For the 50+ Traveler

Stephen Henson spent more than 4 decades in the business world, including being the founder of Kelley Blue Book's, which he grew into the largest automotive site. Throughout his career, he enjoyed traveling and meeting people the most. That journey has led Stephen to 54 countries and more than 600 cities around the world.

He decided to create to share his stories, photographs, and advice. He has met a lot of people who have also worked really hard and can afford some of the better things in life, but still value getting a good deal. Those people are Stephen's target audience.

Stephen was kind enough to answer a few of our questions below!

Photo courtesy of Stephen Henson.

TA: How many years have you been traveling and what got you hooked?

Stephen: Starting more than 40 years ago as a corporate executive I was fortunate enough to travel to amazing cities, such as Rome, London, Paris, and many more. Later in my career I left Kelley Blue Book to go to China to help with a similar business. That experience was the clincher, leading to traveling most of my time. And I have always been an amateur photographer.

TA: Do you specialize in a particular type of travel?

Stephen: "Upscale travel on a budget" is for travelers who can afford luxury, but still want to spend wisely. I don't write for the hostel-staying backpacker or those who prefer big tour bus trips. My audience is independent affluent travelers who want to be in control of their experience.

TA: What is the best vacation you've ever taken?

Stephen: That's a really tough question. I travel the globe, but I keep going back to Hawaii -- maybe 20+ times. So I'm going to say that the best vacation is island hopping in Hawaii. Imagine hiking Diamond Head for a view of Honolulu at sunrise, then standing above the clouds at Haleakala Crater for sunset, and then watching Peles flowing lava from Kilauea Volcano create new land. The diversity of extraordinary things to do is pretty hard to match.

TA: What's one place you've always wanted to visit?

Stephen: I would have said Africa, but we finally took a safari in Kenya earlier this year. I have been to Denmark and Sweden, so maybe it's time for Norway.

TA: If you could only give a traveler one piece of advice, what would it be?

Stephen: Step out of your comfort zone. Some people warned me about going to Myanmar just a week before their contentious election, but it turned out to be a safe and highly rewarding trip (despite food poisoning). If you paid attention to every U.S. State Department warning you would never leave home. Do your homework and go!

TA: What's something you ALWAYS bring with you when you travel?

Stephen: I have written a post about carrying "a drug store in a Ziploc bag." Take small amounts of medicine and first aid in the brands you know and trust.

TA: What are some of your favorite travel blogs and communities?

Stephen: I belong to an organization of travel bloggers called TBEX. We meet a few times a year somewhere in the world to share ideas and best practices.

Photo courtesy of Stephen Henson.

TA: What are the top 3 websites you use for research/inspiration when planning a trip?

Stephen: I like to check out the local tourist board sites. They don't have an agenda other than to inspire you to visit.

TA: Do you have any good airport or flight hacks for people traveling by plane?

Stephen: Travel is supposed to reduce stress in your life. Airports induce stress. That's why I try to arrive early and relax in the lounge. I always try to fly nonstop, even if it costs more. Many of my travel horror stories start with a missed connection.

TA: Is there something you think most travelers worry too much about?

Stephen: I have watched travelers schedule their time to a fault. If you are supposed to visit the canals of Suzhou and it is raining, just go tomorrow. That's easier to do if every minute of a trip isn't pre-scheduled. Don't worry about having a plan for every day.

TA: What's a travel scam travelers should be wary of?

Stephen: Don't ever take a non-metered taxi or other vehicle without first negotiating the price.

TA: Which country has surprisingly good food?

Stephen: Visitors to China agree on one thing: the food is amazing. Beijing duck cannot be duplicated outside China. Same with Shanghai dumplings, Sichuan spicy fish, eggplant, hotpot. Go there and you will be an evangelist.

TA: Which underrated destination deserves to be more famous?

Stephen: San Miguel de Allende is only a few hours' drive from Mexico City but it is a world apart. Great mountain climate, 300 restaurants, art galleries, festivals, and affordable.

Learn more about Stephen:

Visit his website:
Follow him on Twitter here.
Find him on Facebook here.
See his photos on Instagram here.
Read his CV on LinkedIn here.
Or connect with him on Pinterest here.

Thanks for taking the time to talk with us!