Jul 31 2019

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Here’s why it’s worth hiring an expert to plan your family trip to Italy

Do you enjoy travel planning? Are you exhilarated by spending weeks or months scrutinizing every possible hotel, restaurant, tour, train schedule and other specifics of your vacation?

If so, this story is not for you.

For me, the endless options and litany of tasks are stressful, exhausting and overwhelming. But at least it all pays off with a dream vacation. LOL. Even after extensive research, I still manage to usually end up with so-so (or worse) meals, in just OK accommodations, getting lost on the way to some humdrum tour.

Scolds tell me those unexpected scenarios are part of the fun and adventure of travel. To them I say: Hard pass.

When my husband, Ron, and I decided to visit Italy last spring to meet up with our daughter Samantha, a college junior on a semesterlong study abroad program, I thought it might be time to try a different approach. Instead of agonizing over the particulars or turning over planning duties to my mate, who is the type to insist the hotel room he once booked is JUST FINE STOP BEING SO FINICKY despite the sputtering, moldy air conditioner and deflated, ratty mattress that someone had recently been murdered on (probably), I called on The Roman Guy, a group- and private-tour operator in Italy. The company had recently added trip-planning services to its offerings.

The Roman Guy charged 99 euros a day (about $112; minimum fee 495 euros) to plot an entire holiday, everything from suggesting destinations and sights to booking transportation, hotel rooms, restaurant reservations, tours and activities. The company will take care of other tasks, too, like getting you an Italian SIM card for your phone. The daily fee covers the planning; vacationers still foot the bill for their expenses. (Since my trip, the travel-planning part of the company operates under the name Finelli & Shaw, but the services and fees remain the same. Plans are in the works to expand to Paris as well.)

“We take care of everything, so you don’t have to worry about anything,” co-owner Brandon Shaw says.

The first step was a phone call with our Rome-based guide, Filippo, who asked what cities were on our must-see list (Rome), whether we preferred tours of famous sites or off-the-beaten-path activities (both), if we might like museums and food and wine tours (yes, yes and yes) and how we’d like to get around (private drivers, trains, vans with small groups, buses, water taxis and gondolas all got the green light).

We had just a few requirements: We needed to meet Samantha on a specific date, and we requested hotel rooms with two separate sleeping areas, so we could enjoy some privacy. We booked the flights ourselves and left almost everything else in their hands.

Filippo suggested starting in the north of the country, spending three days in Venice before heading south for two days each in Florence and Montalcino, a small Tuscan hill town where the renowned Brunello di Montalcino wine is produced. Next would be four days in Rome with the final three on the Amalfi Coast in Praiano, a seaside village he said was a bit less crowded and expensive than the towns it sits between, Positano and Amalfi.

A few days after our call, a 17-page personalized document landed in my inbox with a tentative itinerary accompanied by descriptions and photos of recommended sites, hotels, transfers between cities, tours and eateries with times already booked.

Much of what he proposed sounded wonderful — but not everything. A couple of his hotel choices were too expensive for us or otherwise unappealing. A few of the restaurants didn’t look appetizing, and a tour or two weren’t to our liking.

I felt like I was driving Filippo nuts with my numerous emailed questions and revisions, but he remained genuinely patient and helpful as he cheerfully made alternative arrangements to accommodate my tweaks.

Our final itinerary encompassed many major highlights, including St. Mark’s Basilica and a tour along the waterways of Venice; the iconic David statue and famous pieces in the Uffizi Gallery in Florence; the ancient Colosseum in Rome where gladiators once battled; Michelangelo’s ceiling and other masterpieces in the Sistine Chapel in Vatican City; and a boat ride to Capri, where we browsed the ritzy shops and hopped a ride on the funicular, the cable car/railway that runs up and down a hill.

The company sent along detailed instructions with maps and photos of tour meeting spots — directions so complete, they included how many stops to go on the bus, plus a private concierge phone number in case we ran into problems.

We followed The Roman Guy’s dining advice and sampled assorted versions of prosecco spritz, the ubiquitous fizzy, boozy drink; different types of cicchetti, little bites of snack food (loved the pesto spread accompanied by roasted tomato, hated the baccala mantecato, a pureed cod mousse topped with anchovy); pasta dishes galore; and, of course, gelato.

Filippo and the rest of the team we worked with sent us to places I likely wouldn’t have found on my own, places that were new to Samantha, as well, despite her extensive travels throughout the country.

Many of them turned out to be favorites, like the cooking class we took at Locanda Demetra in Montalcino, where we scarfed down eggplant Parmesan and pasta we’d made from scratch. Another highlight was our visit to the Venetian Ghetto, the 1500s-era quarters where Venice’s Jewish population was forced to live and where five synagogues from the period still stand.

Without their guidance, we wouldn’t have visited Civita di Bagnoregio, a tiny village we could only access via a lengthy walk up a steep bridge, or Orvieto, a hidden gem in Umbria where we stumbled upon a lesser-known but still stunning cathedral.

Having a trip planner was a relief; we could focus on the moment without worrying about every upcoming detail. But we also could be spontaneous because we knew they would handle rearranging plans when we made last-minute changes, like ditching dinner reservations in favor of fried artichokes at Samantha’s favorite place in Rome’s Trastevere neighborhood or canceling a scheduled day trip to Pompeii when we knew we were too pooped to enjoy it.

Ron and I still can — and will — plan future trips on our own, but the process won’t be as easy and stress-free as using a planner.

Worse yet, we’ll have no one else to blame when we find ourselves sleeping on a murder mattress.

Hilary Shenfeld is a freelance writer.

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