My Startup: Cheeky Weekend

Charlie Spargo's picture
by Charlie Spargo
Cheeky Weekend

Eyebrow-raisingly named Cheeky Weekend aims to help busy professionals get away from their desks and on their way to an exciting foreign destination as affordably as possible, and at times that suit them.

It focuses on getting people away for a "cheeky weekend", which they define as leaving after work on Friday and returning late on Sunday, giving you the maximum possible time away. By taking users' preferences Cheeky Weekend's system find the prices, times and holiday locations that suit them.

Its founders, Dave and Russell, are also passionate about keeping prices low - finding the best weekend deals for flights which can vary by hundreds of pounds just depending on the weekend chosen. They drew on their own good and bad travelling experiences to create a solution that's transparent and simple to use.

Founders: Dave Bailey and Russell Trow

Founded: 2018


Dave Bailey, Cheeky Weekend

We spoke to Dave about where Cheeky Weekend came from.

Why did you start Cheeky Weekend?

I love to travel but I hate the experience of booking flights. It always takes longer than expected, and involves making horrible trade-offs like, ‘Is it worth waking up at 3am?’, ‘Is it worth it to have a connecting flight?’ and ‘Is it worth taking time off work?’. Plus, you never really know whether what you’re paying is cheap or not.

I started working on Cheeky Weekend as a way to make the process of booking flights enjoyable. We ask our users for their travel preferences and take a lot of the hard decisions out of the process. For example, all our flights are direct, they all leave outside of working hours, and they all have remarkably low prices compared to nearby dates.

Tell us more about the tech behind the product?

Our service automatically finds all the possible flights that match your preference criteria over the next six months, using algorithms to identify the best value deals, often 60-90% below the average price. Specific trips are presented on a calendar - ready for a quick purchase before the fare disappears. 

My co-founder Russell Trow and I already founded a tech business together called 3 Kinds of Ice, a mobile app that helped Londoners find unusual restaurants in their city. Starting a second business allowed us to hit the ground running and use a lot of best practices we discovered in our last venture.

For example, we’ve optimised our tech stack for continuous deployment, enabling extremely fast iteration even for a small company.

"Is it worth waking up at 3am, or having a connecting flight?"

Where are you at right now?

Cheeky Weekend is available in several cities across the UK including London, Manchester, Bristol, and Edinburgh. Customers can visit hundreds of destinations with cheap return flights in order to make the most of their annual leave.

What are your aims for the next year?

Over the next year, we’re looking to expand internationally and help people all over the world to travel more. We want to build a category-defining product that helps people take a proactive approach to leisure travel.

Using Cheeky Weekend
"Travel is one of the joys of life - we want to remove the obstacles"

What's been the hardest thing about getting Cheeky Weekend off the ground?

Cheeky Weekend started as a side-project to solve one of our own travel pain points. Balancing different projects is always a challenge and it took a lot of patience and discipline to come this far. But having less time to build and more time to think turned out to be an advantage - helping us resist the temptation to add too many features that don’t add value.

Why should more people be using Cheeky Weekend?

Travel is one of the joys of life and we want to help remove the most common obstacles that stop busy professionals from travelling more: money, effort and time off work.

Cheeky Weekend can help you travel more by proactively looking for deals on your behalf. It’s the equivalent of hiring an assistant to look at Skyscanner every day, and curate the cheapest deals that fit your criteria - but at a fraction of the cost.

How much will it cost users, and why is it worth the investment?

Cheeky Weekend has a free service that shows you the best-value trips you can take over the coming month. For people that want to book in advance to benefit from cheaper flights and accommodation, subscribing to Cheeky Premium costs £2.99 per month.

The value comes in our ability to find the best value weekend to visit a particular destination with convenient flight times. And the savings are typically massive, with up to 90% off the average flight prices.

Cheeky Weekend