The Wild Woman's Guide to Traveling the World

by Kristin Rockaway

  “Take a look around.” I gestured to the massive billboards and flashing neon signs that towered above us, in every direction. “This is Times Square. The beating heart of New York City. Each day, over three hundred thousand pedestrians pass through this intersection. On the busiest days, that number soars to almost five hundred thousand. And, of course, during New Year’s Eve celebrations, close to a million people gather here to watch the famous ball drop from the top of One Times Square.”

  I pointed to the building behind me and smiled as I watched my tour group—my tour group!—survey their surroundings.

  “Times Square came of age in the Roaring Twenties, when the area was a cultural hub full of theaters, cabarets, and upscale restaurants and hotels. Then, with the dawn of the Great Depression, the atmosphere shifted to one of danger and disrepute. Some of you may recall Times Square being referred to as a den of sin, brimming with drug dealers, prostitutes, sex shops, and peep shows.”

  The German boys exchanged low titters and I raised my eyebrows at them. “Fortunately, the neighborhood underwent a great transformation in the 1990s, when X-rated movie theaters were replaced with family-style restaurants, and drug dealers were replaced with people in Disney character costumes.”

  “Where’s the Naked Cowboy?” asked Mr. Fanny Pack, looking around.

  “He generally appears on Forty-Fifth and Broadway just before noon. I’m afraid we’re a few hours too late.” Not that I’ve ever spent my lunch hour ogling him or anything.

  I pointed out the television studios overlooking the square, as well as the exact spot in which Chris Evans stood when filming the first Captain America movie. Then I stood silently, allowing everyone adequate time to drink in the environment, to smell the exhaust from the crush of passing taxis, to hear the dissonant babble of a thousand voices mixing with music and car horns and screeching brakes, to be adequately awed by the colorful spectacle soaring above our heads and all around us.

  From there, I led everyone on a slow stroll through the theater district, recounting all the tales of Broadway history I’d picked up over the years. Everyone seemed attentive and happy, even the German kids, who I could tell only understood every third word I spoke. And Mr. Fanny Pack, who by now I’d learned was actually named Bill, was full of enthusiastic questions. Like which theater was the original production of Cats featured in, and how long did it run for?

  And, yes, I knew the answers: the Winter Garden Theatre, and almost eighteen years.

  We wound up meandering through my neighborhood, Hell’s Kitchen, where I gave a brief overview of the now-gentrified community’s crime-ridden, mob-run history and pointed out the buildings that functioned as speakeasies during Prohibition. Then we pressed on toward the Hudson River Greenway, where we stood in the shadow of the Intrepid aircraft carrier and a docked Carnival cruise ship. By then, I had no idea what time it was—and without my smartphone, I had no way of checking—but when Bill announced we’d been walking for two and a half hours, I pressed my fingertips to my lips. Wandering around the city, with no plan and no direction, had made the afternoon go by in a flash.

  “I’m so sorry,” I said. “I went a half hour over our schedule.”

  “Don’t apologize,” he said. “This has been fantastic.”

  “It has,” said his companion, Theo, “but I’m starving. Where’s a good place to grab something to eat around here?”

  Looking up and down the street, I tried to think of the best place for a group of seven hungry people at the beginning of the city’s dinner rush. We’d have to avoid the touristy destinations or anywhere that required a reservation. Then it hit me.

  “I know just the spot. Two blocks from here, there’s a fantastic little German restaurant that’s popular with the locals.” The teens regarded me skeptically and I held out my hands in defense. “Trust me, it’s one hundred percent authentisch. They’ve got Bitburger. And schnitzel platters.”

  They conferred in their native language before shrugging in resignation and followed me east along 45th Street. When we entered Zum Bauer, I approached the host stand, where Wolf flashed a smile at me.

  “Hello, Sophie,” he said, his accent a strange mixture of Bavarian and Brooklynese. “How are you this evening?”

  “Great.” I craned my neck, looking around the room. “Is Kat here?”

  “She took the night off. But don’t worry, Henry’s working the bar right now and he’ll get you whatever you like.”

