The Ultimate Mother-Daughter Journey to Italy: A Tale of Healing, Adventure, and Self-Discovery
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2021 was a year that tested me in unimaginable ways. My daughter’s incarceration was a heartbreaking ordeal that left me grappling with a void I couldn’t fill. Christmas arrived, but it wasn’t the same. The absence of her laughter, her presence—it was like a dark cloud hanging over the season. For the first time, I truly understood the depth of pain that makes the holidays so hard for so many.
Amid that difficult time, my mom and I began talking—dreaming, really—about taking a trip to Italy. We didn’t just mention it casually; we romanticized it. We envisioned the gondolas of Venice, the rolling hills of Tuscany, the grandeur of Rome. It felt like an escape we desperately needed, though it seemed so far out of reach.
But that Christmas, sitting together in the glow of the tree’s lights, something shifted. I realized that waiting for “the right time” was no longer an option. Life was messy and unpredictable, and if I didn’t take this leap now, when would I? I opened my laptop, started researching, and found an 11-day guided tour covering Venice, Florence, Rome, Pompeii, Sorrento, Capri, and more. It was perfect.
I looked at my mom and said, “I’m not leaving until we book it.” And we did.
A Journey Born of Loss and Love
On September 13, 2022, we boarded a plane for the adventure of a lifetime—a celebration of my mom’s last year in her 60s and a much-needed reprieve from the heaviness of life.
Leading up to the trip, we’d call each other daily, excitedly planning every detail. We debated what to pack, researched the weather, and laughed about our shoe choices (because, let’s be honest, it’s always about the shoes!). But no amount of planning could have prepared us for the transformative experience awaiting us.
First things first - Packing!
Packing Must-haves for Italy:
Layers! Warm days, cool nights—be ready for both. My go-to sweater was this one, and it comes in several colors!
Mix-and-match pieces. One carry-on bag for the whole trip? Yes, it’s possible.
A mini umbrella. Be prepared for pop-up showers. (I took this one.)
Portable power bank. Your phone will thank you. (my favorite one here!)
Comfortable walking shoes. Seriously—so. much. Walking. I wore these as my daily sneaker. I also loved these sandals for those dress-up occasions which were still very comfortable (I walked all day in Florence in these with no issues).
Cross-body purse with RFID protection. This is my favorite purse for traveling! It’s small enough that it’s not bulky and fits everything I need.
My favorite jeans! I love these! They can be dressed up or down. Super classic.
A classic skort that can be dressed up or down and mix-and-match with anything. I wore these a lot!
Travel journal. This is a must-have! If you’re like me, time can blur the details. I take mine on every trip!
Things I packed and never used (they only took up valuable space!):
Excess clothing. Trust me when I say that no one cares what you wear! It’s not fashion week. Comfort is more important, so pack things you can mix and match that are comfortable. Think capsule wardrobe.
Refillable water bottle. There are plenty of places to get water.
Extra shoes. They took up so much space and I only wore the two pairs I linked above.
Multiple swim suites. For this trip, they were not needed. One would have been fine.
Backpack. My purse was enough for me.
First Stop, Venice: A Fairytale on Water
We arrived in Venice via water taxi—a magical entrance to a city that felt straight out of a storybook. The turquoise canals, colorful facades, and iconic gondolas took our breath away. At Villa Mabapa, a charming 80-year-old hotel overlooking the Venice Lagoon, we settled in, pinching ourselves. “Can you believe we’re really here?” we kept asking each other.
Our first dinner was an Italian feast of wine and authentic cuisine with our tour group—a lively bunch we’d grow close to over the next 10 days.
The next day, we explored Murano, marveling at the art of glassblowing, then wandered through Venice’s winding streets. We savored bruschetta and pizza at Rosapomodoro, a hidden gem, and glided through the canals on a gondola, serenaded by a singing gondolier.
As the sun dipped below the horizon, we walked along the lagoon, sipping Aperol spritzes and soaking in the beauty of our first day in Italy.
Tuscany & Pisa: A Feast for the Senses
The cool morning air greeted us as we took a ferry off the island of Venice and boarded our tour bus, heading deep into the Tuscan countryside. On our way to Florence, we stopped at Fattoria Il Poggio, a winery and olive farm that felt like it was straight out of a storybook.
We wandered through vineyards and olive groves, learning about the art of winemaking, olive oil, and balsamic vinegar. Then, we gathered for a family-style meal paired with tastings of their wines. Let’s just say the wine loosened everyone up, and soon the group was laughing like old friends.
With a little buzz, I couldn’t resist ordering wine, olive oil, and vinegar to be shipped home. No regrets—it was like bringing a piece of Italy back with me.
