Leonardo & His Olives


I arrive in Certaldo pretty late and very tired. 

I get off at the station and an older man walks up to me.

“Need ride to Certaldo? You come with me.” He smiles.
I guess this is Leonardo. I have never seen a photo of him so a guess is as good as it’s going to get.
“Leonardo?” I smile back. Glad he is here waiting for me.
“My name Marco. You come with me. I take you wherever you need to go. I have car. This way.” He gestures aggressively.

Oh okay! Not my host. Just a random creepy old Italian dude. Glad I asked.

“No.” I respond awkwardly already walking towards the main station entrance. I see no one else here. What if he didn’t get my email?

Dammit. Dammit. Dammit!

Certaldo isn’t exactly a thriving metropolis so I imagine accommodation will be limited.

Outside in the parking lot another older Italian man approaches me and takes both of my hands into his.
“Ciao Rachel! You must be tired.”
He has one of the nicest smiles I have ever seen. This is Leonardo. I mean he knows my name, so he must be. He takes my bag and we walk up to an old beat up white van. The seat is very dirty and there are two dingy looking towels folded sitting on it. I actually expected this kind of car from an olive farmer in Certaldo so that’s fine. We drive about twenty five minutes up unmarked dark streets past countless olive trees until we reach a tiny villa. I can’t see very much, but I don’t care.

 I just want that bed! 

He points up to an apartment on the second floor of one of the buildings and tells me that that is his apartment. “All the lights are off because Maria is asleep. I was going to sleep when I saw your email.” He says pointedly still smiling. I can feel my face turning red.
“Sorry about that my train ran a little late.”
(Which was true)
Leonardo curses in Italian. “Italy trains always late! It is big problem. Why you take train?! I told you to fly.” He lectures me loudly. Okay. Umm I didn’t want to fly?

We walk up to a separate house across from his building and he lets me in.
“You will share bed with girl upstairs.. What is her name?” Insert long pause here, “I do not know her name. She is from Australia. But she is asleep because it is late. Tonight you sleep down here in this room.”

He leads me to a room with a single bed and a connecting bathroom.
There is water all over the floor.. Which leads to more cursing in Italian.
Leonardo checks the bathroom and says that the Australian girl must have done something to make this happen.
“Why she do this?” He grumbles walking towards the exit.
“So, what time do I need to be up tomorrow?” I ask.
The sweet smile returns and he tells me that if I am tired I can sleep in a bit but breakfast is at seven at his place. I tell him I will see him at seven and he leaves. I set my things down on the wet floor because I have no other option and immediately crawl into bed. There are no sheets. Just a thick moldy smelling blanket and one pillow with no case. Eww. Luckily, I am too tired to care and i pass out pretty quickly.


The next morning I wake up at 6:30 and put on my dirt stained gardening jeans, a t-shirt, my men’s flannel button down, and pull my hair up. I am so ready to harvests some Tuscan olives.

I walk to Leonardo’s apartment and walk in to find one of the other workawayers already at the breakfast table. He is a tall cheery man from Gambia whose name is Emam. He smiles kindly at me and introduces himself but is otherwise quiet. Soon after I sit at the table, the other workawayer walks in. She is about my height with long blonde hair. She doesn’t say anything to me and actually looks kind of angry. Her name is Jennifer and she is the girl from Australia. Emam asks her how she is doing today in an apologetic tone. She gives him a look and he smiles. A small older frizzy grey haired woman walks in and starts setting things on the table. Emam and Jennifer start eating immediately keeping their eyes on their plates. They must be pretty hungry.

The older woman is Leonardo’s wife and she doesn’t speak one single word of English. She looks at me with an expression I cannot read and suddenly starts yelling really really loudly gesturing about wilding.
I can’t think of anything I could have possibly done wrong.. I look helplessly at the other volunteers. Jennifer doesn’t look up from her plate and Emam smiles looking at me expectantly. “She wants to know if you want coffee or tea.”
Oh. “Coffee..Por favore?”
I smile meekly at her. I watch her go and look in the (Italian coffee thing) and sit it on the stove. Five minutes later I am drinking someone else’s old coffee reheated. The food on the table is plain vanilla yogurt, uncooked porridge, stale bread that is hard as a rock and marmalade. I am confused.
Leonardo walks in soon after wearing the same shirt he was wearing yesterday when he picked me up. “Eat,” He smiles, “We will not eat again until one and you don’t want to be hungry.”
I dont know what to eat, so I copy Jennifer and pour about half a cup of raw porridge onto about half a cup of yogurt. It is not delicious.
We all put on our Wellies and pile into the white van. Leo gives me an extremely old and extremely dirty baseball cap and a pair of gardening gloves that are equally dirty with countless holes in the fingers. 

What is the point of gloves if they have that many holes in them?

They are about two sizes too small for my hands and wearing them makes grabbing ahold of things difficult. I am not putting that hat on either.
We drive about five minutes to one of his olive fields and unload the van. We each carry three crates and Leo carries a tool with a long handle that sort of looks like an electric rake.
We walk down a steep hill until we reach an two lines of trees with long green nets beneath them. Here I help the other volunteers stretch out large tan nets under certain trees and pin them together with sticks we get from the ground. It is hard enough to walk sideways on such a steep hill, but to do so on the slippery dew covered nets is almost impossible and we all slip onto our backs several times during this process. Leo uses the machine which is an olive “tickler” to knock the olives from the branches and we go behind crawling under, up and around the tree getting all the stubborn olives left behind. 

