A weekend in Cheltenham: A 48-hour itinerary

Best known for its festivals, spa and horse racing, my home town of Cheltenham isn’t the most obvious UK city break destination. It can get overshadowed by its more famous touristy neighbours – with Oxford on one side, Bath on the other and picture-postcard Cotswold villages all around it. But it’s makes for a great weekend break destination in its own right, with gorgeous Georgian architecture and plenty of great places to eat, drink and shop. So here’s my guide to how to spend 48 hours in Cheltenham.

Read more weekend guides

Cheltenham Town Hall

Friday evening

Check in to the Malmaison Cheltenham, in the heart of Montpellier – Cheltenham’s most stylish district, with plenty of bars, restaurants and boutiques. Set in a white Regency villa, the hotel is classically grand from the outside but inside it’s modern and stylish, with lots of contemporary furniture and artworks, and modern tech like paperless check-in and in-room iPads (see my review of their sister hotel in a converted prison in Oxford). There’s lots of space to relax, with a cosy lounge-come-library and a Victorian conservatory as well as a smart bar, restaurant and spa. Double rooms start from £125 a night.

Take a walk through Montpellier to the Daffodil for dinner. The restaurant serves modern British food in a converted art deco cinema, full of gorgeous original 1920s design features (I love it so much I got married there!). Head upstairs for a drink in the Circle Bar first, with a great cocktail list and half-price bubbly and two-for-one gin cocktails on Fridays from 12pm. Then walk down the sweeping stairs to the restaurant – where the cinema screen used to be you can now watch the chefs in action in the open kitchen.

Art deco style at the Daffodil

Saturday morning

Start the day off with a walk through Montpellier and Imperial Gardens. Cheltenham is a big festival city – with annual jazz (May), science (June), music (July) and literature (October) festivals. The parks are used as festival venues, with marquees, shops, cafés and lots of free events. But even if you’re not there for a festival, you can grab a coffee from one of the park cafés and take a walk around the gardens. Carry on down the Promenade, Cheltenham’s main shopping street lined with elegant Georgian buildings.

For some background on the town, join a history and architecture walking tour. The Blue Badge guides have lots of interesting stories about Cheltenham’s Regency buildings and its days as a holiday destination for upper-class spa-goers. Walks start from the Wilson Art Gallery and Museum at 11am and take 90 minutes (adults £5, children £3). At the end of the tour, head back to the Wilson for a look around the galleries. It recently reopened after a big refurbishment and has a mix of exhibits, from Arts and Crafts furniture to the story of local hero Edward Wilson – one of Scott’s team on his ill-fated 1912 Antarctic expedition.

The Wilson Art Gallery and Museum

Saturday afternoon

Refuel with a stop at the Well Walk Tea Room for afternoon tea. It’s one of Cheltenham’s oldest shops and inside is packed with quirky antiques and crafts. Don’t miss a slice of their cake – from an unusual courgette sponge to a Cheltenham Dripper, the local version of a lardy cake – served on vintage crockery. Then burn it off with a walk to the Pittville Pump Room, about 20 minutes north of the town centre. Built in the 1820s, this was Cheltenham’s largest spa building, surrounded by manicured lawns and ornamental lakes. You can still taste the medicinal spa waters from the pump (open 10am–4pm, unless closed for an event).

If you’re a real ale fan, pop into the Jolly Brewmaster for a pint, a traditional-style pub with a great selection of beers on tap and a big beer garden with summer BBQs. Or if wine’s more your thing, head to The Grape Escape, an unstuffy tasting room with a big selection of wines and red and white tasting flights. Have dinner at Koj, a Japanese restaurant that specialises in sharing dishes (and doesn’t do sushi) run by a MasterChef finalist. Then finish the day with a dose of culture, with either a show at the ornate 1890s Everyman Theatre or a film at the Screening Rooms, a luxe cinema with armchairs and waiter drinks service.

The Pittville Pump Room

Sunday morning

If the sun’s out (or you’re feeling brave), start the day with a few laps at Cheltenham’s 1930s Sandford Parks Lido, one of the UK’s largest outdoor heated pools with a 50-metre main pool as well as childrens’ pools (adults £4.80, children 5–15/seniors £2.60). Or if that sounds too energetic, then try out the Hotel du Vin’s ESPA spa, for a relaxing massage, facial or body scrub. Head to the Boston Tea Party next for brunch, with everything from the full English ‘Boss’ breakfast to Scotch Pancakes with bacon and maple syrup.

If you’re in the mood for shopping, you can find the usual high-end, high-street shops (think White Company, Cath Kidston and Space NK) on Cheltenham’s Promenade. Or the area around Montpellier and the Suffolks has lots of interesting independent shops to explore. Check out the Triton Gallery for antiques and interior design inspiration, Bodega for women’s clothes and accessories, David Hayward for bespoke jewellery, Curious City Print Shop for quirky artwork and the Suffolk Anthology book shop.

Cheltenham’s Promenade

Sunday afternoon

Cheltenham is surrounded by gorgeous countryside, so take a walk out of town to explore some of it on a loop around Cleeve Hill (it’s a short car or bus ride on the 606 service to the starting point). The walking route covers about 4 miles up through woodlands and meadows, with panoramic views across the Cotswolds, to Gloucester Cathedral and right across over to the Black Mountains in Wales. It’s part of the Cotswold Way, a 100-mile walking route from Chipping Campden to Bath. Finish the weekend off with lunch at the Rising Sun on Cleeve Hill, a pub with fantastic views across five counties from its beer garden.

Views across the Cotswolds

Have you visited Cheltenham? Do you have any tips to add on what to see, do and eat? And if you do visit get in touch – I am always happy to take people on a cocktail tour!

Pin it

This article contains affiliate links, where I get a small commission at no extra cost to you – thanks.