traveled alone in years. I went to a Club Med in the Turks & Caicos last December but that doesn’t really count
since it was like summer camp for adults with “free” drinks. As I recall, I was rarely without a beverage in hand
which constitutes an escape rather than an adventure. However, after my “escape” I decided it was time to get
back on the proverbial travel horse.
My mom had 3 favorite sayings when I was a child: 1) you can do anything
you put your mind to 2) if you fall off your bike or roller skating, get back on or up and keep going, and 3) look it up (I
had a propensity to ask a lot of questions particularly about spelling and what foods were “good for” what and
why. You know, like spinach is good for your muscles so you can be strong like Popeye, carrots are good for your eyes, etc.)
That’s probably a big reason for my HUGE win of the 5th grade spelling bee which I’m not shy about
bringing up when the opportunity presents itself… I digress.
I have wanted to travel around the world for as long as I can remember.
Fear and finances have been relentless excuses to stay close to home. As you know, I am a dating disaster. I consistently
pick the wrong men to spend my time with. They’ve ranged from high powered executives, field professionals, business
owners, older, younger, stocky, thin, and funny to not-so-funny to just-your-average-Joe. The one quality, however, that is
unbroken with my eclectic focus group is they’re all well-traveled.
I started the year off
with New Years in San Diego to visit a nice young man I met two weeks prior, NYC in May alone for the weekend, Miami in August
with a friend but I still felt trapped. I had the finances to hop on a plane but the fear of going alone was still there.
NYC was a stepping stone but it was still only a 3-hour car ride from home.
So, this fall, I decided
it was time to see Chicago, alone. As I walked through O’Hare, I wished I had the foresight to take the barf bag. I
was immediately overcome with anxiety. “Who would I talk to for 3 days?” “Who will I eat with?” “What
am I going to do with myself?"
I got to my hotel, which I booked through www.quickbook.com (awesome site and great room, I was VERY pleased, btw) then headed to Wrigley Field. I sat
behind home plate for a Cubs game, had a few beers and pulled myself together. The Cardinals were mercilessly beating the
Cubs so I left in the fourth. Not that I had an affinity for either team but when the score is 8-0 in the first, it’s
not much of a game. When I got back to my hotel, I took a walk towards the lake to mull over my predicament; no friends to
speak of and no plan.
Those words of wisdom started to percolate in my psyche; “you
can do anything you put your mind to” and “if you fall, get up.”
Can I just
tell you? I was going to have fun if it killed me, damn-it. So, I got comfortable with the subway system and picked up a Chicago
Day by Day book. I circled all the places I wanted to see and made a plan. That night I went to a jazz bar in a seedy area
of town, I got there a little early so I parked my ass at the bar at a little Indian restaurant down the street and chatted
with the bartender for an hour and a half then headed back to my place of immediate interest, The Green Mill. It was packed
by the time I got there but I found a great seat at the bar with a perfect view and let the melodies seep into my soul. Honestly,
I felt like I could have listened to that music until the day I died. Then, from out of nowhere, a gigantic man blocked my
stellar view. I thought to myself, “Seriously?” When he turned around, I gasped. It was none other than my dream
date, Vince Vaugh, with a woman much too young for him, of course. Bastard.
The men sitting to my right
started to kibitz back and forth, they couldn’t place Vince. I swooped in with an assist just as the band was taking
intermission. We laughed about the movies he was in and then got the low-down on each other. I told the men my story and they
invited me for brunch the next morning followed by sailing on Lake Michigan. My very practical self considered the danger
of going off with two perfect strangers on a very deep lake especially since the only stroke I’ve mastered is the doggy
paddle. However, they were Canadian so I shrugged my shoulders and said, “Sure, pick me up at 9!” So much for
not talking to strangers; that was another pearl of wisdom from my mom that always seems to be an afterthought.
We had a
blast. It turned out to be a beautiful day! One of the men lived in the city; the other was a friend visiting from Toronto.
Neither of them had done the intensive tour I had planned for myself so, they tagged along with me for the rest of the weekend.
We followed up sailing with a trip to the famous Second City comedy club where the likes of Chevy Chase and Bill Murray got
their start. From there, I went to Buddy Guy’s Legends Blues Club and met up with them later. That place was packed
too but two women in the front row let me join their table. I told them I was from Boston and they said, “Too bad you’re
not visiting in January because Buddy Guy comes in all the time.” Truthfully, I wouldn’t have known Buddy Guy
if he kicked me in the shin but I didn’t say anything.
Well, wouldn’t you know it? A man got up on stage, the crowd
erupted and a waitress handed him an amber shot of something. I half expected him to dramatically whip down the glass to shatter
on stage but, he didn’t. I immediately got on the internet from my blackberry to look up Buddy Guy. I held the picture
on my phone up to the stage to see if there was a resemblance. Sure enough, it was him.
finished their set, I wanted to buy a CD. One of the band members caught my eye and invited me to sit and chat on stage. I
couldn’t stop smiling; there I was on Buddy Guy’s stage, who, I had just learned, was the inspiration to Jimi
Hendrix. History, man.
On my last day, I managed to fit in everything I wanted to see up until minutes before
I had to leave for the airport.
What a difference? On my way into the city, I was beside myself thinking,
“How am I going to manage this alone?” On my way out, all I could think was, “What city next?”