Eat, Slay, Love: Italy Edition – From Milan to Rome with Jan

duration
8 days · 7 nights
travel date
Sep 2 - 9, 2025
activity level
Light
group size
10
transportation
Group vehicle, train
Your TourHero
tourhero
Jan van Vianen
bio

As a femme identifying gay man, my digital presence works to inspire other members of the LGBTQIA2S+ community to live authentically. My social media pages marry my love of fashion, beauty, and travel, while inspiring others like me to live authentically and take up space unapologetically.

I believe that fashion is genderless and gender is a construct. Therefore, my trips are designed to create a safe space for LGBTQ travellers and their allies. I know how difficult it can be to travel somewhere as a LGBTQ person; therefore, I’m here to promote safe parties, safe spaces, safe activities, and safe countries to travel to, and to bring you along!

Social media allows us to connect with creatives all around the world and fashion has the power to enhance the message of inclusivity and diversity; my vision is that we live in a world that celebrates and accepts individual uniqueness.

I’m looking to build my LGBTQ community while partying around the world and I want you to be part of it.

Countries I’ve travelled to:

China, United States, Mexico, Brazil, United Kingdom, Spain, Portugal, Italy, Switzerland, France, Hungary, Netherlands, Belgium, Germany, Ireland, Scotland

Stay femme

💖🏳️‍🌈

Italy > Eat, Slay, Love: Italy Edition – From Milan to Rome with Jan

Pack your best looks and get ready to live your main character moment in Italy’s most iconic cities — Milan, Florence, and Rome. This trip is your ultimate glam getaway, blending high fashion, history, and plenty of vino. Strut through the streets of Milan with a local designer, shop Florence’s artisanal markets with an expert chef, and snap content-worthy pics at legendary spots like the Duomo, Pantheon, and Ponte Vecchio. There’s gelato in Rome, rooftop views in Florence, and stylish bar crawls to keep the nights just as fabulous as the days. Perfect for fashionistas, beauty lovers, and anyone who believes life’s too short for boring travel – this is a week of glamour, laughter, and unforgettable experiences that will have your followers begging for more.

Itinerary timeline
Day 1 · September 2, 2025 · Milan
Arrive at Milan Malpensa Airport
Private group transfer from airport to hotel
Check-in at NH Collection Milano Touring (or similar according to availability)
Free time
Welcome dinner (includes 3-course menu with 1 drink)
Day 2 · September 3, 2025 · Milan
Breakfast at hotel
Milano fashion tour & workshop with an Italian designer (2.5 hours)
Free time
Day 3 · September 4, 2025 · Milan & Florence
Breakfast at hotel and checkout
Train from Milan to Florence (second-class ticket)
Check-in at Cellai Boutique Hotel (or similar according to availability)
Walking tour of Florence with 1-hour wine tasting in city center
Free night
Day 4 · September 5, 2025 · Florence
Breakfast at hotel
Food tour of Sant'Ambrogio Grocery Market with an expert local chef (3 hours)
Free time
Day 5 · September 6, 2025 · Florence & Rome
Breakfast at hotel and checkout
Train from Florence to Rome (second-class ticket)
Check-in at Napoleon Hotel Roma (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 · September 7, 2025 · Rome
Breakfast at hotel
Free day
Rome bar crawl (3 - 4 hours)
Day 7 · September 8, 2025 · Rome
Breakfast at hotel
Free day
Farewell dinner (includes 3-course meal with drinks; vegan and vegetarian options)
Day 8 · September 9, 2025 · Departure
Breakfast at hotel and checkout
Private group transfer to Rome Airport
Journey ends
Details
Day 1 · September 2, 2025
Ciao, bella – welcome to Milano!

-Touch down in the fashion capital of Italy – Milan, darling! After a smooth private transfer from Malpensa Airport to your stylish hotel, it’s time to settle in and refresh.

-Once you've unpacked those OOTDs and snapped a quick “just arrived” selfie, the rest of the afternoon is yours. Explore the city’s iconic streets or just relax and recharge.

-In the evening, we’ll kick things off in true Italian style with a fabulous welcome dinner – three courses and wine await. Cheers to an unforgettable week ahead!

Day 2 · September 3, 2025
Strike a pose during a high-fashion day

-Fuel up with breakfast at the hotel because today, you’re stepping into the world of high fashion. We’re talking a next-level Milano fashion tour led by a local designer – think behind-the-scenes insights and tips straight from the catwalk. This exclusive workshop will have you feeling like a runway star while learning how to infuse that Italian flair into your wardrobe.

-The afternoon is yours to explore. Maybe hit the boutiques of Via Montenapoleone or snap that perfect Duomo pic for the 'Gram. Either way, Milan is your runway today. Live it up!

Day 3 · September 4, 2025
From Milan to Michelangelo – the journey to Florence

-Rise and shine for one last breakfast in Milan before we board a train to the birthplace of the Renaissance – Florence!

-After a scenic ride through the Italian countryside, you’ll check into your next hotel, a true Florentine gem.

-Once you’re settled, lace up your walking shoes (or stilettos – you do you) for an afternoon tour that blends history, art, and a touch of glamour. Wander through Florence’s cobblestone streets, see iconic sights like the Ponte Vecchio, and head to the city center to conclude your tour with a wine tasting, showcasing some of the best libations of the region.

-The evening? Totally yours. Whether it’s pasta in a charming piazza or a moonlit stroll to the Duomo, Florence is calling.

Day 4 · September 5, 2025
Feast in Firenze

-Start your day with a cozy breakfast at the hotel before diving into Florence’s culinary scene. Today’s highlight? A food tour through the vibrant Sant’Ambrogio Market, led by a local chef who knows all the secrets to Italian cooking. Wander through colorful stalls filled with fresh produce, artisan cheeses, and cured meats while picking up tips on Florentine flavors and traditions. You'll get to sample some local specialties – think truffle spreads, fresh focaccia, and the best olives in town.

