How To Make The Most Of A Business Trip To Winchester

View from St Giles, Winchester

Following my business trip for Winchester Fashion Week last week, I thought it would be fun to put together something a little bit different for this blog. A guide about how to make the most of your business trip to the historic city of Winchester. 

Love them or loathe them, for many of us business trips are an essential part of our business lives. So it makes sense to make them as enjoyable and productive as possible. When I used to travel for work, I generally kept my business trips as short as possible, not least because I was expected to get back to the office quickly! This meant I saw little of the place I was visiting, and more often than not, ended up retreating to my hotel room for cable TV and overpriced room service. Sound familiar? 

Now that I’m my own boss, I can be more intentional about how I plan my business trips and build in downtime for exploring as well as a little me-time. This means I come away from my business trip energised by my new experiences and feeling like the time away has been both enjoyable and restorative. 

The way events were structured for Winchester Fashion Week meant I had plenty of downtime to explore this stunning, ancient city. Here’s what helped to make my recent business trip to Winchester so enjoyable.


When I’m visiting a new place and preparing my itinerary, I generally consult the relevant Lonely Planet guide as well as the travel blogs I follow. A Lady In London is a favourite travel blog as she often writes about day trips from London, like this one she wrote on Winchester

Winchester is one of the oldest cities in Britain, with stunning architecture from every era. The Romans established a town here, and after they left, Winchester became the English capital under the Saxons. Its most famous landmark is the cathedral. The building itself is impressive, being one of the world’s longest medieval churches. What’s inside is equally impressive with Jane Austen and other important historical figures buried here.

How To Make The Most Of A Business Trip To Winchester


The explosion of services like Airbnb means that there has never been a wider range of places to stay for a few nights. The advantage of Airbnb is it offers a home from home experience, rather than an impersonal hotel room. The owner is often on hand to give a local’s perspective on the area’s “must sees” and “must dos”.

I stayed with Joanne and Bert in their pretty Victorian home, a short walk from the train station and city centre, and close to where the cover photo below was taken. If you haven’t tried Airbnb before, I highly recommend it. If you’re booking for the first time, use this link and Airbnb will give you a £25 travel credit.


I needed to find somewhere quiet to work for a few hours, so I went to the Winchester Discovery Centre, home to the main library and a truly world-class centre for creativity, learning and culture. The Centre also houses a 180-seat theatre which features tours from acclaimed singers, musicians and performers.  With more than 150 events, gigs, concerts, talks, shows and exhibitions taking place every month, you're likely find something to interest you. Alternatively check out what's on at the Everyman Cinema.


The city has a large centre, laid out on a grid plan by the Saxons, and is packed with buildings of all ages. Guided tours are an excellent way to explore the city. Winchester Tourism Information Centre lead two tours daily. (See their website for times). Tickets can be purchased on the day of visit from the tourist information office. You'll also find leaflets with a number of free self-guided trails so that you can explore the city at your own pace. There are a range of trails to suit individual interests. Here's where you can download a copy in advance online. Do bear in mind that Winchester is quite hilly and comfy shoes are a must!

The City Walk is a great place to start if you want to fully immerse yourself into Winchester city life whilst following the footsteps of the legendary King Alfred. The beauty of this particular walk is it’s divided into three loops, so you can choose how much of the walk you’d like to do. Each loop is about 1 mile and takes approximately an hour to complete. 

While you're in Winchester, you won’t want to miss the Great Hall, a 13th-century medieval aisled hall with a round table rumoured to be that of the legendary King Arthur. Outside you’ll find a secret herb garden with an arched walkway of pink roses in summer.

While you’re exploring the city, be sure to find Flat Whites’ Citroen van which is parked up just outside the big Jigsaw. Stop here for excellent coffee and take it with you whilst you continue to potter.

Winchester Cathedral


I need no excuse to visit a tea room, and Winchester’s St George’s Tea Room didn’t disappoint. Close to the Cathedral, this tea room has an elegant dining room and pretty walled garden. During the summer, they plan to open until 7pm so that customers can enjoy the warmer evenings outside. 

I spent a happy hour there, reading my book while enjoying a pot of Lady Winchester tea, a blend of Assam, Sumatra, Darjeeling black teas, exquisitely flavoured with orange, grapefruit and bergamot. 


Winchester has an abundance of independent shops. My starting point for exploring these was Monica Welburn’s  ‘Winchester Travel Guide: The Most Stylish Independents In The City’ written for her blog, The Elgin Avenue. 

An independent shop I loved was Char Teas which has a bricks and mortar store opposite the Tourist Information Office, and sells their teas online. I always like to bring something back from a trip away. A packet of their Winchester tea fitted perfectly into my corner of my case and is a daily reminder of a lovely few days away. 


When you’re traveling on your own, finding somewhere you feel comfortable to eat out – and get a nutritious evening meal – can be tricky. I received a warm welcome at Dim T, making me feel instantly at ease. So much so that I went there for dinner twice. Serving Asian food, it turns out Dim T is a small group of restaurants with five outlets in London as well as this offshoot in Winchester. 


Traveling for business is hard work so I like to treat myself a little, whether that’s having a relaxing massage in the hotel’s spa or a facial at a local beauty salon, on this occasion at the Winchester Hotel and Spa.

If I’m away for a few days, I always book a Blow Dry at a local hair salon. I like to travel light and not be weighed down by a hairdryer, brushes, clips and the assortment of hair products I need to tame my curly hair! Plus, hair stylists are a great source of local knowledge. On the recommendation of Monica Welburn, I had my hair blow dried at Lord Hair Salon and it didn’t disappoint. 

That brings my round up of how to make the most of your business trip to Winchester to a close. Have you been to Winchester before? If so, is there anywhere I’ve missed out that you would particularly recommend? I’d love to know.


How do you make the most of any business trips you take? I love reading your feedback so please do take a moment to share let me know in the comments box below.


Did you miss?

If it's your first time here, you may also want to check out the resources I've curated to help you grow your business. These include some of my most popular content.


To start a conversation about whether we’re a good fit to work together:

  • Check out my Services page where you’ll find details of my business consulting executive coaching and marketing services.

  • Book a consultation appointment, or if the times I’ve given don’t work for you, e-mail me to arrange a coffee chat wherever suits you best – your office, my office, the Harbour Hotel in Brighton or Chichester or virtually. 


The Weekend Edit is my weekly newsletter, sent out every Friday lunchtime to my email subscribers. I love putting together this email, and my intention is that it supports you on your business journey.

If you are interested in signing up to The Weekend Edit, you can do so here