City Breaks

South East England boasts some of the UK's most attractive cities to visit, providing some of the best UK's city breaks destinations, full character and personality, history and culture. From the cosmopolitan vibes of Brighton to the rich maritime history in Portsmouth, Southampton's cultural scene to the ageless grandeur of Oxford, the charm of Canterbury, the ancient treasures of Winchester and Chichester and the modern lines of Milton Keynes.  With eight fantastic cities to choose from its easy to book a last-minute city break to the South East, and experience a spot of culture or simply enjoy exploring a new destination.

Best City Breaks in the UK

Creative Brighton

East Sussex’s most famous seaside resort, Brighton has a vibe like no other, a city of creativity and passion, a foodie heaven, ideal for culture vultures looking to dive into its festival feel and discover its award-winning attractions, flamboyant events and Victorian history. Brighton, voted as one of the top 10 city beach break destinations in the world, is a popular choice along the South coast. Brighton is easy to reach from London, with the fastest trains travelling from London to Brighton in under an hour, making this an ideal choice for an escape from the capital. Choose to soak up the cosmopolitan vibes, try one of the many water sports, visit Sea Lanes - the National Open water swimming centre, explore the Brighton marina and discover a city by the sea. Open all year-round, with an seafront promenade, wide open beaches, historic arches crammed full of art and souvenirs, a Victorian pier packed with family entertainment and the famous 'Lanes' to wander through and discover.

Discover more about a Brighton city break or head on over to VisitBrighton to find out more.

Brighton is full of artistic creations and a fantastic array of cultural experiences and night-time entertainment. Brighton is a great choice for a last-minute city break as it is packed full of great places to stay and with so much to see and do, its definitely a city that needs more just a day visit. Stay on Brighton's famous seafront at the iconic Brighton Grand Hotel, steeped in British history or if you prefer to stay out and travel in, Tottington Manor is just 8 miles away and located on the edge of the South Downs National Park. 

>>> Search & Book Brighton Accommodation

Cultural Southampton

Southampton is a cultural hot spot in the South East, home to the largest theatre on the South Coast, the Mayflower Theatre, a bustling cultural quarter which is full of live music venues, museums and glorious galleries. It is the perfect shop til you drop destination, boasting high end as well as high street brands with West Quay Shopping Centre in the heart of it all. Situated on England's South Coast this vibrant city is also the cruising capital of the UK, with over 400 cruise ships visiting a year. Southampton hosts the world famous International Boat Show every year, offers some great family-friendly attractions like Seacity Museum and Locked in a Room.  A Southampton city break brings together old and new, with a treasure trove of hidden gems, arts and entertainment to enjoy. Don't miss the chance to visit the free Southampton City Art Gallery, walk the historic city walls or visit the old town where you will come across the magnificent Tudor House built in the late 15th Century.

Discover more about a city break in Southampton or head over to Visit Southampton for more.

An hour and a half from London by train, Southampton is the largest city in the county of Hampshire, by population. It's a city with an array of places to stay as individual as the city itself, including the Hilton Southampton - Utilita Bowl, home of Hampshire Cricket, the Southern Vipers and Southern Brave. Southampton is a great destination for exploring with easy access to both Portsmouth and Winchester, it also borders the New Forest National Park so you can combine both city and countryside on this city break in 2025.

>>> Search & Book Southampton Accommodation

Maritime Portsmouth

Portsmouth the Great Waterfront city, famous for its historic dockyard and naval history, is the second largest city in Hampshire. Even today, many of Portsmouth's most stunning features and most popular attractions are found near the harbour. From the elegant yet imposing Spinnaker Tower, to the historic HMS Victory and Henry VIII's flagship the Mary Rose. Take a stroll along the seafront promenade, watch the ships passing in and out of the historic harbour, make a visit to D-Day Story, the only museum in the UK dedicated to the allied invasion. Enjoy waterfront shopping in Gunwharf Quays with its 60% off standard retail prices, ice cream on Southsea beach, or a visit to one of the cities two piers. Situated on England's South Coast with direct train links from London Waterloo and London Victoria, Portsmouth can be reached in an hour and a half from the capital. Portsmouth also provides connections to the Isle of Wight, Gosport and the continent. 

Discover more about a Portsmouth city break or head over to Visit Portsmouth for more.

A city break to Portsmouth combines time by the sea with all the fantastic amenities and cultural experiences you'd expect from a large city. Portsmouth is the UK's only island city, surrounded by water, which plays a big part in a city break to Portsmouth. An ideal destination for a family break at any time of the year with lots of do and see. Looking to book somewhere to stay for a city break in Portsmouth, The Queens Hotel is located on the edge of Southsea Common, many of the rooms offering seafront views.

>>> Search & Book Portsmouth Accommodation

Charming Chichester

West Sussex's only city, once an historic Roman settlement, its an ideal choice for nature lovers and history buffs. Chichester sits at the foot of the South Downs, is home to a host of historic sites including the magnificent Chichester Cathedral which is the site of the Shrine of St Richard of Chichester, Fishbourne Roman Palace - the largest Roman home in Britain - and Chichester Cross, a shelter for market sellers in times gone by which sits in the centre of North, East, South and West streets, at the city heart. Chichester Harbour is National Landscape, previously known as an Area of Outstanding Natural Beauty, wander to the harbour front and enjoy the stunning views over Thorney Island, Hayling Island and onto the Isle of Wight. Bishop Palace Gardens, is a hidden gem ideal to enjoy some peace and tranquillity or take a stroll along the Chichester Canal with its wonderful wildlife. In the evening pay a visit to Chichester Festival Theatre, this award-winning production house has seen many of its shows transfer to the West End and beyond. What to explore further? Head to beautiful West Dean Gardens, with 13 working Victorian glasshouses or to Fishers Adventure Farm Park an ideal place to take the kids on this city break.

