Globetrotter Deborah Jackson celebrated her 50th birthday by challenging herself to visit 50 cities around the world – in a year.
A self-professed ‘extreme day trip fanatic,’ she started on her 49th birthday on December 5, 2024, by going to Pisa for the day, and returned to the Italian city exactly a year later for her 50th.
Deborah, who had only done two extreme day trips a year prior to starting her bucket list challenge, says: “I wanted to mark turning 50 in a memorable way. It’s a milestone birthday and I wanted to set a goal to mark it. I like to make the most of every moment.
“I set myself the challenge of seeing 50 cities in one year. I did 39 extreme day trips, which means I left and came back on the same day.
“I started the challenge last year on December 5 in Pisa and finished exactly a year later – again in Pisa. I went up the leaning tower, then took the train to Lucca, where I went to a Christmas market and saw illuminations projected onto the amphitheatre.
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“Sometimes I’ve seen two cities in one day trip – for example Pisa and Lucca, Rome and the Vatican City. Nothing beats having freshly-made traditional pizza in Italy for lunch. It simply tastes so much better with a stunning view.”
Deborah took two ferries, six Eurostars, one Air Baltic trip and 78 Ryanair flights during the year. She made nine solo trips – with the rest either being with her husband Matthew, 54, an IT product manager, her son Tom, 19, or daughter Madeleine, 16, or with both her children.
She says: “My highlights included taking the funicular railway to watch the sunset in Bergamo (Italy), visiting the floating saunas in Oslo (Norway) and getting the ferry from Helsinki (Finland) to Tallinn (Estonia). I was blown away by the beauty of Riga (Latvia). My favourite places were walled cities with cobbled streets. And I loved Florence (Italy) because there is history and beauty in every corner. I have seen and done more on a day trip than on a week’s holiday!”
Deborah says she loves extreme day trips (EDTs) because there is something thrilling about seeing a new country in a day and making it back home in time for bed. She adds: “There is something so amazing about seeing places for the first time with your own eyes. I love doing EDTs, the feeling travel gives me, it’s such a buzz.
“If I was choosing which would top a list, then I adored all three Baltic states, and Berlin (Germany) was my favourite ‘big’ city. I think my favourite country has been Italy, it’s never disappointed. As a child I only holidayed in the UK. But with EDTs you can go here, there and everywhere- it’s incredible. Life is an adventure, life is for living. I’ve always been a glass half full person and I want to make the most of every day.’”
Deborah works two days a week as a display rep and says her job provides the flexibility to go on EDTs – with most either being on weekends, Tuesdays or Wednesdays. Her cheapest EDT was to Gdansk (Poland) – where she and Matthew spent £30 each, including a nice meal – with flights costing just £27 return.
She tends not to spend more than £35 on return flights, although she made an exception for return flights to Lapland, which cost £60. Deborah uses the Go Anywhere function on Skyscanner to look for the best deals. She continues: “I’m very fortunate, I’ve paid off my mortgage and don’t have a lot of outgoings. I don’t pay more than £35 for return flights and don’t have to pay to park, as I live next to Stansted Airport.
“I love doing EDTs because I love leaving early and coming back in time to sleep in my own bed. It feels like a real adventure. EDTs are also a fantastic way to find out if you like somewhere and I’ve never not enjoyed one. I had some trepidation when I first started doing EDTs, so I did some with family as a safety net at the beginning and didn’t go too far while I found my feet. But once you’ve done a couple of solo trips the world is your oyster!
“I’ve got big plans for 2026. Next on my list are South Eastern Europe – Serbia, Montenegro, Bosnia, Croatia. To anyone thinking of going on an extreme day trip, or doing solo travel I say ‘go for it – you’ll never regret it. It’s life-changing.’”
List of Deborah’s trips:
Dec ‘24: Pisa, Lucca, (Italy) Brussels, Bruges (Belgium) Lille (France), Edinburgh
January 2025: Cardiff, Lisbon (Portugal) Gdansk (Poland), Alicante (Spain), Milan, Bergamo (Italy)
February: Billund (Denmark), Berlin (Germany)
March: Madrid (Spain), Bratislava (Slovakia), Wroclaw (Poland), Dublin, Rovaniemi (Lapland), Helsinki (Finland), Tallinn (Estonia),
April: Eindhoven (Holland), Barcelona (Spain), Gothenburg (Sweden), Luxembourg
May: Oslo (Norway), Nantes (France), Vienna (Austria), Baden-Baden (Germany), Prague (Czech Republic), Cologne (Germany)
June: Limerick, Katowice (Poland), Florence (Italy), Bucharest (Romania)
July: San Marino (Italy), Cork
Sept: Cologne, Hamburg, Lubeck (Germany), Venice (Italy), Vilnius (Lithuania), Riga (Latvia)
October: Boulogne (France) Budapest (Hungary), Rome (Italy), Vatican City (Italy), Sofia (Bulgaria)
November: Copenhagen (Denmark), Malmo (Sweden)
December (2025): Pisa, Lucca, Florence, Prato (Italy).
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