Discover fun, unusual and totally romantic ways to spend a day in Winchester
Whether you’re on a weekend getaway with your special someone, exploring the city for the evening, or just want to enjoy a lovely day out, check out the most romantic things to do in Winchester. We've rounded up a selection of award-winning restaurants, beautiful city strolls, unique activities and romantic overnight stays for you to choose from. Because you deserve to spend time with the person you love in a place you love, too!
Read on for romantic things to do year-round in Winchester.
Curated by the Visit Winchester team. Updated: 10 February 2026.
Watch a spectacular theatre performance
If you’re planning a night out for two, a trip to the Theatre Royal Winchester is a great focal point to your evening. With everything from opera and comedy to cinema screenings and jazz brunch, there is truly something for every taste to enjoy. Discover what's on their fantastic programme this season!
Making a night of it? The Theatre Royal Winchester is located in the heart of Winchester's cultural quarter, meaning you're spoiled for choice when it comes to pre-show dinner spots and charming cocktail bars.
📍Theatre Royal Winchester, Winchester City Centre
Travel on a vintage steam train
Sit back and relax on the Watercress Line, a heritage railway through the heart of Hampshire. On standard travel days, you'll be treated with scenic views of the South Downs National Park. Hop on and off throughout the day, exploring the historic town of Alresford and the history of the line on the platforms.
On selected days throughout the year, you can experience everything from murder mystery and wine-tasting evenings to the popular Real Ale Train. Check out The Watercress Line's dining experiences for a date night to remember!
📍The Watercress Line, Alresford
Learn how to make a perfect cocktail
Did you know that the world-famous Bombay Sapphire Gin is distilled just 15 miles from Winchester? Laverstoke Mill is home to the Bombay Sapphire Distillery, which offers plenty of romantic experiences (with gin, of course)!
During their Gin Cocktail Masterclass, you can take a your of the distillery, including the iconic glasshouse, followed by a masterclass on creating delicious gin cocktails.
Don't fancy making the cocktail? Sit back and relax with a complimentary cocktail and your favourite films during one of their after-dark movie nights.
📍Bombay Sapphire Distillery, Laverstoke
Explore Britain's oldest bookshop*
Book-lovers flock to P&G Wells on College Street for its cosy ambience, gorgeous frontage and excellent selection of books. Browse classics, new-releases, local authors and non-fiction at this Winchester staple.
*P&G Wells is said to be Britain's oldest bookshop (probably) because the shop itself has been based in Kingsgate for nearly 300 years. The Wells name, on the other hand, has been associated with the shop at 11 College Street for nearly 200 years. A visit here will put you in good company; past patrons include John Keats and Jane Austen!
📍P&G Wells, Winchester City Centre
Walk in the footsteps of a famous poet
The English Romantic poet, John Keats, stayed in Winchester during the late summer and early autumn of 1819. Keats enjoyed a daily walk through the Cathedral Close and water meadows to St Cross, which inspired his ode ‘To Autumn’. The area, with its breathtaking natural beauty, has changed little in the 200 years since Keats visited.
Use the self-guided Keats Trail to experience the the walk yourself. It will direct you to The Hospital of St Cross, where you can explore the tranquil gardens and Norman chapel of this medieval almshouse. Be sure to get the Wayfarer's Dole (a traditional offering to pilgrims) from the Porter's Lodge and stop by the HMH Tearoom for a sweet treat before you make your way back to the city.
📍The Hospital of St Cross, Winchester City Centre
Enjoy an award-winning meal out
Winchester has a whole host of places to eat no matter what you are in the mood for. But, if you are looking for an open fire, oak beams and delicious, locally sourced food then it has to be the Chesil Rectory, featured in The Times as the third most romantic restaurant in Britain.
For cosy and casual dining, Lucky Lychee at The Green Man is The Good Food Guide's best local restaurant for 2025! This standout Malaysian restaurant is run by husband-and-wife duo James Harris and Nicole Yeoh and serves up delicious, seasonal dishes that won’t break the bank.
For a pub option, we're yet to meet a person who doesn't love The Wykeham Arms. This 18th-century pub, situated between Winchester Cathedral and Winchester College, is a multi-time winner of Fuller's Pub of the Year award, as well as earning two AA rosettes for culinary excellence for 13 consecutive years.
Read: Winchester’s award-winning food and drink experiences
