Back to Florence

Our next and last Italian adventure with Mom and Becky led us to Florence – one of my favorite cities in the world.

We braced for train drama but surprisingly had none despite a couple transfers with tight connections and some weakened legs from all the Cinque Terre hikes.

We had rented an AirBnB in Florence that we were again very pleased with.  The place had a maze like four levels with contemporary decor.  One of the best features was the roof-top deck built perfectly for our crew of four.  We could gather up there to sip a glass of wine, watch a Firenze sunset and take in the surreal view of the Duomo.  Writing this makes me want to be back there.




We had a couple hours to burn before we started our evening plan.  With that time I decided to do a self instructed yoga class.  Peter worked.  Mom and Becky went in search for their new love, Italian bruschetta, which they easily found a couple blocks away.

We reconvened at our flat shortly before sunset, packed some wine, and began our walk to the Michelangelo look-out point.  It was really fun for me to now know my way around Florence to the point that I could lead my Mom and Becky around the city without a map.  Peter stayed behind to work with plans to meet us at dinner.

Watching the sunset from Michelangelo is one of my most favorite things to do in Florence.  The view looks more like a painting than a reality.  You can sit back, relax, sip a glass of vino in public, and typically listen to a local musician strum an instrument and sing some classic favorites.  The three of us had one of those magical moments of looking at each other, not saying a word, but knowing we were all thinking the same thing – “Wow this moment is really incredible.”

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After our viewing pleasure, we charged it back to the city center to meet Peter for dinner.  We had reservations at the self-described “Tuscan Chic” Osteria del Olio, a restaurant conveniently located next to the Duomo.

We stopped by the Duomo for a quick photo shoot.  While we were surveying the best angle a Japanese man asked me to take a picture of him and his wife.  I obliged and figured I would ask him to return the favor.  He grabbed my camera then proceeded to lay his body entirely flat on the cement ground to get the best angle.  With just his head propped up to take the perfect picture he called out, “a little to the right…little more.”  The guy was dedicated, focused and really entertaining.  I started to feel under-committed to this guy with my picture taking and on queue, as if my Mom was in my mind, she calls out, “my daughter will retake your picture.”  Before I had an opportunity to think about it, I was laid out on the ground in perfect imitation of my new Japanese friend.  Pretty sure I nailed the shot.


We arrived to the restaurant moments later where Peter was sitting at our table. My Mom proceeded to explain that his wife was just laying on the ground next to the Duomo taking photos.

I fired back, “My mom made me do it.”

Peter simultaneously smiled, raised his eyebrow, and shook his head.  At this point in the game, when Peter reunited with us after leaving us to our own devices this facial tick had now become a reflex.

While at dinner I asked the waiter if he knew my friend Allie or Tyler, regulars at the restaurant. I was name-dropping a bit.  Not only did he know Tyler, but explained that his girlfriend was working. “I’ll go get her,” he muttered.

So I hadn’t seen Tyler in four years and I wasn’t caught up on his life.  I didn’t even know how to introduce myself to his girlfriend.  Within a few minutes a gorgeous olive skinned woman with a huge smile, and deer brown eyes walked over to our table.

“Hi, I’m Gabi.  You are friends with Tyler?”

Her sweet and smiling demeanor instantly put me at ease.  I explained how I had met Tyler through a mutual friend Gian and had hung out with Tyler, Allie, and Brianna four years ago when I was doing a solo trip through Europe. She had just moved out to Florence from the US to be with Tyler and this was her first night at her new job.  Not a bad place to move.  She came over throughout the night to check on us.  I told her I’d reach out to Tyler to see if we could all meet up.  This entire encounter elated me because it made me feel like a local.

Regarding the restaurant, it is excellent.  The food, service, outdoor cozy patio.  Totally Tuscan chic. Three out of four of us ordered the pasta that comes with prosciutto and truffles and every single bite was distinctly delicious.

After hitting up our favorite gelato spot, La Carraia, which was conveniently located on our way home and just a few blocks from our flat, we called it a day.  The next morning we were off to enjoy a tour of Tuscan wines while Peter stayed back for work.

I had booked us with Grape Tours for the Super Chianti tour which started at 9:00 am.  This seemed early for wine tasting, but it was the highest reviewed tour so who was I to argue? In addition to ourselves the group comprised of a married couple from Singapore, a couple from North Carolina who were celebrating their 25th wedding anniversary and our tour-guide Matteo.

The tour consisted of two wineries, a lunch at Solo Ciccia in Panzano owned by the famous butcher, Dario Cecchini, and ended in a small village in Chianti named Greve.

