Group Trip · Italy
Gay Group Trip: Tuscany Explorer
Fixed departures
Dates and itinerary set, organised end to end. Tailor-made available too.
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
Stay in a 600-year-old castle in Tuscany, perched on a hillside overlooking vineyards and a historic village. You'll be exploring one of the most beautiful parts of Italy with 30 gay travelers. Sun yourself by the private pool, explore the castle, and take day trips to Siena, Florence, and Pisa. You'll be returning to the castle every night.
This will be a bucket list trip where you will join a group of other LGBTQ+ travelers in Italy.
Read more
Your adventure begins in Rome. You'll spend a night in the Eternal City and have a classic Italian meal in Rome's gayborhood. It's a two-hour train ride the following morning from Rome to Tuscany. You'll be spending seven days in the castle, no less. There are various accommodation options at the castle. These include poolside cottages and elaborate suites with private rooftops. You'll have two trip leaders throughout to guide you through Rome and Tuscany.
The laid-back nature of this trip means you'll have plenty of room for spontaneity—no stressful early mornings or limiting daily itineraries. Relax, explore, and have fun with new friends.
You can join the trip as a solo traveler, with a partner, or as a group of friends. Solo travelers will need to pay extra for a private room or can be paired up with another solo traveler at no extra cost. Joining a group trip organized by destination experts is a great way to ensure you see the best of the region in one trip. All you have to do is show up and enjoy the ride.
Day by day
Group departures follow a set route so everyone travels together. The nights and the order are fixed, but your specialist can add time either side. Prices are an entry-level guide; your quote will be exact.
Day 1: Rome
You’ll land in one of the most beautiful and historic cities in the world. You can arrive a little earlier if you’d like to explore Rome properly – we’d definitely recommend it.
We meet at 4pm on day one. You’ll get to meet your fellow travellers and two tour guides. You’ll wine and dine in Rome and find out more about the adventures we have planned. Let us know if you’d like us to arrange an extension for you in Rome.
Day 2 and 3: Tuscan Castle
After breakfast we’ll take a train to the heart of Tuscany. The castle compound is truly spectacular – we’ll begin with a tour of the castle.
We’ll explore the village of 2000 inhabitants and explore nearby wineries and towns. Back at the castle it’ll be time to grab a Chianti and enjoy your first night in a Tuscan castle.
Day 4: Pisa and Tuscany
Today we’ll visit Pisa where you can take that mandatory selfie by the leaning tower. Who messed up that famed tower? We shall take a deep dive and find out. A local tour guide will show us around Pisa and help to unravel its 3000 history.
There’s so much more to Pisa than the architectural curiosity people take selfies in front of. It’s a great art city, full of charming alleys, squares and markets. After exploring Pisa, we’ll head to Lucca, a fabulous medieval city. Its distinctly Italian architecture is a must-see in Tuscany.
Day 5: Siena
Siena is a 30-minute drive away. It’s famed for the Palio horse race. It’s quite brutal and it’s been going since the 11th century. Siena was a rich and independent city state, until it was defeated and descended into poverty. The original medieval buildings were left standing as they couldn’t afford to build new ones. Now it’s a must-see destination that gives you a glimpse of old world Italy.
Dinner in Siena in a beautiful patio restaurant.
Day 6: Tuscan Castle
Feel free to spend the day relaxing by the castle’s pool. If you’d like to explore some more, you can join us as we explore more local villages and delve deeper into Tuscan cuisine.
Day 7: Florence
Florence is just 80-minutes away from the castle. It’s one of the most magical cities in Europe. Famed for its stunning Renaissance art and architecture, it’s a monument to Italian culture. Our local guide will take us for a tour and discover some of the great artworks. Florence is the birthplace of gelato and the modern Italian language itself.
In the evening, we’ll explore Florence’s nightlife have dinner. We’ll then head back to the castle for our last night in Tuscany.
Day 8: Departure
It’s time to take the Roman road and say goodbye to our 14th-century castle. We can arrange an extension for you if you’d like to visit Venice, Milan or the Amalfi Coast.
Departures
Prices are per person sharing. A single supplement applies to solo travellers and your specialist will confirm it with your quote.
Further information
Castle Accommodation
Nestled amidst the picturesque Tuscan hills, this meticulously preserved 20-suite castle offers an enchanting retreat. Each room boasts a private bathroom and modern A/C, with a selection of options – some rooms are ideal for couples, while others cater to solo travelers. Dive into the serene private swimming pool, explore the beautifully restored grounds, and immerse yourself in the charming village that envelops the castle. Experience 800 years of history, together with the comfort of the 21st century, and enjoy an unforgettable week together.
Rome Accommodation
You’ll stay at the Monti Palace Hotel in Rome. Nestled in the heart of the city, this recently unveiled establishment serves as an ideal launchpad for your explorations. A mere 10-minute stroll from the entrance, you’ll find yourself gazing up at the iconic Colosseum and the awe-inspiring Roman Forum. Inside the hotel, you’ll find contemporary design, a rooftop restaurant, and incredibly comfortable rooms.
Italy Information
What’s the Climate Like?
The period from June to September offers abundant sunshine in Italy. Daily temperatures are expected to range between 75°F and 85°F (24-30°C). With minimal rainfall during this dry season, it’s advisable to pack ample sun protection. Nevertheless, as weather can occasionally be unpredictable, it’s wise to include some ‘just in case’ rain gear in your packing list.
What’s the Currency?
The Euro is the primary currency in Italy. Having some cash on hand is recommended for purchases like souvenirs and tips. Most shops and restaurants accept Visa and Mastercard, though American Express is less widely accepted. ATMs are readily available throughout the trip for additional cash.
What Are The Excursions?
You’ll enjoy a series of thrilling excursions, including guided day trips to Siena, Florence, and Pisa, as well as enchanting dinners at the castle and the local village. Some of these are already covered in your trip expenses. Nevertheless, you’re free to deviate from the schedule if you have other specific interests.
What’s the Phone Service Like?
Many cell phone carriers offer international roaming on Italian networks. Contact your provider to confirm coverage and inquire about cost-effective international service plans. We will have data and call connectivity throughout the trip, and the accommodations provide complimentary WiFi.
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.
Our family of 12 had a dream trip to Italy for our 50th anniversary, and not one glitch.
Diane
It was great to have help from someone who lived in Italy and could give us that point of view.
Jenna M.
When we were thrown off schedule in Italy, the team jumped right in. Excellent planning and support throughout.
Prickett
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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.
Speak To Us About This Group Trip
Tell us which departure interests you and one of our LGBTQ+ travel specialists will confirm availability and talk you through the trip, including any tailor-made extensions you would like to add before or after the group dates.
One named specialist, first enquiry to homecoming. No call centre, and nothing is charged until you decide to book.