A Letter from our Traveler: An 11-Day Cultural Pilgrimage Through Italy’s Heart and Soul with Eskapas Travel
There is a moment, somewhere between the second glass of Chianti and the first glimpse of the Florentine sunset, when Italy stops being a place you are visiting and becomes a feeling you are carrying inside you.
I had dreamed of Italy for years—the way you dream about a first love or a reunion with an old friend. But dreaming, I discovered, is pretty different from actually standing in the shadow of St. Peter’s Basilica, or watching the morning sun set the canals of Venice on fire with light. When I finally decided to stop dreaming and start packing, I chose to travel with Eskapas Travel on their 11-day “Italian Discovery” tour. It promised to take me from the ancient grandeur of Rome to the sun-drenched cliffs of Sorrento, with countless treasures squeezed in between.
What followed wasn’t just some checklist tour of Italy’s greatest hits. It was a deep, immersive experience that engaged all my senses and left me forever changed.
Day 1: Benvenuti a Roma! – The Eternal City at Dusk
My heart was doing jumping jacks as the wheels touched down at Rome’s Fiumicino Airport. Stepping into the arrivals hall, I was instantly put at ease by the sight of an Eskapas rep holding a sign with my name. Such a small thing, but it immediately dissolved that “I’m alone in a foreign country” anxiety. The private transfer whisked me through the wonderfully chaotic Roman traffic to my hotel right in the heart of the city.
After settling in and freshening up, I met my fellow travelers for our first group experience: the Rome by Night Guided Walk. As dusk settled in and the tourist crowds finally thinned out, the Eternal City showed us a more intimate, romantic side. Our local guide led us from the bustling Largo del Tritone through narrow cobblestone streets that kept opening suddenly onto these beautifully lit piazzas. The Trevi Fountain sparkled under spotlights, its waters shimmering like liquid silver. Following tradition, I tossed a coin over my left shoulder—ensuring, they say, that I’ll eventually return to Rome.
The tour ended near the Colosseum, its ancient arches dramatically lit against the night sky. Standing there, I could almost hear the echoes of gladiators and the roar of ancient crowds. It was my first taste of how Eskapas blends structured experiences with moments of personal discovery—the tour ended there, but the night was mine to wander, to linger, to begin falling in love.
Day 2: Medieval Marvels – Rome to Assisi, Siena, and Florence
The next morning, we gathered before dawn, boarding a deluxe coach that would become our home-on-wheels for the next ten days. Our tour guide, a passionate Italian with an encyclopedic knowledge of his country’s history, welcomed us aboard with a warm “Benvenuti!” and outlined the day’s adventure.
Our first stop was Assisi, this tranquil hilltop town that feels frozen in time. Encircled by ancient stone walls, Assisi is where St. Francis was born, and its spiritual essence just seeps into every cobblestone alley and quiet piazza. We had time to explore at our own pace—a format I came to really appreciate throughout the journey. I wandered up to the magnificent Basilica of St. Francis, where Giotto’s frescoes depict the saint’s life in these vibrant, soulful scenes that transcend language and belief.
After a simple lunch of truffle pasta at a local trattoria, we rejoined the coach and continued to Siena. A UNESCO World Heritage Site, Siena is dominated by its magnificent shell-shaped Piazza del Campo, one of Europe’s greatest medieval squares. Our guide shared stories of the famous Palio horse race, a centuries-old tradition that still sees the city’s neighborhoods compete with fierce, friendly rivalry twice each summer.
As the golden hour approached, we departed for Florence, the Cradle of the Renaissance. Arriving as the city’s lights began to twinkle, we checked into our hotel and shared our first group dinner together—a lively affair of pasta, wine, and the happy exhaustion of travelers who’ve already collected a lifetime of memories in a single day.
Day 3: Florence – The Cradle of the Renaissance
Waking up in Florence feels like waking up inside a living museum. After a hearty breakfast, we set out on foot to explore the city that gave birth to the Renaissance. Our guide led us to the Piazza del Duomo, where the magnificent Cathedral of Santa Maria del Fiore dominates the skyline with Brunelleschi’s iconic dome—an architectural marvel that still inspires awe more than 500 years later. We admired Giotto’s elegant Bell Tower and the Baptistery’s bronze doors, which Michelangelo himself called the “Gates of Paradise.”
