Hi friends! I’m Katie, a Washington, DC area-based lifelong preppy grand millennial adventurer. I am a firm believer that every hour is happy hour and have a huge passion for creating community wherever I go. That’s why I curated my very-own trip to Italy which will include happy hours, museum hopping, and experiencing all that this beautiful country has to offer - preppy and grand millennial style. Everyone on this trip is a friend and will leave this trip with long-lasting memories and friendships for years to come - come join me for an unforgettable experience in a preppy grand millennial fashion!
Experience the ultimate Italian escape, where style, fashion, food, and wine take center stage. From the chic streets of Milan to the Renaissance beauty of Florence and the timeless grandeur of Rome, this journey is a curated blend of elegance and indulgence. Stroll through high-fashion districts, sip Tuscan wine in hidden piazzas, taste your way through bustling markets, and explore iconic landmarks — all while embracing the effortless charm of la dolce vita. Pack your suitcase and put on your best dress. I can already picture how stunning our fit checks in Italy will be.
-Welcome to the fashion capital of the world! Step off the plane and into a city where every street is a runway and every corner tells a story of style and elegance.
-Glide through the streets of Milan in comfort as you take in the city’s effortless sophistication and timeless charm.
-After checking in, get some free time to yourself. Whether you want to sip an espresso at a corner café, take a leisurely passeggiata, or dive straight into high-end shopping, the city is yours to explore.
-Kick off this unforgettable Italian adventure with a curated three-course meal paired with a perfectly chosen drink. Toast to la dolce vita with your new travel besties—because in Italy, every meal is a celebration.
-Step into the world of haute couture as you explore Milan’s most iconic fashion spots.
-Then, get hands-on with an exclusive workshop led by a local designer. Learn about the in and outs of creating the perfect piece of clothing.
-Whether it’s browsing the luxury boutiques of Via Montenapoleone, indulging in a long lunch with a glass of prosecco, or capturing that perfect Instagram shot at the Duomo, the city is your playground for the rest of the day.
-Savor one last taste of Milan with a leisurely breakfast before we set off for our next destination — Florence.
-Settle into your seat and watch the Italian countryside unfold like a Renaissance painting as you glide toward the heart of Tuscany on a train.
-Step into a dreamy Florentine retreat and drop your bags off.
-See the best of Florence on a walking tour before indulging in a curated wine tasting experience.
-Enjoy a free night to soak in the timeless beauty of Florence.
-Wake up to the aroma of fresh espresso and flaky pastries, the perfect start to another dreamy day in Tuscany.
-Immerse yourself in Florence’s vibrant food culture as you explore the local food scene alongside an expert local chef. Taste artisanal cheeses, fresh pastas, and rich olive oils while learning the secrets of Tuscan cuisine.
-Spend the afternoon your way. Every corner hides a masterpiece, so go explore!
-Watch the Tuscan hills give way to the grandeur of the Eternal City as you speed toward Rome in effortless style.
-Explore the historic streets of Rome, from the Colosseum to Trevi Fountain, on a guided walking tour. Pause for gelato (two flavors, because why not?) and skep the line at the awe-inspiring Pantheon.
-Enjoy a free evening under the romantic Roman lights.
-With an espresso and buttery cornetto, we'll start our final full day in Italy.
-The Eternal City is yours to explore! Wander through ancient ruins, sip espresso in a sun-drenched piazza, or hunt down the best cacio e pepe in town — today is all about indulgence.
-End this unforgettable journey with a stunning three-course meal, perfectly paired with wine and laughter. Tonight, we toast to adventure, each other, and the magic of Italy.