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The Adventures of Italian-American Man

A Case of Vertigo at Castle Montalcino

Marc Edward DiPaolo (April 5, 2008)
Colin had no problem with heights. But that tower was more intact than the one I foolishly went up...

What's the best way to impress a girl? Collapse in a quivering mass of fear at the top of a castle tower in Montalcino, of course.



The next major outing was to see a castle in Montalcino. Olansky chartered a bus to take us all to the structure, which stood in the middle of the most beautiful scenery I had ever seen in my life. Describing it is virtually impossible. I try to put it into words and wind up falling back on “rolling green hills covered in mist.” Such clichéd words never fail to conjure up an image for me of a misty-eyed Irishman talking about the old country. But the words do fail to conjure up Montalcino.


I wonder if I had ever really seen a horizon before that day on Montalcino. Growing up in the crowded suburbs, I’ve rarely had an opportunity to see a clear sky, or miles of undeveloped land. Before that day, the closest I got to seeing untouched land was watching farm houses go by as I drove along the expressway to my college in upstate New York. And both the farm and the highway were there to spoil the expansiveness of the grass.


The castle was obviously man-made, but it was so old and made of stone, which is a very natural material, so it seemed almost as if it grew out of the ground. Olansky gave us some time to wander around the castle, and I don’t think I’ve ever seen Colin so happy in my life. He ran up and down the battlements whooping out with joy. As a lifelong Dungeons and Dragons fan, as well as a devout worshipper of the move Braveheart, perhaps he had felt that he had come home.


I, on the other hand, was moving very carefully along the crumbling battlements, wondering how anyone could stand guard on such a precarious position, let alone defend it during a siege. One false move and you were a bloody pancake on the floor.


Colin stopped running around long enough to notice how unsteady I was on my feet.


“Don’t tell me you’re scared.”


I smiled sheepishly.


“You got to be kidding. This is the coolest thing ever, and you’re scared?” He laughed and then continued running around, pretending to brandish a sword.


Eileen appeared with Drusilla at her side and the two began exploring the part of the castle I had already discovered. At each corner of the castle there was a tower that rose another fifty feet above the level we were standing on, which was already very high. Eileen made her way to one such tower and stared up at a very long ladder made of sturdy pieces of wood.


“That looks scary,” she said.


She started hesitantly up the ladder and stopped halfway. She looked down and laughed at herself, embarrassed at being afraid.


“It’s okay,” I said. “Just head on up. Don’t look down.”


She nodded and crept her way up. When she disappeared through the hole at the top of the tower, a series of thoughts ran through my head. If I darted up the ladder as quickly as I can, I can impress her by being extra brave. I can also be alone with her at the top of the tower. Maybe that would be a good time to kiss her. I can kiss a lady in a tower. Colin’s Arthurian Romance high was becoming contagious.


Without looking down, I climbed the ladder as quickly as I could. Reaching the top, I leaned through the hole and landed on what was probably the smallest elevated platform I had ever stood on. The half-ruined tower was missing large chunks of its wall, so there would be no barrier preventing anyone who wanted to from simply walking off the edge. Everywhere I looked, I saw a huge drop. I front of me there was a sheer drop along the side of the castle. On my left was another drop where I could splatter myself all over the castle interior. Behind me, I could fall to my death down the ladder.


Eileen tossed her arms back and breathed in the open air. “What a wonderful view!” she cried.


“Oh, my God,” I murmured.


I was feeling dizzy. I didn’t want to move my legs because any step would take me closer to the edge. But not moving my legs made me feel wobbly. Each time I wobbled, I saw the drop. Maybe I should just go back down the ladder. I got up it, I could go down.


I looked at the ladder, and realized that the first run was so far down that I’d have to lower myself waist-deep into the hole until my feet found support. Then I saw the drop past the first rung.


I dropped myself to the floor and hugged my knees to my chest, too afraid to do anything but stare off into nothingness. I wouldn’t allow my eyes to register the sky around me. I had always been afraid of heights, but I’d never had such an attack of anxiety. I’d never felt so vulnerable.


“Are you okay, Marc?” Eileen asked. She rested a hand on my shoulder. “What’s wrong?”


God, why does she have to see me like this? Why do I have to be so weak in front of a woman? I have to be strong. I have to impress her so she loves me. I want to be worthy, but how can I be if I’m so afraid?


Drusilla popped her head up from the hole in the ground. “Ah, it’s nice up here.” She hoisted herself up off the ladder and out of the hole onto the tower.


“What’s wrong with Marc?” she asked as she got settled.


“Nothing. I’m okay,” I said.


Two more people climbed up, including my fellow Blessed Augostino Novello fan, Mark Newcomb, and I wondered how we could all fit on such a small tower. As they walked around the hole in the floor, they had to avoid bumping into one another. None of them seemed scared.


“What a beautiful view,” said Colin, when he joined us.


Eileen moved closer to me and said as gently as she could, “Do you want me to help you down the ladder?”




“Do you want me to go down first and you follow, or do you want me to help lower you down?”