Our first winery, Corzano e Paterno was located on a sprawling 150 hector farm.  The winery specializes in wine, of course, but also cheese and olive oil.  To our delight we tried everything.

To begin, Matteo led us around the grounds.  We started in the vineyards where we were allowed to pick and eat grapes right from the vines.  Wine grapes from the vine are delicious, so much better and different than any grapes I’ve purchased at a grocery store.  I hadn’t eaten breakfast so I might have overindulged on grapes.  I formed this conclusion when Matteo abruptly stopped this grape-tasting session while I was essentially underneath a vine shoveling grapes into my mouth.



We next visited the cellar where we learned that Italian wine has to go through vigorous rules and regulations to be appointed DOCG (Denominazione di origine controllata e Garantita).  This is the label to look for if you are seeking wine that guarantees that the strict wine laws of Italy were obeyed.

There are currently 73 regions in Italy with this designation.  In Tuscany there are 18 DOCG regions.  Matteo also taught us about Super Tuscan wines.  The laws for DOCG were made back in the 60′s and called for a yield of up to 30% white grapes in Chianti to make it fruity and diluted.  At the same time French wines were being regarded for sophistication.  This contrast has created a reputation that has plagued Italian wine for a long time.

Then came a winemaker by the name of Marchese Piero Antinori who started to grow international grapes such as Merlot, Cabernet Sauvignon and Syrah in Tuscany. Unconcerned with the DOCG regulations, he just made good wine from good grapes. As a result, Super Tuscan wine was developed to keep up with the ‘Jones’ of France and even New World wines and to chip away at the old stereotypes. This rouge move started to work and in the 80′s Super Tuscan wines began to really flourish.

This movement has also changed some of the strict DOCG guidelines to be less stringent.  Meanwhile IGT was created to govern the Super Tuscan wines while still giving winemakers lots of freedom to create the wine that they want. The designations, politics and business of wine sometimes feels as complicated as the grapes and terroir itself. 

After the cellar tour we were off to taste wine, cheese, and the best olive oil in the world.  Tuscan olive oil is not what I even thought olive oil tastes like.  It should have a different name because it is in a league of its own.  All of us actually drank olive oil out of a little cup and it was like butter.  The following picture is of our group at our first tasting.



Next up was lunch at the famous butcher shop of Dario Cecchini.  He is an 8th generation butcher and considered the “best in the world” at what he does.  He has been asked to open restaurants across the world including, Paris, New York, and France, amongst others, but he chooses to stay at home in Italy.  We had the pleasure of meeting him.



We walked into the shop and were handed a glass of Chianti and invited to walk around the shop to sample meats, cheeses while listening to rock music, specifically AC/DC.

















We were escorted to a different room where we were served delicious meat dish after delicious meat dish.  This included a plate of raw meat.  Becky the brave indulged and reported that it was actually quite tasty.

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Up next was our second tasting at Montecalvi, but first a random picture taken just outside the restaurant.  Could have been fueled by the Chianti at lunch.



Montecalvi is owned by a woman winemaker by the name of Jackie.  She was my favorite of the day.  She lives on her vineyard with her husband and three children.  Her father originally started the business and when he passed, her mother had no interest in continuing the vineyard.  Neither did Jackie, but she felt responsible for her father’s work to stay in the family.

Jackie slowly learned the wine making process and joked that everything had to be explained in laymen’s terms as she was not “scientific.” I was floored.  What a dream life.  Living on a vineyard with your family.  Creating amazing wine. Traveling to promote your wine with a humbleness to your work and pursuit of improvement.  I was in awe.

The winery is just her, her husband, and one other person. They make great wine and even received the DOCG label.  Of the accomplishment she diffused by mentioning that it took “a lot of paperwork.” Seriously so impressive.

One thing I really enjoyed about Jackie was her use of analogies while describing wine making.  ”Using French Oak is like salting a salad, but you want to be careful of over salting.”  She talked about growing vines close together because it will make them stronger because of the need to work harder for sun and water.

She produces three wines and inquired on our favorite after tasting.  I loved her Super Tuscan that is a Merlot/Cab blend.  I asked her the same question and she compared it to asking her which one of her three children was her favorite.  She then described her three children – each one compared to each one of her wines.  ”My Chianti Classico is like my oldest.  Everyone likes her and she is reliably good.”

The following photos are taken on Jackie’s vineyard.




Our tour ended with a quick trip to the capitol of Chianti, Greve, then we were back to Florence.

For dinner that night we went back to the pizza place Peter and I loved so much, O Munaciello.  After the day of wine tasting, butcher shop lunch, and pizza dinner, I wanted to start sprinting around Florence to rid my body of the gluttonous albeit glorious day. Instead we walked for gelato.

