"I travel literally every month," said Ward. "My favorite places are southern Africa, Argentina, and I absolutely love Paris, France."
Ward also loves to "land" a travel upgrade.
Anne Banas with SmarterTravel.com says there are plenty of secrets to moving up in style without paying big bucks.
"A lot of travelers think that upgrades are for VIPs or celebrities, but the truth is average travelers can get upgrades for airfare, hotel and even car rentals if they know where to look," said Banas.
With airfare, look at the type of coach ticket you're buying. Make sure it qualifies for upgrades, minus fees. Know that the best day for upgrades is Saturday. That's when fewer "elite" travelers hit the skies. Or try your luck during the off-season.
"A lot of times, airlines will announce new routes," said Banas. "A lot of people don't know about it yet, and that can be an optimum time to get up to the front of the cabin."
Or get to the front of the cabin by shopping around for deals and promotions.
"Look online and sign up for each airline's individual newsletter," said Banas.
You can also try message boards. And although experts say it's rare, asking nicely may do the trick on international flights. It worked for Ward on a recent trip to South Africa.
"And the agent said, 'Well, Mr. Ward, there are no upgrades for sale today, but we're pleased to offer you a complimentary upgrade,'" said Ward.
At hotels, popping the upgrade question can go a long way.
Kim Orlando, with TravelingMom.com, says asking can be a great strategy when you're celebrating a special occasion, like a wedding or birthday. So let the front desk know.
"When you're on a family vacation, it can be a little more difficult," said Orlando. "So either leave the kids in the car and then ask for the upgrade, or just, you know, warn them, 'Shhh.'"
Or try a late check-in. That's when hotels know which rooms are still available.
Another tip? Try tipping: $10 or $20 can go a long way.
On the road, car rentals are determined by supply and demand.
"So if you book, say, an economy-class car, there's actually a great chance that you will be upgraded because a lot of those lower-mileage cars are in high demand," said Banas.
Finally, from the air to the ground, our experts agree: Loyalty programs will always pay off.
"Whether you travel a lot or a little," said Orlando. "That's because most of them are free to enter anyway, free to become a member of, and they don't expire."
Jeff Ward is a member of several loyalty programs, but will never forget his free airline upgrade.
"I felt pretty darn special," said Ward.
Orlando says loyalty programs are the best way to "sail" to an upgrade on cruises.