-After the tour, the day is yours. Explore Florence at your own pace — hunt for leather goods, take in panoramic views from Piazzale Michelangelo, or simply sip wine by the Arno.

Day 5 · September 6, 2025
When in Rome, see the sights and eat gelato

-After breakfast, say arrivederci to Florence and hop on a train to the iconic city of Rome, where ancient history meets modern style.

-Once you’ve checked into your charming hotel, it’s time to hit the cobblestone streets for a guided walking tour of the Eternal City. Discover must-see landmarks, soak up the Roman vibes, and skip the line to marvel at the stunning Pantheon. And, of course, what’s a day in Rome without gelato? Two scoops are included to keep things sweet as you explore.

-When the sun sets, the night is yours to rest, relax, or explore. Toss a coin into the Trevi Fountain or grab a drink at a trendy rooftop bar. Let the energy of the city take over. Ancient fare meets modern pleasures.

Day 6 · September 7, 2025
Roam around Rome – a free day and a Bacchus night

-Start your slowly with a leisurely breakfast at the hotel –there’s nowhere to be until the sun goes down. Wander through ancient sites like the Colosseum or Roman Forum, shop in the trendy Monti district, or channel your inner Audrey Hepburn with a Vespa ride through the city. Looking for something artsy? Head to Galleria Borghese or take in sweeping views from Janiculum Hill.

-By nightfall, get ready to turn up the vibe with a lively Rome bar crawl – from cozy wine bars to buzzing piazzas, you’ll sip, toast, and make unforgettable memories under the Roman night sky. Cin cin!

Day 7 · September 8, 2025
La dolce vita, your way

-Enjoy a relaxed breakfast at the hotel before heading out for your final full day in Rome. It’s a choose-your-own-adventure kind of day. Explore iconic spots like the Vatican Museums and St. Peter’s Basilica, take a leisurely stroll through Trastevere’s charming streets, or shop for last-minute finds at Via del Corso. Prefer something off the beaten path? Visit the Aventine Keyhole for a unique view or check out the Appian Way for a historic walk outside the city center.

-As the sun sets, we’ll gather one last time for a glamorous farewell dinner, complete with a three-course meal and drinks to toast an unforgettable week in Italy. What are you toasting tonight? What will you remember forever?

Day 8 · September 9, 2025
Arrivederci, Italia!

-Enjoy one last breakfast at the hotel before packing up your memories (and those fabulous Italian finds) for your journey home.

-A private group transfer will take you to the airport, where it’s time to say ciao to Italy – but never to the experiences and friendships made along the way. Until next time… and remember, Italy always welcomes you back with open arms (and a glass of wine).

Tour Price
USD 2,990
per person
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
NH Collection Milano Touring (or similar according to availability)

The NH Collection Milano Touring offers a perfect blend of classic elegance and modern comforts in the heart of Milan. Ideally located near the iconic Milano Centrale station and the trendy Brera district, it’s a fantastic base for both business and leisure travelers. The hotel boasts a range of stylish rooms and suites, featuring sleek, contemporary designs with thoughtful touches like Nespresso machines and premium bedding to ensure a relaxing stay. Guests can enjoy a delicious breakfast buffet and dine at the chic on-site restaurant offering Italian and international dishes. With amenities like a well-equipped fitness center, meeting facilities, and impeccable service, the NH Collection Milano Touring makes exploring the fashion capital of Italy both convenient and luxurious. Room type/configuration: Double occupancy.

Cellai Boutique Hotel (or similar according to availability)

The Cellai Boutique Hotel in Florence is a stylish, art-filled retreat that perfectly captures the city’s romantic charm. Nestled in a prime location, it’s just a short walk from Florence’s iconic landmarks like the Duomo, Uffizi Gallery, and Ponte Vecchio, making it an ideal base for exploring the birthplace of the Renaissance. The hotel’s rooms are a blend of classic Florentine elegance and modern comfort, featuring curated antiques, plush bedding, and unique artistic touches. Guests can unwind on the charming rooftop terrace with stunning views of the city, or enjoy cozy common spaces like the library and piano lounge. With thoughtful amenities and a warm, inviting atmosphere, Cellai Boutique Hotel feels more like staying in a chic, historic home – perfect for travelers seeking a sophisticated and memorable Florence experience. Room type/configuration: Double occupancy.

Napoleon Hotel Roma (or similar according to availability)

The Napoleon Hotel Roma is a charming, family-run hotel offering an elegant retreat in the heart of Rome. Located just steps from the iconic Colosseum and a short walk from Termini Station, the hotel is perfectly positioned for exploring the Eternal City’s historic landmarks. The spacious rooms blend classic Italian style with modern comforts, featuring plush bedding, soundproof windows, and thoughtful touches to ensure a restful stay. Guests can unwind at the cozy bar, relax in the inviting lounges, or enjoy a meal at the on-site restaurant serving traditional Roman cuisine. With warm hospitality, a prime location, and a boutique feel, the Napoleon Hotel provides a welcoming and sophisticated base for discovering Rome’s timeless charm. Room type/configuration: Double occupancy.

Included
  • 2 nights accommodation in Milan

  • 2 nights accommodation in Florence

  • 3 nights accommodation in Rome

  • Double occupancy in accommodations

  • All breakfasts at hotel

  • Dinner days 1, 7

  • 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 Jun 29, 2025 at 11:59 PM local time (GMT +2), 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 Jun 30, 2025 at 12:00 AM local time (GMT +2) onwards, no refunds will be issued.

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