What to do in Winchester | A 2-day itinerary

Located at the western end of the South Downs National Park, Winchester with its history & heritage, beautiful medieval architecture, bustling market stalls and award-winning eateries is a great short break destination.

England's ancient capital and the seat of Alfred the Great, Winchester is home to the world-famous Winchester Cathedral (it has the longest medieval nave in Europe) but that is not the only reason to visit the city. Winchester offers plenty more to its visitors to explore and enjoy during their stay as we learned from our visit to this beautiful city last month.

 So, take a look at how you can spend a weekend in Winchester.

Winchester Weekend Break

Ad | This trip was organised by Visit Winchester, however, all views, opinions and photos are our own and remain the copyright of 'The Globe Trotter'. The post may contain affiliate links.

Day 1 in Winchester

Winchester Cathedral (and Kings & Scribes Exhibition)

Start off Day 1 with a visit to Winchester's most popular landmark, Winchester Cathedral. It is one of the largest cathedrals in Europe and also holds the distinction of having the longest nave and overall length of any Gothic cathedral in Europe.

The Cathedral has a fascinating history and we recommend that you take the guided tour that is free as a part of your entrance ticket. The tours run at regular intervals throughout the day and last around 1-1.5 hours. The guides are trained & knowledgeable and offer a great insight into the Cathedral's history. We loved the tour. It was very informative and we learnt a lot about the cathedral - its history, the architecture and construction methods, the stained glass, the key people involved with the Cathedral and the power struggle. We wouldn't have had so much insight into the Cathedral had we not taken the tour. So, it definitely comes recommended.

You can also take the Crypt tour (included in the price of the entrance ticket) and explore one of the oldest parts of the Cathedral or go for the Tower tour (separate ticket, £7.50) and enjoy great views across Winchester.

Vaulted Ceiling at Winchester Cathedral

The Great Screen at Winchester Cathedral

Stained Glass Windows at Winchester Cathedral

Post the guided tour, we headed to the Kings and Scribes exhibition. Housed across four galleries, the exhibition was interactive and informative and catered to all ages.

Kings and Scribes Exhibition at Winchester Cathedral

Overall, the Cathedral is an absolutely stunning structure, both inside and out, and certainly one of Winchester's most popular attractions. The Cathedral is open every day of the year and admission prices (at the time of publishing this post) are as follows: Adult £9.50, Concession £7.50, Student £6.00, Children under 16 (with family) go free.

For more information on the Cathedral, visit www.winchester-cathedral.org.uk

City Museum

Located close to the Cathedral is the City Museum which could be your second stop for the day. The museum is spread over three galleries and tells the story of Winchester - from its origins as an Iron Age trading centre to the last journey of Jane Austen. Although the museum is not large, there are some really fascinating exhibits on display like an amazing 1870 model of Winchester city, real Jane Austen artefacts, a Roman collection and jewellery in the Winchester Art style. The interactive hands-on exhibits are also fab.

The City Museum in Winchester

The City Museum in Winchester

The City Museum in Winchester

It is a very interesting museum and around an hour should be sufficient to explore it. Entry is free but a donation is recommended.

For a list of the current events, visit the City Museum’s website.

Winchester College Guided Tour 

Next, head to the Winchester College to gain an insight into life at the oldest of the original nine English public schools. The guided tours at the college last a little over an hour and with a knowledgeable guide taking you around, you are sure to have a fascinating time learning about the history of the college buildings and its alumni.

Winchester College was founded in 1382 by William of Wykeham, Bishop of Winchester and has existed in its present location for over 600 years. We loved the guided tour. As we progressed through it, we not only learnt about the college, its founders and the architecture but also about the history of education in the country. Our guide was fabulous, had a passion for her work and answered all queries expertly. It was a fantastic tour (you get to visit the Chapel, College Hall, Cloisters and the 17th Century School building) and is totally recommended if you are a fan of architecture and history.

Winchester College Tour

Winchester College Tour

Winchester College Tour

Winchester College Tour

Winchester College Tour

For more information on the guided tours and to book yourself into one, visit Winchester College’s website.

Winchester College Treasury

The Winchester College Treasury is not a part of the guided college tour and is open to the general public every day between 2 pm and 4 pm. It is home to the college's collections of art and archaeology including artefacts from Egypt, Greece and Rome, casts of the Parthenon Frieze and some Chinese ceramics.

The Winchester College Treasury

The Winchester College Treasury

The Winchester College Treasury

The museum is compact and located in the medieval Warden's Stables and all though the collection is not vast, the objects on display are inspiring. You can spend as much or as little time as you like exploring exhibits.

