Few cities can rival Chester when it comes to history, especially of the Roman variety. Britain’s most complete Roman city walls remain so well preserved that you can orient yourself by walking a two-mile route along their tops. Although the city has spread far beyond the millennia-old fortifications, and the area beside the River Dee is gorgeous too, it’s in the walled historic centre you are likely to spend most of your time. Here you’ll find heritage sites, medieval half-timbered buildings, and ancient inns intermingling with cool shops and streetwise cafes. Don’t miss the open-air Roman amphitheatre, Britain’s largest, where picnickers have replaced gladiators; the 1,000-year old Chester Cathedral; and Chester Castle, founded by William the Conqueror in 1070. Unique to the city are the Rows, a series of covered stone galleries on four streets, thought to date to the 13th century and now housing independent stores, coffee shops, and delis. It all adds up to a city that’s made for wandering.

Chester is a well-connected, centrally located Cheshire city, linked by the M53 motorway, and with a railway station. It’s easy to explore on foot, by hiring bikes, or using the local bus network. Those who drive might find it easiest to use one of the park-and-ride car parks further out, from which buses run into the centre. Interesting Cheshire towns Nantwich and Knutsford are 30 minutes by rail for half-timbered buildings and great restaurants. Liverpool John Lennon Airport (LPL) is about 30 minutes’ drive away, or 1.5 hours on public transport, by bus from the airport to Liverpool station and then train to Chester. Manchester Airport (MAN) is about 40 minutes to drive, two hours by train. Both have car hire and taxis.

To make the most of the outdoor bars and restaurants by the river, come on a sunny springtime or summer day. On the other hand, a bit of rain isn’t the end of the world — the fact that the Rows are covered means you can still enjoy browsing streets of independent shops without getting wet. There’s usually a wide range of food and drink festivals in spring and summer, and several music festivals in July and August. The Chester Heritage Festival celebrates the city’s history in June, while December brings a twinkling Christmas market with dozens of stalls making it a cozy time of year to stay in one of Chester’s cottages.

River Dee

For all your sunny afternoon needs, head to the banks of the River Dee where the Groves, a paved promenade, leads to pubs with floating beer gardens and restaurants. You can hire kayaks and rowing boats here to paddle under the impressive suspension bridge. Grosvenor Park is another riverside draw: there’s a large park with ornamental gardens perfect for picnics, and an adventure playground to please the kids.

Behind the scenes at Chester Cathedral

The extravagantly decorative cathedral offers behind-the-scenes tours where you’ll get to enter the Victorian bell tower, examine the stained-glass windows up close, and climb 216 steps up the tower for amazing views of the city, across five counties, and even to Wales. Be sure to visit the cathedral cafe, in the grand 13th-century monks’ dining hall.

Hoole

More independent shops and some well-reviewed restaurants can be discovered in the up-and-coming suburb of Hoole in the east of the city — dubbed “the Notting Hill of Chester” or “Notting Hoole” after the smart London neighbourhood, on account of its villagey feel.