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Italy: Milan to Rome

Discover Bel Paese—The Beautiful Country—on our gay Italian escapade.

From Milan to Rome, this 10-day gay culinary crusade will immerse you in Northern Italy’s art, history, food and wine. Alongside a group of like-minded folks, you’ll wallow in the luxury of Lake Como and Lake Maggiore, learn to make perfect risotto in Piedmont, uncork the viticulture of Barolo and follow a truffle farmer into the Monferrato woods. You’ll visit bucket list sites like the Colosseum, Milan’s Duomo and Vatican City. Best of all will be the sense of rapture as you gaze upon some of the world’s greatest masterpieces including Michaelangelo’s ‘David’. Prego! Er… You’re welcome!

Please note: this tour has special booking conditions. Please click here for more details.


Quick Facts


HIGHLIGHTS

  • Stroll the cobblestone streets of Milan, Florence and Rome on private walking tours
  • Relive the glory (and gory!) days of gladiators inside Rome’s Colosseum
  • See some of the world’s greatest masterpieces firsthand and learn about the artists during private tours
  • Enjoy some good ol’ Catholic guilt while touring the smallest country on earth: Vatican City
  • Discover the natural beauty of Lake Como and Lake Maggiore
  • Tour the gardens of Villa Carlotta with an Italian botanist
  • Follow a truffle farmer into the woods of Monferrato and sniff out the region’s black truffles
  • Learn to make the perfect plate of risotto in Piedmont during a private cooking class
  • Sip and swirl famous Italian wines such as the bodacious Barolo
  • Taste Italy’s rich culinary heritage, including pasta, pizza, gelato and tiramisu
  • Wake up each morning to the world’s best espresso and/or cappuccino
  • Swing by Rome’s “Gay Street”, aka Via di San Giovanni

DATES AND PRICES

2025
June 6-15, 2025 (From $8,595 USD)
OPEN
  • Single Supplement (Optional) - All single supplement prices are in USD and additional to the tour price
    • Single Supplement: $1,750.00 per person
  • Payment Terms: 25% Deposit - Balance due 90 Days prior to trip
  • Guides and Hosts for this trip: Frano Novljan
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From $8,595 USD

Bookings have been temporarily disabled due to a scheduled server upgrade. Check back after 11:59PM on July 13th or email info@outadventures.com to get started.

We can’t wait to help you plan an awesome adventure, but due to a high level of fake inquiries we now record your IP address when you submit an inquiry. This helps local authorities identify and prevent harassment against Out Adventures, or any intended recipients.

Tour Map

ITINERARY

Day 1 Milan

Ciao! Welcome to Italy! Today our adventure begins with a short Welcome Meeting at 1PM before we enjoy an extraordinary walking tour of the fashion capital of the world. Highlights will include Scala Theater and Cathedral Square. From the square we’ll gaze upon one of the most famous churches in the world, Duomo di Milan, before taking the lift to its towering roof for a bird’s-eye view of the city. Afterwards we continue to Galleria Vittorio Emanuele II, one of the world’s oldest shopping malls. Together we’ll stroll the mall’s roof for panoramic views, including a gorgeous vantage of the neighbouring Duomo’s spires. This evening we will get our first real taste of Italy’s world-famous cuisine during our official Welcome Dinner.

Day 2 Lake Como & Stresa

Buongiorno! After a simple Italian breakfast, we’ll enjoy a private transfer (approximately 2 hours) to Tremezzo on the shores of the evocative Lake Como. Upon arrival, we’ll hop on a ferry to Villa Carlotta to wallow in the region’s posh lakefront properties and enjoy guided tours of the art and gardens with a local guide. After another ferry ride, we’ll arrive in the picturesque town of Bellagio, located on a promontory overlooking Lake Como. Here, we’ll have some free time to explore the quaint, cobbled lanes and elegant architecture. Lunch will be optional and at your leisure; we recommend one of the boutique cafés in the town centre. After the ferry returns us to Tremezzo we depart for our hotel in Stresa on Lake Maggiore, about a 1.5 hour drive away. Tonight we’ll break bread together at a charming local restaurant.

Day 3 Stresa, Lake Maggiore & the Borromean Islands

Buona mattinata! Today, we’ll be island-hopping to the gorgeous Borromean Islands via ferry boats on Lake Maggiore. Think of it as a mini-cruise where each captivating stop is adorned with blossoming gardens, historic buildings, and elegant villas. First, we’ll explore Isola Bella’s sumptuous Baroque palace and vibrant gardens. Then we’ll hop over to Isola dei Pescatore, a traditional fishing village that’s chock full of adorable Mediterranean architecture. We recommend enjoying an optional lunch at one of the many trattorias that can be found amongst the cozy laneways. Finally, we’ll arrive at Isola Madre, the largest Borromean Island, where we’ll stroll through its renowned botanical gardens at a relaxed pace. Afterwards, the ferry will return us to Stresa where we’ll have the evening free to explore and dine at our leisure.

