Detours Gay Travel Blog
POV: Waking Up in Your Tuscan Castle
- Detours
- May 22, 2025
Ever dreamed of staying in a castle? A real castle, with sweeping views of vineyards, thousand-year-old walls, and lush Italian gardens that feel like something out of a fairytale? Now’s your chance to live that fantasy! 💫
Oh, and don’t worry, it’s not all medieval. There’s high-speed Wi-Fi, modern A/C, and a sparkling pool. Because let’s be honest, royalty should never have to choose between charm and comfort. 👑💻☀️
Welcome to Castello delle Serre, your home base for eight unforgettable days in Italy with Detours gay group travel. This trip is all about exploring the heart of Tuscany while living like you own the palace — and yes, it’s better than it sounds.
Welcome to Your Italian Castle
Perched on a hilltop in the rolling countryside of Tuscany, Castello delle Serre is a lovingly restored medieval castle that perfectly blends centuries-old elegance with modern comfort. This isn’t just a hotel — it’s an experience from the moment you walk through the gates. Picture this: fresh espresso in the courtyard, afternoons by the pool, and evenings sipping wine as the sun sets behind the hills. 🌄🍷
Parts of the castle date back over 1,000 years, with the main structure standing strong for over 500. In 1995, the property was purchased from a debt-ridden contessa (yes, for real) by the Gangale family, who have poured years of love, vision, and painstaking restoration into it. Original frescoes and architectural details have been carefully recreated, preserving the historic soul of the castle, while making it a comfortable and luxurious place to stay.
And the rooms are stunning! Each one comes with A/C, a private bathroom, and sweeping views of the Tuscan countryside that make waking up every morning feel like stepping into a painting.🎨🪟
Whether you’re a history buff, a hopeless romantic, or just someone who’s very into wine and a good poolside moment, trust me, this castle delivers.
The Trip of a Lifetime
This eight-day Italian adventure is all about laid-back exploration, authentic local experiences, and our signature structured spontaneity. That means enough guidance to keep things stress-free, but plenty of room for you to do your thing.
We kick things off in Rome, where you’ll meet your two Detours trip leaders and your small group — aka your new travel fam. 🧑🤝🧑🌈
Our first night includes a warm Italian welcome: a group dinner at a charming Roman trattoria (hello, fresh pasta), followed by a celebratory night out in the city’s buzzing gayborhood. Laughter, Aperol spritzes, and instant connections? Count us in! 🍝🥂🌃
The next morning — don’t worry, we keep it leisurely — we hop into private transportation for a two-hour drive through the gorgeous Italian countryside, headed straight for your castle in Tuscany. And that’s when the magic begins.
Tuscany Awaits
For the next seven nights, Castello delle Serre becomes your royal headquarters. No packing and unpacking, no switching hotels — just a home base that feels like a dream.
From the castle, we’ll take daily trips to explore the best of Tuscany. Some days are filled with iconic cities and must-see landmarks. Other days, we slow down and wander through hilltop villages or stop at a vineyard that seems plucked straight from a postcard.
Here are just a few of the unforgettable stops along the way:
Siena: Medieval charm at every turn 🏰
Siena feels like stepping into a storybook. Its narrow, winding streets, towering cathedrals, and red-brick piazzas are packed with history and charm. Whether you’re wandering through its UNESCO-listed historic center or climbing the Torre del Mangia for panoramic views of Tuscany, this medieval city invites you to slow down and soak it all in. Get lost on purpose — you’ll be glad you did.
Florence: Art, architecture, and aperitivo 🎨
Florence is where the Renaissance was born — and it shows. Masterpieces by Michelangelo and Botticelli, stunning architecture like the Duomo, and streets buzzing with creativity make this city an absolute must-see. Spend the afternoon exploring world-famous galleries or just strolling the Arno River with a gelato in hand. Florence has a way of making everything feel a little more beautiful.
We’ll also visit olive groves, explore local markets, and enjoy long, leisurely meals that always seem to end with a toast (or three).
Pisa: Yes, the tower is here (and so much more)
Sure, everyone comes for the Leaning Tower — but Pisa is more than a photo op. After you’ve nailed the classic tourist pose (no shame!), explore the surrounding Campo dei Miracoli, visit the cathedral, and wander off the beaten path to discover cafes, quiet side streets, and a lively student vibe that keeps this historic city feeling fresh and vibrant.
Wine Country: A toast to the good life
Tuscany’s wine country is every bit as romantic as you imagine. Rolling hills lined with cypress trees, ancient stone farmhouses, and endless rows of vines set the scene for some truly unforgettable tastings. Learn the winemaking process from passionate locals, sip world-class Chianti, and enjoy long, leisurely lunches overlooking the vineyards. It’s not just a tasting — it’s a lifestyle. 😏
Hidden Hilltop Villages
Away from the big-name cities are Tuscany’s true hidden gems: hilltop villages that feel untouched by time and full of unique experiences. These are the kinds of places where you can wander without a plan, discover local markets, chat with friendly shopkeepers, and stumble upon the best meal of your trip. They're small, unassuming, and unforgettable — the kind of magic that doesn’t show up in guidebooks.
Life at the Castle
While the adventures are incredible, castle life is a highlight all on its own. Every morning, wake up in your private room, grab a cappuccino, and breathe in the warm Tuscan air. The mornings are peaceful. The afternoons are for relaxing; lounging by the pool, reading under a lemon tree, or grabbing a spritz while enjoying a social opportunity with a new Detours friend.
Evenings at the castle? Pure magic.
Whether it’s a homemade dinner in the courtyard, a casual wine tasting with local winemakers, or a spontaneous dance party with the group, every night has its own kind of charm.
One of our favorite experiences? A private wine tasting at the castle, led by a passionate Tuscan vintner. Imagine: the glow of candles on ancient stone, stars overhead, and the kind of laughter that only happens after a couple of glasses of Chianti. 🍷🌙
And because the vibe is so laid-back and flexible, you’ll have space for everything — group bonding, solo reflection, or that mid-afternoon nap you didn’t know you needed. 😴🛏️
This isn’t just a vacation — it’s a reset; a chance to slow down, soak it in, and reconnect. Tuscany has a way of making time feel... different. Maybe it’s the rolling landscapes, the food, the wine, or the history. Maybe it’s the people. Or maybe it’s just the magic of waking up in a castle and realizing — this is real life, at least for a little while. 🏞️
Tuscany Awaits
So, picture it:
Morning light spilling into your room through ancient shutters. Olive trees swaying in the breeze. Long dinners, easy laughter, late-night swims. The best wine you’ve ever tasted. And a group of authentic travelers who feel more like friends.
Whether it’s your first trip to Italy or your 10th, there’s something about Tuscany — and Castello delle Serre — that sticks with you. You won’t want to leave. And honestly? That’s kind of the whole point.
We’ll see you in Italy. 🇮🇹❤️🍷