  “Actually, I’m gonna need a table. See, I’ve got this tour group with me, and—”

  “You’re a tour guide?” Wolf’s eyes lit up. “How cool! I didn’t know that about you.”

  “Yeah.” I paused to revel in the moment. I’m a tour guide. How cool. “Anyway, we’ve just finished an exhausting walk around Midtown, so I was hoping we could get a big table in the back. Someplace sort of semiprivate, where we can all talk, maybe?”

  He nodded and peeled seven menus from the side of the podium. “Absolutely. Right this way.”

  The German kids followed closely behind Wolf, chatting him up in their mother tongue. Bill and Theo went after them, commenting on the billowing flags and the posters adorning the walls. I brought up the rear, with my hand in the pocket of my blazer, my fingers tracing the edges of the six red bus tickets I’d collected. The payment I’d received for providing a service I loved so much, I’d do it for free.

  But maybe next time I could actually earn some cold hard cash.

  CHAPTER TWENTY-SIX

  First things first: I needed a plan.

  Yes, even though I was calling them “Sophie’s Spontaneous Tours,” I still had to figure out how to spin this awesome idea into a lucrative business. I couldn’t very well give the same bumbling speech day in and day out and expect to turn a profit. People wanted variety in their sightseeing tours; they wanted choices. Plus, I had to prepare for contingencies: What if it rained? What if a suspicious package closed down everything north of Union Square? These things happened in the city, all the time. I wanted to show I could handle any unforeseen circumstances and still give my clients what they paid for, unlike the double-decker bus company, which was now my competition.

  After exchanging good-byes with the members of my inaugural tour group, I raced up the stairs to my apartment, bursting with enthusiasm for my new undertaking. Dusting off an old laptop I hadn’t touched since college graduation, I immediately set to work developing a business plan: defining a mission statement, establishing goals, identifying areas of strength and opportunities for growth. Finally, my strategic planning skills were being used on a project that actually mattered to me.

  I settled on a pricing structure designed to lure tourists away from CityLights: ten dollars cheaper than the bus ride for a tour that lasted two hours, featured loads of exercise, and ended at a place to grab some grub. Also, the tickets would be fully refundable, transferrable, and reschedulable. Sophie’s Spontaneous Tours were about seeing the best sights the city had to offer, but they were also about flexibility and fully acknowledged the fact that not everything was under our control. Some things just had to be left up to the roll of the dice.

  One thing I couldn’t leave to chance, though, was my budget. Initial revenue projections for my fledgling business were a paltry fraction of what I’d earned at McKinley, and if I didn’t make some major modifications to my spending habits, I’d wind up draining my savings account in a matter of weeks. Armed with my trusty spreadsheet of personal finances and a thick stack of old bank and credit card statements, I analyzed each purchase I’d made over the past six months, determining where I could make the deepest cuts.

  Slashing expenditures turned out to be an easy task, since most of my money went to supporting a lifestyle I’d no longer be living. Those latte macchiatos I guzzled to stay alert while hopping time zones? Deleted. The takeout I constantly ordered because I was always on the road? Gone. My available funds increased with each expense I removed from my spreadsheet. While I knew this
all meant I’d be forced to take a hiatus from globe-trotting for the foreseeable future, it was the price I was willing to pay to pursue my dream job.

  Perhaps my greatest thrill came from knowing I’d never have to pay another dry-cleaning bill. Each month, I’d spent absurd amounts of money to launder my work attire, designer duds I didn’t even enjoy wearing; the stuffy blazers and demure dresses felt more like armor than apparel. Since they certainly wouldn’t be practical choices for leading walking tours, I happily deleted the dry-cleaning expense from my spreadsheet, then opened the door to my organized closet to survey the neatly pressed items suspended from slim velvet hangers. A double-breasted seersucker jacket. Wool pinstripe trousers with painted wood buttons. An A-line skirt with embroidery ringing the hem. They’d cost me a fortune when I bought them off the rack at Brooks Brothers. Maybe I could earn some of that money back.

  One by one, I removed every article of clothing from my closet and, using my laptop’s webcam, photographed each item before posting it on all the online resale shops I could think of. By the time I published my final listing, it was well after midnight, and my eyes were starting to close of their own volition. There was still more planning to do, but it would have to wait until morning.

