Tuscany & Rome with Sarah Looper

Benvenuto in Italia! Our adventure through the world’s premier wine destination begins in Florence, the Tuscan capital brimming with art, culture, and positively exquisite cuisine.  

We’ll ease into our first day with an unhurried afternoon at the hotel, luxuriating in the opportunity to refresh and get settled after our long transatlantic flights. In the evening, we’ll wander over to one of our favorite trattorias in the city. Over welcome drinks and plenty of bright, local fare, we’ll learn more about Sarah and her love affair with Italy.

We’ll even make room for a nightcap as we fawn over Florence from a rooftop bar and toast to the adventure ahead.

This morning, we put our sweet tooth forward. With Sarah—an exceptional baker and pastry enthusiast—at our side, we dive into the world of coffee and gelato. Through the Oltrarno district, we’ll veer off onto the sidestreets only to zero in on a few local favorites who make some of the most coveted and authentic coffee in Florence.

Afterwards, we’ll meander 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). Our final stop is 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. There’s so much to experience here, and with the help of our expert guide we’ll skip the lines and enjoy a beautifully curated tour.

Dinner tonight is fiercely local and special—we’ll convene at Trattoria Sostanza, a charming trattoria beloved by locals.

Today is a day of culinary and cultural exploration as we bid arrivederci to Florence and journey through the scenic Tuscan countryside; our first stop, one of Sarah’s favorite wineries, for an exquisite tasting through its vintages.

Our appetites piqued, we stop for lunch at the extraordinary Officina della Bistecca. Dario Cecchini is an international legend, Netflix star and the beating heart behind this cozy neighborhood restaurant and ethical butcher shop — he’s renowned throughout Italy for his commitment to honoring the animal and using all of its parts. Over a spread of seared carpaccio, Florentine steaks, and innovative vegetarian entrees, we’ll toast to the unparalleled splendor of a morning well spent in Tuscany. 

After lunch, continue your Chianti journey with a short drive to Istine, a boutique winery in the heart of Radda. In this charming village with ancient origins surrounded by towering medieval walls, you’ll enjoy a private tasting of their exquisite wines, crafted with passion and care from organically grown vineyards.

As the day draws to a close, we’ll check into our new hotel and unwind amidst the tranquility of Tuscany’s rolling hills. After settling in, we’ll indulge in a delicious dinner featuring locally sourced ingredients, and reflect on the day’s adventures as you savor the beauty and charm of Italy’s timeless countryside.

Today, we’ll drive to Val D’Orcia, home to picturesque hills, vineyards, and towns like Pienza, known as the “Ideal City” for its Renaissance charm. We’ll explore Pienza, a UNESCO World Heritage site, with its harmonious central piazza and Renaissance architecture. Our journey continues to an organic dairy farm, where we’ll indulge in a cheese-making experience and savor Pienza’s renowned Pecorino cheese.

From Pienza, we’ll embark on a short drive to Montalcino for a delightful two-hour wine tasting and lunch at Cerbaie. We’ll immerse ourselves in the world of Brunello, one of Tuscany’s most celebrated wines. Surrounded by Montalcino’s picturesque rolling hills, we’ll savor a meal crafted to complement the estate’s outstanding vintages.

After lunch, we’ll make our way through the scenic Tuscan countryside to Montefalco, your gateway to Umbria with a visit to the famed Umbrian Cashmere boutiques. From there, we’ll check into our new hotel nestled amidst historic streets in the old town before regrouping for a dinner crafted from local Umbrian ingredients, offering a warm and flavorful welcome to this enchanting region.

The day begins with a short drive to Spello, a charming Umbrian village renowned for its cobbled streets, flower-filled balconies, and ancient Roman heritage. Take a leisurely stroll through its picturesque alleys and soak in the tranquil beauty of this enchanting town. Once we’ve taken in the sights, we’ll head back to Montefalco, known as the “Balcony of Umbria” for its stunning panoramic views. Here, you’ll spend the late morning indulging in a private wine tasting and lunch with Giampiero Bea, a visionary winemaker celebrated for his organic and biodynamic practices. Relish a curated selection of wines paired with seasonal local dishes, offering a profound connection to the terroir and traditions of the region.

After lunch, we’ll transition from the rolling hills of Tuscany to the verdant heart of the Umbrian mountains and the Monti Sibillini National Park (about 2 hours drive).

Here, we’ll immerse ourselves in an adventure all about truffle hunting in the mountain village of Pettino, guided by Luca, Alessandro, and Francesca—three cousins whose families have been hunting and breeding for generations. Following highly trained dogs as they hunt, we’ll enjoy amazing views in every direction as we stroll the countryside and relax in a panoramic spot for a glass of wine. Then, back at the village, we’ll discover some of the secrets of the family’s culinary tradition.

Post-hunt, we’ll engage in a hands-on pasta-making experience, then enjoy the fruits of our labor with a rustic truffle-laden dinner. Join in and lend a hand, or simply sit back, watch, and enjoy an assortment of homemade specialties such as truffle bruschetta, capocollo, and pecorino cheese, accompanied by some great local wine. Finally, we’ll sit down to a big traditional mountain meal where family and friends from the village will probably join for a relaxing, fun, and totally authentic Umbrian get-together.

Begin the day with a serene journey into the Lazio countryside, driving to the village of Vitorchiano to visit the Trappist nuns winegrowers. These dedicated sisters have produced exquisite organic wines from their monastery’s vineyards, cultivated according to natural and sustainable practices, for more than three decades. We’ll experience their unique approach to hospitality and tradition first-hand as we taste their handcrafted wines and share a warm, communal, convivio-style meal with them, celebrating the simple pleasures of good food and event better company.

From there, we’ll continue our journey onto Rome and check into our hotel before reconvening for a walking tour before heading to dinner at Roscioli, a Roman institution renowned for its unparalleled fusion of tradition and innovation in Italian cuisine—the perfect toast to an extraordinary day.

This morning we immerse ourselves in the rich tapestry of the Eternal City’s history, culture, and culinary delights. Our adventure begins with a vibrant food walking tour through iconic neighborhoods and their gastronomic treasures. Begin in the Jewish Ghetto, famed for its ancient bakeries and the legendary carciofi alla giudia. From here, we’ll make our way to Campo de’ Fiori, renowned for its bustling fruit and vegetable market and as the birthplace of the iconic coda alla vaccinara. Continue to Largo Argentina, where remnants of the Porticus Minucia Frumentaria recall a time when Roman citizens received grain, pork, and wine to support their families. Crossing the Tiber River, we’ll arrive in Trastevere, one of Rome’s most charming neighborhoods, to explore its hidden gems and vibrant local spots. Along the way, sample artisanal cheeses, traditional street food like supplì, and gelato from a beloved local shop.

After some free time at your pace, we’ll experience an evening of cooking and conviviality with chef Giuseppe Ruzzettu, of La Tavernaccia Da Bruno. Located in the southern part of Trastevere, not far from Porta Portese, Ponte Testaccio, and the Trastevere Station, this homey trattoria serves a mix of dishes from Umbria and Rome.

It offers a delightful blend of regional specialties, including suckling pig cooked in the wood-fired oven, pappardelle al cinghiale, amatriciana, and coda alla vaccinara.

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