At a glance
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Our group trips are a great chance to travel with others. We also recommend adding in a few extra nights tailor-made to ensure you build the perfect itinerary.
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.
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 laidback 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 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.
More Information
The legal picture in Italy is more mixed than elsewhere in Western Europe. Civil unions have been legal since 2016 and provide most of the practical rights associated with marriage, including inheritance and hospital visitation, though Italy is one of the few Western European countries that hasn’t yet legalized full same-sex marriage. Anti-discrimination laws cover sexual orientation and gender identity in employment, education and services.
In practice, LGBTQ+ travelers will find the destinations on most luxury itineraries entirely comfortable. The cities, the lake regions, the coastlines and the major islands all welcome same-sex couples as standard. Italian luxury hospitality is unbothered, and the staff at the kind of hotels we book have been welcoming same-sex couples for decades.
Italy also has one of the most interesting LGBTQ+ cultural histories in the world. Michelangelo’s love poetry, Leonardo da Vinci’s biography, the writing of Pier Paolo Pasolini and the films of Luchino Visconti are part of how the country has thought about sexuality for centuries. The legal framework may lag behind the rest of Western Europe, but the cultural ease that comes from that history is real, and it’s what travelers notice on the ground.
- 04 Sep, 2026
- Accommodation as listed
- All transport between itinerary destinations
- All taxes
- Three full day tours with an Italian walking tour guide
- Four dinners
- All full breakfasts
- Two tour leaders throughout your trip
- International Flights
- Travel insurance
- Meals and drinks outside those listed above
- Activities outside those listed above
- Arrival/departure transfers
- Optional gratuities
In detail
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Don't forget that most of our itineraries can be totally customized. Our expert team will be able to talk you through all the options.
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.
More Information
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Don't forget that most of our itineraries can be totally customized. Our expert team will be able to talk you through all the options.
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.
Why book with us?
Personal Service
We want to ensure you have the best experience with us so we’ll keep working on your itinerary until perfect. You will have your own personal dedicated member of our team who will help build a trip that is bespoke to you.
Call our travel experts on +44 (0)20 7157 1570
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