The Itinerary in My Mind

by Erica Bethe Levin – November 29, 2010

Traveling with a companion – any companion – can be a very stressful undertaking.  Especially when it involves eight days, five flights, three cities and a handful of sundry friends and family.

I can honestly say that – in retrospect – I am one helluva traveling buddy.  So is Boyfriend.  Phew.

I just got back from my first “real” vacation in years.  Years.  It came to be because of a precarious situation involving a last minute wedding cancellation.  You see, we were supposed to fly to Rochester, New York for said wedding (in which I was a bridesmaid), then peace out to Manhattan for five days of post-wedding relaxing/vacationing/indulging.  When we found out the wedding was cancelled (and came down from the shock of realizing that our plane tickets were of the non-refundable variety), we opted to fly to Washington DC/Virginia instead (so long, upstate New York in November)…then peace out to Manhattan.  What resulted?  The best eight days of my life.

Sure, the fact that we were able to hit up some of DC’s historical landmarks (the National Holocaust Museum is not to be missed – the world would be a better place if every man, woman and child absorbed this exhibit); spend time in Richmond, Virginia with long-time friends and their children (hello, bonfires, fried turkeys, an extreme night of live, cover band dancing and campfire songs); eat our way through Manhattan (13 restaurants in 4 1/2 days) and experience sights, sounds and smells we haven’t enjoyed in years (the Statue of Liberty, swindling cab drivers and New York pizza), didn’t hurt.  But it was something beyond all of this that made it the “best eight days of my life.”

It’s quite normal – and highly expected – to worry a bit before embarking on a lengthy (eight days!!!) vacation with your significant other for the first time.  Sure, we’ve done one or two day-ers in Galena and downtown Chicago (I love me a Chi-town staycation), but over a week in three different states?  Well, that’s a whole ‘nother story.  Would I be a nuisance?  Would I be overbearing?  Would he want to sleep in too late?  Would he forget his gym shoes?  Would we have to use the bathroom at the same time (gasp!)?  Would we argue over aforementioned sights, sounds and smells?  Would he want pepperoni on his New York-style pizza while I preferred ricotta and basil?  The list is endless.  Shit.

But…get this…everything was perfect.  And perfection involves releasing expectation and imbibing in cooperation.

You see, I’m an overzealous, Type-A, major planner person.  Boyfriend is a go-with-the-the-flow, relaxed, completely Type-Opposite-Of-A, non-planner person.  I could afford to take it down a notch – perhaps he could afford to take it up a notch?  But the vacation that resulted was the hybrid progeny spawned by an anxious planner and a blasé non-planner.

We knew what we would be doing during our brief stay in DC, we knew we would be relaxing at home in Richmond with friends and family, but we didn’t know what Manhattan would have in store for us.  I was extremely uncomfortable with this.  I begged…please let me make dinner reservations, let me buy Broadway theatre tickets, let me write a detailed itinerary from 8:30 am to 11:30 pm each day.  “Absolutely not,” I was told.  “I want to relax, we’re on vacation, let’s see where that takes us.”  Oy.  I compromised.  I insisted upon making one dinner reservation with family, one dinner reservation with friends for a double date night and tickets to one Broadway show on one designated night.  We were both okay with this.  But in my itinerary-less mind, I didn’t know if we would be able to accomplish everything else on my mental to-do list: see Ground Zero, go to Battery Park to view the Statue of Liberty, hit up Wall Street, traipse through Times Square, eat a slice of NY pizza each day, find the best crumb cake in New York City, see a few Manhattan-residing friends, etc. etc. etc.

But lo and behold!  We did it all!  With NO plan of action.  And…guess what…it was relaxing.  I was relaxed and cool and calm and cucumber-like.  We ventured out of our swanky hotel room every morning, grabbed a bite and started walking.  We actually walked 21 miles in 108 hours, and via our path, we came across Battery Park, the Statue of Liberty, tons and tons of pizza, Wall Street, a few historic churches, a few homeless people, the New York equivalent of Boystown, a handful of friends (a chef, a photographer, a writer, an actor, a teacher, a healthcare worker), NO crumb cake (unfortunately) and the Fifth Avenue Veteran’s Day parade.  I’d say that’s a pretty impressive roster – itinerary or no itinerary.

But just when I thought all was accomplished, I moped to LaGuardia realizing that I had not found a piece of my favorite, New York-bred pastry – the elusive crumb cake.  Dammit… Then while waiting for our much-delayed Southwest flight – sad to be going home and a little bit tired – Au Bon Pain saved the day.  At the 11th hour, I mentally crossed off the last thing on my to-do list and indulged in about 700 extra calories – hey, I’m on vacation!

So here begins the story of the overzealous, Type-A, major planner person who met her non-planning, non-Type-A counterpart and actually allowed his nonchalance to permeate her first vacation in years (as well as her OCD mindset).  And she liked it.

About the Author: Erica Bethe Levin

Erica Bethe Levin is the Co-Founder and Editor-in-Chief of CheekyChicago.com. She loves to write, but she also really loves her dog Pippin, spaghetti, wine and Billy Joel.