Watch a show at Theatre Royal Winchester

Time to end your day, with a culture fix at Theatre Royal Winchester.

Theatre offers something that you just cannot get watching a movie or the television. And what better place to experience it than at Theatre Royal Winchester, a beautiful Edwardian-style theatre in the heart of Winchester. The theatre is considered as 'one of the most beautiful theatres in the south of England' and offers a good selection of entertainment to suit all tastes.

Theatre Royal Winchester

When we visited in early March, we watched a thriller called Revenge (by Robin Hawdon). It was fantastic. From the curtain going up at the start of the show to the Curtain Call at the end of a performance, it was an excellent all-round experience. Kept us guessing right to the end.

The theatre though small has a lot of charm. The seating was comfortable, the staging, lighting, special effects - everything was great and the staff friendly. A great entertainment evening out.
If you are a lover of theatre, you will appreciate and enjoy watching a show at Theatre Royal Winchester. Check out what's currently on at the theatre, here.

Day 2 in Winchester

The Great Hall

Start the second day with a visit to the Great Hall. The Hall, along with the Sally Port, is all that remains of the medieval Winchester Castle.

The Great Hall has served as a royal residence, a courtroom, a defence bastion, a filming location (BBC’s Wolf Hall, The Hollow Crown), a wedding venue and now as a visitor attraction and a museum. Guided tours are available which throw light on a number of different topics like the court cases tried at the hall, the hall's Gothic architecture, the history of Winchester Castle and the myths and legends associated with the Great Hall. The legend of King Arthur is the most popular one with many visitors coming in to see the "King Arthur's Round Table", one of the greatest symbols of medieval mythology.

The Great Hall in Winchester

The Great Hall in Winchester

Also interesting is the Long Gallery where you can learn more about the key characters associated with the Great Hall - from Kings and Queens to judges and executioners and more.

The Long Gallery at the Great Hall in Winchester

Walking trails in Winchester

If you love walking, Winchester has a vast number of fantastic paths and trails for you to enjoy. There are two walks that we recommend. The first one is the River Itchen and Weirs Walk. Cross the beautiful City Bridge (it's the river's ancient crossing place and also the entrance to the city) and follow the Weirs Walk to the water meadows and St Cross. It is a short and level walk with plenty of seats on the way should you wish to sit down and admire the scenery.

The Weirs, Riveside Walk in Winchester

The City Bridge in Winchester

The other walk is a romantic, circular walk through the historic eastern part of Winchester taking in some of the city's beautiful buildings and scenery. It is also referred to as the 'Sunset Walk' as it takes you to St Giles Hill from where you not only get a lovely view of the city but can also catch the final minutes of daylight.

You can download a copy of the 'Sunset Walk' here.

Shopping in Winchester

Winchester is a shopper's paradise with an impressive selection of stores. One of the main places to shop is the Brooks Shopping Centre which is located right in the centre of Winchester and houses some popular brands like New Look, T K Maxx, HMV and Beales. Another popular place to shop is the High Street of Winchester which not only has trendy boutiques and independent stores but also some lovely, historical buildings. We visited over the weekend and Saturday was the day for the street market with several stalls selling everything from hand-made art/jewellery to fruits & vegetables and from unusual gifts to local foods & confectionery.

Shopping in Winchester

All of these markets are located in close vicinity of each other. You can wander around the main High Street and then explore the quaint side streets and you will realise why Winchester attracts many keen shoppers – it has such a great choice of big-name brands and boutique, independents shops. And you are sure to find something unique and special for a loved one or something to spoil yourself.

Spa time at ANA spa

End your day with a spa experience that is sure to leave you feeling rejuvenated and relaxed. The ANA Spa at The Holiday Inn Winchester has a range of facilities including a hydrotherapy pool, Himalayan salt sauna, Sensory Shower, a steam room and bubbly foot spas. Although not big, the newly refurbished spa is well maintained and the friendly team are on hand to make your experience a good one.

If you are staying at the Holiday Inn Winchester you can use the spa facilities for a charge of £25 per person while for non-hotel residents the price is £35 per person. The price includes a complimentary non-alcoholic drink on arrival; towel & robe hire and flip flops.

The spa also offers a long list of treatments using the luxury British skincare brand Elemis. A half-day spa experience is priced at £85 while facials start from £45 onwards. I tried out one of their Elemis facials and it was lovely. My therapist, Robyn, had a look at my skin and picked products based on my skin type and concerns. The facial was excellent from start to finish - very relaxing and my skin felt lovely afterwards.

