A holiday gets awkward when the people who like walking assume everyone else is waiting to be persuaded. It gets just as awkward when the walkers feel they must abandon the hills to keep the group together. You can solve both problems by giving each morning a purpose and making lunch the shared point of the day.

Cheltenham is a useful base for that arrangement. There is genuine hill country close to town, while the town itself offers art, parks, shopping and cafés. The non-walking group has somewhere interesting to go, rather than a spare hour in the car while the walkers finish their circuit.

Start together on Clarence Street

Boston Tea Party on Clarence Street is our breakfast choice. Its central location and breakfast-and-brunch offer suit a group with different appetites. Published facilities include step-free access, but ask about the entrance, seating and toilet arrangements that your group specifically needs.

Use breakfast to agree the lunch booking, the contact number and how the walkers are getting back. This is the organiser’s useful five minutes. It avoids the lunchtime messages that begin with ‘we are somewhere near the top’ and end with everyone looking at a cooling meal.

For the walkers: Leckhampton Hill

Leckhampton Hill and the Devil’s Chimney give the walking group a real countryside morning. Choose a mapped route and starting point that fit the available time. Paths can be steep and muddy, and the exposed parts feel different in poor weather. Take appropriate shoes and leave enough time to return, change and travel to lunch.

The appeal is the change of scale above the town: views open out, the escarpment becomes apparent and the distinctive rock formation gives the walk a clear subject. The distinctive rock formation gives the outing a clear focus. You can enjoy a shorter route here without trying to complete a long section of the Cotswold Way before the restaurant booking.

For the town group: art and a route of your own

The Wilson is the first option for people who want an indoor cultural morning. Check current opening and exhibitions, then choose the collection or show that interests you. A museum visit is a proper activity in its own right, not a consolation prize for opting out of the hill.

Others may prefer the Promenade, shops or a café. Keep that route realistic for the people walking it. A town can be manageable without every pavement, crossing and entrance being equally easy. If someone wants very little walking, arrange a destination and transport rather than describing a long wander as gentle.

A real lunch booking brings the day together

Book The Coconut Tree for lunch. Sri Lankan small plates give the meal a different character from the usual walking-day pub stop. Order for the group’s appetites, talk through allergies and decide whether you want to share; nobody has to pretend they want the same level of spice or the same number of dishes.

This is a planned journey from the hill for the walkers and a town journey for the others. Allow enough time for both. The restaurant’s published Monday-to-Thursday kitchen has a break between lunch and dinner, so a late drifting lunch is not interchangeable with the booked early-afternoon meal.

An afternoon everyone can choose

Pittville Park is one option after lunch. The landscape around the Pump Room and lake has a different feel from the central shopping streets. Choose the section that suits the group, and remember that seeing the Pump Room exterior is not the same as visiting inside; events and access have their own arrangements.

Alternatively, split for a second short outing and meet for dinner. There is no rule that everyone must spend every hour together because they booked the same accommodation. The successful part is agreeing it openly, rather than one person silently tolerating an afternoon they do not enjoy.

Dinner for the whole table

The Bottle of Sauce is a useful casual dinner choice, with pizza and burgers and a sociable pub setting. Book for a group and check the kitchen hours for your day. After an active morning, this can be a more relaxed answer than a formal restaurant booking with a tight arrival time.

If the occasion calls for a more dressed-up meal, Muse offers a different style. Its published access limitations mean it will not suit every group, particularly anyone needing accessible facilities. Choose the venue around the people attending, rather than inviting them and hoping the building works.

Repeat the arrangement, rather than the route

On day two, Cleeve Common can provide another walking option while the town group chooses a different activity. Keep the same principle: breakfast together, meaningful separate mornings, a meeting point and a meal worth returning for. A mixed-pace weekend works when both versions of the holiday are treated as equally worthwhile.