Discover more about a Chichester city break or head to Great Sussex Way for more.

Chichester is just an hour and a half from London by direct train from London Victoria so easy to reach for a weekend city break. If your looking for somewhere to stay the The Cottage sits at the eastern end of the city, whilst West Dean College or Chilgrove Farm are both just 6 miles from Chichester city centre. Stubcroft Farm campsite is only 9 miles away from Chichester town centre making it ideal for a weekend camping city break here. With so much to see and do the hardest decision is how long to stay for. 

>>> Search & Book Chichester Accommodation

Historic Winchester

Hampshire's historic cathedral city Winchester, is one of the oldest settlements in Britain and the ancient capital of England. The city is dominated by the statue of King Alfred the Great, Winchester Cathedral, which dates back to 1070 and is one of the largest cathedrals in Europe. A great place to explore on foot and discover the cobbled streets, hidden courtyards and crooked buildings. You'll find a city with great places to eat, historic public houses and coffee shops to take a break in plus some great cultural experiences to enjoy.  Discover the grave of one of the most popular literary figures in the country, Jane Austen, get futuristic and hands-on at Winchester Science Centre, enjoy a show at the intimate Edwardian-style Theatre Royal Winchester. Head just a short way out of city for a delightful day out with all the family at Marwell Wildlife, just 7 miles from the city centre - with so much to do, its hard to decide if to stay for short city break away or to make it a holiday! Winchester is an hour by train from London Waterloo, leaving plenty of time for exploring and making it feel like a real escape away with a a year-round events calendar making it a fantastic choice whenever you decide to visit. 

Discover more about a Winchester city break or head over to Visit Winchester for more.

Looking for somewhere a little different to stay? Spend your weekend city break staying in a Norwegian log cabin, set in the centre of South Winchester Golf Club or time at The Winchester Royal Hotel, a unique hotel is situated in a prime location in the heart of the city.

>>> Search & Book Winchester Accommodation

Academic Oxford

The world-famous City of Dreaming Spires, Oxford is a picture-perfect historic destination set in the heart of the Oxfordshire countryside. Famous for its universities and academic links, but also full of fascinating museums, libraries, and galleries.  A destination full of surprises, amazing architecture, and a host of fun Instagram-able moments, with its strong film and TV links. Steeped in history, it has been the home to an array of famous people including Oscar Wilde and many British Prime Ministers, with a thriving high street, the modern Westgate Shopping Centre, plenty of cinemas, art cafes and music venues, there's something for everyone here. Enjoy views over the city at Oxford Castle and Prison and be regaled with stories stretching back a 1000 years, hop on board and explore the city by bus with City Sightseeing. With so much history to uncover a guided tour is a must and a great way to introduce one of the best city breaks in the UK.

Discover more about a city break in Oxford

Accessible in just under an hour from London Paddington, Oxford is a great choice for a city break in 2025. Whether you choose to stay in the heart of the city, Royal Oxford Hotel or just a short hop away at Courtyard by Marriott Oxford South, you'll find a wealth of accommodation choices to suit most budgets and styles. Combine your Oxford city break with a visit to the Southern Oxfordshire countryside to complete the perfect getaway.

>>> Search & Book Oxford Accommodation

Charming Canterbury

The city of Canterbury in Kent is home to some of the most historic and well-known buildings in Britain. With its character and heritage, it's no wonder that Canterbury is one of the most popular destinations in the south. As soon as you arrive, you can’t help but notice the famous Canterbury Cathedral. The cathedral, together with St Augustine's Abbey and St Martin's Church, make up the city’s World Heritage Site. Visit Canterbury and discover a city full of Kentish fare, unmissable experiences, stories of Romans, Saints and Pilgrims. Visit the Roman Museum and explore the city walls, head to Westgate Gardens for a riverside stroll or the Beany House of Art and Knowledge for an afternoon of art and culture. There is so much history to discover book a tour with the South East England Tourist Guide Association to make sure you don't miss anything along the way.

Discover more about a Canterbury city break

Taking just over an hour and a half from London Charing Cross, London St Pancras, and London Victoria to Canterbury by train, this destination is a wonderful choice for a weekend city break. Choose to stay overlooking the city in the Beverley Farmhouse at the University of Kent (year round) with its self-catering rooms or head a little way out and stay in the Kent countryside, combining your time with a visit to the city, exploring the countryside and visiting the coast. 

>>> Search & Book Canterbury Accommodation

Modern Milton Keynes

Milton Keynes in Buckinghamshire became the eighth city in South East England in 2022. A modern city designed with a grid road system, lots of open spaces, and some fantastic family-friendly attractions to enjoy. Home to the FI Red Bull Racing team, the historic Bletchley Park, Xsacpe Milton Keynes entertainment centre and Snozone, Europe's largest indoor snow centre. Look out for the many art installations in and around the city, including the famous Milton Keynes cows, a sculpture created by the Canadian artist Liz Leyh, which can now be seen today on a visit to the Milton Keynes Museum. Experience the MK International Festival a ten-day arts festival in July, and explore the 6,000 acres of woodland, parkland and lakes on offer.

Discover more about a Milton Keynes city break

Taking between thirty to forty-five minutes by train from London Euston, Milton Keynes if one of the most accessible city break options in the South East. Book a stay at the stunning Horwood House, miles from the city centre. This country-style manor house and 38 acres gardens, offers easy access to Milton Keynes and provides the perfect escape to the countryside.

>>> Search & Book Milton Keynes Accommodation

We look forward to welcoming you for a city break in South East England in 2025. Planning your trip? Then look a little further and discover the host of events and attractions you can enjoy whilst here in South East England.