The average train between Winchester and Skegness takes 4h 53m and the fastest train takes 4h 5m. There is a train service every few hours from Winchester to Skegness. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.
Trains run every 2 hours between Winchester and Skegness. The earliest departure is at 5:19 AM in the morning, and the last departure from Winchester is at 11:24 PM which arrives into Skegness at 11:53 AM. All services require a transfer at London Waterloo Station and take an average of 4h 53m. The schedules shown below are for the next available departures.



4h 35m • 3 changes



4h 6m • 3 changes



4h 35m • 3 changes



4h 6m • 3 changes



4h 35m • 3 changes



4h 6m • 3 changes



4h 35m • 3 changes



4h 6m • 3 changes



4h 18m • 3 changes



4h 5m • 3 changes



4h 5m • 3 changes



4h 6m • 3 changes



4h 11m • 3 changes



4h 10m • 3 changes



4h 12m • 3 changes



4h 10m • 3 changes
Want to know about travelling from Winchester to Skegness? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.
No, there is no direct train from Winchester to Skegness. However, there are services departing from Winchester station and arriving at Skegness station via London Waterloo. The journey, including transfers, takes approximately 4h 53m.
Winchester to Skegness train services, operated by South Western Railway, depart from Winchester station.
Winchester to Skegness train services, operated by South Western Railway, arrive at Skegness station.
Book your Winchester to Skegness train tickets online with South Western Railway, London Underground (Tube) and 3 other operators.
The distance between Winchester and Skegness is 257.3 km. The road distance is 373 km.
You can take a train from Winchester to Skegness via London Waterloo Station, Waterloo station, Euston station, King's Cross, and Grantham in around 5h 7m.