The Travel Test: Would Our First Trip Be A Disaster Or A Delight?

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To be honest, I'm not a natural traveler, and several close friends have refused to board another plane with me. So when my boyfriend of a mere five months offered to whisk me away on a romantic trip to Italy, I was hesitant.

On one hand, I'd never been whisked as far as the corner deli, so the prospect was tempting. On the other, I was having horror-movie flashbacks of a crappy (dutch) weekend in Mexico with a guy who was angered by my clumsy scuba diving and amused by my seasickness. That relationship barely made it through customs.

This time, everything was going so well. Did I dare tempt fate with nine days in a foreign country?

Wednesday: Somewhere Over The Atlantic Ocean

Who was I kidding: What girl is going to turn down a free trip to Europe? Not I, I thought, rather smugly, five hours into our six-and-a-half-hour flight, pleasantly tipsy on Alitalia's cheap red wine. Suddenly, someone poked me in the ribs. It was the boyfriend, who'd noticed something peculiar on the little screen on the back of his seat.

"Look!" he said. "The plane is going back to New York!"

We were indeed making the world's largest U-turn. A passenger had gotten ill and needed to be dropped off immediately.

In Newfoundland.

Of course I felt horrible for someone who was sick enough to merit an emergency landing on the tundra, but the glitch also gave me pause: Was it an omen?

After a two-hour layover in Canada, the plane took off again. Five hours after that, we landed in Milan, smelly and delirious, to find that we had missed our connecting flight to Venice.

My first thought was of my bag and the carefully planned wardrobe inside. Since childhood, I've had recurring nightmares about losing my luggage.

I shared that thought with the boyfriend.

"Yes, but have you ever actually lost one?" he asked. "There's nothing to get upset about yet."

Thursday: We Open In Venice.

Three hours later, the Venice baggage claim was finally in our grubby view. Around and around it chugged, past the smartly dressed Italian officers and their handsome German shepherds, only to grind to a halt, having failed to produce our bags.

Another omen? I slumped into a black leather airport chair. But before I could finish my mental tally of what everything in my brand-new suitcase was worth, the boyfriend presented me with the airline's toiletry kit (complete with three-bristle toothbrush and dog comb) and whisked me out the door. He had quickly hatched a plan: "Distract her with bright, shiny things."

Bypassing the creaky and cheap ferry, he hailed a bright, shiny water taxi that took us directly to our hotel for a mere $100. Even unbrushed teeth, a day without sleep, and dirty clothes couldn't diminish my first glimpse of Venice. I've heard it called "the Disneyland of Italy," but what's wrong with that? The city seems to float on top of the sea like a fairytale come to life, a bit of the 17th century preserved in amber.

The boyfriend had chosen a luxurious hotel called Dei Dogi, a former palazzo in the Cannaregio Sestieri residential area. At that point, I could have slept in an abandoned gondola, so I crawled into the ornately carved bed while he went out foraging for really important stuff, such as wine and underwear.

When he woke me up bearing a demurely sexy white lace bra (in the right size) and a new pair of undies (ditto), as well as bread, a wedge of brie, and a bottle of Chianti—"They sell it right out of giant casks!"—that he found on San Leonardo, it struck me that this one might be a keeper.

The next day, after only three or so hours on the phone trying to find our bags and bump back our departure date to make up for the time we'd lost visiting Newfoundland, we set out to explore the city.

I had learned that the ornate, brilliantly colored chandeliers in the Dogi’s lobby were made on the nearby island of Murano, and decided we had to visit. It's definitely worth a trip. After a demonstration of the centuries-old art of glassblowing, you view More Glass Objects Than You've Ever Laid Eyes On. Yes, it's all designed to make you buy some insanely expensive thingamajig to take home, but the candy-colored glass is so beautiful you don't mind.

I discovered a grove of lamps shaped like bunches of grapes. I've wanted to possess such an item for nearly 15 years—don't ask me why—so I was thrilled and touched when the boyfriend announced I should pick my favorite for my birthday/Christmas/ Valentine’s/Arbor Day gift. Suddenly, the absence of my luggage didn’t seem so tragic.

Still, a girl can't live on handblown glass grapes alone. A trip to one of Venice's ornate houses of worship for a little spiritual sustenance was the next order of business. Basilica di San Marco may get most of the attention, but a local tipped us off to Santa Maria Gloriosa dei Frari in San Polo. Its carved marble skeletons, pyramids, and saints are so exquisitely over-the-top that I couldn't bear to dilute their memory with a glimpse at another church until we got to the Vatican.

