With its spectacular architecture, vibrant dining scene and plenty of entertainment to choose from whether you're into sports, art or theatre, Cheltenham is a fantastic destination for a date.
SoGlos rounds up 14 of the best places to go on a date in the Regency town, to help you impress your beau.
Casual dining date night
The Brewery Quarter boasts a whole host of casual dining destinations to satisfy almost every taste, so it's ideal for a date night in Cheltenham – with plenty of entertainment options on offer, too.
Share a tapas board at The Cosy Club, chow down on burgers and wings at BrewDog or Hub Box, try one of The Botanist's famous hanging kebabs, enjoy a theatrical dinner and drinks at The Alchemist, spice things up at Mowgli or Pho, or satisfy your inner carnivore at Son of Steak. There's even Creams Cafe where you can share a sundae with your sweetheart.
Challenge your date to an Escape Room
Whether you're a naturally competitive couple, or fancy going head-to-head with your besties on a double date, Escape Hunt at The Brewery Quarter offers a variety of challenges.
There are five different escape rooms to try, from the King Arthur-themed Excalibur to the mind-bending Alice in Puzzleland, with games suitable for two to six people.
Try something sporty with your significant other
Active couples have plenty of fun activities to choose from in Cheltenham town centre – with The Brewery Quarter being home to Hollywood Bowl, Mr Mulligans Adventure Golf and social darts venue Flight Club.
Slightly further afield, Boulders at Centrum Park offers indoor climbing and bouldering for adventurous couples; while Ian Coley Sporting on the outskirts of Cheltenham offers clay pigeon shooting surrounded by idyllic Cotswold countryside.
Book a ticket to Cheltenham's underground SpeakeaZy
Hidden away in an underground venue below popular pizza pub The Steam & Whistle, famous Cheltenham resident Dom Joly hosts a monthly SpeakeaZy night with a lineup of super secret special guests.
While you'll never know who you'll be seeing until you're there, previous guests have included comedy legend Jenny Eclair and 90s icon Babybird – promising a surprising date night that's bound to impress.
Go all out with fine dining
From the freshest sushi and sashimi at KIBOU, swanky small plates at Sam's Montpellier, dinner with a view at Cheltenham's only rooftop restaurant The Nook, to Indian fine dining at the Gloucestershire Lifestyle Awards Restaurant of the Year 2025 Prithvi, foodies with a taste for the finer things in life are spoiled for choice in Cheltenham.
Cheltenham even boasts not one, but two Michelin-starred restaurants in Le Champignon Sauvage and Lumiere.
Take a steam train ride from Cheltenham to Broadway
Take your lover on a date with a difference by hopping on board the Gloucestershire Warwickshire Steam Railway – with a station at Cheltenham Racecourse.
GWSR offers everything from afternoon tea to fish and chip specials aboard the Cheltenham Fryer and even murder mystery evenings, where partners in crime can team up to try and discover whodunnit.
Watch the sun set from Cleeve Hill
Pack a picnic and hike up to the top of Cleeve Hill to cuddle up under a blanket and watch the sun set.
Offering spectacular views across Cheltenham and beyond, this romantic spot is perfect for outdoorsy couples who don't mind a bit of a trek to be rewarded with incredible sights.
Say cheers to love with a brewery tour and tasting
Brewhouse & Kitchen at Cheltenham's Brewery Quarter isn't just a pub, it's actually a microbrewery – and it offers beer making experiences with one of its master brewers, including breakfast, lunch and a mini keg to take home.
Not a beer fan? Not a problem! Dunkertons Cider in Charlton Kings offers regular cidery tours with cider and cheese pairings – not to mention an array of street food and regular evening entertainment, from live music, DJ sets and comedy to quiz nights, tarot readings and paint and sip socials, if you fancy making a night of it.
Go to a show together at Cheltenham's Everyman Theatre
Theatre-loving couples will be in their element at the Everyman Theatre, with its auditorium – designed by Frank Matcham – providing a spectacular setting for a special evening.
Watch everything from West End smash hits, big-name comedians, homegrown productions and even beautiful ballets.
Soak up some culture at Cheltenham's museums and art galleries
With its rich Regency heritage, Cheltenham is a wonderful place for sapiophiles to enjoy a mind-expanding date.
Take in the artworks and artefacts at The Wilson Art Gallery and Museum, learning all about its namesake Arctic explorer, Edward Wilson; admire art created by people in the community at the Gardens Gallery in Montpellier; or take a stroll towards Pittville and pop into the Holst Victorian House to see the birthplace of Cheltenham's famous classical composer, Gustav Holst. The annual Art in the Park event makes for a great sunny summer date for artsy couples, too.
Take a dip at Cheltenham Lido
Cheltenham's heated outdoor lido is a fantastic place for a summer date, providing acres of grounds to lounge in a sunny spot and a 50-metre outdoor pool to cool off in.
There's also a sauna bringing some Scandi vibes and a cute cafe where you can grab coffee and a bite to eat once you're all dried off. It also offers sunrise and midnight swims for extra special experiences.
Indulge in a couples spa day
Ellenborough Park's Spa Garden Retreat offers a indulgent way to spend quality time with your date, with a 50-minute treatment each and a two-course lunch with prosecco included.
Once fed and fully relaxed, couples can while away the afternoon with 90 minutes in its secluded spa garden, complete with private hot tub, ice bath, heated outdoor pool and sun loungers, as well as indoor facilities including jacuzzi, sauna and steam room.
Go rowing on Pittville Park's lake
A stroll around Pittville Park is romantic enough itself, but during the summer months, couples can recreate the iconic scene from The Notebook by hiring a rowing boat and heading out onto the water.
Stop by The Boathouse Cafe, spend an hour on the lake taking in the sights and sounds, then hop back on to dry land for a coffee or an ice cream afterwards. Swoon!
Catch a movie together in Cheltenham
It's a classic for a reason – who doesn't love grabbing popcorn and a drink to share and cuddling up close to watch a movie on the big screen?
Cineworld at The Brewery Quarter shows all the Hollywood blockbusters, as well as National Theatre screenings and special anniversary events, too.