“I don’t know,” I said, my voice wavering. As mortified as I was, I tried to be big about it and laugh at myself. I managed a smile and a small laugh.


“You have to tell me, or I can’t help you,” said Eileen.


“I’ll go first.” I moved slowly towards the hole in the ladder and then stopped abruptly.


“I can’t,” I said.


“Do you want me to go first?” Eileen whispered.






Eileen walked over to the hole and tried to figure out how to lower herself onto the ladder. She sat on the edge of the hole, dangling her legs in the air over the first rung. She then planted her hands on either side of the hole and pushed her bottom over the edge. She hung in the air a moment, supported only by her locked arms. Then she bent her elbows and her feet found ground. Once this was done, she had to do an awkward maneuver to turn herself around so she could back down the stairs.


After a moment, she was ready and climbed quickly down the stairs. Several seconds went by.









“I made it down.”






“Come and see.”


I slowly leaned forward and peered into the hole. She was at the base of the ladder, looking up at me.


“You can do it, Marc.”


Colin, who was still on the tower with me agreed. “You can do it, man.”


I exhaled sharply through my nose. “Okay.”


I stood up and tried to will myself to the ladder. I was posed as if I would start walking at any moment, but I wasn’t moving. A long moment passed with me standing there.


“What are you trying to do, use the Force?” asked Mark Newcomb. “Just go down the fucking ladder.”


I laughed, and that joke was all I needed to break the tension. I’d had it with looking the fool in front of Eileen.


Focusing only on her face, I duplicated the same maneuver she used to find the first rung of the ladder. The moment my feet reached the rung, I knew I was home free. I went down the ladder as quickly as I could. Suddenly, I found myself at Eileen’s side again.


She gave me a thumbs up sign. “There you go. You made it.”


“Thanks,” I said. “That sucked.”


She pointed up at the hole in the tower where Colin had appeared to make his descent. “You looked so cute when you’re head appeared up there, looking down on me. You had this adorable, frightened chipmunk face on.”


I pictured it in my mind and laughed. “Good lord, I can imagine.”


On the bus ride back to Siena, Eileen was oddly cool to me. We sat next to one another, but she seemed to not want to speak to me at all. Saying she was no feeling well, she placed headphones over her ears and started listening to her Ringo Starr and His All-Starr Band CD. She didn’t speak the entire trip back.


After reaching the hotel, I complained to Colin about her for twenty minutes. He agreed with everything I said about her, but no longer opposed my continued passive pursuit of her. He just couldn’t care enough to oppose it because he didn’t want to see me with a girl he hated so much. I would later feel the same way about his girlfriend, Monica, so I can no longer fault him, in hindsight.


Shortly after nightfall at 6:30, I went to Eileen’s room. I sat on her bed beside her as she made up a list of all the Mets games of the current season and tried to calculate how many she’d be able to realistically see commuting from Connecticut. She spoke rapidly and nervously as she told me about it, once again an odd mixture of tension and eagerness in my presence. Half of her seemed to be screaming out for me to kiss her while she other half just wanted to make me go away.


“Do you want to take a walk?”


It was two hours earlier than we would usually walk with Drusilla and Colin, so the request was definitely special, especially considering what had been going on with us over the past few days. I had also failed to mention asking either of our friends to accompany us.


She considered it for a moment before giving an only slightly hesitant, “Yes.”


It was a cold night out. The two of us walked side by side to the D’Uomo, the main church of Siena. It was her favorite building in the city, and we would often include it on her walks, but she was particularly insistent that we head directly for the church. It was a none-too-subtle way of telling me she was still confused about our relationship.


When we reached the church, she asked that we go to the other side of the main square and sit on a low all across from its façade. I sat next to her on the cold stone and looked with her at the dozens of saints’ statues on the Gothic structure. She looked like she was considering saying something about the artistry of the church, but stopped.


As I sat there with her, looking at the church, I knew there would never be a better time. She was ready and so was I. This would be something I would remember for the rest of my life.


I reached down and gently placed my hand on hers. She lowered her head and smiled in muted disbelief.


I laced my fingers through hers and moved closer to her.


“I don’t understand,” she whispered. “There must be so many things you’d rather be doing than sitting here with me.”


“There are,” I said, and I leaned forward to kiss her.


She lifted her head to mine, letting my lips touch hers. I placed my arm around her waist and pulled her closer to me as I kissed her. I felt a rush of excitement as I felt the warmth of her body through her coat.


Once the kiss started, we abandoned all the inhibitions that had been crippling us from the beginning and let ourselves let in the moment. She put her arm tentatively around my neck and kept kissing me, not doing anything to push me away as she had done so often over the past weeks.


I wondered how it was that this was happening to me, even though I had helped make it happen. How was I with this wonderful person? What did I do to deserve her?


I shoved the unwanted thoughts aside. Even though I knew that Eileen and I might never be together again after we returned to America, I felt happy, and I felt alive. For the first time in years, I wasn’t afraid of living.


As we kissed, I was aware of the D’Uomo beside us, standing there as it had always stood, every day for the past five hundred years.


And it was good.