Postcards from Italy

Staff Inspiration: Matthew’s Dream Trip

Join us over the next few weeks as we share our dream trips through Italy and Switzerland, aimed at informing and inspiring future jaunts to Europe. After last week’s trip with Cristina Tili, Operations Manager for CIUTravel, this week we take you on Matthew Greenbaum, Operations Associate for CIU Travel’s dream trip.

(Photo by CIU Travel via Flickr)

We met Matt in 2018, shopping for a ski jacket for Brian at Patagonia in New Haven, CT. It was a weekday afternoon in February, and we were hosting chef Luisa Scolastra from Villa Roncalli in Umbria. She doesn’t speak English, so we were walking around the store, speaking Italian with her and English to the sales associates. Matt was assisting Brian and he asked what we did that we were in the store in the middle of the day, and with an Italian woman who was experiencing a first visit to the U.S. I told him a bit about CIU, and he asked if we were hiring. We replied that, actually, we were looking to add a part time position, but starting in the office – basically warning him that we wouldn’t be sending him to Italy tomorrow! We received an email from him a few days later, and after a couple of interviews and email exchanges, he came on board. We thought that his love for the outdoors and adventure activity would be a great addition to our team, especially with the then recent addition of Switzerland to our offerings. Although his dream itinerary here is in Italy, after Maria Gabriella, Matt was the first person on our team to become a certified Swiss Travel Expert. We hope you enjoy his dream trip through two of Italy’s wine regions!

A Note from Matthew

I would dub my trip “A Wine’ing Our Way through Italy” and I think I started to dream about it while we were boarding the plane to head home from our honeymoon in Italy and Switzerland last summer. (That trip can be read about here: Trip Inspiration: Venice to Zermatt in Ten Days). However, it wasn’t until I saw a picture of the Piemonte region, with its vineyards surrounded by mountains in the background, that I knew exactly where I wanted to travel to next with my wife. Not to mention that some of our favorite wines come from this region.

Brian Matthew and Maria Gabriella

(Photo by CIU Travel via Flickr)

I like to see as many places as possible when I travel, and Italy is the perfect country to experience so much in such a small amount of time. So, with the Piemonte region as the main focus for our next trip, I began to dream about what other cities and regions we could visit within one trip.

Hopefully soon, my wife and I will be boarding a plane to Milan to live out this trip. But for now, I can’t stop dreaming about it.


Italy’s capital of fashion and design also houses the nearest international airport to the wine country of Piedmont, so we would fly into this chic northern capital and take advantage of an overnight to admire its highlights. We would splurge on a room at the landmark 5-star Grand Hotel et de Milan, one of Milan’s premier Grand Dame hotels since 1863 and perfectly located near the legendary La Scala opera house; indeed, Giuseppe Verdi lived at the hotel for years and many of its common areas and guest rooms are named after iconic opera composers, singers, and operatic works.

MInacce dal cielo

(Photo by Gianni Domenici via Flickr)

Well rested the next morning, we would dip into the Milan’s top cultural sights with a guide to make the most of our time in the city, taking in the spectacular Gothic-style Duomo, elegant Galleria Vittorio Emanuelle II shopping arcade, and Santa Maria delle Grazie, where Leonardo Da Vinci’s famed “Last Supper” decorates the refectory wall. If there’s time, we could even pop into Leonardo’s Vineyard, located just opposite the church.


After the urban bustle of Milan, it will be a relief to head to the quiet La Villa Hotel set in the hills of Piemonte to unwind. We’ll relax in this rustic chic retreat, with its pool, rooftop terrace, and excellent restaurant; if we are feeling ambitious, we could even set out with the provided bicycles to pedal through the picturesque rolling countryside. This would be our base for the next few days of gastro adventures.

Alba and Roero

Today, we would finally begin our deep dive into the world of Piedmont’s wines, concentrating on the area surrounding the historic towns of Roero and Alba (also known for its prized white truffle) in the morning. We would begin with a stop in the historic village of Pollenzo to visit the fascinating Wine Bank and admire its collection of roughly 100,000 bottles, featuring Italy’s top 300 producers.

tartufo bianco

 (Photo by CIU Travel via Flickr)

Then we would set off on a scenic drive through the vineyards of Roero, passing the villages of San Vittoria d’Alba and Monticello on the way to Alba. Once here, we would stroll through town to take in the Duomo di San Lorenzo, San Domenico, La Maddalena, Via Maestra, and other highlights before tucking into a traditional Piemontese lunch. After lunch, we would continue our drive through the villages and vineyards of Barbaresco, Neive, and Treiso – stopping at local wineries for tours and tastings along the way.


