Experience Winchester's most iconic sights on your next weekend getaway.
Want to immerse yourself in the city's rich history, catch a must-see show, explore breath-taking countryside, and discover charming independent shops and restaurants? Read our itinerary for spending three days in Winchester below!
Where to stay?
Winchester city centre has plenty of accommodation, ideally situated for those wanting to take in the sights of the city. The city centre is also easily accessed via car, train and bus. Find out how to get here.
Winchester Royal Hotel is a historic 16th century hotel located in the city centre. They offer a range of rooms, private parking and the award-winning Walled Garden Restaurant. This elegant hotel is the perfect blend of heritage and modernity.
Hotel du Vin is a stunning Georgian hotel nestled in the heart of Winchester. Choose from 24 distinctive rooms and suites, from garden rooms with a private patio to luxurious suites. Refreshments are also never far away at the beautiful Bistro du Vin.
Just a stone's throw from the breath-taking Winchester Cathedral, Winchester Wessex Hotel features bright, airy rooms, a modern British restaurant and covered parking. They are also dog-friendly!
Enjoy a relaxing and romantic getaway at The Winchester Hotel & Spa. The Spa offers luxurious treatments, provided by the team of experienced therapists, as well as a swimming pool and hot tub. This is a great spot to unwind after a day of exploring.
Sandwiched between the Cathedral and the 14th century college, The Wykeham Arms is a luxurious country pub with rooms. The pub, with its crackling fireplace and historic interiors, offers a seasonal mix of high-quality, locally-sourced ingredients.
Image: Winchester Royal Hotel
Day 1
Spend your first day in Winchester exploring the history of the city, from its beginnings as a an Iron Age settlement to its recent literary connections - 2025 marks Hampshire-born Jane Austen's 250th anniversary!
Begin your morning at Winchester Cathedral, one of the finest medieval cathedrals in Europe. Learn about its captivating history and magnificent architecture with a free tour (look out for the Guides in their red sashes). Explore hidden rooms like the crypt, Morley Library and the tower. Be sure to stop by the Cathedral Cafe and Gift Shop!
Top tip: Are there any book-lovers in your group? Visit the Deanery Bookstall (tucked in the Inner Close) for a vast selection of pre-loved books!
Adjacent to Winchester Cathedral, in The Square, is City Museum. It tells the story of Winchester from its origins as an Iron Age trading to the last journey of Jane Austen. This will inform your visit to Winchester's other iconic heritage attractions.
Make the short walk to 878 AD, where you will be transported back to the time of Winchester's most famous resident, Alfred the Great. This family-friendly immersive experience is a must-see for fans of early-medieval history and the spectacular world of Assassin's Creed Valhalla.
After this, make your way to The Great Hall in the Upper City, where you can see the legendary Round Table and the medieval herb garden of Queen Eleanor. Next door is Westgate Museum, a former debtors' prison telling the history of Tudor and Stuart Winchester.
Top tip: Save money on your visit to Historic Winchester attractions (City Museum, The Great Hall, Westgate Museum and 878 AD) with the Super Explorer Ticket. Pay once and visit for free all year!
End your day of exploration with dinner at one of Winchester's award-winning restaurants
Occupying a 600-year-old building, The Chesil Rectory offers a modern British menu featuring simple, classic, seasonal dishes and an abundance of fresh local produce. For a taste of Cornwall in the heart of Winchester, try Rick Stein Winchester. A favourite of locals and visitors alike, Kyoto Kitchen serves up authentic Japanese cuisine from their restaurant on Bridge Street.
Top tip: Keep up to date with the latest dining discounts on the Visit Winchester offers page.
Image: Winchester Cathedral
Day 2
Your second day in Winchester can be spent exploring the like a local, discovering some of the hidden gems along our cobbled streets.
Take a walk around the historic grounds of Winchester Cathedral through the 17th century Curle's Passage and emerge into the Inner Close, a grassy area that was once the main cloister of St Swithun's Priory.
Within the Inner Close, you'll spot Dean Garnier Gardens, a tranquil and beautifully planted walled garden which stands on the site of the monks’ dormitory that was once part of the great medieval site. Continue past The Deanery to the Outer Close, where you'll find The Pilgrim's Hall, a 14th century guesthouse for visitors, the wisteria-clad Prior's Gate, and the Elizabethan timber-framed Cheyney Court.
