Tuscany & Rome with Chris Cosentino

Benvenuto a Firenze! We’ll convene this afternoon for a gentle walking tour of what’s arguably the most beautiful city in the entire world. As we stroll down the same cobbled alleyways and piazzas that Galileo and Dante once trod, we’ll feel the thrill of history in every step. We’ll pay a visit to the Accademia, one of the oldest drawing schools in Europe and home to the largest number of sculptures by the great Michelangelo of any museum in the world. No trip to Florence would be complete without paying homage to his majestic David, but there’s much more experience here, and with the help of our expert guide we’ll skip the lines and enjoy a beautifully curated tour.

In the evening, we’ll reconvene for hors d’oeuvres at our hotel, where we’ll enjoy a very special tour of its contemporary art collection from a local artist. We’ll end the night right here, with a delicious Tuscan dinner artfully paired with local wines courtesy of an expert sommelier — a first glimpse into the vast riches of the region.

Start the day with an optional yoga session, followed by coffee and pastries at Caffè Perseo, a Florentine institution. Next, we’ll head to Mercato Centrale, one of the oldest and busiest covered markets in Europe, where Chris will introduce us to some of his favorite ingredients and sources of inspiration. We’ll taste as we go, sampling Tuscan delicacies; somehow we’ll still have room for our trattoria lunch.

In the afternoon, we’ll continue our wanderings through the historic Santo Spirito district, paying special attention to the city’s 150-odd buchette del vino, small windows attached to the palaces of grand noblemen from which wine was traditionally sold by the fiasco (glass bottle). We’ll finish our exploring in the shops of the pelletteria district, learning about the traditional leatherwork techniques practiced here for centuries.

In the evening we’ll reconvene for dinner at Cibrèo, another Florentine institution. For those craving an after-dinner nightcap, we’ll have the chance to relax with Chris and enjoy a blind tasting of different non-alcoholic digestivi, from hemp-based amaro to the beloved Italian staple Crodino with its distinctive blends of bitter herbs.

After breakfast, we’ll head out for a day of exploration. Our first stop will be the perfectly preserved town of Lucca, whose medieval walls encircling the centro storico form a vast green space perfect for cycling. We’ll enjoy lunch at a typical Lucchese trattoria, where we’ll sample local dishes like gramugia, a spring soup of fava beans, asparagus, and artichokes, and tordelli, a hearty pasta stuffed with Swiss chard and pine nuts. As we dine, Chris will tell us all about the traditions of cucina povera he learned from his grandmother Rosie, and how this approach to using every scrap of an ingredient has informed his cooking.

Our next stop will be Pisa, where we’ll visit the majestic (and aptly named) Campo dei Miracoli complex, a UNESCO World Heritage site, with its piazza of monuments including the duomo, the baptistry, and the Bell Tower, better known as Leaning Tower. Pisa is just a stone’s throw from the Tuscan riviera, and we’ll end our time there with a leisurely bike ride along its sandy beaches, breathing in the salty sea air and admiring the pounding turquoise surf of the Tyrrhenian sea, before heading back to Florence. Dinner tonight will be on our own.

We’ll bid farewell to Florence and head out into the Tuscan countryside, to explore the storied region of Chianti following its narrow lanes lined with spires of cypress trees. Lunch is at the restaurant of eighth-generation butcher (and good friend of Chris) Dario Cecchini. Anthony Bourdain once called Dario the most famous butcher in Italy; we’ll enjoy his handiwork today over plates of bistecca panzanese, a cut of beef first popularized in the Middle Ages and single-handedly resuscitated by Dario.

After lunch, we’ll visit a local winery nestled in vine-covered hills, where we’ll learn all about the trademark features of Chianti. Wine-making in this region dates back all the way to the Etruscan period, but Chianti as we know it is only 300 years old, the brainchild of Cosmio III, Grand Duke of Tuscany, who first delimited its production zone, one that has barely changed over the centuries. Today is our day to get to know Chianti better, exploring every nuance of its tart, spicy, herbaceous profile.

