Jun 5 — 14, 2026Land TripMediterranean

Italy: Milan to Rome

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Out Adventures

9Nights

6Locations

20Max Guests

Out Adventures

A Journey Worth Savoring

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 Michelangelo's 'David'. Prego! Er… You're welcome!

A 10-day gay Italian escapade through Northern Italy's art, history, food and wine — from Milan to Rome via Lake Como, Lake Maggiore, Monferrato and Florence.

Steven Krumholz

310.560.9887 — steven@kgaytravel.com

Steven Krumholz is the guy who actually picks up the phone — and the one who knows which cabin, which resort, and which party is worth your time. Decades of access, zero booking fees, all heart.

$0Booking FeeNEVER A FEE — HASSLE FREE.

Don't forget travel insurance.Need an airport transfer?

A Journey Worth Savoring

A 10-day gay Italian escapade through Northern Italy's art, history, food and wine — from Milan to Rome via Lake Como, Lake Maggiore, Monferrato and Florence.

Steven Krumholz

310.560.9887 — steven@kgaytravel.com

Steven Krumholz is the guy who actually picks up the phone — and the one who knows which cabin, which resort, and which party is worth your time. Decades of access, zero booking fees, all heart.

What's in the package

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
$50 USD Rainbow Railroad donation to help resettle LGBTQ+ refugees

Not included

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

Detailed Itinerary

Day01JUN 5

Milan

Milan is Italy's queer trailblazer and the high-fashion capital of the world, renowned as one of the top gay travel destinations in Italy. The city boasts the largest variety of LGBT-friendly clubs and venues, with a vibrant and welcoming LGBTQ+ community. Milan made history as the first Italian city to register civil unions between same-sex people, cementing its progressive stance. The city offers a cosmopolitan atmosphere perfect for gay travelers seeking a fabulous city break experience.

Day02JUN 6

Lake Como & Baveno

Lake Como is a stunning Alpine lake in northern Italy offering a romantic getaway with picturesque lakeside towns, historic villas, and breathtaking mountain scenery. The region, including the charming town of Baveno on nearby Lake Maggiore, is renowned for its elegant architecture, fine dining, and welcoming atmosphere for all travelers. Lake Como appeals to diverse visitors seeking cultural experiences, outdoor activities, and the authentic beauty of Italy's Italian Lakes region.

Day03JUN 7

Lake Maggiore & the Borromean Islands

Lake Maggiore is a stunning natural paradise located in the Piedmont region of northern Italy, offering year-round attractions and a mild climate. The lake is home to the famous Borromean Islands, which are essential stops on any itinerary. Visitors can enjoy a variety of sports activities including hiking, biking, golf, and horseback riding in the surrounding areas. The lake combines natural beauty with cultural heritage, making it an ideal destination for both adventure seekers and those interested in historic palaces and spectacular gardens.

Day04JUN 8

Monferrato

Monferrato is a picturesque hilly region in northwest Piedmont, Italy, renowned for its stunning landscapes, rolling vineyards, and authentic medieval villages. This wine-producing area combines rich history with exceptional cuisine and wine culture, offering visitors charming small towns like Casale Monferrato, Cella Monte, and Ozzano set amidst breathtaking countryside perfect for cycling, wine tasting, and cultural exploration.

Day05JUN 9

Monferrato

Day06JUN 10

Florence

Florence is the capital city of Tuscany in central Italy, renowned as the birthplace of the Renaissance and a world-leading center of medieval European art and architecture. The city is famous for its stunning cathedral (the Duomo), iconic artworks including Michelangelo's David, and masterpieces by Leonardo da Vinci. Florence's rich cultural heritage, picturesque streets, and artistic legacy make it one of Italy's most visited destinations. The city also has an established LGBTQ+ community with a welcoming gay scene centered around the Santa Croce neighborhood.

Day07JUN 11

Florence

Day08JUN 12

Rome

Historic port city serving as gateway to Rome's ancient landmarks. Home to iconic attractions including the Colosseum, Vatican, Trevi Fountain, and 2,000+ years of history.

Day09JUN 13

Rome

Historic port city serving as gateway to Rome's ancient landmarks. Home to iconic attractions including the Colosseum, Vatican, Trevi Fountain, and 2,000+ years of history.

Day10JUN 14

Rome

Historic port city serving as gateway to Rome's ancient landmarks. Home to iconic attractions including the Colosseum, Vatican, Trevi Fountain, and 2,000+ years of history.

9Nights

6Locations

20Max Guests

$0Booking FeeNEVER A FEE — HASSLE FREE.

Don't forget travel insurance.Need an airport transfer?