Interview with Jane and Duncan Dempster-Smith, from “To Travel Too”

Back in the summer of 2016 I had the pleasure of meeting Jane and Duncan Dempster-Smith, the co-founders of “To Travel To.” In 2013, Jane and Duncan decided to leave the corporate world behind and see the world. Read more about Jane and Duncan in my interview with them: 


1. Tell us a little about yourself: Who are you? Where are you from?

Jane – Co-Founder, Flashpacker, Travel Guru 

Over the past four decades, Jane’s passion for travel has taken her to over 50 countries. She has lived and worked in Australia, UK and Singapore. With extensive experience in all aspects of travel from airport ground staff to air hostessing, retail, corporate and group travel, she has flown in two seaters, hot air balloons and even the Concorde. Jane offers her skills to baby boomers who want to change their lives; to travel light and travel far.

Duncan – Co-Founder, Flashpacker, Philosopher

Having travelled for both business and leisure, Duncan has lived in Malta, UK, Hong Kong, Australia and Singapore. In his past life he held senior roles with global multinationals in manufacturing, distribution and sales. In 2013 he embraced a life change based on the philosophy: ‘chase time not money’. His ambition is to support fellow baby-boomers who want to fly the empty nest and see the world.

What we do:

Jane and Duncan, have created “To Travel Too,” a travel blog focused on the baby boomer, transition to retirement and retired folks. The blog creates content and partners with other related travel and lifestyle providers to inspire folks to take action.

We have gained experience in leaving the corporate worlds, downsizing/empty nesting. We have strategies to assist baby boomers take the first step to let go of the corporate worlds, downsize the family home and to travel longer term. We provide strategies in how to travel on a budget and we show by example how the baby boomer can chase time not money. We offer special bespoke travel planning services in particular airfare checking and itinerary planning.


2. What is your blog about and how did you start blogging?

Our eldest son was on a late gap year and we caught up with him in Santorini, Greece back in 2012. We had been stalking him on Facebook and enjoyed his travels throughout Central and South America and Europe. If he could take a late gap year why couldn’t we? In 2013 we left the corporate world behind, created To Travel Too and have not looked back since. We are continually on the road writing about our adventures, reviewing hotels and tours to provide inspiration for our readers. To Travel Too is targeted at the baby boomer, transition to retirement and the retired folks globally.


3. Do you travel for work or for pleasure?

Definitely pleasure. We are fortunate to be able to travel continuously and write about our experiences. Each destination particularly if it’s for the first time provides us with nourishment. We love getting the feel of a new culture and it’s exciting when the fives senses are experienced in the travels.


4. What is the most stunning place that you have ever visited?

Wow! That’s a hard one! For Jane it was Machu Picchu, Peru after we trekked for 4 days to get there! For Duncan, it was Petra, Jordan. It was simply magical to arrive into Jordan and to travel to Petra. We experienced camping and sleeping in the desert, which was followed by days wandering Petra. Petra is mystical, magical, serene and very quickly once you enter you escape and fall into an ancient world. You can feel the vibe and explore the bygone ages before reentering your own 21st Century Petra.


5. Do you feel that blogging takes time away from your social or family life?

No, it is our life now, our boys are on the road, and we Skype with family and friends regularly. We also take the opportunity to travel with family and friends more than we would have if we were still in the corporate world. We have found our network of friends has expanded, we meet fellow travelers on the road and we get to meet and engage with locals. Our travels are much slower than when we started, this allows us to connect with the destination and to peel back the tourist veneer to get to the core of a destination.


6. What is the one thing that is too large or impractical to travel with that you wish you could take with you when you travel?

We love our green markets and if we could take a nutra-bullet with us this would be smoothie heaven.


7. Are there any countries that you would not consider visiting and why?

The only countries currently would be Syria or North Korea (which you cant visit as a tourist anyway).


8. Do you have any funny travel stories?

We have a few, but the first one that comes to mind is when we flooded a hostel in Florence. We had a great terrace that overlooked the Duomo and one late afternoon we were joined by some young Australians our boys ages who were travelling around. We joined them for a few drinks early afternoon and it extended into the evening. We had washing soaking in the bidet, unfortunately with the tap running slowly. A few hours later a passing guest noticed water coming out from under the door and alerted us to the fact. One of the guys was a project manager, the other a builder and we all pulled together to quickly stop the water flowing with thousands of towels. After cleaning up the boys left to go and get something to eat and we were left trying to get the soaking wet towels down to the laundry in a one-man lift.


9. What is the most adventurous thing you have ever done?

Trekking Machu Picchu with no prior trekking experience and for Jane no camping experience. The altitude was something that we had expected never the less it is was an issue for Duncan and thankfully we had planned to acclimatize in Cusco. Thank Goodness!


10. What is your favorite mean of transportation (plane, train, car, ship)?

Jane – Up until this year I would have said bus but we have just travelled on a repositioning cruise from Spain to Panama and it was so much fun I would definitely do it again.

