Q&A: Travel Routines with TripStreak

This post originally appeared on Culture With Travel.

Every traveler has one: a routine. How do you prepare for your next trip? What are your routines before, during, and after? That’s where advice from Charles Ralston, founder of TripStreak, the smarter travel search, comes into play. TripStreak is a personalized online travel search that finds the best trip for you. Best of all, it’s free! The search encompasses all the major travel brands, so people don’t have to worry about missing out.

Be sure to join us at 2:30 p.m on Thursday, January 28, 2016, for #CultureTrav with TripStreak as our special guest host. Read the interview to learn about Ralston’s travels and routines, his tips for travellers, and what inspired TripStreak.

How do you maintain your routine when traveling with other people who may have different ones?
Based on my experience, it really depends on who else is in the group. Many of my friends that I travel with are like-minded in that we all operate fairly independently, so if someone wants to do their thing with/without everyone else, they just do it, and it works. I think as long as people are clear about their expectations and desires upfront, then it usually isn’t an issue.

What is the biggest challenge of traveling (during the holidays)? Please share any tips you may have to make (holiday) travel easier and more comfortable.
The holidays are stressful enough without sprinting through an airport or missing a flight. Winter storms and fog can wreak havoc on connections. If at all possible, fly non-stop to your destination, so you don’t run the risk of getting delayed and missing a connecting flight.

If you have to connect somewhere, do it in the Sun Belt (the southern region of the United States) and give yourself at least 90 minutes to connect. Download the airline’s app and also FlightAware or FlightRadar24 to keep an eye on your flight(s). If things start to look dicey, jot down some backup plans in your phone. It’s always helpful when working with the airline agent to rebook your flights if you know exactly what you want.

If issues do come up and you have airline lounge access, go there to get help rather than stand in the long lines at the customer service desks in the terminal. Carry-on whenever possible. If you have to change your flights due to disruptions, airlines generally won’t do it if your bags are checked.

What are the top five items in your carry-on?
In no particular order:

1. Bose QC20 in-ear noise cancelling headphones – these are a must-have, and I’ve found them pretty good for sleeping as well
2. iPad Mini 3
3. USB charger – anything over 6,000 mAh
4. IBM, er Lenovo, Thinkpad T420s – yeah, it’s old, but it’s served me well over the years.
5. Universal Power Adapter – you never need one until you don’t have one.

What are the top 10 destinations remaining on your wanderlist, those that you’d absolutely love to visit?
Australia, New Zealand, Tierra Del Fuego, Croatia, Bali, Burgundy, South Pacific Islands, Morocco, and South Africa.

Have you encountered any fascinating cultural celebrations or traditions? Please feel free to share some examples with us.
I was on vacation in Barbados in 2014, and we went to a local event called the Oistins Fish Fry. This is a weekly occurrence where both locals and visitors come to eat and party. I’ve never seen anything quite like it. The food is amazing, and everyone is dancing and having a great time.

Where during your travels did you experience an interesting tradition around the holidays?
I was lucky enough to go on a trip to Cuba in Dec 2013 – Jan 2014 (fully-approved trip, don’t worry ;)). Our group was near the city of Trinidad and went to a club that was in a cave for New Year’s Eve. Primarily locals, great music, good drinks, and everyone was dancing. You can’t beat that. For me, the interesting aspect wasn’t that it was hugely different from how we celebrate NYE, but as an American, I had a very limited idea of what to expect in Cuba (read, I had no idea what to expect).

On a broader note, our trip took place before the travel restrictions for Americans were lifted, and Cuba has since seen the number of Americans traveling there increase significantly…I think something like 33% year-over-year was the last statistic I saw. It was very common for locals to come up to us on the street, at bars, etc. just wanting to chat, learn about the US, hear our perspective, and vice versa. We had heard that this might happen, but I don’t think many of us expected it to be as eye-opening as it was.

What locations do you mainly travel to over the holidays?
Home for Christmas is an annual standard, especially since I get back to Atlanta only a few times throughout the year. New Year’s really depends on the day of the week on which it falls as well as how burned-out I feel. The last few years, it’s been more of a low-key holiday.

How likely are you to do things differently on a business trip than you would at home or on a leisure trip?
Business trips are usually pretty consistent for me – meetings all day followed by dinner/drinks, so there’s not a lot of time for much else. Given how packed those days can be, I typically try to get in/out on those trips quickly rather than spending an extra night on the road. Leisure trips are much more varying, and it really just depends on where, for how long, etc.

Please tell us what inspired the creation of TripStreak.
The idea for TripStreak came out of my own frustration with searching for my own trips, both business and leisure. Basically, I got fed up with having multiple browser tabs open, using spreadsheets to calculate frequent flier mile earnings, and, of course, the massive amount of time required to do all this before clicking the ‘purchase’ button. In numerous conversations with others, I found that I wasn’t alone and there was a resounding need for a more efficient process. Clearly, every individual will have his or her own set of preferences and system of doing things, so it became clear that the solution was to allow people to define their personal preferences and use those in the planning process to create the best trip for them.

What is (or was) your typical travel planning routine? What are your biggest frustrations?
For the longest time, it was something like the below:

• For business trips on short-notice or with very finite appointments, the process was somewhat faster because fewer options could be considered; in other words, I just needed to get there.
• If I had some time to play with the schedule, for business and leisure trips, then that’s when things would get much more complicated with spreadsheets and so on. That process was very time-intensive, and it had a lot of potential to get frustrating due to price changes, schedule changes, etc.

On a recent business trip to India, I was able to find exactly what I wanted on TripStreak in a matter of seconds, without having to deal with spreadsheets or extra tabs. I’ve also made bookings for some upcoming trips in a similar fashion. It’s really removed the burden of tracking down a lot of information from different sources.

Don’t forget to join the TripStreak #CultureTrav chat on January 28 to share your routines and get answers!