kavanaugh had been an attorney with Genentech—something that would “get their brains moving again,” recalls Stroh, and would also incorporate their love of Italy. Stroh, who is Italian on her father’s side, spent six months there as a teenager and wed in Lake Como. Kavanaugh is Italian on her mother’s side, lived there during a two-month sabbatical and later returned with her children for a three-month stint. 

In Tuscan Travel Group, they’ve created a business that allows them to share this special destination with others, including insider knowledge of central Italy (their blog is filled with helpful information). Initially, the company was focused on booking villas for clients; recently, it expanded to allow various levels of concierge service. Now, at the gold level, TTG assists travelers with itineraries by providing recommendations. At the platinum level, Stroh and Kavanaugh make reservations on their clients’ behalf, such as walking tours, cooking classes or wine-tasting excursions. (They don’t handle airline and rental-car bookings.) 

One of the properties they just started working with—which they are especially excited about—is a former palazzo and convent in Pienza. While the stone exterior maintains its rustic charm, the interiors’ eight bedrooms have been stylishly updated, and the expansive open-plan kitchen is ideal for groups. The grounds include an infinity pool that overlooks a nature reserve. “It’s country-chic and just beautiful,” says Kavanaugh. (Room rates from €1,750 per week; complete buyout €17,000.) 

Great Outdoors
The pool and picture-perfect views are among the amenities at a Pienza property in the TTG portfolio.

The duo frequently returns to Tuscany to visit places they’re partnered with to make sure they still meet TTG’s high standards, as well as to find new accommodations and attractions to suggest to clients. They are also focused on establishing expertise on areas near Tuscany—like Rome or Cinque Terre—that might be of interest for side trips. “It’s really about making the unknown process of travel personal,” says Stroh. 

Originally published in the November issue of
Silicon Valley

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