Next, we needed an art fix. Venice is filled with museums devoted to Byzantine, Renaissance, and Baroque masterworks, but I had just finished reading Art Lover, a biography of Peggy Guggenheim, who amassed an enviable collection of 20th-century art (and more than a few artist lovers) and spent her waning years in the Palazzo Venier dei Leoni on the Grand Canal. So I took the boyfriend to the palazzo, now a light-filled museum, to see surrealist and cubist works by Max Ernst, Piet Mondrian, Marcel Duchamp, and Guggenheim discovery Jackson Pollock.

In return, he took me someplace that showcased his favorite Italian "art." Enoteca al Volto Calle Cavalli (rumored to be a favorite of Elton John's) is a rough-hewn ristorante tucked away on a winding street near the Rialto bridge. While the boyfriend adores "challenging" food and likes everything with ten kinds of sauce, I could live contentedly on protein bars, so I felt pretty adventurous letting the server choose what we should sample—salty creamed fish spread, tiny spicy langoustines, and pasta tossed in anchovy sauce. All delicious.

Cliché or not, we set off for a Bellini nightcap at Harry's Bar at the Hotel Cipriani. Who can resist a Hemingway haunt? I was tempted to snatch a signature ashtray—they are so bright and shiny, after all—but they’re less expensive than a drink, so we bought one instead.

By the time we got home from dinner, our bags had arrived, just in time for the drive to Florence. I was never so happy to see an inanimate object in my life.

I showered the suitcase—and the boyfriend—with kisses.

Friday: Finding Firenze

I'd pictured a scenic jaunt through the Italian countryside, with stops to tour lush vineyards and chat with ruddy-cheeked locals. I had forgotten to take into account the male need for speed. The boyfriend drove our tiny rental car in excess of 130 kilometers an hour on the windy Autostrassa while I, the girl with no sense of direction whatsoever, attempted to figure out if that town we just passed was anywhere on the map I was reading. In Italian.

Missing the exit into Florence—and dealing with the boyfriend's reproach—blew the last wisps of my romantic Venetian cloud away. And once we entered the city, the next hurdle was where to stay, since we hadn't made hotel reservations. Miraculously, one of the places I'd found on the Internet was actually close to a street I'd been able to find on the map. "Let's just go here," I said, jabbing it with my finger.

"Here" ended up being the Una Hotel Vittoria on the Via Pisana. Bright, shiny, and oh-so-postmodern, it was just the thing to get me out of my navigating funk. A giant floral mosaic spiraled through the lobby, echoed by a huge plush red couch in the bar. Our room was like a sexy little stage set, with tiny, dimmable twinkling lights surrounding the bed, and, behind a wall of translucent glass, a huge tile shower—a lavish, overgrown fish tank for exhibitionists. Best of all, when we walked in off the street, we paid much less than the going rate, due to vacancies.

As far as I was concerned, this was the coolest place in town. But we were in Florence, after all, so bright and early the next morning we queued up to see the most famous penis in the world, on Michelangelo's David.

If Venice is a courtesan turned semi-respectable countess, Florence is a prim dowager who supports the arts and goes to bed early, so marble nudes are about it for racy fun. Unless, of course, your favorite deadly sin is gluttony. Everyone I know who's been to Florence has told me to dine at Il Latini on the Via Palchetti.

Picture Studio 54 in its heyday, and you'll have a sense of the effort and enthusiasm required to get into this rustic Tuscan ristorante. The waitstaff plied us with complimentary glasses of wine while we waited in the alley outside and tried to keep other sneaky tourists from cutting in line. Finally, a bunch of business-tripping Gucci executives swept us in with their party, and we were seated for one of the most lavish meals of my life.

It's family style, so we got a giant jug of red wine to share with our new favorite strangers. Then came the antipasti of local liver spread—the boyfriend dived in immediately—and bruschetta and cold cuts. Next came pasta with red or white sauce; a main dish of rabbit, chicken, or beef; and sparkling wine and biscotti to finish. It was a minor miracle we managed to drag our drunken, satiated selves across the cobblestone bridge to our hotel.

The next morning, five pounds heavier but with light hearts, we set off for one of my favorite Italian attractions: the Prada outlet in Montevarchi.

It's not clearly marked, but any local can point you toward the unassuming warehouse. Inside is a treasure trove of past collections from Prada, Miu Miu, Helmut Lang, and more, all a whole lot cheaper than retail price. I tried on an armload of dresses and sweaters before settling on a very Audrey Hepburn gray wool A-line shift with a fur-trimmed hem for the (relatively) inexpensive price of $400. I also nabbed a pair of electric-green suede Miu Miu boots for the boyfriend for around $100.

