Jessica Osborn
- Jan 8, 2020
- 6 min read

Memorable Moments in Venice, Siena and Florence

When I “accidentally” booked a non-refundable hotel in Venice, I knew we had to go. My husband agreed without too much of a fuss — so, kicking and screaming we went, leaving our 2 year old daughter in the loving care of “the village” — our neighbors, Gigi, G-pops and brother and sister in-law.

Here are the top 10 most memorable moments from our 9 days in Venice, Siena, Cinque Terre, Florence and the surrounding Tuscany region.

1. Venice boat getaway

Our first day in Italy kicked-off early because of jet lag. I witnessed the city of Venice waking up at sunrise, preparing for the thousands of tourists who would be stepping onto the small, sinking island. Little did I know and with a little stretch to my imagination, we would be making our “great escape.”

Right after guarding my breakfast from the pigeons who didn’t hesitate to swipe my chocolate hazelnut torta, I reached out to the concierge to help us with the logistical dilemma of “how do we get to Murano Island?” We were in luck because he “had a friend” who could give us a private ride to the island to their family’s glass company with “no obligation to buy.” And it just so happened that his friend was waiting outside to deliver us to the boat where he would make the hand-off.

As promised, Leonardo DiCaprio’s Italian doppelganger met us at our hotel and led us as we quickly doubled our pace to keep up, ducking and weaving through the narrow streets and over canals to the Grand Canal just as the wooden Italian speedboat arrived. We jumped onto the boat, landing onto the plush white leather seats and just like the “Italian Job,” we zipped away — dodging the arriving ferry boats crammed with tourists — leaving Venice behind.

2. Act 3 of Madame Butterfly

Venice’s Teatro La Fenice is arguably one of the most beautiful opera houses in the world — every detail laced in gold, plush red velvet seats, a blooming chandelier draped in jewels anchors the blue ceiling with the depth of the sky. Like being inside a jewelry box and candy for my eyes to devour.

We were able to purchase discounted tickets an hour before the show to see the opening night of our first opera, Giacomo Puccini’s Madame Butterfly. If you’re not familiar, it is a story about a geisha in Japan known as Butterfly who weds an American navy officer, Pinkerton who doesn’t take the marriage very seriously. He leaves her behind with a family who disowns her for converting to Christianity.

There is a moment in the 3rd act when Pinkerton learns of his child and identifies that he is a “wretch” for playing with her heart and realizes she would have to give up her child so he can have a better life. The moment is powerful as the music bursts into a crescendo and the singers belt out the loss, regret and sympathy in a passionate ensemble of separate dialogues. I was overwhelmed with emotion and my heart ached seeing a Mother in pain and I missed my sweet Noelle.

Teatro La Fenice

3. Intimate dinner at a Palazzo all to ourselves

On our last night in Venice we splurged on dinner at a former palazzo. Built by the Coccina family on the Grand Canal in the 16th century and revitalized in 2011 as the stunning AMAN luxury hotel. The experience was almost eerie as we seemed to be the only people in the hotel. We creeped up the narrow staircase, tea candles on each step lead the way as we followed the noise of the piano playing a romantic and haunting melody.

The second floor dining room featured frescoes, tall mirrors and chandeliers as extravagant as Versailles. The enchanting atmosphere made for a romantic night for us to enjoy each other’s company. We took the time to savor the melt in your mouth burrata with candied figs and the deconstructed tiramisu with coffee ice cream and cocoa snow. We drank to good health next to the grand marble fireplace as the piano played for us all night in what we imagined to be a palace all to ourselves.

4. The vibe on Fondamenta dei Ormesini Street

With the thousands of food options and specialties in Venice, we decided to sign up for a food tour to help navigate the cicchetti culture – the Venetian version of tapas. At the end of the tour, our guide recommended a visit to the Cannaregio neighborhood in Venice. It only makes sense to trust a local’s recommendation so later that night, we went.

The Cannaregio neighborhood is known for the 16thcentury Jewish Ghetto. It is now a popular local hangout with casual canal-side restaurants and bars. We matched the surrounding conversations in volume and laughter and as the locals do, dangled our feet along the canal with a delicious locally priced wine from Timon in hand. On Fondamenta dei Ormesini Street in the Cannaregio neighborhood, the love, laughter and camaraderie is tangible.

One of our favorite cicchetti spots on our food tour

5. Getting stuck in Montalcino

We hired an Alfa Romero to explore more of the Tuscan countryside, to take the opportunity to visit the renowned Brunello di Montalcino wineries. At some point the GPS started recalculating on our way to Ciacci Piccolomini. Since technology was failing us, our only option was to navigate with instinct and our bad sense of direction.

We started winding up a small hill town in hopes we would find the winery on the other side. We quickly realized it was not the right direction when we got stuck on a narrow street with no room to turn around down the hill. Miles inched the car forward and backwards. All at once I think the entire town raced out of their shops and homes waving their hands and yelling in Italian, “FERMO!”

We all worked together to move a couple boulders and other obstacles until finally we were able to turn the car around. Unfortunately we missed the cellar tour which included meeting their domestic wolves that guard the property; however, we were able to pass the time with a complimentary glass of wine in their olive grove until we could rejoin the group in the tasting room.

6. Cellar tour in Siena

After a long day in Tuscany, we decompressed at a cozy restaurant, Osteria le Logge. Wine lovers can ask to visit the wine cellar nearby. Housed in a tunnel of Etruscan origin, each floor led us down into ancient history with dwellings dating back to 500 BC. We geeked out over the vintages, rare labels and stories the sommelier shared about the wines he’s poured.

7. Contrade Palio Race

Siena was once a prosperous city, competing on the same level of civilization and grandeur as Florence. To our benefit, the black plaque decimated the city, keeping the medieval architecture frozen in time. Now, every summer as it has done since the 6th century, Siena celebrates the seventeen remaining neighborhoods “Contrade” that make up the city in a passionate horse race on the Piazza del Campo. Each Contrade displays their own flag and mascot like the Eagle, Snail, Unicorn, Dragon, etc.

We were staying at Palazzo Ravizza in the Panther Contrade the night they were running their own annual Palio race. Stacks of hay lined the corners of the winding streets. You could hear the thunder of the sleds on wheels as they raced down the cobblestones. We cheered along with the locals as the kids ran after the sleds to keep up with the racers and to give a final push to the finish line. We delighted in their laughter echoing the ancient city walls.

8. Vespa Tour

Our introduction to Florence was with the Vespa tour of a lifetime. I hopped on the back of our tour guide Lucca’s bike and held on for dear life as we zipped through the narrow streets of Florence, dodging people like an action scene from a 007 movie.

We left the buzzing city and winded our way through the Tuscan countryside. We made a couple stops in Fiesole and Piazzale Michelangelo for impressive views of Florence. Lucca treated us to ice cream before we continued on the tour. The ride was truly authentic with the smell of Lucca’s heavy cologne and his pony tail tickling my nose. We rode at top speed and the rest of the group had trouble keeping up with us – in fact we actually lost the group at one point. Lucca’s Vespa ride was peaceful and thrilling, making our turns with the sun at it’s perfect height to show off the colors and textures of the Chianti wine striped hills.

As the sun set, we stopped at a small village near Greve in Chianti for aperitivo time — my favorite time in Italy. Time and place was at a perfect harmony and I didn’t want to be anywhere else but in that moment in time.

Don’t stop exploring!

Jessica

Here are more photos from our memorable trip.