They travelled across Portugal and the UK, as well as France and Switzerland before jetting over to Asia and visiting the Philippines, Malaysia, Indonesia and Bali.
And when they fell pregnant with surprise baby Leo, now three, they ignored criticism and advice to take him on holiday aged just two weeks.
Sharing parenting travel tips online to fellow nomads saw Jenna’s audience grow until she was able to give up her stressful job as locum doctor in February.
They explored Cyprus and the Greek islands in 2019, as well as Italy, before travelling across the US - with a quick jaunt to the Bahamas - and finishing in New York.
Just a few months after she launched www.thetravelmum.com it's so successful Joao quit his job as a civil engineer to work on the website full-time too last month.
Now they go on holiday most months, and fund their life in Worksop, entirely from advertising and hits on their site and social channels.
Jenna said: "We earned £6,000 last month from our website and have realised we could do everything we did before, just with a baby.
"We don't have to live a boring life to provide for him.
"It's getting to the point where we can travel and be nomadic and live the life we want to live.
"Taking Leo to Portugal at two weeks old was so easy - he slept the whole flight and was happy enough in Portugal.
"We had bought Glastonbury festival tickets before I knew I was pregnant and decided to take Leo with us.
"It went really well and we realised we could do whatever we wanted to do and it would make him confident and adaptable.
"Joao handed in his notice just a couple of weeks ago and I've been working on the website since February.
"The income we get is significant enough that we can both survive and we know this is the life we want."
In April, 2017, Jenna attended a hen party in Albufeira, Portugal, and when it came to leaving decided she wanted to stay and see more of the Algarve.
Then training to be a doctor, she ditched the flight and booked a hostel in Lagos - then found herself on Tinder looking for someone to hang out with.
After matching with Joao on the app, the couple spent a few weeks exploring the beautiful beaches of the country and spending time together.
"During the hen party we would go out and lie by the pool, and when it came to leaving I realised I'd barely seen any of the Algarve," she said.
"I ditched the flight home and booked a hostel in Lagos but quickly realised the hostel was a bit dead and there wasn't much to do.
"I went on Tinder to find someone to hang out with and matched with Joao.
"I explained I was in Portugal for a few weeks and he showed me the lesser-known beaches - we went camping on this beach and cooked food outside and just had the best few weeks, it all felt really natural.
"I had texted my friends after one of the first times I'd met him, saying 'I'm going to marry this man and have his babies' as a joke.
When she had to leave, they continued to talk on WhatsApp - and Jenna swiftly booked another trip out the Algarve to see him again.
In August, they decided they wanted to give things a go and began a long-distance relationship, meeting up in England and Portugal, and travelling to the Philippines and Bali together.
In April 2018, Joao moved to England to be with Jenna who was living in her parents' house at the time - and it was only a few months later that they discovered they were expecting a child.
"He moved in with me in England and only a few months later discovered I was pregnant - I had previously tried for a baby for years and had been told I was infertile," she said.
"I told all of this to poor Joao and said we didn't need to be too careful, so when I found out I was pregnant I was shocked.
"It felt like it was bad timing, but secretly deep down I had been wanting a baby for so long and knew Joao was a good guy - we had already established it was a serious thing.
"I knew when we looked back, we would think it was perfect timing and we've now been trying for a second baby for two years and it hasn't happened, so Leo is definitely a bit of a miracle baby."
Leo Carr-Paias was born on March 15, 2019, and the couple quickly realised they could do everything they did before - just with a baby along for the journey too.
When Leo was two weeks old, they went to Portugal so Joao's family could meet him and that summer they even took him to Glastonbury festival with them - when he was just 12 weeks old.
Next, with Leo, they explored Cyprus and the Greek islands in 2019, as well as Italy, before travelling across the United States - with a quick jaunt to the Bahamas - and finishing in New York.
Jenna's website and her big following on TikTok, where she posts under the username @thetravelmum, since February 2020, now allow her, Joao and their son to travel the world.
So far in 2022, they've spent time in Italy and have plans to visit Japan later this year.
Jenna set up the website - www.thetravelmum.com - in March 2021 to support her social media account, where she gives out budget travel tips to her thousands of followers.
Her top five tips for travelling on a budget include;
1. Pack light by using a rucksack as your free personal item so you don't have to pay extra for checked-in luggage.
2. Travel mid-week when flights are less in demand and therefore cheaper.
3. Travel off-season - April to May and September to October usually still have great weather with massively reduced prices compared to summer months.
4. Use flight and hotel comparison sites to look for the best deals - package deals are often more expensive than doing it yourself.
5. Look for rooms with a kitchenette and a nearby supermarket - a bit of effort making a meal or two can save you a lot of money.