Taste of Tuscany and Rome: Exploring Italy with Two Travel Gurus
In March 2025, 41 travelers— including Sugarmill Pond residents Sandra Booher, Tanya Ellis, and Micah Ellis—set off on a 14-day journey through Italy with Two Travel Gurus. What began as a 3-day pre-tour in Rome turned into an unforgettable adventure through Tuscany and Bologna. Experiencing Rome during the 25th Jubilee Year made it especially meaningful for our Catholic travelers. With a perfectly planned itinerary and the freedom to explore independently while breaking away from the group, this trip struck the ideal balance of structure and spontaneity.
March 1–2: Arrival in Rome
The pre-tour group departed the U.S. on March 1st, arriving in Rome on the evening of March 2nd. After settling into Hotel Massimo D’Azeglio—an elegant, centrally located property that made sightseeing a breeze—we were greeted by our local travel director and treated to a cozy welcome dinner at the hotel.
The pre-tour group departed the U.S. on March 1st, arriving in Rome on the evening of March 2nd. After settling into Hotel Massimo D’Azeglio—an elegant, centrally located property that made sightseeing a breeze—we were greeted by our local travel director and treated to a cozy welcome dinner at the hotel.
March 3: A Catholic’s Dream Day
We started the day at a relaxed pace before heading into the heart of Rome. Some travelers branched off to explore the Colosseum on their own, while the rest joined a guided city tour. The highlight came in the afternoon with a private 25th Jubilee Tour of the three major Papal Basilicas: St. John Lateran, St. Mary Major, and St. Paul Outside the Walls.
We started the day at a relaxed pace before heading into the heart of Rome. Some travelers branched off to explore the Colosseum on their own, while the rest joined a guided city tour. The highlight came in the afternoon with a private 25th Jubilee Tour of the three major Papal Basilicas: St. John Lateran, St. Mary Major, and St. Paul Outside the Walls.
We walked through the Holy Doors—a privilege offered only during Jubilee years—and even climbed the Holy Stairs (Scala Sancta), the same steps Jesus walked up on the day He was condemned. As Catholics, it was humbling, sacred, and unforgettable.
March 4: Behind the Vatican Walls and a Taste of Rome
In the morning, we joined “What a Life Tours” for a VIP skip-the-line Vatican experience. The guides led us through the Vatican Museums, the Sistine Chapel, and St. Peter’s Basilica—then took us to exclusive areas including the papal apartments and the Kiss Room, where pilgrims once paid homage to the Pope.
In the morning, we joined “What a Life Tours” for a VIP skip-the-line Vatican experience. The guides led us through the Vatican Museums, the Sistine Chapel, and St. Peter’s Basilica—then took us to exclusive areas including the papal apartments and the Kiss Room, where pilgrims once paid homage to the Pope.
That night, we wrapped up our Rome experience with a fun, flavorful Trastevere Walking Food Tour hosted by Secret Food Tours. What an awesome treat! Wine, pasta, cheese, dessert, laughter—it was the perfect sendoff. If you haven’t visited this off-the-beaten-path area of Rome, you want to!
March 5: Tuscany, Here We Come
We boarded our luxury coach and headed north to Montecatini Terme, a spa town that would serve as our home base in Tuscany. At Hotel Ercolini & Savi, we reunited with the rest of our group, who flew in. Our new tour director, Guillo, welcomed us with warmth and energy, and we enjoyed a group dinner to kick off the next phase of the trip.
We boarded our luxury coach and headed north to Montecatini Terme, a spa town that would serve as our home base in Tuscany. At Hotel Ercolini & Savi, we reunited with the rest of our group, who flew in. Our new tour director, Guillo, welcomed us with warmth and energy, and we enjoyed a group dinner to kick off the next phase of the trip.
March 6: Lucca, Legends, and Tuscan Wine
Our first Tuscan day took us to Lucca, a charming city enclosed by Renaissance-era walls, followed by Borgo a Mozzano and the famous Devil’s Bridge (Ponte del Diavolo). We learned about the Gothic Line and WWII history at the Museum of Liberation, then capped off the day with a wine tasting at a scenic vineyard.
Our first Tuscan day took us to Lucca, a charming city enclosed by Renaissance-era walls, followed by Borgo a Mozzano and the famous Devil’s Bridge (Ponte del Diavolo). We learned about the Gothic Line and WWII history at the Museum of Liberation, then capped off the day with a wine tasting at a scenic vineyard.
March 7: Florence and Leather Treasures
We headed to Florence via train, where the art, architecture, and atmosphere swept us off our feet. After a guided tour of the city’s highlights, many of us bought beautiful leather goods from a local artisan shop—authentic, well-priced, and unforgettable keepsakes.
We headed to Florence via train, where the art, architecture, and atmosphere swept us off our feet. After a guided tour of the city’s highlights, many of us bought beautiful leather goods from a local artisan shop—authentic, well-priced, and unforgettable keepsakes.
We visited the gothic style church, Santa Croce, where the famous Michael Angelo was buried. Alongside him are other notable burials.
March 8: Siena’s Medieval Magic
What a wonderful surprise! We wandered Siena’s narrow Gothic streets, learned about the famous Palio horse race, and felt the pride of its 17 contrade (neighborhoods), each with its own flag and history.
What a wonderful surprise! We wandered Siena’s narrow Gothic streets, learned about the famous Palio horse race, and felt the pride of its 17 contrade (neighborhoods), each with its own flag and history.
