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The Perfect Weekend in Chepstow: A 2-Day Group Itinerary

Friday: Arrive, Settle In & Start the Weekend

Make yourself at home

Once everyone arrives in Chepstow, get settled into The Elements Residence and give everyone a chance to unpack and relax.

With several interconnected suites and shared spaces, the house is designed to make group stays easier — giving everyone their own space while still having plenty of room to come together.

Explore Chepstow

Before dinner, head into Chepstow for a relaxed wander around the town.

Take in the historic streets, browse the local shops or simply enjoy a walk through the town before settling in for the evening.

If you have time, you can also make your way towards the River Wye for some fresh air and views.

Dinner with the group

One of the best parts of a group weekend is getting everyone around the table.

Chepstow has plenty of options, from Italian and Indian food to Greek cuisine and riverside dining.

For more ideas, take a look at our guide: Where to Eat in Chepstow: 5 Places Worth Trying

Saturday: Adventure, Food & Time Together

Start with breakfast at the house

There's no need to rush out first thing.

Make breakfast together, grab a coffee and plan the day before heading out.

Having a shared kitchen and dining space means everyone can start the morning at their own pace before coming together for the day's activities.

Get out on the Wye

For an active morning, head out and explore some of the activities available around Chepstow and the Wye Valley.

Canoeing is a great option for groups, combining time outdoors with something a little different from the usual weekend away. If you'd prefer to stay on dry land, there are plenty of other activities to choose from too.

Looking for more ideas? Read our guide to Things to do around the Wye Valley for more group-friendly activities and inspiration for your weekend.

Take a break for lunch

After a morning outdoors, it's time to slow things down with lunch.

You could head back towards Chepstow for a relaxed meal, find somewhere riverside, or choose one of the local restaurants featured in our Chepstow food guide.

For larger groups, booking ahead is always a good idea.

Spend the afternoon your way

The afternoon can be as relaxed or as active as you like.

For something cultural, explore Chepstow Castle and discover a little more about the area's history.

Alternatively, head back into the Wye Valley for a walk, explore the surrounding countryside or simply enjoy some downtime at the house.

Not every part of a group weekend needs to be planned. Sometimes the best moments are the ones where everyone has time to relax and catch up.

Back to the house for the evening

After a full day, head back to The Elements Residence and make the most of having everyone under one roof.

Put your feet up, have a drink, play some games and spend some time together before heading out for dinner — or keep things simple and enjoy an evening in.

For a large group, having comfortable communal spaces can make a big difference. You're not restricted to meeting in a hotel lobby or trying to squeeze everyone around a small table.

Sunday: Slow Down Before You Go

Take the morning slowly

After a busy Saturday, there's no need to rush.

Enjoy a relaxed breakfast, another coffee and some time together before packing up.

If you have a little more time, take a final walk around Chepstow or head towards the river for one last look at the Wye Valley.

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Make your next group weekend one to remember

The best group weekends aren't necessarily about fitting as much as possible into two days.

They're about having somewhere everyone can stay together, finding a few things everyone will enjoy, eating well and having time to actually spend together.

With Chepstow, the Wye Valley and a range of activities on your doorstep, you can build your weekend around whatever your group enjoys.

And when the day is done, The Elements Residence gives you a place to come back to, relax and enjoy the evening together.

Ready to plan your own Chepstow weekend?

Explore The Elements Residence and see how the interconnected suites can work for your group.