Let's Dream Together

When I was a preteen, I used to hop in the car with my parents on a Sunday afternoon after the lunch dishes were cleaned up, and drive leisurely through our city’s “nice” neighbourhoods, looking for show homes. When we’d spot one, we’d trundle out of our Oldsmobile 88 and go looking through some of the fanciest places I’d seen. Experiences like this made me into an aspirational person. My mom would always end our drives, as we pulled up to our small one-storey home in a not-so-nice neighbourhood, with “I still like our house best.” It was a nice blend of aspiration and contentment. A feeling I still have today. I am content, but I love to dream.

That’s probably what inspired “Your Dream Vacation Mondays.” It is my way of saying, “Let’s dream together.” Let’s breathe deeply of the grape-infused Tuscan air and imagine a family or friends trip marked by lingering long around a beautiful table filled with the rich produce of the land. Let’s envision long days by the pool, soaking in the laughter of our family’s kids, splashing and making memories against a backdrop of Italian cypresses.

Every Monday, I’ll feature one complete trip. Not a mood board. Not a someday wish. A real place, on real dates, with real prices, built for a real group. Because here’s what those Sunday drives taught me: walking through the dream is how you find out it might actually fit you.

A Private Tuscan Villa for Large Groups and Multigenerational Families

For our very first feature, I chose the corner of Tuscany that Renaissance painters couldn’t stop painting. The Val d’Orcia is a UNESCO World Heritage landscape in southern Tuscany, all rolling hills, vineyards, and hilltop towns like Pienza, Montalcino, and Montepulciano. Time passes slowly here, and you get to enjoy every second of it.

Home base is Villa Serenzia, a traditional Tuscan farmhouse near the medieval town of Cetona, about two hours from Rome. Here’s what makes it special for a big group:

The space. Ten bedrooms and seven bathrooms sleeping up to 20 guests, divided into four independent residences under one roof, each with its own private entrance. Grandparents get their quiet mornings. Teenagers get their own corner. Everyone gathers when it’s time to gather.

The comforts. Air conditioning (a real gift in an Italian August), a private pool, housekeeping and a mid-week linen change, all included.

The freedom. The trip includes three vans for your entire stay, because this is countryside made for wandering. The nearest town is six minutes away. Pienza, Montepulciano, and Montalcino are easy drives. And for a day in Florence, you leave the vans at the Chiusi train station and arrive in the historic centre in under two hours.

The wine. Six wineries sit within a 20-minute drive of the villa’s front door, and a full wine tour experience in Brunello country is 50 minutes away. This is the land of Brunello di Montalcino and Vino Nobile di Montepulciano. You will not go thirsty.

The food, your way. One of my favourite things about a villa trip is that dinner becomes whatever you want it to be. Cook together with market-fresh ingredients from the local shops and the Coop in San Quirico d’Orcia for around $35 per person per day. Book a table at a family-run trattoria in a medieval hill town, where a full dinner with house wine runs $35 to $50 a plate. Or hire a private chef for the week and let Tuscany come to you. Most groups do a blend of all three, and honestly, that’s the version I dream about. If you’re wondering what to pack, our packing guide has everything you need for a Tuscan summer.

The Numbers

This is the part that surprises people. When 20 people share something extraordinary, extraordinary becomes affordable.

Per person, including the villa for ten nights (August 9 to 19), three vans for the full stay, the damage waiver, and roundtrip flights to Rome:

That’s a private Tuscan villa summer, wine country at your doorstep, for less than many resort packages. Food, the local visitor’s tax (a few euros per person per day, paid in cash on arrival), fuel, and activities are extra, and I’m happy to help you budget those too.

One important note: these prices were accurate when this post was written, but villa rates, airfares, and exchange rates change without notice and are not confirmed until a reservation is booked and paid in full. If this trip speaks to you, the best thing to do is reach out soon.

VILLA SERENZIA ✦ VAL D’ORCIA

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VILLA SERENZIA ✦ VAL D’ORCIA

Your Turn to Dream

Now I want to hear from you. Every Monday, I’ll choose one dream and build the whole trip, exactly like this one. Real villa, real flights, real numbers.

You can drop them in the comments on our social posts, or send them straight to hello@gatherwelltravel.com. Your dream might be the next Monday feature.

And if the dreaming turns into something more, that’s what Gatherwell Travel is here for. We create family experiences of a lifetime, handling every detail from flights to wine tours so all you have to do is show up and be together.

I still like my house best. But I also believe in the drive, the wandering through, the wondering what if. Let’s dream together.

Julie Day
Founder, Gatherwell Travel
hello@gatherwelltravel.com ✦ (888) 664-3090

Meaningful Travel, Beautifully Planned ✦

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