(Photo by CIU Travel via Flickr)

The Barolo Valley

We are true wine lovers, so one day of winery hopping wouldn’t be enough for us. Today, we would continue exploring by car through the hills and the vineyards of La Morra, Barolo, Castiglione Falsetto, Serralunga and Grinzane Cavour – opting for a guide and driver today to avoid the hassle of reading a map and instead concentrate on the stunning views. We would tour the historic vineyards of the Marchesi di Barolo where everything started 200 years ago, as well as a small boutique winery, and visit a local enoteca for an introduction to the history of the Langhe region and a wine tasting dedicated to the area’s great reds made from Nebbiolo: Barolo and Barbaresco.

Bologna via Parma

After two days steeped in Piemonte and its outstanding wines, we would start heading south, stopping in the Food Valley outside Parma for a private gourmet tour, including a stop at a parmigiano dairy farm to watch the cheese being made, followed by a balsamic vinegar producer for a tasting, and then a visit to a prosciutto producer. In the afternoon, we would spend a few hours exploring the elegant town of Parma before continuing on to Bologna.

After checking into the family-run Hotel Touring in Bologna’s city center, we would head out for dinner at one of the city’s many extraordinary traditional restaurants, making sure to sample local delights like tortelloni and tagliatelle al ragù.


(Photo by CIU Travel via Flickr)

The next morning, we would try to burn off a bit of the previous days’ abundance with a walking tour of Bologna’s historic sights, including its kilometers of porticoes, imposing Basilica di San Petronio, and the city’s university, one of the oldest in the world. We would cap off our cultural stroll with a tasting of local specialties at a local “osteria”, tucking into fresh pasta, mortadella, prosciutto, parmigiano cheese, bread, balsamic vinegar, and artisan chocolate to refuel.


 (Photo by CIU Travel via Flickr)

After days of tastings and samples, we would dedicate our final afternoon in Bologna to rolling up our sleeves for a hands-on cooking lesson in a private local kitchen. After learning how to prepare some of the city’s iconic dishes, we would relax over dinner to enjoy the fruits of our labors with our teacher and host.

Castelnuovo Berardenga via Siena

As we head further south into Tuscany, our focus would shift from cuisine to culture. We would stop in the medieval hill town of Siena to marvel at its iconic Piazza del Campo, home to the raucous Palio di Siena, and lavish Duomo. If we time it right, we may even catch the extraordinary duomo floors uncovered.


(Photo by CIU Travel via Flickr)

After a leisurely Tuscan lunch, we would set off to Castelnuovo Berardenga and Borgo San Felice, a unique hotel that is actually a medieval hamlet. This Relais & Chateaux estate comprises a main palazzo and smattering of cottages, as well as a vineyard, restaurant, and spa featuring wine- and grape-based treatment. Set in the hills of Chianti, this is the perfect base to explore the nearby villages and wineries.

Montepulciano, Montalcino, and Pienza

We would spend a full day kicking around the postcard-perfect hill towns of Montepulciano, Montalcino, and Pienza – perhaps booking a sommelier guide in the first half of the day to visit local producers of the area’s flagships Brunello and Vino Nobile wines. After a winery lunch, we would head to lovely Pienza, stopping at an artisan cheese producer to sample the town’s famed pecorino sheep cheese.


(Photo by CIU Travel via Flickr)

Florence via Chianti

Before our final stop in Florence, we would explore Chianti by car, taking in historic hill towns like San Gimignano, Radda, Gaiole, and Monteriggioni. No jaunt through this area would be complete without tasting its famed Chianti Classico wines, so we would relax over a vineyard lunch featuring classic Tuscan dishes paired with the estate’s own wines.


(Photo by CIU Travel via Flickr)

After lunch, we would head to Florence, “Cradle of the Renaissance” and a must-see when visiting Italy. We would check into the Antica Torre di Via Tornabuoni boutique hotel, a CIUTravel favorite set in a 13th-century medieval tower on the elegant Via dei Tornabuoni in the heart of the city. After our morning of driving and wine tasting, we would certainly spend time relaxing on the panoramic roof terrace overlooking the city.


(Photo by CIU Travel via Flickr)

The next day, we would make every moment count by exploring the city with the insights of a guide on a walking tour of the city’s highlights and a stop at the Accademia to marvel at Michelangelo’s David. In the afternoon, we might even end our day with a romantic row down the Arno River via a traditional “barchetto” with a “renaioli”, or historic boatman, at the helm. We would likely have an early flight to catch in the morning, so dinner would be a simple affair in one of the city’s many old-school trattorias followed by a pensive stroll through the city streets by night, while we reflect back on our food-and-wine-filled dream trip coming to an end.

Travel Specialists

Maria Landers

Brian Dore