Tuscany & Rome with David Cilli

Day 1: Florence

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. Nestled at the heart of Florence’s city center, Gallery Hotel Art is an oasis of quiet luxury and stylish, thoughtful touches.

It’s also the perfect backdrop for our first bites of the trip—tonight, we’re paying homage to one of Italy’s long-standing traditions: the aperitivo. Over welcome drinks and plenty of bright, local fare, we’ll learn more about David and his profound connection to the land—as well as its legendary vines.

Day 2: Florence

As the sun makes its giddy debut over bright-eyed Florence, we can seize the day with an optional running tour and yoga session. Later in the morning, we’ll head together over to Mercato Centrale, one of the oldest and busiest covered markets in Europe, where David will introduce us to some of his favorite ingredients and sources of culinary inspiration. We’ll taste as we go, sampling local delicacies before sitting down for a traditional Tuscan lunch at one of the market’s most storied stands.

Feeling buoyant and inspired from our exquisite market spread, we’ll meander onwards 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.

In the evening we’ll reconvene for dinner at Osteria dell’Enoteca, another Florentine institution. After our meal, David’s inviting those craving an after-dinner nightcap for cocktails and an informal Q&A.

Day 3: Siena & Tuscany

We’re bidding adieu to Florence this morning and making the short (and ridiculously scenic) drive to 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. Here, we’ll wind through the same cobbled lanes that locals walked in the middle ages, learning about the city’s rich history of art and cuisine. Along the way, we’ll stop for small bites and pastries at local shops and quaint cafes, testing out the best of Siena’s flavors.

Lunch today is a special treat: an insider’s look at traditional Tuscan cooking. In an old-world osteria at the heart of the city center, a local chef will lead us through an in-depth cooking demonstration. Afterwards, we’ll sample our handicraft over an exquisite lunch of regional specialities.

Glowing with the unique joy of a deeply satisfying meal, we’ll float onwards to a nearby azienda where farmers and artisans work in harmony with the land. Here, we’ll sample a lineup of truly farm-fresh fare: think gem-toned jams, pestos, and Tuscany’s famed Chianina meat (ground zero for Florentine steak!). As the grand finale to a day of impeccable culture and cuisine, we’ll round out our evening at our hotel, joining David and one very special guest for an unforgettable masterclass in Italian wines.

Day 4: Marina di Grossetto

This morning, we’ll head to Marina di Grossetto for a day of aquatic adventure. With white sand beaches that stretch for miles, the region is a stunning exemplar of Tuscany’s natural beauty—which, of course, we’ll be exploring in style. From breezy sailboats, we’ll bask in the magnificence of our surroundings, cooling off with a swim or snorkel before a hyperfresh lunch onboard.

For dinner, we’re taking advantage of our coastal location and indulging in a Tuscan seafood feast. As we breathe in the salty sea air at a nearby restaurant (a favorite among locals), we’ll share our favorite memories from the day and savor the impeccable flavor of just-caught frutti di mare.

Day 5: Tuscany

We’re starting the day off in elevated luxury—literally. As the sun rises over the countryside, we’re floating high above Tuscany’s patchwork quilt of rolling vineyards, medieval towns, and ancient forests in vibrant hot air balloons. It’s a pinch-yourself moment, but the vineyard brunch that follows is an equally extravagant affair, dominated by local wine and a symphony of fresh, seasonal offerings.

After our jaunt in the sky, we’re heading back to our hotel, the afternoon ours to reflect on the magic of our morning. Drink in the warm afternoon sun from the terraced garden, or hit the reset button with a nourishing massage at the in-house spa. We won’t meet up again until later in the evening for dinner, and trust us on this one—it’s a truly remarkable experience. While we don’t want to give any spoilers, we’ll leave it as this: we’re in for an intimate evening of celebration, heartfelt flavors, and friends we’ll cherish for the years to come.

Day 6: Tuscany

This morning, we’re rounding out our adventures through Tuscany with a horseback ride—it’s an unforgettable immersion into the region’s fabled countryside. Atop our steeds, we’ll wind through peaceful valleys and timeless vineyards, reveling in views so beautiful they beg to be made into a postcard.

Of course, riding horses is no small feat, so after a morning in the saddle we’ll head onwards to Terme di Saturnia for an afternoon of sumptuous relaxation. Tucked away within 120 hectares of secluded Tuscan countryside, these ancient hot springs are rich in minerals and healing bioplankton—they’re also outrageously beautiful: we’re talking otherworldly blues and glimmering turquoise as far as the eye can see. Surrounded by natural beauty, it’s the perfect conclusion to our time in Tuscany. Next stop: Rome!

Day 7: Tuscany to Rome

It’s time to swap Tuscany’s tranquil delights for the hustle and bustle of Rome. We’ll commence our adventures through Italy’s capital city with an exclusive tour of the Villa Borghese, the country’s largest and most famous art museum that’s set in a verdant park in the heart of the city. Afterwards, the afternoon is ours to relax back at the hotel or wander through Rome’s endless offering of breathtaking plazas and ancient streets.

Dinner tonight is at an all-time Roman favorite: Rimessa Roscioli. This traditional trattoria is run by one of Rome’s famous baking families and it’s the perfect celebration of the city’s classic dishes. As a special treat, David’s hand-picked the wines for tonight and we can’t wait to sit back and savor his thoughtful choices.

We’ll end the day with the ultimate when-in-Rome adventure: zipping around the city in classic, candy-colored Fiat 500s. Some three million of these iconic little beauties were produced between 1957 and 1975, and nothing could be more quintessentially la dolce vita than this very special nighttime excursion.

Day 8: Rome

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 way 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. Later, we’ll tuck into the fruits of our labour for dinner, but not before we raise a glass to toast David, our new friends, and la bella Italia—we know our lives have been forever enriched by this time together.

Day 9: Departures

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