Next, we made a quick stop in Pisa to see the famous leaning tower. And yes, we took the obligatory “holding up the tower” photos—it’s a rite of passage!
Florence: A Celebration of Beauty and Love
Florence stole my heart. It’s a city of charm, art, and history, and we were lucky enough to be there for Mom’s 69th birthday.
Walking through the city, we turned a corner and saw it: Florence’s Duomo. The sight stopped us in our tracks, tears welling in our eyes. It was a moment of awe and gratitude, standing before something so magnificent, sharing it with someone I loved so deeply.
We spent the day wandering leather shops, buying art from local painters, and treating ourselves to jewelry—something rare for my selfless mom, and I was proud of her for doing it! Later, we took a pasta-making class, the one thing she wanted to do while in Italy! We had the best instructor who made it so much fun and the best classmates. Everyone was celebrating mom’s birthday with us! We laughed so much, then feasted on our creations with plenty of wine to toast the occasion.
That evening, at a Chianti winery, our group serenaded Mom with “Happy Birthday” as she was presented with a cake adorned with sparklers. She was embarrassed but beaming, and I couldn’t have been prouder to celebrate the woman who has been my rock through life’s storms. Seeing her joy made my heart so full. It was, without question, the best day of the trip.
Rome: Walking Through History
Rome was overwhelming in the best way—a living museum of ancient wonders. From the Roman Forum to the Colosseum, each site left us in awe of the history beneath our feet.
When we arrived at Vatican City, we toured the Sistine Chapel and St. Peter’s Basilica, marveling at Michelangelo’s artistry. Knowing he was only 30 years old when he began painting the chapel reminded me that it’s never too early—or too late—to chase greatness. He wasn’t even a painter! He was a sculptor! Talk about having self-confidence and going for it!
We ended our Roman adventure with a whirlwind tour of the Trevi Fountain, the Pantheon, and the Spanish Steps, though the chaotic cab ride through the city’s narrow streets was an adventure in itself! (Real-life Mario Cart, no joke!)
Sorrento: A View to Remember
We checked into The Towers Hotel in Sorrento and the moment we walked into our room, we were struck by the beauty of the place.
Our room on the second floor had floor-to-ceiling windows that opened onto a view of the Bay of Naples. Just below, the beach stretched out, and the sound of waves filled the air.
Standing together in the window, Mom and I were initially quiet, letting the moment sink in. The water shimmered in the fading light, and the scent of the sea drifted through the open windows. One of us finally spoke, sharing how much we had enjoyed the trip and how grateful we were—not just for the places we had seen, but for sharing them.
That evening, we sat on the beach and talked about life. We opened up about the weight we were carrying—my daughter’s incarceration and the impact it had on all of us. There was sadness in the conversation but also hope.
“I hope someday I can take a trip like this with her,” I said. Mom nodded, her hand resting on mine. “She’ll get through this,” she said. “And when she does, you’ll have your adventure together.”
Even now, three years later, I still long for that moment. I dream of standing in a place like Sorrento with my daughter by my side, sharing the view and the gratitude that filled me then.
Capri: A Moment of Clarity
The island of Capri was the crown jewel of our journey. From the chairlift ride to Anacapri’s summit to a boat tour around the island’s stunning cliffs, every moment felt like a dream. It was a clear, sunny day and was perfect for sipping Limocello and eating lemon cookies (mom’s favorite).
Sitting atop the island, looking out over the shimmering Bay of Naples, I felt something shift within me. For the first time in years, I allowed myself to breathe, to feel joy untethered from life’s struggles. It was a moment of clarity, of realizing that life’s messy parts don’t define us—they’re just chapters in a much larger story. Without the messy parts, I don’t think we are able to truly enjoy the good parts.
Lessons from Italy
This trip wasn’t just about seeing beautiful places but about rediscovering ourselves. For my mom, it was a rare chance to spoil herself. For me, it was a reminder that I can’t pour from an empty cup.
We left Italy with full hearts, cherished memories, and a newfound resolve to say yes to life’s adventures. Because here’s the truth: life is short. Don’t wait. Book the trip. Take the chance. Say yes to the things that make your heart sing.
Also, NEVER tell yourself “I can’t!”, because you absolutely can! If Michelangelo can do it at 30 with no experience and go down in history as one of the greatest and most influential of all Renaissance figures, then why can’t you go for it?
So here’s my promise to myself—and to you: I will never again hesitate to live boldly, to love deeply, and to celebrate the moments that matter most.
Take the trip. You’ll never regret it, Babe!
