CrossCountry
East Midlands Railway
What are the train times from Chepstow to Skegness?
Get from Chepstow to Skegness in as little as 5 hours 37 minutes on the fastest trains, so you can make the most of your time.
The average train journey from Chepstow to Skegness takes around 8 hours 6 minutes. There are around 10 trains that operate on this route daily.
As there are no direct trains between Chepstow and Skegness, you'll need to make 1 change.
Transport for Wales, East Midlands Railway and CrossCountry trains operate on this route.
Booking in advance often results in cheaper ticket prices.
With our Journey Planner, you can check live train times, compare prices and check routes.
What do people frequently ask about the train journey from Chepstow to Skegness?
Want to know more about your journey from Chepstow to Skegness? We've compiled some of the most frequently asked questions by our customers to help you plan your journey.
How close is Chepstow to Skegness by train?
Is it possible to get from Chepstow to Skegness without flying?
What is the best way to travel from Chepstow to Skegness?
What time does the first train from Chepstow to Skegness leave?
What time does the last train from Chepstow to Skegness leave?
How often are trains from Chepstow to Skegness?
Do you need to book the train from Chepstow to Skegness in advance?
How do I find cheap train tickets from Chepstow to Skegness?
As most UK train companies increase their prices as the departure date approaches, our Trainline team of experts have put together these tips to help you find the cheapest tickets.
1. Sign up to Ticket Alert
If you're planning a trip more than 12 weeks ahead, sign up to our Ticket Alert to get notified when Advance tickets are released for your travel date.
2. Use a Railcard
National Railcards offer a 1/3 off eligible train tickets in the UK and can be a great investment if you travel throughout the year. Buy one with us and you'll be able to store it digitally in our app, so you'll always have it on your travels.
3. Book split tickets
Our handy feature SplitSave will 'split' your train journey into multiple tickets, which can be much cheaper than buying a single ticket. Find out more about split tickets.
4. Travel Off-Peak
If you can be flexible with your travel times, Off-Peak and Super Off-Peak tickets are usually cheaper in the UK. Generally, Off-Peak times are any time at weekends and outside of Monday to Friday morning and evening rush hours.
5. Consider a Season Ticket
Best for commuters, if you catch a train on the same route more than 3 times per week, you could save money with a Season Ticket. With annual, monthly, weekly and flexi options available, find out if a Season Ticket for Chepstow to Skegness is right for you.
For more money-saving tips on UK and European train travel, read our cheap train tickets guide.
§Advance adult single fare. Excludes booking fee. Prices seen by Trainline customers in the last 30 days. Availability limited.