  I crawled into bed and buried my face in the pillow, waiting for sleep to envelop me. But instead of peacefully drifting off, I was jolted awake by the heady scent infused in my sheets. The distinct spice of Carson’s aftershave prickled my nose, reminding me of his abrupt departure, the terrible words we’d exchanged, the back of his head as he disappeared down 42nd Street. Had that really happened only twelve hours earlier?

  Willing myself to forget these vivid images of our final encounter, I turned on my side with my eyes wide open and saw a speck of light glinting off a small, shiny object atop my nightstand: the spare key to my apartment, the one I’d left on my kitchen counter for Carson earlier that morning. Beside it was a crumpled piece of vellum, and even though I didn’t need to unfold it to know it was his five-year plan, I did anyway. I wanted to see his handwriting, the smudged pencil strokes, the tangible evidence of his love for me. Though after the way we left things, who knew how he felt about me now?

  * * *

  Sleep didn’t come easily. All night, I faded in and out of consciousness, my brain cycling between excitement for my new venture, despair for my lost love, and anxiety for how drastically my life was about to change. At the first peek of sunlight, I gave up the fight and put on a pot of coffee, ready to turn my full attention back to my business. But first I tucked Carson’s five-year plan out of sight, in the very bottom of my nightstand drawer. Nothing was going to distract me today.

  The next item on my task list was to design my itineraries. My goal was to have several different walking tours throughout Midtown, each with a rough agenda that remained adaptable based on current events or even the whims of the attendees. Instead of creating all my itineraries from scratch, I decided the most expedient way to get my enterprise off the ground would be to dig up all those travelogues I used to write, back when I took those weekend tours around New York City. I still had them all, waiting for me on the bookshelf of my childhood bedroom.

  I threw on a comfortable pair of jeans and a casual top—my new daily uniform for the foreseeable future—and walked downtown to Penn Station. The 8:37 train to Woodbridge was pleasantly empty, since most commuters were heading into Manhattan to begin their days at work. I slid right into a window seat with no one else around me and sank into the vinyl cushion, watching the crowded platform fade from view. But as the train ducked into a tunnel and sped beneath the Hudson River, panic set in. Because for all the planning I’d done, I still had no idea how I was going to break the news to my grandmother.

  She’d always thought my love for traveling and tourism was frivolous, dangerous, and foolish. I cringed to envision her reaction when I announced I’d quit my stable, prestigious, high-paying job to hang out with tourists in the city all day. She didn’t understand what it meant to me, and there was nothing I could say that would make her happy, no way I could convince her this sudden upheaval in my life was a positive development. Which is why I didn’t warn her I was coming over. I didn’t want to give her the chance to ruminate before my visit or to prepare some big derisive speech.

  Also, I didn’t have a phone with which to call her.

  So when I showed up on her stoop at 9:30 and rang the doorbell, it wasn’t surprising to see the confusion written all over her face. And, of course, since it was my grandmother, the confusion immediately turned into worry.

  “Sophie, what are you doing here?” she said, holding the screen door open for me to enter. “Is everything okay?”

  “Yeah, I’m totally fine, Gram.”

  “Why aren’t you working today?” She followed me into the foyer, her voice trembling with worry. “Is this some kind of emergency? Has your building been evacuated?”

  “No, it’s nothing like that. Really, everything’s fine.” I advanced toward the kitchen with my eyes on the worn parquet floor. “Can I have some coffee?”

  “Of course.” She approached the kitchen counter and poured the warm liquid into my mug, the same one with the purple cartoon cats. As she measured out the milk and sugar, I took a seat at the table and twiddled my thumbs, looking everywhere but in her direction. Finally, she sat down and placed the mug in front of me. When she saw the sheepish look on my face, her eyes went wide.

  “Oh God,” she said. “You’re not pregnant, are you?”

  “No, Gram, I’m not pregnant.” I buried my face in my hands, mortified. But if Grandma was already jumping to such far-fetched conclusions, surely the real reason for my visit wouldn’t seem so bad. It was time for me to just spit it out. So I lowered my hands, took a deep breath, and said, “I quit my job.”

