Italy: Milan to Rome

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.

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.

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.

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!

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’.

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.

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.

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.

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.

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.