ANA spa at Holiday Inn Winchester

ANA spa at Holiday Inn Winchester

ANA spa at Holiday Inn Winchester

For more information on spa days and treatments at ANA Spa, visit www.anaspa.co.uk

Staying Longer?

If you are planning a longer holiday in Winchester, then you could include the following in your itinerary.

  • Winchester’s Military Quarter - It is a group of six regimental museums all located close to each other and featuring fantastic collections of medals, paintings and other military objects. The six museums are the Gurkha Museum, the Museum of The King's Royal Hussars, the Royal Hampshire Regiment Museum, the Rifles Regimental Museum, the Royal Green Jackets Museum and the Adjutant General's Corps Museum. Three of the museums are free to visit while three have a ticketed entry.
  • Winchester Water Mill - Restored and managed by the National Trust, Winchester City Mill is probably the oldest working watermill in the UK. Visitors to the mill can learn more about its history as well as see the mill in action and learn how stone-ground wholemeal flour is produced using the power of water. Entry is free for National Trust members and Hampshire and Isle of Wight Wildlife Trust members.
  • Winchester Science Centre and Planetarium - It is one of the largest and the leading science and discovery centre in the South of England. The centre has a number of interactive exhibits, hosts live science demos and shows, has a nature-based experimentation zone and is also the UK’s largest standalone planetarium. Makes for a fun day out for the entire family.

Other places to visit include the Hospital of St Cross, Winchester Science Centre & Planetarium, Wolvesey Castle and Palace and the Westgate Museum.

Where to stay in Winchester

Whether you are travelling as a couple, a family or as a solo traveller, you are sure to find accommodation in Winchester to suit your style and budget. You can take your pick from country house hotels, city centre hotels, cosy B&Bs or self-catering properties.

Holiday Inn Winchester

We stayed at Holiday Inn Winchester which underwent a major refurbishment in 2019, including the opening of a new restaurant and luxury spa & leisure facilities. The 4-star hotel is located a short distance from the city centre on the edge of the South Downs National Park making it a great location not just to explore Winchester but also the Hampshire countryside.

Holiday Inn Winchester

The hotel has 100+ well-appointed, air-conditioned bedrooms and the room we stayed in was spacious, clean and quiet - ideal for getting a good night’s sleep after a day of exploring. It was kitted out with all the amenities one would expect in a such a room - en suite facilities with complimentary toiletries, a desk workstation, flat-screen LCD TV, iron and ironing board, hairdryer, tea/coffee making facilities, complimentary Wi-Fi etc.

Bedroom at Holiday Inn Winchester

Bedroom at Holiday Inn Winchester

Breakfast (buffet style) is served in the Odyssey Restaurant.

Breakfast at the Odyssey Restaurant in Winchester

Free parking is available at the hotel and if you are arriving by public transport, then bus no 64 that runs between Winchester bus station and Alton is the one for you. If you love walking, you can easily get to the city centre by walk as well. There is a path near the Science Centre & Planetarium (which itself is near the hotel) that takes you past Wykeham Park and Magdalen Hill Cemetery right up to St Swithun's School from where you can continue on Alresford Road to the city centre. If you have the time and the inclination, this is a wonderful way to take in the beauty of the chalk grassland.

We loved our stay - from the great standards of accommodation & food to the spa experience and the friendly service; everything was good. We give it bonus points for its superb and peaceful location.

Holiday Inn Winchester | Telegraph Way, Morn Hill, Winchester, SO21 1HZ

Book your staty at the Holiday Inn Winchester here.

Where to Eat and Drink in Winchester

In Winchester, there is no dearth of cosy pubs, bustling cafes and restaurants. Whether you are after traditional British fare, Indian, Thai, pizzas or anything else that tickles your fancy, Winchester has you covered. Here are some of the places that we recommend if you are heading to Winchester:

The Eclipse Inn

Located next to the City Museum, the Eclipse Inn is a great little pub with a fantastic atmosphere. The pub building dates back to 1540 and has a beautiful Tudor facade. It was packed with regulars and tourists when we visited and everyone seemed to be enjoying their food and drinks.

The pub has a good selection of drinks but the food choices for vegetarians were limited. We, however, enjoyed the pies that we ordered. They were served piping hot and were tasty.

Vegetarian pies at the Eclipse Inn in Winchester

Vegetarian pies at the Eclipse Inn in Winchester

Cabinet Rooms

Located opposite Theatre Royal is Cabinet Rooms, a café-bar serving light meals, speciality coffee & teas, wines, classic cocktails and unusual spirits. Founded by Gary and Marcus in 2014, Cabinet Rooms is open all day and is the perfect place to enjoy a light lunch or pre-theatre drinks and nibbles. It is a cosy little place and very popular based on how busy it was when we visited. The food/drinks were amazing and both the vibe and service were on point.

