Tuscany & Rome with Amanda Cohen

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 Amanda and her connection to the land and its bounty.

Day 2: Florence

As the sun makes its giddy debut over Florence, we can seize the day with an optional yoga session. Later in the morning, we’ll head together over to Mercato Centrale, one of Europe’s oldest and busiest covered markets, where Amanda will introduce us to some of her 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.

After, 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.

In the evening we’ll reconvene for dinner at Osteria dell’Enoteca, another Florentine institution. After our meal, Amanda’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. 

Upon arrival, we’ll roll up our sleeves to do what every pilgrim to Italy must: learn how to make the finest pasta in the world. At a professional kitchen in the heart of the city center, a local chef will lead us through an in-depth masterclass on Tuscan classics and traditional pastas. Afterwards, we’ll sample our handicraft over an exquisite lunch, sitting back to savor the fruits of our labor as Amanda regales us with stories of her time in Tuscany. 

Glowing with the unique joy of a deeply satisfying meal, we’ll float onwards to our hotel for the night, a dreamy villa with postcard views of the surrounding countryside. Sip a Negroni at the library bar or wander outside to explore the medieval hilltop village. We won’t meet up again until dinner, and trust us on this one, it’s a real treat. At a chic cellar restaurant, we’ll tuck into a feast of Tuscany’s finest, raising our glasses in toast to the magical day and adventures still to come. 

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; fresh, seasonal offerings; and unforgettable tales of mountain pizza, courtesy of Amanda.

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 dinner, reconvening at the hotel’s award-winning restaurant for an evening of celebration, heartfelt flavors, and friends we’ll cherish for the years to come. 

Day 6: Tuscany

This morning, we’re diving into the world of Italian organic farming. We’ll visit a scenic agroturismo deep within the Tuscan countryside that produces all the key ingredients you’ll find in any traditional trattoria—think: fragrant honeys, fresh cheese, and plenty of bright, seasonal vegetables. As we meander through the stunning grounds, we’ll learn more about the farm’s commitment to sustainable agriculture, sampling as we go. 

Inspired by our farm-fresh fare and bucolic surroundings, we’ll drift 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.

For dinner tonight, we dive deep into an Italian classic: la pizza! We’ll meet at an intimate neighborhood joint that’s an all-time favorite among locals, where each bite it its own revelation—think: creamy mozzarella and bright tomato sauce; delicate zucchini flowers and crusts at once crisp yet sumptuously soft. As a special treat, Amanda has thoughtfully selected the wines tonight, and we’ll sit back to learn more about her pairing philosophy and advocacy for women-owned labels. 

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 Amanda, 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 Amanda and to each other, knowing the memories we’ve made will stay with us for a lifetime. Until we meet again!