  “What?” She pressed her palms against the tabletop. “What do you mean you quit your job?”

  “I’m done. I submitted my resignation yesterday and walked out.”

  “I don’t understand. Did you get a better offer?”

  I shook my head. “No.”

  The worry on her face increasingly gave way to anger. “Why would you do that?”

  “Because I was miserable,” I said. “I’ve hated that job for a really, really long time. I’d finally had enough.”

  “How are you going to pay your bills now?”

  “I’ve decided to start my own business.”

  “Doing what? Consulting work?”

  “Kind of,” I said, forcing a smile. “I guess you could call me a travel consultant.”

  “Stop beating around the bush, Sophie,” she said, her nostrils flaring. “What are you up to?”

  Here we go. I took another deep breath before confessing. “I’m becoming a tour guide. I’ve got it all planned out. See, I’m going to be giving these walking tours around New York, and—”

  “A tour guide?” Grandma’s face screwed up in disgust. “What the hell kind of a job is that? How much are you getting paid?”

  “Well, I won’t exactly be making a steady salary. I’ll be charging thirty-nine dollars per person for each tour, so it depends on how many customers I get on any given day.”

  “So you’ll obviously be taking a pay cut.”

  “I certainly won’t be making McKinley money anymore,” I said. “But I’ll be much happier.”

  “How the hell are you gonna pay your rent?”

  I fought to keep my voice even and subdued, despite the tension building in my chest. “Well, I’ve got enough savings to last me through the rest of my lease. When that’s over, I was thinking about looking for something more affordable in Queens.” But never, ever in New Jersey.

  Grandma got to her feet and began pacing around the kitchen, her hand fluttering over her chest.

  “Calm down, Gram,” I said. “This is good news, I promise you.”

  “This is a mistake, Sophie.” Her slippers scuffled against the floor as she trudged from the ba
y window to the refrigerator to the kitchen table and back again. “You’re going to regret this one day.”

  “No, I won’t.”

  “Yes, you will. Mark my words.”

  “You know what I’d regret? Not taking this chance. I would regret always wondering what my life could’ve been like if I’d been brave enough to follow my dreams.”

  She stopped in her tracks, her veiny hands gripping the back of her wooden chair. “Your dreams?”

  “Yes. My dreams. Remember when I applied to college? I was looking at all those schools that offered degrees in travel and tourism.” I swallowed hard, afraid to say the next words. But I knew they needed to be spoken. “You threw all the brochures away. You said I shouldn’t pursue it. That it wasn’t a real job.”

  “Because it wasn’t a real job,” she said, throwing one hand in the air for emphasis. “It still isn’t. It’s a crazy idea. I thought you’d have outgrown it by now.”

  “You don’t outgrow your passions, Gram. I can’t live my life making choices simply because you want me to make them. I won’t compromise my happiness for you. Not anymore.”

  I pushed back from the table, causing the chair legs to squeak against the parquet floor, and retreated to the hallway, where I climbed upstairs. As I blinked back tears, I chided myself for getting so upset. I knew this was the reaction Grandma was going to have. I never expected her to be supportive or understanding.

  But I guess it would’ve been nice if she’d been a shade less scornful. Or perhaps demonstrated the least bit of respect for my autonomy, my ability to make decisions about my own life. Then again, why did I think things could be different than they ever were before? She still treated me like an irresponsible child who wasn’t trustworthy enough to run her own life. Just like she always had.

  I hadn’t come to New Jersey to seek her approval, though. I was here to get my old New York City guidebooks. They were right where I’d left them, on the four-tier beechwood bookshelf in the far corner of my childhood bedroom. I knelt on the mauve plush carpet and ran my fingertips along their worn spines, inspecting the titles. Walking New York, Streetwise Manhattan, Urban Adventures in the Big Apple. Alongside them were three spiral notebooks—my handwritten travelogues. A wave of nostalgia washed away my melancholy, and I flashed back to all the fun I used to have touring through the city. How I used to dream of leading my own group of travelers around the streets. You’re making the right decision, no matter what she may think.