The next morning was another early one.  This time to see Michelangelo’s David at 7:30 am before it opened to beat the crowds.  The museum has other works of art, but the David is really what you go to see.  I don’t know how to describe it without sounding trite.  It is  simply a must-see in person.  Pictures do not do it the justice as what it looks and feels like to be in the presence of it.

















That afternoon the ladies checked in for a little retail therapy.  Since we left in July I had done zero shopping because I didn’t really have room in my bag to buy much and shopping is Peter’s least favorite activity.  I bought my first real Italian leather jacket and a pair of boots after being stiff armed by both my Mom and Becky (pictured below).  Becky, in the most matter of fact tone, stated, “I wouldn’t leave here without either of those items if I were you.” Those two are dangerous to shop with.

















After shopping we headed over to Astor, the bar that Tyler owns, to meet up with him and Gabi.  Tyler was the same.  Personality bigger than life and always up to something, but I never could figure out what.  He impressed my Mom and Becky with his fluent Italian.  He was a gracious host as he entertained us with stories and bought us a round of drinks.

We decided to head home after sunset.  We were running out of steam, the trip was winding down, and we had another early morning the next day, which was our last.

Becky and I headed out the next morning to climb the stairs to the top of the Duomo before it opened to beat the crowds.  It was quite an adventure to start the day with a climb 463 steep steps through narrow winding staircases. My claustrophobia set in a couple times.  At the top of the dome just before you walk outside for the view of the city you get to take in Giorgio Vasari’s ‘Last Judgement’ on the ceiling which is mesmerizing in it’s depiction of heaven and hell (the latter linked above).

The following pictures are the views from the top and the stairs going back down.

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The rest of the day stayed super busy.  Peter and my Mom joined us outside the Duomo where we went inside to explore the Basilica Santa Marie del Fiore.  Well, except my Mom because her knees weren’t covered and they wouldn’t let her in.  We strolled through Santa Croce, then enjoyed the Boboli Gardens only before eating one last Italian pizza at O Vesuvios (delicious).

Peter and I then dropped my Mom and Becky back off at the Uffizi Gallery for a tour. They looked exhausted. We looked exhausted. This was the last afternoon of a three week tour of Italy and we were all spent.  We waved good-bye and predicted that they might develop a bit of narcolepsy mid Botticelli viewing at the Uffizi.

Below is a picture taken at the Boboli gardens.



When we reunited after their tour they relayed the fact that they essentially slept walked through the Uffizi. But despite this they wanted to go out for one last dinner before we went our separate ways the next morning.

We went to another favorite of ours in Florence, Osteria Santo Spirito.  My Mom did actually fall asleep while sitting up.  This was a great sign.  This was success! Peter and I had pushed them to the point of exhaustion just before they were leaving.  We had done Italy and we had done it right.

After dinner Becky and my Mom headed home while Peter and I did one last gelato stop at Cantina where I ordered a peanut butter scoop and ate it with just the tiniest bit of sorrow.  My days of eating Florentine gelato were done for now, or maybe it was knowing I had to say good bye to my Mom and my Aunt.  I think it was the double whammy of both situations.

The next morning was even earlier.  We were catching a flight to Munich to relax and unwind at Oktoberfest.

I hugged my Mom and Becky with a heart full of gratitude that they came to join us on our year long journey.  It was a trip of secrets (what happens in Positano….), frustration (luggage blocked walkways) embarrassment (claiming flatulence), laughter (daily) and one that Peter and I will cherish forever.

Thank you Mom and Becky.  We love you both dearly.

As always thanks for reading!



  • Becky Lessley

    Jaime and Peter, thanks for the memories. It was a trip of a lifetime, one that Rosemary and I could never have done without the two of you. The Duomo was my favorite!!! Seeing that painting up close was incredible!!! Why am I so infatuated with “hell”? Perhaps I may be going there one day? I hope not! Love to you both!!!! I promise to get my guest blog done soon.

  • The hell portion of the fresco was mesmerizing. What a fun morning that was. Thank you so much for joining us on our adventure. It was so special to have you both be a part of it. Love you.

  • Rosemary Hodges

    Wow!!!we did a lot in a short amount of time in Florence. No wonder Becky and I were dead on our feet. The tour of the museum came closer to breaking me than almost any other one thing. I remember sitting down at one point and feeling myself start to doze off. I loved our wine picnic at the Michelangelo …a great kickoff experience. How about the guy who took our picture at the Duomo? So hysterical. Both you and him. The wine tour was nothing but top drawer and the people were such a great mix. Gosh I want to be back there doing all those fun things with people I love. Florence was great. Thanks for recapturing it all for me to enjoy again and again.