Duncan – Love to travel by bus as we get to enjoy the landscape, check in is easy and its often much cheaper than other forms of travel.


You can follow Jane and Duncan on: 

Google+: totraveltoo



This is a post for The Weekly Postcard Blog Link-up

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22 Comments on “Interview with Jane and Duncan Dempster-Smith, from “To Travel Too”

  1. Hi Anda,

    Jane and Duncan have a great story!

    They show you can start traveling at any age. Wonderful.

    I vibe with their take on Peru. I missed MP – got a bit sick – but struggled with the altitude for a few weeks in Cusco. Not many places on earth that are 2 miles high. When I first lugged my suitcase up 4 flights of stairs, I felt it! In a major league way.

    Thanks for sharing.

    Ryan Biddulph recently posted…5 Travel Photography Tips for the Postcard Perfect ShotMy Profile

    • @Ryan Thanks for passing by..

      We have found the experiencing rich and s we let go of more we are receiving more time, more experience, more inner happiness. Certainly we can emphasize with you re Cusco. love to have you along with us in the journey we are currently in Mexico and then off to Cuba , Barbados and then to Europe.

      Do you have plans for travel coming up ?

      Duncan & Jane

  2. Same problem with altitude in Cuzco, so I’m kind of glad we didn’t think about trekking to Machu Picchu. We were there on our honeymoon in 1982. It hadn’t been quite “discovered” yet by the mass market tourism crowd and the Shining Path Maoist revolutionary group was acting up violently, so it was a good time to visit. We did our only multi-day hike on the South Island of New Zealand, the Milford Track. No altitude problems and there aren’t even any dangerous wild animals nor insects, so it was great for inexperienced hikers.

    • Hi Suzanne..

      We plan to visit New Zealand later on in the years as our Australian neighbor. It’s interesting how many of us experienced Cusco and the altitude. Peru was a stimulant for us re-culture, colors and textures. We are finding this experience the most enriching time in our lives having spent time with our careers and family..

      Do you have plans for 2017/18 travel wise ?

      Best Wishes

      Duncan & Jane
      Jane Dempster-Smith recently posted…Budva The Disappointing Jewel of MontenegroMy Profile

    • Mary Bless you

      Yes, we do hope to inspire the Baby Boomers and all folks. having said that the Baby Boomers have kind forgotten their vibe and the days they traveled Europe, US and Asia back packing in a Combi Van .. going to festivals and being free.

      it’s time to reach back to more love and less hate and travel allows this

      Where would you like to travel to and how long do you think you might ?


      Jane & Duncan
      Jane Dempster-Smith recently posted…Budva The Disappointing Jewel of MontenegroMy Profile

  3. Really enjoyed reading this interview – very inspiring. This is something we plan to do – moving this year to country number 6 (Australia) and looking at ways of perhaps working for 6 months and travelling for the next 6 – with a view to increasing travel time when we get our pensions at 60. Great stuff! Off to connect and read more!
    Tracy recently posted…A Virtual Cuppa – January 2017My Profile

    • Tracy

      That’s a great plan and we are pleased you have been inspired by our interview. We do wish to show folks that it can be done.

      Interesting to see and hear your plan. Where were the first 5 countries ?

      Australia is certainly a big country and expensive so yes slower, longer travel is definitely the plan. Many ways including low-cost Asia as part of the length of travel with Australia allows the daily rate to come down. House Sitting is a way to travel low cost and is very acceptable in Austalia. Lets us know if you need information on any of this


      Jane & Duncan
      Jane Dempster-Smith recently posted…Budva The Disappointing Jewel of MontenegroMy Profile

  4. Ahhh! What an inspiring couple! I would like to sit and hear their many travel stories. Flooding a hostel sounds interesting. It has never happened to me but I remember staying in a hotel where one of the rooms flooded in the middle of the night. Two of our friends had to stay for a couple of hours in our room because the smell wasn’t that nice.
    Ruth recently posted…A Perfect Day in Toledo: Travel ItineraryMy Profile

    • Jessica

      Yea the Hostel was a highlight especially as it was the oldies that caused the issue and Gen Y bailed us out literally.

      Pleased you enjoyed the interview, we were blessed to have met Anda and was a great way to continue to get to know her and be inspired by her story.

      Are you planning any travels in 2017/18


      Duncan & Jane
      Jane Dempster-Smith recently posted…Budva The Disappointing Jewel of MontenegroMy Profile

  5. Kudos for hiking to Machu Picchu! I didn’t choose that option, but that location is a spiritual experience that is not like any other. I also admire Jane and Duncan for the type of blog and audience they focus on. It’s good to see people encouraging others to travel no matter their age!
    Brooke of Passport Couture recently posted…Chinese New Year 2017 InspirationMy Profile

  6. I feel like I’ve learned so much about Jan and Duncan. I will have to start following their travels as it sounds like they’ve been to some great destinations. Flooding a hostel! Yikes! #TheWeeklyPostcard

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