Also under these trees are plants with fuzzy sticky things that cling relentlessly to my gloves, my jeans, and get tangled in my hair. I decide the dirty baseball cap is worth wearing after all.

We throw these olives onto the net until the tree is completely barren and then we unpin the nets and shake the olives into a pile. We pick out any large sticks from this pile and then transfer those olives into plastic bins. Two people carry the bins back up the steep hill and load them into the back of a red truck parked there. It is unequivocally the hardest work I have ever done. The nets and bins are extremely heavy. Climbing up and crawling under the trees involves a lot of arm and leg strength as well. By one o’clock I am absolutely exhausted. We have lunch which is stale bread, Parmesan cheese, a salad of carrots and scallions soaked in vinegar, and a couple walnuts. This is not nearly enough food to fuel me for the amount of physical labor required to pick these olives. The silverware is really dirty. The knife used to cut the cheese was actually covered in dirt..from the ground. Not to mention that I noticed Maria only use cold water and no soap to “wash” the dishes this morning after she let her two dogs lick our breakfast plates.

AND I have yet to see Leonardo ever wash his hands.

Thinking of these things makes me almost gag but I need fuel! So I eat everything given to me as if it is the best food I have ever eaten.

We start work again at two and work until five pm only stopping when it is too dark to see the olives on the trees. Through out the day, Leo directs us to place the nets a certain way and no matter how diligently we follow his instruction he moans that we do it incorrectly. 

Every. Single. Time.

“Why you do this?!”

“Please. Just listen. Please!”

“What is the matter with you? I see an olive in that tree. I am old, but I think that maybe you are blind. I said pick every olive!”


Jennifer says that her and Emam accepted the fact that they would never do anything right a long time ago and just to ignore him.

Which is hard because sometimes he gets right up in me or Jennifer’s face when he lectures us. But never Emam. Emam seems to get treated with a lot more respect for no apparent reason other than the fact that he is a man. Leo takes us out for pizza one night and yells at the waitress, but I have never witnessed him yell at another man.

At one point he leaves to drive the full truck of olives home to his garage and Emam plays rasta music and we all chat. It is so much more fun and seemingly more productive picking the olives by hand than straining to find just a couple olives from each tree. We talk about Africa, relationships, travel…
They are both so nice and really funny.
Jennifer says that she is in a bad mood because the night before Leo had  yelled at her for waiting for him to come home and cook supper. Even though he had initially said for them to wait on his return before he left. He said because she was a woman, she should know it was her responsibility to feed Emam…because he was a man.

Wow. This will not do.

Dinner is cold soup and there is barely enough to go around. We have this same soup for dinner for the next three days. The last day they throw the same noodle and vegetable broth soup into a blender to make it seem like a different soup.. But it actually makes it more disgusting.

I really need an exit strategy but there is no wifi here. No telephone. No way to get to civilization by foot.

There is no exit.

The three of us make a lot of slavery related jokes. We imitate Leo’s accent yelling at each other for having blue eyes and other things that can’t be helped. We play mental strategy games and sneak pomegranates off the neighbors tree to attempt to get full.

One day the three of us work alone and it is great. I am really sore, but I actually like the physical labor part of it. It’s like a really long steady workout. I ask when our days off are and they say that they have worked ten days straight with no day off.

That’s it.

This is the first workaway either of them has ever done, so they must not know better. This isn’t going to work for me.

Here is the way Workaway works:

(Or at least the way it is supposed to work)

For five out of every seven days you work for a maximum of five hours a day. You do this in exchange for meals and accommodation. You do this for the cultural experience of living with actual locals versus the hostel tourist market.

Workaway, for me, has been a wonderful experience thus far. It has taken me to places I never would have gone to and led me to meet people I never would have otherwise met. I have lived like a local, completed the tasks given to me to best of my ability, and saved a lot of money in the process.

When the rules are followed by both the host and workawayer, I think it is one of the best ways to travel on a budget.

Leonardo is getting free labor. We are working without complaint for double the amount of time agreed on without any days off. Which I might gladly do for a nice hot Italian meal..

Or to be honest, I wouldn’t even care about the awful food. Maybe he can’t afford to feed us well. I wouldn’t hold that against him..

IF he were only kind..

but he is not kind.

It is that simple.

(Plus he can definitely afford to feed us.
He is just stingy and simply abusing the system.)


Before I arrived, Jen says they were working on another farm where they hand picked all the olives and it was great. She says the hours were the same, but they had traditional filling Italian meals every night. She describes a large group of pickers, conversation, wine and celebration at the oil mill when the work was done.

Just what I imagined..

One of the pickers from the last farm actually texts Jennifer and invites us to Radda in Chianti for a night.

After explaining the guidelines of workaway to the other workawayers (including the fact that we can report him if we want to) we decide to go to Radda.

Now we just have to tell Leonardo…

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