You’ve booked a villa with a pool, a long table under a pergola, and a view that justifies the deposit. But now the group chat has gone quiet, because everyone’s realised a problem: we have three days and no idea how to plan them.

The villa is the easy part; filling the days inside it are where things get trickier.

So here’s a complete three-day itinerary that focuses on the experience. It gives the weekend a shape, a rhythm of arrival, celebration, and a soft landing, so it feels like a proper holiday and not a logistics exercise.

Adapt it freely to your group (but keep the relaxed, focussed core).

The principle: one anchor a day, and let it breathe

The rule that makes everything else work: plan one real anchor event or activity per day, and leave the rest open.

The activity or event is the thing you’ve booked and built the day around. Everything else (the pool, the long lunch, the wander into town) fills the generous space around it.

Three days with three anchor moment. That’s enough cause a weekend stuffed with five activities a day is how groups end up exhausted.

Day 1, Friday: Arrive and settle

The mistake everyone makes is scheduling something big for the first evening, when half the group is still in transit or tired. Don’t. Friday’s job is simply to let everyone land, physically and as a group.

Afternoon: Arrivals, room sorting, the first delighted lap of the villa. Get the kettle or the prosecco going. Let people unpack at their own pace.
Early evening: A welcome aperitivo on the terrace: a few bottles, some local cheese and salumi, olives, bread. This is the single best-value “activity” of the weekend, because it does all the social work of an icebreaker while everyone’s just standing around a table with a drink.
Dinner: Keep it easy. Either a relaxed group cook (pasta and salad, nothing ambitious) or a booked table at a nearby trattoria. Avoid anything that needs a long drive or a tight reservation; people are tired.
Night: Let it end when it ends. Friday is not the big night. Guests trickle to bed when they want. Save everyone’s energy for Saturday.

The whole day is designed to get the group comfortable with each other before anything is asked of them. By the time you go to bed, strangers have become a group.

Day 2, Saturday: The core day

This is the heart of the weekend, the day the trip is really about. It deserves the one experience you most want to remember.

Slow morning: Coffee, pastries, no alarm. Let people drift down.
Late morning, the anchor: This is where I’d place the yoga and wine experience, and it’s purpose-built for exactly this slot. The gentle group practice can happen right at the villa, weather permitting outside, so you enjoy every moment of that location you chose; then the sommelier-led tasting of Italian wines is held at a nearby winery or other licensed venue, which turns the day into a celebration. It works for the whole group at once, every age, every ability, drinkers and non-drinkers alike, which is precisely what you want from the centrepiece of a hen. (More on why it suits a hen so well.)
Long lunch: Roll straight from the tasting into a leisurely lunch, at the villa if it can provide catering or you have a private chef, or at an agriturismo or restaurant nearby.
Open afternoon: Pool, naps and a wander and gelato in a cute medieval borgo. Deliberately nothing scheduled.
Saturday night: This is your big evening, if you want one: a fancy dinner out, a toast to the bride, and on into the night as far as the group fancies.

Day 3, Sunday: Recovery and a soft landing

The temptation is to cram one last thing in. Resist it. A scrambled (possibly hungover…), packing-in-a-panic Sunday undoes a lot of the weekend’s goodwill. Build the last day to be kind.

Late breakfast: Long, slow and coffee. Have someone popout a get a load of dainty little Italian pastries from a local pasticceria.
A gentle recovery option: If Saturday ran late, this is the perfect morning for a short, restorative session of gentle yoga, movement and breathing to bring everyone back to life before travel. (It’s the same tool from the day before, used in reverse.) Alternatively, a quiet swim or a short stroll.
A little something, if there’s time: For groups not flying until evening, this is the slot for one easy, low-commitment outing: a nearby town, a local must-see site or attraction, a final gelato. If you’re near Pisa, my guide to things to do in Pisa beyond the tower has the genuinely good stops.
Departures: Unhurried. Hugs, group photo, promises to do it again.

The arc, at a glance

Day	Energy	The anchor
Friday	Settle	Welcome aperitivo on the terrace
Saturday	Celebrate	Yoga & wine, long lunch, big night
Sunday	Recover	Gentle restorative session, gentle day out, soft landing

Three days, three anchors, and a great deal of pool time in between. That’s a weekend people remember warmly, not a checklist they survived.

Make it yours

This itinerary is a skeleton; your group is the character. Swap the Saturday anchor for a cooking class or a vineyard visit if that’s ‘more your bride’. But keep the arc, arrive, restore, celebrate, recover, because that’s what turns three days in a nice house into an actual hen weekend.

If the yoga-and-wine Saturday sounds like your bride’s kind of celebration: I bring the yoga to you and arrange the sommelier-led tasting at a nearby winery, tailored to your group. Small groups of 4–12+. For the full planning picture, start with the complete hen-do guide; when you’re ready, tell me about your weekend and I’ll send a quote within 24 hours.