Day 4 Monferrato

This morning we’ll navigate the North Italian countryside en route to a farming estate in the province of Vercelli. Founded in 1123 by Cistercian Monks, Vercelli was the first Italian region to grow rice. Upon arrival we’ll delight in some homemade risotto—one of Italy’s many famous dishes. Obviously, we’ll enjoy the fruits of our labour paired with a glass of regional wine. After we’re well fed, we’ll venture over to our gorgeous boutique accommodation, a restored farmhouse surrounded on all sides by vineyards, rolling hills and striking country vantages. We’ll have a wee bit of downtime before regrouping for dinner at a cozy family-style restaurant. Buon appetito!

Day 5 Monferrato

After a leisurely countryside breakfast, we’ll enjoy the remarkable experience of truffle hunting! Along with an Italian farmer, we’ll venture into Monferrato woods in search of black truffles. Next we’ll uncork the region’s viticulture in the comune of Barolo. The region’s famously elegant, tannic and rich vintages will have you proclaiming Barol-WOW! After some wine tasting and light sightseeing there will also be time to have an optional lunch. Later this evening for dinner we’ll learn how to prepare the typical Piemontese dishes from ‘la nonna’.

Day 6 Florence

Sadly, it’s time to bid arrivederci to Monferrato as we’re off to fabulous Florence via a 4.5 hour private transfer. This afternoon you’ll have free time before an included dinner where you’ll get your first taste of Florence’s world-renowned wine and cheese.

Day 7 Florence

Today we’ll travel back in time to the sensual Renaissance and Italy’s little-known queer past. Together we’ll stroll the city’s cobblestone streets learning about the Medici Family and gay life during the Renaissance, when Florence was the active center for gay relationships. We’ll visit the Accademia Gallery to see some of the world’s greatest masterpieces including Michaelangelo’s titillating and glorious David. We’ll take our time here, indulging our senses in Michaelangelo’s artisanship while our guide regales us with stories of the artist’s personal and sentimental side. We’ll also learn more about Michaelangelo, including scandalous details on his homosexual lifestyle and his true relationship with Roman popes in the 1500s. Expect dark intrigue and corruption aplenty! Flushed and flustered we’ll step out into the open-air museum at Signoria Square and end our walking tour at the splendid Ponte Vecchio, known as the “Old Bridge” and an everlasting symbol of Florence. You’ll have plenty of free time for lunch and dinner before gathering for a final magnificent stroll at dusk through Piazzale Michaelangelo. Snacks and wine await.

Day 8 Rome

Rise and shine, Gentlemen, as the Eternal City awaits! After a quick breakfast at our hotel we’ll board a high-speed train bounding for Rome proper. Upon arrival we’ll drop our luggage at our accommodation before venturing over to the Colosseum to relive the days of gladiators and spectacles. Later in the day we’ll enjoy a walking tour around some of the city’s most exciting neighborhoods. Specifically, the historic Jewish Quarter and Trastevere. Later this evening we’ll gather for dinner at a nearby restaurant. Afterwards perhaps you can scooter over to Via di San Giovanni, the city’s well-situated gay street located underneath the Colloseum.

Day 9 Rome

Today we head to the smallest country on earth: Vatican City. Our tour starts with the Vatican Museums. At first sight, you will be caught by the modern entrance built for the Jubilee in 2000, but then—inside the museums—the Sistine Chapel will amaze and enthrall. The famed ceiling was painted by Michelangelo between 1508 and 1512. The artist was originally enlisted to paint the twelve apostles, however Michelangelo demanded a free hand in the pictorial content of the scheme. He painted a series of nine pictures that have become some of the most recognizable paintings in the world. After an afternoon at leisure, we’ll wrap up our spectacular journey during a fab Farewell Dinner. If the group is up for it we can also head to a gay bar for one last Aperol Spritz.

Day 10 Rome

Alas! It is our final day and there are no activities planned. If you have time, be sure to swing by Rome’s other famous sites including the Column of Marcus Aurelius, the Pantheon, Trevi Fountain and of course the Spanish Steps. Safe travels and grazie mille for joining our big gay Italy tour. 


GUIDES AND HOSTS

HOST

WHAT’S INCLUDED?

  • Arrival & departure transfers to/from Out Adventures’ joining/finishing point hotel
  • An Out Adventures Host from beginning to end of tour + local day guides for included tours
  • 9 Breakfasts, 1 Lunch and 7 Dinners
  • Gratuities for day/city guides, drivers, included meals and porters
  • All activities mentioned in the itinerary, including city guides and heritage site access
  • All land transportation in comfortable, air conditioned vehicles as well as high-speed trains
  • A $50 USD Rainbow Railroad donation to help resettle LGBTQ+ refugees. Read more here.