From there, we wound our way through narrow streets to the Piazza della Signoria, an open-air sculpture gallery featuring the Palazzo Vecchio and a copy of Michelangelo’s David (the original lives in the Accademia Gallery). The Basilica of Santa Croce, final resting place of Michelangelo, Galileo, and Machiavelli, offered a moment of quiet reverence.
For lunch, Eskapas had arranged a special treat: a meal at a typical Tuscan restaurant in Piazza Santa Croce. Sitting at an outdoor table, savoring handmade pappardelle with wild boar ragu and watching Florentine life unfold around me, I felt this profound connection to place that no guidebook could ever provide.
The afternoon was free for personal exploration. While some in our group opted for the optional excursion to Pisa to see the Leaning Tower, I chose to get lost in the Oltrarno neighborhood, browsing artisan workshops and discovering a tiny gelateria that served the best pistachio gelato of my life.
Day 4: Porticoes, Piazzas, and Culinary Delights – Bologna to Venice
Leaving Florence behind, we journeyed north to Bologna, a city often overlooked by first-time visitors but absolutely beloved by those in the know. Known as “La Dotta” (the Learned) for its ancient university, “La Grassa” (the Fat) for its incredible food, and “La Rossa” (the Red) for its terracotta buildings, Bologna immediately charmed me with its elegant porticos—covered walkways that stretch for over 38 kilometers through the city.
From the bustling Piazza Maggiore to the unfinished facade of the Basilica of San Petronio, Bologna just exuded this sophisticated, lived-in authenticity. Being a total food lover, I couldn’t resist a quick lunch of tortellini in brodo—tiny, hand-filled pasta parcels swimming in rich capon broth, a dish that tastes like centuries of tradition.
In the afternoon, we made a brief stop in Padua to visit the magnificent Basilica of St. Anthony, one of the most important pilgrimage sites in the Catholic world. Then, with anticipation building, we continued toward Venice.
Arriving in the late afternoon, we checked into our hotel in Mestre (the mainland gateway to Venice) and enjoyed dinner together, dreaming of the watery wonderland that awaited us in the morning.
Day 5: Venice – The Magic of the Serenissima
No amount of photographs or film can truly prepare you for Venice. Stepping off the vaporetto (water bus) into St. Mark’s Square felt like stepping onto a movie set. The Basilica’s Byzantine domes gleamed in the morning light, the Campanile stretched toward a perfect blue sky, and pigeons scattered across the paving stones in beautifully chaotic fashion.
Our guided tour took us inside St. Mark’s Basilica, where golden mosaics cover every surface, telling biblical stories in shimmering detail. We crossed the Bridge of Sighs—so named, our guide explained, for the sighs of prisoners catching their last glimpse of beautiful Venice before being led to their cells—and admired the ornate Gothic architecture of the Doge’s Palace.
The afternoon was gloriously free. I did what every visitor to Venice absolutely must do: I got lost. Wandering away from the tourist crowds, I discovered quiet canals where laundry fluttered from windows, where gondoliers tuned their voices in practice, where the real Venice—not the postcard version—revealed itself in fragments. I eventually found my way to a tiny osteria where I enjoyed squid ink pasta and a glass of local wine while watching the light dance on the water.
Day 6: Tuscany’s Wine Region – Montepulciano
Leaving Venice behind, we journeyed south into the heart of Tuscany, bound for the hilltop town of Montepulciano. This was the day I had been waiting for—a chance to experience the region’s legendary wine country firsthand.
Perched high above rolling hills carpeted with vineyards and olive groves, Montepulciano is the very picture of Tuscan perfection. Its Renaissance palaces, ancient churches, and winding streets all lead to the magnificent Piazza Grande, which has served as a backdrop for films including the Twilight saga (the town stood in for Volterra in “New Moon”).