Pre-theatre drinks and nibbles at Cabinet Rooms in Winchester

Pre-theatre drinks and nibbles at Cabinet Rooms in Winchester

Pre-theatre drinks and nibbles at Cabinet Rooms in Winchester

Gary and Marcus host the Ginchester Christmas Market (Winchester’s local Gin festival) annually. If you happen to be in Winchester during the festive season, this is not to be missed.

The Old Vine

This has to be probably one of the best inns we have been to. Set just a couple of minutes’ walk away from Winchester Cathedral, The Old Vine is an eighteenth-century inn that holds the distinction of having been awarded Four AA stars (Bronze in the Tourism Pub of the Year category at the Beautiful South Awards 2018/19).

With a great location, fab interiors, fantastic food/drinks and friendly & efficient service, there was nothing to not like about the place.

The Old Vine in Winchester

The Old Vine in Winchester

There was a good choice for vegetarians and the drinks menu was impressive as well. We ordered a vegetarian mezze platter followed by sweet potato & cashew tart and chickpea, lentil, mushroom and spinach curry with rice and everything was delicious - a perfect balance of flavours all around. And the service was incredible. Should we return to Winchester, we will definitely be heading back here.

Vegetarian mezze platter at the Old Vine in Winchester

Drinks at the Old Vine in Winchester

Chickpea, lentil, mushroom, red pepper and spinach curry with rice at the Old Vine

Lightly spiced sweet potato and cashew tart at the Old Vine

Ice cream at the Old Vine Winchester

To book a table at The Old Vine, visit www.oldvinewinchester.com

The Odyssey Restaurant at Holiday Inn Winchester

As we were staying at the Holiday Inn, we dined in the hotel’s restaurant one of the evenings. The Odyssey has its very own pizza oven and serves a range of delicious, hand-stretched pizzas in addition to dishes made using local produce. The choice for vegetarians was good and the service was fabulous. It is a good option if you are staying at the Holiday Inn and do not want to step outside the hotel for dining.

Dinner at The Odyssey Restaurant in Winchester

Dinner at The Odyssey Restaurant in Winchester

Dinner at The Odyssey Restaurant in Winchester

Dinner at The Odyssey Restaurant in Winchester

How to get to Winchester

Surrounded by Hampshire’s beautiful countryside, Winchester is just one hour from London and is easily accessible by car. It can also be easily reached from other cities like Bath, Bristol, Southampton and Portsmouth. And if you are not travelling by car, the rail and bus connections to Winchester from major cities across the UK are equally good.

National Express operates up to 8 services per day between London and Winchester and the journey time is under 2 hours making it a great option even for a day trip.

South Western Railway operates regular services from London Waterloo to Winchester and the journey time is just 53 minutes! We loved our train journey - it was comfortable, convenient and the greenest of all options available.

You can check for all rail services to Winchester from across the UK with South Western Railway at www.southwesternrailway.com

Once you have reached Winchester, you can take a bus into town or simply walk. The city centre is just 10 minutes away. Exploring Winchester on foot is the best way to ensure that you don't miss any of its quirky charms. And since most of the city's popular attractions are located close to each other, this is the best way to explore them. For attractions further afield, you can use the local bus services like Stagecoach or Bluestar Buses.

In conclusion

So, that's our guide to spending a weekend in Winchester. All in all, it is a beautiful city that offers an astonishing amount of history and culture and makes for a great weekend trip away, whether you are based in London or any other city in the south-east of England.

You can check out the Visit Winchester website for more ideas on things to do and events in Winchester.

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Winchester 2-day itinerary

Have you had the opportunity to visit Winchester? If so, what did you enjoy the most? Let me know via the comments section below.


  1. wow the cathedral looks amazing and so beautiful

    1. It is beautiful, both from the outside and the inside.

  2. Ive never been to Winchester, what a fantastic review!! Its on my to do list when things go back to normal xx

    1. 2-3 days should be ample to explore all that the city has to offer. Hope you enjoy your visit to Winchester, once travel restrictions are removed.

  3. Wow I have never been, it looks stunning. Alot of hidden treasures, the food at the old vine looks incredible

    1. Yes, lots to see and do. And a visit to the Old Vine is definitely recommended.

  4. I've never been to Winchester but I like the look of the walking tours, especially along the river.

    1. There are a number of walking tours/trails in the city. I liked the River Itchen and Weirs Walk too. It's a short, circular walk tracing the beautiful River Itchen and takes you past some of the city's popular sights.

  5. Winchester Cathedral looks magnificent!


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