Table of Contents

a man at a desk near his computer.
Jonathan Tallman at his office in the Tallman Group building. He checks flights to destinations he wants to see three times per week.

From dumpy motels in Jacksonville...

It all began when Jonathan Tallman started his first internship in Jacksonville, Florida, when he was 18. The Niceville-based financial advisor and leader of the Tallman Group spent the Summer in the east coast city for his work. Too short to get a rental. But hotel stays were pretty expensive, too.

So, like any other 18-year-old, he looked up what he could afford and booked that. He ended up at a hotel called the Suburban Inn.

It wasn’t great.

“I stayed there for like two weeks. It was the worst hotel experience ever,” Tallman said, “fights outside, people drunk wandering through the hallways at night. I was like, ‘I gotta find something else, because this isn’t working. I can’t stay here – it isn’t safe.”

His resolution to get a safe place to stay instead of a dump he thought he’d be robbed in when he got back from work every night started him on a wild adventure that ended up at some of the city’s best hotels.

Tallman ended up moving from hotel to hotel night-to-night to take advantage of last-minute vacancies – which meant he got the room at a steeply discounted rate while staying at places like the Hyatt and the Grand Regency in downtown Jacksonville.

He’d pay about the same price as the Suburban Inn.

“So that’s where I started learning about flexibility because I would go to work. And I wouldn’t know where I would stay that night. But I just knew, ‘Okay, I’ll get a room; it’s not a big deal. There’s plenty of rooms available; I’ll get one later.’ He moved from hotel to hotel that Summer, keeping his stuff in the car as he roamed from lobby to lobby of the fanciest places in town.

He says – the stuff he learned along the way can save you thousands of dollars on every trip – and let you travel the world (even with kids!) at a steep discount. He’d know. He’s been to more than 50 countries with his wife. They’ve even taken their kids on many of their adventures together.

But, it requires knowledge of how the system works and, most importantly, the flexibility to enact the plan.

Here's what you need to do and know to start taking trips all around the world (from Niceville)

Semper Gumby

The Marine Corps has a motto. 

No, not the official motto, the other motto. 

Semper Gumby: always flexible. To travel-hack well from Niceville, Crestview, or Eglin Air Force Base – you will need a couple of kinds of flexibility. 

If your travel plans – for one reason or another – don’t allow you to be flexible, then this is probably not going to work for you. “I had someone the other day tell me, ‘I want to go to this specific city. I want to stay at this specific hotel, and its during this time during this specific event – can you hack this for me?’ And I was like ‘I can’t,'” said Tallman.

Here’s how to ensure you’re flexible enough to make travel hacking worth your while:

You’ll need to be flexible on your travel dates, but everyone knows that. Tuesday flights will cost less than Friday, Saturday, or Sunday flights. No surprise there. You’ll also need to be willing to go to places that are less likely to be traveled to. That one is pretty common knowledge, too

1. Repeat after me: "There will always be a hotel room."

Despite the planner’s need to plan – Tallman says that the best hotel deals are the ones you get at the last minute. You may not get to pick the exact fancy hotel you stay, but you will have a fancy hotel to stay in that night – at a deeply discounted rate. There will always be room at the inn. Plan to get your hotels for a trip about a week in advance.

2. Compromise on where you are going - even on your way back from a trip

While the knee-jerk reaction to travel planning is to pick a place that you want to go and find the way to get there – Tallman says that the most cost-efficient way to do things is to choose a region or area you would like to see and then look for the least expensive flights. Google Flights mapping option is an excellent tool. Once you have zeroed in on a city with good flight deals, you can use the calendar tool. This will help you see if any dates are cheaper than the ones you are looking at. 

Tallman and his family once took a trip to see Alaska by cruise. When traveling home to Niceville, their Sun Country flight (which flies from Seattle to Minneapolis and is only twice a week, like Allegiant) was canceled. That means they were stuck in Seattle. Tallman changed plans and got flights from Seattle to Las Vegas because Allegiant has a direct flight to Destin-Fort Walton Beach Airport. There was at least a day between flights – so the crew headed to a Katy Perry concert which happened to be taking place to enjoy their night! 

a man uses a computer.
Jonathan Tallman begins his search for the next perfect (and inexpensive) trip with a look at the Google Flights website.

3. Travel from bigger airports using these methods:

The most significant cost-savings you can get from travel hacking is on flights. And luckily, living in our area means there are great ways to make that happen. Because we live near Destin – there are plenty of Cheap-O Air flights from VPS to airports near (but not in) major worldwide travel hubs. “Allegiant Air is amazing,” Tallman said. When he took his family to Egypt earlier this year, he took an Allegiant flight from VPS to Newark, New Jersey, costing about $70 per person. The family of four got the train into JFK and flew out to Istanbul, Turkey (more on that later) before flying from Istanbul to Cairo. The flights from JFK to Cairo cost about $300 per person. The family of four spent about $1,500 total in airfare to travel from VPS to Cairo. Right now (on a flight on July 8), you would pay $1,952 per person to go to Cairo – meaning the Tallman’s saved about $6,500 on one trip’s airfare. 

a family on camelback in the foreground of the pyramids at Giza.
The Tallman family enjoys a camel ride a stone's throw from one of the famous pyramids of Giza.

4. One-way car rentals from VPS to MCO or ATL

One-way car rentals are another way to cut the costs of flying out of larger airports within several hours of drive, Like Atlanta (ATL) or Orlando (MCO). Driving one way to these destinations often costs less than paying for parking at VPS’s parking lot. “Because you are renting [a car] for one day if you are going somewhere for a week or something like that,” Tallman notes. 

