Explore the ancient city of Winchester with the advice of real people who have grown up in the city

How often do we end up on a web page that isn't really relevant to the topic that we wanted to read about or that has been written by either AI or someone who clearly doesn't know a great deal about the subject about which they have written?

This guide to exploring Winchester, England has been curated by people who have grown up in the city and really do know the spots to discover and explore!

Yes, Winchester Cathedral and The Great Hall are worth a visit, but what the normal guide books don't tell you about are the back streets, the hidden treasures and the 'must visit' spots that only the locals know about

9:30am – Start with coffee at Cadence Clubhouse (known to most local as The Handlebar Café)

Begin your day with breakfast or coffee at this unique, community-led café just a 10 minute walk from King Alfred's Statue at the bottom of the High Street. Perched on the Viaduct Way cycle path, the cafe has views over the surrounding water meadows and the River Itchen

• what3words /// The simplest way to talk about location

• Indoor and outdoor seating

• Winchester Cadence — Cadence Cycle Club

10:00am – Climb St Catherine’s Hill

Just behind the café is this scenic chalk hill. A short (but steep) climb rewards you with sweeping views over Winchester and the Itchen Valley.

The 2500-year-old Iron Age hillfort, an ancient yew-tree maze and generally doesn't get too crowded

• Find the start of the easiest path to the top (a 7 minute walk from the cafe) at what3words /// The simplest way to talk about location

• It is a steep walk but worth it for the views!

11:30am – Riverside Walk to the City

Walk back down the hill the way that you went up and then head right back towards the city centre via the Itchen Navigation path, a tranquil riverside walk with views of water meadows, wildlife, and historic mills. You will pass the cafe where you had coffee earlier but then just follow the riverbank path for as far as you can go

12:00pm – Quiet Corners of the Cathedral Grounds

While the Cathedral itself is magnificent, the quieter side is the Inner Close and Dean Garnier Garden, a tucked-away walled garden with views of the cathedral’s flying buttresses.

• Tip: Enter from the east side of the Cathedral for fewer crowds.

• Optional: If you'd like to see inside, visiting earlier or just before closing is quieter.

1:00pm – Lunch at The Bishops on the Bridge (or picnic nearby)

This riverside pub just off the High Street has a peaceful garden by the water. Alternatively, pick up something from Open House Deli and enjoy it in the Abbey Gardens, a lesser-visited park nearby.

2:00pm – Explore Winchester College's Outer Grounds

The College offers quiet beauty and a historic atmosphere without the bustle. You can wander past old school buildings, see the cloisters, and enjoy the quiet of the Meads.

• College Street, just behind the Cathedral.

2:45pm – Visit the Wolvesey Castle Ruins (English Heritage)

Free to enter and often almost empty, these romantic ruins of a medieval bishop's palace are right near the College and offer beautiful views of the river and gardens.

• A secret gem — few tourists find it.

• Allow 30–40 minutes to wander.

3:30pm – Tea Break at The Orangery or Coffee Lab

Choose a peaceful spot for tea or cake. The Orangery (near the Cathedral) has a lovely garden, or try Coffee Lab for quiet seating upstairs.

4:30pm – Visit The City Museum or The Arc Winchester

• The City Museum is compact and usually quiet, offering an engaging look at Winchester’s Roman and Saxon past.

• The Arc is a contemporary arts and culture space with exhibitions, a gallery, and a calm atmosphere.

6:00pm – Early Dinner at The Chesil Rectory

A characterful restaurant in a 600-year-old house — historic, peaceful, and ideal for rounding off a day of gentle exploration.

• Reservation recommended, especially for early evening.

Optional Twilight Stroll

If the weather is fine, take a short walk along the Water Meadows path towards the Hospital of St Cross (it may be closed, but the walk is beautiful at sunset).

Need more help or advice? Just drop our friendly, local team an email on hello@experiencehampshire.uk and they will be happy to offer you some assitance