Kayak Rolling on the River Dee in Chester: Our Honest Review

If I had a pound for every time Georgia warned me about “ending up upside down in a kayak,” I’d have enough to set her up for life when one of these stupid adventures eventually claims me.

She always says she couldn’t hack being a young widow, so the more survival skills I’ve got, the better for both of us.

We’d been looking for ways to level up our van life plans, and kayaking kept popping up—mainly because I wanted to learn something new that didn’t involve breaking bones.

So when GetYourGuide kindly offered us the chance to try out Kayak Rolling on the River Dee in Chester with Paddle the Dee, it felt like the perfect opportunity to prove I could handle it (and maybe convince Georgia I wasn’t a total liability on open water).

We had the option of white water rafting or learning to roll a kayak, and I’ll be honest…my practical side won out. If I’m going to spend more time in a kayak, it makes sense to know how to get myself out of trouble.

We booked the session, crossed our fingers for decent weather, and set off at 6am for the two-hour drive to Chester.

Disclosure: This post contains affiliate links. Our kayak rolling session with Paddle the Dee was gifted by GetYourGuide, but we’re under no obligation to give a positive review. All opinions are our own.

Kayak Rolling on the River Dee:
What It’s Really Like

Here’s how my session went.

Instructor & Setup

When we pulled up at Sandy Lane Car Park (free for four hours, which is rare enough to be worth mentioning!), it was just a short walk to the sailing club where the session started.

Joe, my instructor, met us there—super friendly, and straight away, it was clear this wasn’t going to be a generic group session.

It was just me, him, and two hours of training, even though it was advertised as 90 minutes.

Right from the start, Joe asked what I wanted out of the session.
I explained I was hoping to make kayaking a regular thing, especially when we hit the road full time, and he was clearly keen to set me up for solo success, not just tick the “you did a roll” box.

He got me to adjust the kayak for my height, taught me how to carry it on my own (handy for solo adventures), and gave loads of practical tips you just don’t get in a group taster.

What to Wear & Gear

If you’re booking through GetYourGuide, heads up—the info said no shoes, which nearly left me in a pinch since I’d only brought new walking boots for a day in Chester after.

Joe kindly lent me his own trainers so I didn’t trash mine, but next time I’d bring an old pair just for the river. There are changing rooms, and wetsuits are available to borrow if needed.

Confidence Building

Before we even hit the water, Joe focused on safety and basics.
He explained how spray decks work and why they’re important, then got me to practice releasing myself from the kayak.

We did this by closing my eyes, and releasing myself so I’d be confident finding the pull tag even underwater.

It sounds simple, but this bit really boosted my confidence before I was actually upside down.

Getting in the Kayak

Out on the water, the first thing I noticed was how much less stable this kayak was compared to the “sit-on-tops” you get at the beach.

These are smaller and more nimble, which is perfect for rolling—but also means you have to get used to it.

Joe had me paddle around while he watched, then we did some “baby steps” like shifting my weight to tip the kayak without going under, just to build confidence in staying upright.

Everytime something went wrong/right, we talked through it: Why did that happen? What part of the body did I use to do that?
This makes you actively think about each movement you make and is really insightful.

Skills & Going Overboard

We worked on technique: turning, paddling in squares, and quick turns. Inevitably, I tipped and went under (see action shot below).

Thanks to Joe’s earlier safety briefing, I found the pull tag and got myself out without drama, and he was there in a flash just in case.

He also showed me how to get back into the kayak from the water which is definitely useful if you ever end up swimming in a river by accident.

The Main Event: Going Upside Down

To get comfortable being upside down, we practiced just rolling and holding my hands out of the water (managed 26 seconds—felt like 10 minutes).

He took this opportunity to teach me about “T Rescues”, and how to do them safely, then getting used to flipping back upright.

The first sort-of-roll I did was actually by accident, but with Joe’s help, I made it the whole way around…just not with much dignity left.

By the end, we tried a full roll with the paddle. I didn’t manage to nail it this time, but Joe reckoned with another session or two I’d have it sorted.

So, Is It Worth It?

I went in thinking this would be a one-off, but I’m already thinking about my next session.

I’m genuinely excited to try some of the other activities Paddle the Dee has to offer. They run activities like white water rafting, kayaking excursions, and SUP, and if the kayak rolling is anything to go by, I’m expecting more soggy socks, plenty of laughs, and some actual skills by the end of it.