You can then explore Kingsgate Village, a hub of independent shops including P & G Wells, Cornflowers, and Kingsgate Books & Prints. Stop for lunch at the historic country pub, The Wykeham Arms. Kingsgate is also home to iconic landmarks such as the medieval Winchester College, the tiny St Swithun-upon-Kingsgate Church, and the house where Jane Austen spent her final weeks.
Top tip: Winchester College runs tours of their medieval buildings, grounds and War Cloister throughout the year. You can also visit their Treasury for free!
One of the city's best kept secrets is The Hospital of St Cross and Almshouse of Noble Poverty, a short walk from Kingsgate Village through the water meadows (also known as Keats' Walk). Visitors are welcome to explore the stunning and tranquil heritage site, walk around and worship in the majestic de Blois Chapel, and enjoy the stunning Master’s Gardens with breath-taking views of St Catherine’s Hill.
Top tip: End your visit with a call into the Porter's Lodge, where you can receive the 'Wayfarer's Dole' of bread and medieval ale traditionally served to visiting pilgrims.
Later, indulge in an evening of fantastic food before catching a show at The Arc or Theatre Royal Winchester.
Jewry Street, once the city's Jewish Quarter, is now a hub of independent restaurant, bars and cultural venues. Enjoy dinner at 5 Boroughs Pizza, Overdraft, and Bangkok Bistro, or stop for drinks at Margaux Lounge, Green's and Cabinet Rooms.
This leaves you just a stone's throw away from Theatre Royal Winchester and The Arc, both of which offer a varied programme of dance, comedy, music and theatre.
Top tip: Outside The Arc, spot the statue of Licoricia of Winchester, known as the most important Jewish woman in medieval England. You can learn about Licoricia and the city's Jewish history with our Medieval Jewish Trail.
Image: The Hospital of St Cross
Day 3
Use your final day in Winchester to explore one of the district's market towns, known for their charming independent shops, delicious eateries, countryside walks and rich local history.
Alresford is a Georgian town just 15 minutes by car and 20 minutes by bus (64 bus route) from Winchester. It is perhaps best known as the centre of the UK's watercress industry. From here, you can hop aboard The Watercress Line, a heritage steam railway with scenic views through the Hampshire countryside.
The town offers a host of independent boutiques (House of Gallet, Delilah, Moda Rosa) and cafes (Josie's, The Town House, Tiffin Tearooms), as well as unique local gems such as Long Barn home and garden shop and Laurence Oxley bookshop.
After browsing the town's charming shops, explore the surrounding countryside by following the Millennium and Alre Valley Trail. From the town centre, you will walk along the river Alre to discover Old Alresford, including Eel House, Alrebury Park House and panoramic views of the Alre Valley.
Top tip: you can discover more of Alresford's hidden gems and historic landmarks with our Alresford town guide.
Bishop's Waltham is another of Winchester's charming market towns, 20 minutes by car and 50 minutes by bus (69 bus route) from the city centre. The town is known for its quaint independent shops, medieval palace ruins and its heritage, country and nature trails.
Begin your visit at Bishop's Waltham Palace, where you can explore ruins dating back to 1135. The palace was home to the medieval Bishops of Winchester, including Henry of Blois (who also established The Hospital of St Cross). The palace was expanded upon by William of Wykeham (founder of Winchester College and New College, Oxford) in the late 14th century.
From here, meander down the High Street, stopping by independent boutiques (Labels, Luvvit Want It, Tashinga), eateries (Josie's, Stainers Bakery, No. 60 Coffee & Wine Bar) and traditional pubs (The Crown Inn, The Barleycorn Inn, The Bunch of Grapes).
Top tip: Marwell Zoo is a 10 minute drive from Bishop's Waltham. Tie in a visit to this outstanding family day out, featuring hundreds of animals across the 140-acre parkland. Be sure to check out their latest events and activities here.
Spend your final evening in Winchester enjoying local, hearty flavours at one of our traditional pubs. Highlights include The Wykeham Arms, The Bishop on the Bridge, The Royal Oak and The William Walker.
