I leave for Italy in 39 days.

I only recently bought my plane ticket, and just last week decided exactly where I will spend the days following my volunteer work in Umbria. I have not booked a single night at a hotel, pensione, hostel or airbnb.

This is highly unusual for me.

By now I would have secured a room for all of my nights, and outlined a rough itinerary of my days – making certain I knew when each museum closed.  I learned this from my friend Tim, who saved the Louvre for his last day in Paris, not realizing it closed on Tuesdays.  He has lovely pictures of the outside.

I would have purchased my train tickets and made copies of my passport.  My travel books would be dog-eared and yellowed with highlighter.

I have done none of this.  I’m not sure why.

And so I find myself tucked into a big chair in the back of the Book Cellar, pouring over travel guides – more out of necessity than anything.  Fodors.  Rough Guide.  Lonely Planet.  Thick books on the whole of Italy.  Thinner versions on Rome, Florence and Tuscany.  Artist Date 86.

I recall my first travels overseas – press trips to Germany and Israel.  I was in my 20s and had dreamed of traveling abroad.  Everything was handled for me.  Flights.  Hotel.  Itinerary.  And yet, I sat at San Francisco International Airport before each trip – terrified.

Flying out of SFO in 1999 to Spain – my first overseas trip with my then boyfriend, now ex-husband — felt wholly different.  I wasn’t alone.

One Saturday morning we somewhat impulsively bid on Priceline tickets to Madrid.  By afternoon, we were sprawled out on the floor of Borders Books – leaving a few hours later with copies of Frommers – Europe on $100 a day and Madrid, Barcelona and Seville.

We traveled overseas together several times over the next few years – me carefully crafting an itinerary each time.   Yet, a part of me longed to travel alone, as so many of my friends had done after college.

And at 37, I do it.

At the time, I feel too old to throw a rucksack on my back, sleep in hostels and shower in train stations.  I find a trip volunteering in the south of France, building walls as part of an architectural restoration project.

I spend a few days in Paris by myself when I arrive.  It does not feel glamorous and exciting as I had imagined.  It feels scary and lonely.  I wander the streets alone, slightly drunk and call my then husband — crying.  A few days later I join my team in Avignon.  Surrounded by volunteers from around the word, ranging in age from 21 to 73, I feel joyous and free.  I have found my place, my role.  I am the friendly American who drinks too much and gives massages.

Eight years later, (I will turn 45 in Italy) I do not drink anymore.  I do not have a husband anymore.  These things that I leaned into ceased to serve me long ago.  This time, this trip, I must lean into myself.  My hesitation in planning suddenly makes sense.  I am afraid.

And yet, I have a plan, a purpose – I am again joining volunteers from around the globe.  This time, at the Altrocioccolato Festival – known as the “other chocolate festival” – outside of Perugia.  This time, my alone time is on the back-end of the trip – and I will have a better sense of place.  This time I have people, “waiting” for me in church basements.  People who also used to drink too much but don’t anymore – people like me.

My friend Pam says I will go to Italy and meet a boy on a scooter and never come home.  She tells me that I am brave.  That she doesn’t know anyone else our age doing what I am doing – traveling, alone.  I do not feel brave.

And I remember what I’ve been told, that bravery isn’t the absence of fear, it is walking through it anyway.

Or perhaps flying through it – direct from Chicago to Rome on Alitalia.  Or riding a scooter through it – an Italian boy in front, and chocolate in my pocket.