Tailor-made Vacation · Italy
Milan, Venice, Florence and Rome
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
Experience the quintessence of Italian elegance and history with this luxury tour. This journey invites you to immerse yourself in the diverse cultural tapestry of Italy, exploring its most iconic cities.
Your Italian sojourn begins in Milan, the world-renowned fashion capital. Here, amidst the glamour of Via Montenapoleone and the historical grandeur of the Milan Cathedral, you will discover the city's unique blend of modern chic and classical beauty.
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Next, let the enchanting city of Venice captivate your heart. Known as the City of Love, Venice is a labyrinth of picturesque canals, historic bridges, and opulent architecture. Glide through the serene waterways on a romantic gondola ride, and meander through the storied streets, visiting landmarks like Piazza San Marco and the Rialto Bridge.
In Florence, the cradle of the Renaissance, you will be surrounded by some of the world's most incredible art and architecture. Visit the famed Florence Duomo, marvel at the artistic genius in galleries housing works like Michelangelo's David and Botticelli's The Birth of Venus, and soak in the city's rich artistic heritage.
Conclude your Italian adventure in the Eternal City of Rome, exploring its ancient sites. The journey culminates with a visit to Vatican City, where Renaissance art is explored with a focus on its gay themes, offering a unique perspective on this historic site.
This Milan, Venice, Florence, and Rome itinerary is a perfect fusion of Italy's fashion, romance, art, and history.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Day 1 and 2: Milan
When you arrive into Milan airport or railway station, your driver will meet you and take you to your hotel. Explore the city and enjoy dinner in one of the Milan’s best restaurants.
Whilst in Milan, you’ll take a gay-friendly walking tour of Milan with visits to via Montenapoleone, the Milan Cathedral, the Galleria Vittorio Emanuele II and the most important historical and artistic attractions.
After the tour, take an aperitif at Blanco, one of the Milan’s best known gay bars in town during happy hour and, in the evening, explore the gay nightlife of Milan.
Be sure to leave time to explore the boutiques and fashion stores of Milan which have coined many of fashion’s most famous looks.
Day 3 and 4: Venice
You’ll take a high-speed train to Venice which takes around two and a half hours before checking into one of our favourite Venice boutique hotels.
Be sure to step on board a gondola whilst in Venice – which is known by many as the City of Love – before taking a walking tour of the city, with break in a typical “osteria” (tavern) to taste “cicchetto e piattini” (Venetian glass of wine and small dishes of food). Also visit the famous Piazza San Marco (St Mark’s Square), the Rialto Bridge and other wonderful locations.
Day 5 and 6: Florence
Hop aboard your next high-speed train for the two-hour journey from Venice to Florence.
Explore the beautiful streets of Florence with a guide who will take you to Piazza della Signoria, Santa Maria Novella Church and other wonderful locations.
Florence is a hub of Renaissance art and architecture. Indeed the Duomo is perhaps its most famous building, thanks to its terracotta-tiled dome. Its art galleries and museums also display some of Italy’s finest works such as Michelangelo’s sculpture of David and Botticelli’s The Birth of Venus.
Day 7 to 10: Rome
This morning you’ll leave Florence by high-speed train which takes an hour and a half. Stay in one of our favourite boutique hotels in the heart of the city.
Whilst in the city, take a gay-friendly walking tour of Ancient Rome, to discover the Colosseum and the Imperial Fora, followed by light lunch at Coming Out, the best known gay bar in the capital.
Explore Vatican City to discover the untold story of gay Renaissance artwork. A guide will show you many paintings and statues with underlying, or even overt, gay themes.
Our Experts
Italy is one of the best places in Europe to experience culture, food and beautiful scenery. With so much character and colour, the Amalfi Coast is a personal favourite of mine.
I never get tired of planning luxury vacations in Italy. There are so many magical cities and experiences to be enjoyed. Beaches, mountains and rolling countryside, there really is something for everyone.
Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first inquiry to homecoming. No call center, and nothing is charged until you decide to book.