Tailor-made Holiday · Italy
Milan and Lake Como
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Every trip built from scratch around your dates, pace and preferences.
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At a glance
Experience the allure of Italian sophistication and serenity with this specially crafted itinerary in Italy. Perfect for fashion enthusiasts, culture seekers, and nature lovers alike, this trip offers a seamless blend of urban exploration and lakeside relaxation.
Begin your Italian escapade in the bustling streets of Milan, a city that stands at the forefront of global fashion and design. Here, delve into the world of high fashion, discovering the latest trends in the city's chic boutiques and historic shopping arcades.
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Milan is not just about fashion; it's also a treasure trove of artistic and historical gems. Follow in the footsteps of Leonardo da Vinci, exploring the city's rich artistic heritage at renowned institutions like the Pinacoteca Ambrosiana and the Museum of Ancient Art in Sforza Castle.
For those interested in Milan's vibrant LGBTQ+ scene, there's an opportunity to embark on an optional walking tour to experience the best of Milan's gay nightlife. Discover the city's lively bars and clubs, where the spirit of inclusivity and celebration is palpable.
The journey then transitions to the serene and picturesque Lake Como, an area renowned for its natural beauty and tranquil atmosphere. Stay in the iconic towns of Bellagio and Como, where you can unwind amidst stunning landscapes and explore historical villas.
Lake Como, with its azure waters and majestic mountains, provides a peaceful contrast to Milan's bustling streets. A boat trip on the lake is the perfect way to soak in the breathtaking vistas and elegant villas that line its shores.
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: Milan
Private transfer from the airport to your 5* Hotel. You’ll receive a welcome cocktail and then meet your guide.
This first day will be devoted to the discovery of the main tourist attractions of Milan with a private tour by car. You’ll visit the ‘Galleria Vittorio Emanuele’, one of the most elegant shopping malls in the world, the worldwide famous Duomo and the ‘Teatro alla Scala’ and its museum.
Later in the day, you’ll explore gay life in Milan on an optional walking gay tour where your guide will show you the best gay clubs in Milan.
Return at leisure to your hotel and overnight.
Day 2: Milan
Today you’ll follow in Da Vinci’s footsteps trying to shed light on his mysterious life. Da Vinci was famous for being a misanthrope but it’s believed he had a gay love story with a young trainee called Sala and this relationship influenced him a lot.
You’ll start with a visit to the ‘Pinacoteca Ambrosiana’ with a detailed explanation of its large collection of drawings and writings – in particular, the Atlantic Code of Leonardo – and continue by visiting the Museum of Ancient Art sited in the Sforza Castle. Once there you will admire the ‘Sala delle Asse’ and its ceiling
The highlight of the day is the visit to the Cenacle, the mysterious fresco that became even more famous after appearing in the popular bestseller “The Da Vinci Code” by Dan Brown.
In the afternoon you visit the Leonardo di Vinci Museum of Science and Technology, an interactive museum with both historical artefacts and modern day wonders. Overnight.
Day 3: Milan
This is the perfect day to enjoy the city of haute couture. Your guide will allow you to discover the city of fashion and style. You’ll meet designers and tailors in person for a closer look at how luxury clothes are made.
We’re visiting the fashion houses of Versace, Gucci, Prada, Cavalli and many other famous brands in the fashion world.
Free time for shopping in the afternoon and in the evening. Overnight.
Day 4: Bellagio
You’ll set off by private transfer to Bellagio and your 5* hotel – the perfect place to soak up the lake’s famous panorama. The stunning village is renowned for its century-old buildings and picturesque cobbled streets. You’ll find shops aplenty showcasing the finest Italian wares.
In the afternoon, take a boat trip on the lake and take in the breathtaking views.
Day 5: Bellagio
In the morning you’ll visit two of the most beautiful villas in Italy: Villa Melzi and Villa del Balbianello. Villa Melzi is surrounded by beautiful gardens, waterways, woods and sculptures. You’ll explore the “Orangery” in the grounds, a greenhouse where oranges ripen in the winter period and which is now home of the Archaeological Museum.
Next, it’s Villa del Balbianello, a romantic villa famous for having been the set of various film productions, like Star Wars and Casino Royale from the 007 series.
In the afternoon you’ll return to Bellagio where you’ll sample the traditional dish called “Toc” and sip on fine local wines.
The rest of the day is yours to relax and drink aperitifs and cocktails. Overnight.
Day 6 and 7: Como
The final two days are spent in Como. Wander the romantic streets of this quaint, yet renowned, Italian destination. Visit the Cathedral of Santa Maria Assunta, famous for its gothic style, as well as many other monuments.
Soak up the atmosphere of Como in one of its numerous excellent restaurants and bars.
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.
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, 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 personalised 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 travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, 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, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
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 personalised 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+ travellers 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 travelling 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 enquiry to homecoming. No call centre, and nothing is charged until you decide to book.