WHAT ISN’T INCLUDED?

  • International airfare
  • International departure taxes
  • Meals and drinks not mentioned in the itinerary
  • Drinks with included lunches and dinners
  • Travel insurance is mandatory for all travellers. Click here for more details.
  • Gratuities for Out Adventures Host (budget between $70 – $100 USD)
  • All items of a personal nature (laundry, drinks, etc.)
  • Visa fees

LGBT INFO FOR Italy

IMPORTANT INFORMATION

What to bring, visa information, required
vaccinations, travel insurance and more.
TELL ME EVERYTHING!

EXAMPLES OF ACCOMMODATIONS

Milan
Hotel Bianca Maria Palace
Exterior
Milan
Hotel Bianca Maria Palace
Comfort Room
Milan
Hotel Bianca Maria Palace
Bathroom
Stresa
Grand Hotel Bristol
Exterior
Stresa
Grand Hotel Bristol
Pool
Stresa
Grand Hotel Bristol
Superior Room w/ Lake View
Stresa
Grand Hotel Bristol
Bathroom
Monferrato
Agriturismo Tenuta La Romana
Exterior
Monferrato
Agriturismo Tenuta La Romana
Junior Suite w/ Balcony
Monferrato
Agriturismo Tenuta La Romana
Junior Suite w/ Balcony
Monferrato
Agriturismo Tenuta La Romana
Bathroom
Monferrato
Agriturismo Tenuta La Romana
Pool
Florence
Hotel Glance
Comfort Room
Florence
Hotel Glance
Bathroom
Florence
Hotel Glance
Rooftop Pool
Florence
Hotel Glance
Rooftop Terrace
Rome
Hotel Dei Mellini
Exterior
Rome
Hotel Dei Mellini
Superior Room
Rome
Hotel Dei Mellini
Bathroom
Rome
Hotel Dei Mellini
Terrace



Reviews

Some from our travellers

Jim & Rob

Great locations and extensive tours.
Italy: Milan to Rome
Rating:

Great locations and extensive tours. Our host was outstanding, and our local guide was great. They made sure all details were handled and that all we had to do was enjoy the trip.

ACCOMMODATIONS:
TRANSPORTATION:
MEALS:
GUIDE:

Dave P

It was nice to travel again after a two-year hiatus.
Italy: Milan to Rome
Rating:

Traveling solo in Italy (or anywhere really) is much nicer when you’re doing it with a new group of friends plus two hosts that take great care of you!

ACCOMMODATIONS:
TRANSPORTATION:
MEALS:
GUIDE:

Philip W

I might even do this a second time
Italy: Milan to Rome
Rating:

As a solo traveller (70), I was a little hesitant about taking this journey, but it was nothing but an experience with a lifetime of amazing memories. I loved every minute of this 4-star tour; the company and our cheeky and engaging guide – Frano – made it hugely entertaining. Great food, sumptuous hotels (esp. Lake Como, country villa), lovely places to visit, such kind and friendly companions. I highly recommend it. I might even do this a second time.

ACCOMMODATIONS:
TRANSPORTATION:
MEALS:
GUIDE:
See All Reviews


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CHOOSE YOUR DEPARTURE

From $8,595 USD
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We can’t wait to help you plan an awesome adventure, but due to a high level of fake inquiries we now record your IP address when you submit an inquiry. This helps local authorities identify and prevent harassment against Out Adventures, or any intended recipients.

Who's it for?

While these trips typically attract gay men, all genders are welcome, and we encourage friends and family to join the fun as well.

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Accommodations

All accommodations on Out Adventures tours include breakfast and are located in areas central to our activities. All amenities are examples only, and may differ from hotel to hotel.

4-Star Hotels: Very comfortable and well-decorated rooms along with quality amenities such as a stylish restaurant and/or bar, a fitness centre, and a pool/sauna. Customer service is very good, and there is usually a concierge.

B&Bs: This tour includes an evening in a beautifully restored farmhouse B&B. Expect plush beds, spacious rooms, a hearty Italian country breakfast and top-notch customer service.

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Physical Rating: 2 - LIGHT

Learn More

This trip is fully booked but cancellations occur. If you’d like to be contacted if space opens up, please click “Book Now”, select the appropriate departure and you will be prompted to provide limited information.

If you are a solo traveller willing to share a room with another solo traveller, please select Shared/Twin Room when booking this tour.

If you are a solo traveller interested in booking a private room, please select single supplement when booking this tour (based on availability). If you are willing to share a room with another solo traveller, please select Solo Shared.

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This departure is almost sold out. Book now to guarantee your spot!

This departure is open for booking!

This trip is available but we are close to departure and will need to confirm services such as hotels and activities before confirming you on the trip. The process can take up to 5 business days. If you are seriously interested in this trip, please complete the On Request Booking form and one of our team members will get back to you with next steps.