But the highlight of the day was definitely our included lunch at a local winery. Seated at a long wooden table overlooking the Val d’Orcia, we sampled the region’s famous Vino Nobile while our hosts explained the winemaking process with such obvious passion. Course after course arrived—crostini, cured meats, pecorino cheese, pici pasta with garlic and tomato, and finally, simple yet perfect cantucci with Vin Santo for dipping. This wasn’t just lunch; it was communion with the land and its traditions.
Returning to Rome in the evening, I felt this strange sensation of coming home to a city I had only left days before. The Eternal City had already become a touchstone, a familiar presence welcoming me back.
Day 7: Rome – The Vatican and Ancient Wonders
Our second day in Rome was devoted to its two greatest treasures: the Vatican City and the archaeological wonders of the ancient empire.
Entering the Vatican Museums, I was immediately overwhelmed by the sheer abundance of beauty. Gallery after gallery housed masterpieces collected by popes over centuries—ancient sculptures, Renaissance tapestries, and frescoed ceilings that seemed to defy gravity and imagination. The experience culminated in the Sistine Chapel, where Michelangelo’s Genesis and Last Judgment surround you in this silent, sacred symphony. Photography is forbidden, which actually forces you to just be present, to absorb the genius without the mediation of a screen.
St. Peter’s Basilica, the largest church in Christendom, inspired a different kind of awe—one of scale and grandeur. Bernini’s baldachin soars above the papal altar, and Michelangelo’s Pietà, sculpted when the artist was just 24, moved me to tears with its tender depiction of Mary cradling her son.
After a break for lunch, we crossed the Tiber to explore ancient Rome. The Colosseum rose before us, its damaged facade belying the incredible engineering within. Standing on the arena floor, I could almost hear the roar of 50,000 spectators. Nearby, the Roman Forum spread across the valley between the Palatine and Capitoline Hills, its ruins hinting at the grandeur of the empire’s political and social heart.
That evening, exhausted but exhilarated, I dined al fresco in Trastevere, watching the neighborhood come alive with the laughter and conversation of Romans doing what they do best: just enjoying life’s simple pleasures.
Day 8: The Scenic Road to Sorrento
Leaving Rome behind once more, we traced the route south toward the legendary Amalfi Coast. Our destination was Sorrento, a charming town perched on cliffs overlooking the Bay of Naples.
The journey itself was breathtaking. As we wound along the coast road, each turn revealed a new vista—deep blue sea meeting rugged cliffs, villages clinging impossibly to steep slopes, terraced lemon groves scenting the air with citrus. We arrived in Sorrento in the late afternoon, just in time to watch the sunset paint the sky in shades of orange and pink from a waterfront café.
Sorrento’s historic center charmed me immediately. Narrow streets lined with shops selling limoncello, ceramics, and leather goods just begged to be explored. That evening, we gathered for dinner at our hotel, sharing stories of the journey so far and anticipating the adventures still to come.
Day 9: The Enchanted Isle of Capri
If Sorrento is charming, Capri is positively glamorous. A short hydrofoil ride across the sparkling Tyrrhenian Sea delivered us to the island’s main port, Marina Grande, where we transferred by funicular up to the town of Capri.
From there, we took an open-top bus along this hair-raising road to Anacapri, the island’s quieter, higher town. The views from the Gardens of Augustus were nothing short of spectacular—cliffs plunging into emerald water, the famous Faraglioni rocks rising from the sea like ancient sentinels.
I spent the afternoon wandering the whitewashed streets, peeking into chic boutiques and discovering hidden viewpoints. Some in our group took a chairlift to the top of Monte Solaro for panoramic views across the Bay of Naples. Others found a quiet spot by the water and just soaked up the sun. Capri has a way of making even the most industrious traveler slow down, breathe deeply, and appreciate the moment.
Returning to Sorrento in the evening, I joined new friends for a final dinner on the coast—fresh seafood, cold white wine, and the kind of easy conversation that only develops after days of shared adventure.
Day 10: Pompeii – A Journey Through Time
Our final full day of touring brought us face to face with one of the world’s most extraordinary archaeological sites: Pompeii.