Having dallied a bit too long in the shoe racks, we'd fallen behind schedule to get to Rome. We were hurtling through Umbria when we realized we were lost again. Neither of us wanted a reprise of the tension we'd felt on our way into Florence, so we both stayed quiet, still flying along. Then the crumbling tower of a monastery appeared on the horizon.

"Let’s check that out," said the boyfriend. A sucker for adventure, I agreed, and we pulled off the road. What looked like a scenic ruin was in fact La Badia di Orvieto, a 12th-century abbey converted into a luxury hotel and restaurant, now more or less deserted in the off-season. We both wanted to stay, but doing so would have sacrificed reservations in Rome. "We should come back sometime, in the summer," the boyfriend mused. As the sun set over Umbria's rolling vineyards, it occurred to me that perhaps we should.

Sunday: When In Rome

That was before I realized he'd left our plane tickets, our itinerary, and my carefully researched "places to go" folder in the dresser drawer in Florence.

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We circled around and around the center of Rome trying to find either an Internet café or our hotel.

"It's around here somewhere, let's just keep looking," he said, as I silently seethed.

Dumb luck led us to the Via di San Basilio and the Aleph. Lavish and slightly cheesy in that endearing Italian way, the Aleph's décor is based on Dante's Inferno, and everything—bar, restaurant, library, lobby—is a brilliant shade of red. The hell theme seemed very appropriate when we checked in and found a message from the fun folks at Alitalia questioning the change in our departure date. After another hour on the phone, we were told that neither it nor our missing tickets would be a problem. I suggested that we have the documents FedExed from Florence, but the airline assured the boyfriend this wouldn't be necessary.

And so we set off to sightsee. Rome is a blend of the old and the new, with flashy, perma-tanned couples in Dolce & Gabbana inspecting the treasures of the Vatican. The streets smell like sautéed garlic and wine, and the pace of the city sweeps you from ancient monument to trendy restaurant.

Because a friend of mine spent six months in Rome working on Wes Anderson's The Life Aquatic, I knew about a few off-thebeaten- path places of which the cast and crew had grown fond.

Tucked away in a cobblestone courtyard on the Via della Croce, near the Spanish Steps, Otello alla Concordia was a favorite of theirs, and of Fellini's. The boyfriend stuffed me with Roman specialties: fried zucchini florets, fried anchovies, and zuppa de pesce.

For the boyfriend, an inveterate history buff, Rome is the cradle of civilization, the road map to the modern world. To me, it's a lot of crusty old buildings. But I was finding out what made him happy—and finding that that made me happy—so I agreed to learn about gladiators as long as I got to go to Gucci.

My shopping was strictly of the window variety (the Prada outlet and that ridiculously expensive grape lamp from Murano had filled my quota), but the boyfriend was in a buying mood. As he tried on an insane mustard plaid mohair suit at Etro, I remembered that a friend once compared my personality to a crazy outfit that many men might admire but few could, or would, actually wear.

But here was a guy not only willing to try on the crazy outfit, but also eager to buy it—if only it were his size. "They only made one for all the stores," said the apologetic shopkeeper. "Some things, too strong!"

Instead, the boyfriend bought a black wool Gucci coat (I hoped the metaphor ended there), and we had one last night out in Rome. We went to Trastevere, the bohemian district famous for its lively piazzas. As I watched the street performers, jugglers, and stilt walkers, the magnitude of the gift I'd been given began to sink in.

The trip wasn't just a vacation; it was an amazing life experience. With an amazing person. Who, despite everything, was still speaking to me. And I to him. Un miracolo!

Tues: Basta, Alitalia!

The next morning at the airline check-in counter, however, my warm glow turned into extreme anxiety. Despite the multiple, lengthy phone calls, the airline had no reservation information of any kind for our return. And since our tickets were still in Florence, we had nothing to prove we were on this—or any other—flight.

With the last plane leaving for New York in less than an hour, there wasn't time to argue. We'd already stolen an extra day, and jobs, commitments, and reality awaited us back home. The boyfriend threw up his hands, forked over the credit card, and charged $3,000 worth of new tickets. I dragged him to the airport police station to fill out a stolen-ticket report, hoping we'd get the cash back eventually, then we raced to catch the flight and plopped down, spent, into our seats.

Shortly after takeoff, an episode of The Flintstones came on the boyfriend's tiny TV, and he began laughing merrily.

"How can you be in such a good mood?" I demanded.

"This is the most expensive flight of my life," he said. "I may as well enjoy myself."

And suddenly, the future seemed rather bright and shiny.

Kendall Morgan married the boyfriend, Tim, six months later. Their next trip was to Jamaica for their wedding and honeymoon.