In Piazza del Campo, the heart of the city, we imagined the energy of race day and admired the stunning Siena Cathedral’s marble detail. With postcard views, cozy cafés, and quiet piazzas, Siena felt like a living storybook. If it’s not on your bucket list yet—it should be.
March 9: Pisa and Pizza
Pisa brought plenty of laughs and must-have photos at the Leaning Tower—but it surprised us with so much more. We stepped inside the stunning Cathedral of Santa Maria Assunta and the Baptistery, where the architecture and acoustics were truly awe-inspiring. With time to shop, snack, and explore the surrounding piazzas, we discovered Pisa isn’t just a quick photo stop—it’s a fun, fascinating place worth savoring.
Pisa brought plenty of laughs and must-have photos at the Leaning Tower—but it surprised us with so much more. We stepped inside the stunning Cathedral of Santa Maria Assunta and the Baptistery, where the architecture and acoustics were truly awe-inspiring. With time to shop, snack, and explore the surrounding piazzas, we discovered Pisa isn’t just a quick photo stop—it’s a fun, fascinating place worth savoring.
March 10: Cinque Terre by Train & Hands-On Cooking
With the water route closed, we reached the colorful villages of Vernazza and Manarola by train. The views were stunning, and lunch by the sea was unforgettable. In the evening, we rolled up our sleeves at Agriturismo Buccanne Farmhouse for a cooking class like no other. Split into small groups, we each took full responsibility for preparing the meal from scratch—no shortcuts! We kneaded dough for homemade pasta, seasoned and prepped pork loin, peeled and roasted Tuscan-style potatoes, built the perfect bruschetta, and even competed in a tiramisu contest to see who made the best one. The chefs simply popped it all in the oven—we did the rest. Add in plenty of wine and laughter, and it was a night none of us will ever forget.
With the water route closed, we reached the colorful villages of Vernazza and Manarola by train. The views were stunning, and lunch by the sea was unforgettable. In the evening, we rolled up our sleeves at Agriturismo Buccanne Farmhouse for a cooking class like no other. Split into small groups, we each took full responsibility for preparing the meal from scratch—no shortcuts! We kneaded dough for homemade pasta, seasoned and prepped pork loin, peeled and roasted Tuscan-style potatoes, built the perfect bruschetta, and even competed in a tiramisu contest to see who made the best one. The chefs simply popped it all in the oven—we did the rest. Add in plenty of wine and laughter, and it was a night none of us will ever forget.
March 11: San Gimignano and Pecorino Paradise
In San Gimignano, the medieval towers and vineyard views were picture-perfect. We visited a cheese farm to see how fresh pecorino is made and enjoyed generous tastings. Then, we headed to Acetaia Gambinini Zoccoli for a tour and tasting of their aged balsamic vinegars—rich, smooth, and utterly addictive. Oh my! What an awesome treat.
In San Gimignano, the medieval towers and vineyard views were picture-perfect. We visited a cheese farm to see how fresh pecorino is made and enjoyed generous tastings. Then, we headed to Acetaia Gambinini Zoccoli for a tour and tasting of their aged balsamic vinegars—rich, smooth, and utterly addictive. Oh my! What an awesome treat.
March 12: The Road to Bologna (with Cheese!)
As we headed to Bologna, we stopped at the Madonne Caseificio Parmigiano Reggiano factory and got a behind-the-scenes look at how Italy’s king of cheeses is made. After arriving in Bologna, we had the evening to wander through this often-overlooked gem of a city—known for its food, fashion, and authenticity. So much fun just checking out our centrally located area! We stayed at the beautiful Monrif Royal Hotel Carlton.
As we headed to Bologna, we stopped at the Madonne Caseificio Parmigiano Reggiano factory and got a behind-the-scenes look at how Italy’s king of cheeses is made. After arriving in Bologna, we had the evening to wander through this often-overlooked gem of a city—known for its food, fashion, and authenticity. So much fun just checking out our centrally located area! We stayed at the beautiful Monrif Royal Hotel Carlton.
March 13: Bologna’s Hidden Treasures
Our final full day took us through Bologna—a city you don’t want to miss. At San Petronio Church, some in our group received confession, a sacred and unforgettable experience during the Holy Year. We visited the University of Bologna, the oldest in Europe, and then explored the city’s lively markets and hidden boutiques. From food to history to fashion, Bologna delivered. We wrapped it up with an exceptional lunch (and wine!) at Tamburini.
Our final full day took us through Bologna—a city you don’t want to miss. At San Petronio Church, some in our group received confession, a sacred and unforgettable experience during the Holy Year. We visited the University of Bologna, the oldest in Europe, and then explored the city’s lively markets and hidden boutiques. From food to history to fashion, Bologna delivered. We wrapped it up with an exceptional lunch (and wine!) at Tamburini.
Final Thoughts
This wasn’t just a tour—it was a thoughtfully woven tapestry of culture, faith, fun, and freedom. The itinerary was perfectly paced, the logistics seamless, and the experiences beyond what we expected. Best of all, travelers always had the option to break away, explore on their own, and rejoin the group whenever they wanted. It was structured without being strict—and that’s what made it so special.
This wasn’t just a tour—it was a thoughtfully woven tapestry of culture, faith, fun, and freedom. The itinerary was perfectly paced, the logistics seamless, and the experiences beyond what we expected. Best of all, travelers always had the option to break away, explore on their own, and rejoin the group whenever they wanted. It was structured without being strict—and that’s what made it so special.
For Tanya and Micah Ellis, Sandra Booher, and everyone else in our group, this 14-day Italian journey was more than memorable. It was transformational.