Fit Checks in Italy with Katie

duration
7 days · 6 nights
travel date
Apr 11 - 17, 2026
activity level
Light
group size
8 - 10
transportation
Group vehicle, train
Your TourHero
tourhero
Katie Thompson
bio

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!

Italy > Fit Checks in Italy with Katie

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.

Itinerary timeline
Day 1 · April 11, 2026 · Milan
Arrive at Milan Malpensa Airport
Private group transfer from airport to hotel
Check-in at Hotel Canada (or similar according to availability)
Free time
Welcome dinner (includes 3-course menu with 1 drink)
Day 2 · April 12, 2026 · Milan
Breakfast at hotel
Milano fashion tour & workshop with an Italian designer (2.5 hours)
Free time
Day 3 · April 13, 2026 · Milan & Florence
Breakfast at hotel and checkout
Train from Milan to Florence (second-class ticket)
Check-in at Hotel Silla (or similar according to availability)
Walking tour of Florence with 1-hour wine tasting in city center
Free night
Day 4 · April 14, 2026 · Florence
Breakfast at hotel
Food tour of Sant'Ambrogio Grocery Market with an expert local chef (3 hours)
Free time
Day 5 · April 15, 2026 · Florence & Rome
Breakfast at hotel and checkout
Train from Florence to Rome (second-class ticket)
Check-in at Hotel Floris (or similar according to availability)
Guided walking tour of Rome (includes 2 flavour ice-cream and skip-the-line tickets to the Panthenon; 2.5 hours)
Free night
Day 6 · April 16, 2026 · Rome
Breakfast at hotel
Free day
Farewell dinner (includes 3-course meal with drinks; vegan and vegetarian options)
Day 7 · April 17, 2026 · Departure
Breakfast at hotel and checkout
Journey ends
Details
Day 1 · April 11, 2026
Buongiorno, Milano

-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.

Day 2 · April 12, 2026
Haute couture

-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.

Day 3 · April 13, 2026
The charm of Florence

-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.

Day 4 · April 14, 2026
Local food fare

-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!

Day 5 · April 15, 2026
All roads lead to Rome

-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.

Day 6 · April 16, 2026
Toast to the end

-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.

Day 7 · April 17, 2026
Tour Price
From USD 2,497
per person
Flexible payment plans available
19 people are interested
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Your fellow explorers
Age range
18+
Travel interest
Fashion, art, wine & good eats, history & culture, exploration
Your local guide
A leading DMC with more than four decades of experience, Europe Incoming is ready to help make your travel dreams in Europe come true. They’ve curated countless tours over the years, both pre-made and customized, and they have a deep understanding of each unique region of Europe. From Norway to Croatia and everything in between, they can create the perfect trip for you, handling all of the minute details.
Accommodation
Hotel Canada (or similar according to availability)

Hotel Canada Milan is a stylish and comfortable 3-star hotel located in the heart of the city, just a short walk from the iconic Duomo and major attractions. Ideal for both leisure and business travelers, the hotel offers modern, soundproofed rooms with free Wi-Fi, air conditioning, and minibars. Guests can also enjoy a daily breakfast buffet, concierge services, and convenient access to public transportation for exploring Milan with ease. Room type/configuration: Multiple options available. See packages at checkout.

Hotel Silla (or similar according to availability)

Hotel Silla is a welcoming 3-star hotel in Florence, nestled along the picturesque Arno River in the historic San Niccolò district. Housed in a charming 16th-century building, the hotel offers elegantly furnished rooms with modern amenities, free Wi-Fi, and a scenic terrace perfect for relaxing with views of the city. Its prime location places guests within walking distance of the Ponte Vecchio, Uffizi Gallery, and Florence’s vibrant cultural attractions, making it an ideal choice for travelers seeking both comfort and convenience. Room type/configuration: Multiple options available. See packages at checkout.

Hotel Floris (or similar according to availability)

Hotel Floris is a charming 3-star accommodation situated in the heart of Rome, just 150 meters from the Opera Theater and a short walk from Termini Station. Housed in a 19th-century building, the hotel offers modern, air-conditioned rooms equipped with free Wi-Fi, flat-screen TVs, minibars, and private bathrooms with complimentary toiletries. Guests can enjoy a daily continental breakfast buffet featuring fresh pastries, cold cuts, and hot beverages. Its central location provides easy access to iconic attractions such as the Trevi Fountain and the Spanish Steps, making it an ideal choice for travelers seeking both comfort and convenience in the Eternal City. Room type/configuration: Multiple options available. See packages at checkout.

Included
  • 2 nights accommodation in Milan

  • 2 nights accommodation in Florence

  • 2 nights accommodation in Rome

  • All breakfasts at hotel

  • Dinner days 1, 6

  • 1 group arrival airport transfer

  • 1 group departure airport transfer

  • All activities & tours listed in itinerary

Not included
  • All flights

  • All meals & drinks not mentioned in inclusions

  • Personal expenses not stipulated

  • Optional add-ons

  • Gratuities

FAQ
Cancellation policy

Refunds for deposits
We will hold your spot as soon as you put down your deposit. However, if you decide to cancel your trip, we will be unable to refund your deposit.

Refunds for balance payment
If you cancel your trip on or before Jan 29, 2026 at 11:59 PM local time (GMT +1), you will get a refund of the remaining balance. This may or may not include the deposit amount. See deposit refund section above.

If you cancel your trip from Jan 30, 2026 at 12:00 AM local time (GMT +1) onwards, no refunds will be issued.

You can change or cancel your trip in your TourHero account by clicking on Your Trips.

Trip disclaimer
To offer the best group rates, we need a minimum number of travelers. If that number isn't met—or if unexpected events occur (such as force majeure)—TourHero, the trip host, and the tour operator may need to cancel or reschedule.


If changes happen: You'll be notified by Jan 29, 2026 at 11:59 PM local time (GMT +1), and if the trip is canceled or rescheduled beyond your control, you'll get a full refund. We'll always update you at least 7 days in advance if this date changes.


Book smart: We recommend refundable flights and accommodations to protect your plans from any last-minute changes.

Available add-ons
Private Milan Walking Tour with Duomo Cathedral skip-the-line tickets (2 hours)
USD 94
10 spots left
Private Uffizi Walking Tour with Museum skip-the-line tickets (2 hours)
USD 121
10 spots left
Private Vatican Walking Tour with skip-the-line tickets (3 hours)
USD 119
10 spots left