After our tasting concludes, we’ll continue on to Castel Monastero, a beautifully restored monastery nestled among the corn fields and chestnut forests, and our home away from home for the next three nights. We’ll have time for a quick siesta or stroll around the grounds after checking in, before reconvening for a very special dinner in the estate’s storied wine cellars.

After a sumptuous breakfast, we’ll make our way to gracious Siena. It’s arguably one of the most beautiful cities in all of Italy, with a car-free central district of ancient alleyways and noble squares.

We’ll walk the same cobbled lanes that locals walked in the middle ages, while learning about the rich history of this ancient city. We’ll even stop for dessert in quintessential Siena style— over bites of Ricciarello, a soft almond cookie first baked in Siena in the 14th century.

After this initial immersion, we’ll dive deeper into the unique history of Sienna with a visit to the Contrada museum. Beside medieval relics and interactive installations, our expert guide will chaperone us through the centuries-old tradition that ensures all 17 districts of the city democratically elect representatives, and even challenge other districts to competitions like bareback horse racing.

Dinner tonight is on your own. See you bright and early tomorrow.

This will be a morning of monastery-hopping, as we leave our own “monk’s quarters” to explore the storied abbey of Sant’ Antimo, a stunning masterpiece of Romanesque architecture that for centuries has been the home of Benedictine monks. As we take a leisurely stroll through its vast herb gardens, breathing in the heady scents of anise, bay leaf and oregano, Chris will share with us some of his favorite chef’s tricks for incorporating these herbs into his cooking.

Our next stop is the hillside town of Montepulciano, one of Tuscany’s great wine towns. We’ll enjoy lunch on our own here, and the chance to lazily stroll the sun-filled piazzas, admiring the elegant Renaissance palaces and ancient churches and taking in the sweeping panoramic views over the valley below.

In the early evening, we’ll visit a unique winery that’s home to dense vineyards and gardens bursting with herbs and other edible plants. We’ll enjoy an al fresco wine tasting, followed by an unforgettable dinner among the vines.

It’s time to swap Tuscany’s tranquil delights for the hustle and bustle of Rome. As we speed our way south, we’ll break our journey at an Autogrill—a quintessentially Italian roadside experience!—for a flawless espresso, a buffet lunch, or a little grocery shopping (liters of olive oil and even whole haunches of prosciutto are among the standard offerings). Our ultimate goal is Rome, starting with an exclusive private tour of the Villa Borghese, Italy’s largest and most famous art museum, set in a verdant park in the heart of the city.

We’ll have time back at the hotel before our dinner tonight at a classic Roman trattoria showcasing the bold, aggressive flavors of cucina romana — heavy on the black pepper, bitter greens, sheep’s-milk pecorino and, of course, the offal dishes so dear to Chris’ heart. Once upon a time, these cuts were eaten because they were all people could afford; now, they form the base of iconic Roman dishes like tripe with stewed tomatoes and mint and lamb hearts with artichoke.

We’ll slip right into the teeming street life of Italy’s capital this morning as we enjoy a curated walking tour, visiting and tasting our ways through bakeries, covered markets and gelaterias in the storied Trastevere neighborhood. A morning of grazing will segue into lunch on our own, with the balance of the afternoon for further exploration of Rome’s backstreets and cafe-lined squares, a chance to saunter slowly amid the bustle.

We’ll reconvene late in the afternoon for a deep dive into two of Italy’s greatest culinary gifts to the world: pizza and gelato. First, we’ll try our hand at gelato, learning how to source the very best ingredients and proper mixing techniques. While our gelato sets in the freezer, we’ll turn to pizza, crafting and rolling out our own dough and selecting just the right toppings. Chris will be at our side, preparing a very special pizza to be enjoyed at our farewell dinner tonight. As we raise a glass to toast Chris, our new friends, and la bella Italia, we know our lives have been forever enriched by this time together.

Arrivederci Italia! After eight full days of immersion in the best Italy has to offer, it’s time to say ciao to Chris and to each other, knowing the memories we’ve made will stay with us for a lifetime. Until we meet again!