Tailor-made Holiday · Italy
Private Gay Group Villa Escape in Tuscany
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
This seven-day luxury gay group escape is built around Villa Ardore, an eight-bedroom private estate surrounded by vineyards and rolling countryside.
Sleeping up to 18 guests, it is ideal for a group of friends, couples, milestone birthdays or a celebration that deserves something more memorable than a hotel.
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The appeal is simple. You have the villa to yourselves, with your own heated infinity pool, spa facilities, wine cellar and plenty of space to spend time together.
Your private chef can take care of meals at the villa, while we arrange the transfers, day trips and experiences around you.
There is still plenty of Tuscany beyond the front gates. Spend a day exploring Siena, San Gimignano and Monteriggioni, taste your way through local wineries, head into Florence for Renaissance art and a standout lunch, then come home to dinner, drinks and sunset back at the villa.
Some days are deliberately slower. Sleep late, spend the afternoon around the pool, book massages at the villa or open another bottle of Tuscan wine with the group.
On another evening, bring everyone together for a private pizza masterclass and dinner around the wood-fired oven.
This is not a fixed gay group tour. It is your own private Tuscany takeover, designed around the people you choose to travel with.
We can tailor the pace, dining, excursions and celebrations around your group, whether you are planning a big birthday, an anniversary, a friends' trip or simply an excuse to get everyone together somewhere exceptional.
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: Arrival at Villa Ardore
Arrive in Tuscany and settle into Villa Ardore, your private home for the week.
The villa sleeps up to 18 guests across eight bedrooms and comes with a heated infinity pool, spa facilities, wine cellar and bar. Once everyone has arrived, start the trip properly with champagne and time to explore the estate.
We will arrange your transfers, so there is nothing to coordinate between the group. Unpack, claim your room and gather everyone together for your first evening in Tuscany.
Day 2: Exploring Siena, San Gimignano & Monteriggioni
After breakfast at the villa, head out together for a day exploring three of Tuscany’s most beautiful historic towns.
Start in Siena, with its medieval streets, striking architecture and lively piazzas, before continuing to San Gimignano and its famous skyline of medieval towers. Finish in tiny Monteriggioni, still enclosed by its ancient walls.
After lunch in the countryside, return to the villa for a private chef dinner. No restaurant reservations, no taxis home, just dinner with your group and the Tuscan hills outside.
Day 3: Relaxing Villa Day
There should be at least one day when nobody has to be anywhere.
Have breakfast when you like, take over the infinity pool and spend the afternoon doing very little. Your private chef can handle lunch and dinner, while the villa’s wine cellar and bar make staying in considerably more appealing.
If you want to make the day even more indulgent, we can arrange private massages at the villa.
Day 4: Tuscan Wineries & Pizza Masterclass
Today is about two of Tuscany’s greatest exports.
Head into the countryside with a wine expert for tastings at local wineries, followed by lunch among the vineyards. Pick up a few favourite bottles along the way and bring them back to the villa.
That evening, a pizzaiolo joins you for a private pizza masterclass. Learn to make your own pizzas, cook them in the wood-fired oven and turn dinner into one of those long, slightly chaotic group evenings that usually becomes the part everyone talks about afterwards.
Day 5: Day Trip to Florence
Spend the day in Florence, one of the great art cities of Europe.
We can arrange private guiding around the Uffizi, Accademia or the Duomo, depending on what your group actually wants to see. Stop for an exceptional lunch, explore at your own pace and then return to Tuscany.
Back at the villa, your private chef prepares dinner, giving you the best part of a Florence city break without having to give up your private countryside base.
Day 6: Relaxing at the Villa
Your final full day belongs to the group.
Stay by the pool, wander through the surrounding countryside, book another treatment or simply settle in for a long lunch that gradually turns into dinner.
For something more organised, we can also arrange a private painting class with a local artist at the villa.
The point is not to fill every hour. The luxury of taking over a villa is having somewhere beautiful enough that you do not always need to leave it.
Day 7: Departure
Enjoy one last breakfast together before your private transfers take you onward.
Or, if seven days does not feel like enough, we can extend the trip with Florence, Rome, the Italian Riviera or another part of Italy.
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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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 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.