Right now (June 22) – you can rent a car for a single day at VPS airport and drop it off at MCO (Orlando, FL) for $126. Returning from Orlando is even cheaper – the rental will cost you about $50If you go on vacation for two weeks – the cost to park your car at VPS airport ($8.50/day plus tax, unless you are a 100% disabled veteran) costs you more than the rental option – and you’ll likely save money on flight costs, too. Orlando parking (between $5 and $11) and Atlanta (between $3.90 and $11) would cost about the same for you to rent a car. 

5. Leverage Layovers

Most people think of layovers as divine retribution for that hand gesture you made in traffic that one time you got stuck on John Sims Parkway because of the new left turn lane. But Tallman says you should see them as an opportunity to have a vacation within a vacation. He scopes out flights with intentionally long layovers because they cost less and allow the family to see a different country. “A lot of people don’t like having to spend the night places because of stopovers, but stopovers, I think, are a hidden gem because it’s really about finding something to do in these places and making the best out of any situation. Someone told me back in the mortgage crisis of 2008. ‘Take advantage of the high times in business and the low times.’ I asked, ‘well, what do you mean by that?’ They said, ‘Well, when times are slow, take advantage of it, spend more time with your family, relax, rest more, or go on vacation; when times are busy, take advantage of it.’ That stuck with me. But it’s the same type of situation.”

Some airlines, like Latin America’s Copa, have gotten with the layover program and even incentivized their passengers to take layovers in other countries and make a short stay out of them. They will charge you the same price, but you can spend three or four days in a location before continuing to your final destination.

two children smile for the camera in latin America.
The Tallman children smile on steps next to a street in Columbia.

6. Whenever you can - book with European-based airlines

Whenever possible – use European-based airlines for one reason: they have way more generous refund policies than American-based carriers. A couple of years ago, Tallman visited the UK and was returning with Norse Airlines when a hurricane formed and looked like it was headed back to Orlando. Well, the airline did not consider the flight cancellation a weather delay because there was no weather to delay the flight. It offered to fly Tallman back to Miami after a three-day stay in a hotel to wait out the ‘storm,’ paid for his rental car to get him to Orlando and wired him $1,500 for his troubles. “I got paid to stay in London for three days,” he said with a smile, “It was literally the best deal ever.”

Additionally, once you’ve found a way onto the European continent, the cost of flying from one place to another decreases significantly. “It’s insanely cheap,” Tallman added.

Best and worst times to travel hack from Niceville

The absolute worst times to travel hack might seem pretty obvious – the weeks of Christmas and Thanksgiving are the most expensive time. But many of the best times to travel are bunched up right next to the worst times. No one wants to take two flights to two vacations twice a month! Look to the weeks between Thanksgiving and Christmas for the best deals. Also, take a gander at the week of Valentine’s Day. Too many people buy chocolate that week instead of plane tickets to go somewhere. The second week of November is the third-best time to travel.

a family in front of the Eiffel Tower
The Tallman family enjoys Paris together.

Factors affecting travel prices in the future

Tallman, a financial planner by trade, sees a couple of factors that could change the prices of flights in the near term – some factors will exert upward pressure and others downward. Overall, he believes travel will become more affordable in the long term.

The COVID glut

A near-term upward pressure on flights and travel, in general, is the pent-up demand getting released for travel to other countries now that the COVID pandemic has ended worldwide.

During COVID, travel was extremely cheap – and significantly different than it is right now, Tallman told me. “During COVID was one of the coolest travel experiences ever,” Tallman said. “we went to Chicago and saw The Bean, and it was literally just me and my wife there.”

But now that COVID restrictions are gone, plenty of people are taking to the skies with renewed enthusiasm to escape their homes for a while. That, of course, means more demand and higher prices – at least in the short term.

Jet Efficiency

The overarching cost of flights, especially long-haul flights, will decrease significantly as more airliners buy the newest fuel-efficient planes like the Boeing Dreamliner. “They are a game changer because their fuel costs are a lot less,” Tallman said.

Freight

Finally, another downward trend for prices – airlines are taking on more freight as they go from place to place – which allows them to lower their passenger costs to compete with other airlines. You’ll see some flights for as low as $19 per passenger due to cargo payment below the passenger deck. On another trip, the Tallmans could fly from Atlanta to Shanghai, China, for about $250 per ticket.

Tools of the trade: travel hack like Jonathan.

So, here are the tools you need to travel hack like Jonathan. 

 Google Flights. Use the ‘anywhere’ option to dive down the rabbit hole and find your next destination. 

• Go light, especially if you are using Allegiant. Ancillary costs make up 50% of the travel company’s revenue – which means they expect you to double the price of your plane ticket in fees (They say so in their annual financial disclosures). If you want to save, don’t bring items that are not essential on your trip. 

• Once you have a destination, keep your finger off the hotel booking trigger until about a week before. Use Skyscanner, Expedia, or Priceline to get good deals on hotel rooms. 

Get in touch with Jonathan and ask him more questions about travel hacking.

Got more questions about travel hacking (or want to talk to Jonathan about his day job, financial planning, insurance, and investments?), give him a shout on his email at jtallman@thetallmangroup.com or head to the Tallman Group website

2 Responses

  1. Thanks so much for these tips! There is a lot more to be said about getting great deals with airlines and I appreciate the recommendation about waiting to make a hotel reservation 1 week prior to arriving at the hotel door step. Thanks for this helpful interview/article. I love to travel and appreciate tips on how to travel more cost effectively.

  2. These are awesome ideas! I like the security of knowing where I’m going and when, but the times things haven’t gone as planned (think frequent French Rail strikes, Greek general strikes, or getting bumped off KLM in favor of horses!) have been great unexpected adventures. Thanks to those flying horses, I got a fantastic two-night stay in Amsterdam, meal vouchers, transportation to the hotel and back to the airport, and such a generous cash compensation I was able to use it to pay half my rent a week later!

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