Walking through the ruins of this Roman city, frozen in time by the catastrophic eruption of Mount Vesuvius in 79 AD, was a profoundly moving experience. Our guide brought the ancient city to life, pointing out details I would have completely missed—the ruts worn into stone streets by chariot wheels, the faded frescoes still visible on villa walls, the poignant plaster casts of victims captured in their final moments.
We saw the forum, the baths, the brothel with its explicit frescoes, and the lavish Villa of the Mysteries with its stunningly preserved Dionysiac frieze. Pompeii isn’t just a collection of ruins; it’s a snapshot of daily life in the Roman Empire, preserved under volcanic ash for nearly two millennia.
After a final included lunch, we made the journey back to Rome, arriving in the evening with mixed emotions. The adventure was nearly over, but the memories would last a lifetime.
Day 11: Arrivederci, Italia!
On my final morning, I woke early to watch the sun rise over Rome one last time. I walked to a nearby café for a cappuccino and cornetto, just savoring the simple pleasure of being present in this extraordinary city.
Then came the difficult task of packing, of folding eleven days of memories into a suitcase. The private transfer arrived promptly, whisking me back to Fiumicino Airport with the same efficiency that had marked my arrival. As the plane lifted off, I pressed my face to the window, watching Italy shrink to a green and gold smudge on the horizon, and whispered a promise: I will return.
The Eskapas Difference: Why This Journey Worked
Looking back on my eleven days with Eskapas Travel, I totally get why this particular tour gets such consistently great reviews from travelers. The itinerary strikes that perfect balance between seeing everything and actually having time to soak it all in. We visited extraordinary places, sure, but we also had time to absorb them, to wander off the beaten path, to make our own discoveries.
The guides were exceptional—knowledgeable, passionate, and genuinely caring. They anticipated needs, solved problems before they even came up, and shared their love for Italy in ways that were absolutely contagious. And our bus driver? The guy navigated impossibly narrow streets with such calm professionalism, earning our gratitude and admiration every single day.
Accommodations were comfortable and well-located, giving us welcome havens after long days of exploration. And the included meals—especially the Tuscan lunch and the winery experience—offered authentic tastes of regional cuisine that went way beyond typical tourist fare.
But maybe most importantly, Eskapas created an environment where connections could really flourish—connections to place, to history, to culture, and to fellow travelers who started as strangers and ended as friends. Our group of forty, guided with skill and warmth, became this temporary little family, sharing meals, laughter, and the profound experience of discovering Italy together.
Practical Tips for Your Own Italian Discovery
If this journey sounds like your kind of adventure, here are a few things I learned along the way:
Pack comfortable walking shoes. Seriously. The itinerary involves a ton of walking, from cobblestone streets to archaeological sites. Your feet will absolutely thank you.
Bring a refillable water bottle. Italy’s public fountains offer free, cold, perfectly safe drinking water. Staying hydrated while reducing plastic waste? Win-win.
Learn a few Italian phrases. Even a simple “buongiorno” or “grazie” will get you warm smiles and sometimes more enthusiastic conversation than you expected.
Embrace the optional excursions. While the included itinerary is solid, excursions like the trip to Pisa or a gondola ride in Venice add so much richness to the experience.
Leave room for spontaneity. Some of my most cherished memories came from totally unplanned moments—a discovered alley, a recommended restaurant, an impromptu chat with a local artisan.
Final Thoughts
Italy, they say, is a state of mind. After eleven days traveling from Rome to Sorrento, through medieval hill towns and Renaissance cities, across wine country and along dramatic coastlines, I finally get what that means. Italy just seeps into you—through the food you eat, the art you absorb, the history you walk through, the people you meet.
Eskapas Travel provided the framework, the expertise, and the support that made this journey possible. But the magic—the moments of transcendence, the connections, the transformation—that belonged to Italy itself. And to me, forever changed by the experience.
Arrivederci, Italia. Until we meet again.
Cathy, November 2025
Have you dreamed of an Italian adventure? Got questions about traveling with Eskapas or visiting any of these incredible destinations? Drop your thoughts in the comments below—I’d love to help you plan your own journey into the heart and soul of Italy.
