The other day I was speaking with my friend C.F., an patent attorney with an undergraduate degree in physics — a smart guy to say the least. C.F. has always liked travel, but after his first trip to Europe his enthusiasm morphed into a monster travel bug.
I always enjoy my conversations with C.F. because he has great natural curiosity and wisdom. On this day, the conversation turned to travel as his mind started to explore a new adventure to Europe. After pelting me with questions and proposing various strategies for ensuring a great trip, he commented, “To get a brilliant travel experience you need to be very savvy.”
I paused with my thoughts for a moment then replied, “It’s actually rather simple if you ask the right questions.”
With that in mind, I offer my 10 best questions for successful travel planning.
1. Is there a better time or place to go?
The hallmark of my travel philosophy is “Contrarian Travel” — traveling when others are not. And who’s better to know the most opportune times to travel than travel providers? An airline can tell you which flights have light loads — and therefore lower fares and better opportunities for upgrades. Likewise, hotels and resorts know best when their occupancy is likely to dip. Sometimes the difference is only a week — but what a difference a week can make if you save money and get prized upgrades.
2. When is the best time to call?
When you need to call a travel provider, schedule the call for maximum efficiency and service. Avoid weekends, when agents are generally swamped; instead, make midweek call and make it midday. If you’re trying to reach a manger of a hotel, speak first to his assistant, who can tell you when the manager is likely to be free. Better yet, make an appointment to call him.
Also pay attention to breaking news that may affect your travel provider’s availability. Last week, during a nasty nor’easter, I called my airline to check on an itinerary that was still seven days away. While I was on hold, the news flashed a weather update announcing that five major East Coast airports had closed. I realized that with all the canceled flights, I was probably looking at a long hold time. Not to mention that I would be taking up an agent’s time on routine matters when she really needed to serve stranded travelers. So I hung up. Two days later, I got right through.
3. Does this flight, stay or rental count toward my elite status?
My friend Tim wrote me last December telling me how thrilled he was to have finally achieved “Medallion” status on Delta Air Lines by taking one flight to South Africa. Unfortunately, Tim didn’t know that the miles he earned on South African Airways would indeed give him Delta points, but they would not count towards Medallion status. I recently experienced a similar situation renting a car from Hertz. Because I rented the car outside the United States, the rental did not count toward my requalification as a “Five Star” member. Many loyalty programs have this kind of two-track system — especially when the transaction involves a third-party “partner.” Your best bet is to always ask — specifically — whether the rate or fare you are booking counts toward the elite status you are hoping for.
4. What rooms offer the best location, view or size?
Those who travel widely and often understand the value of a well-situated hotel room. Whether you want a room on a club floor, a stellar view or just some peace and quiet, an advance call to the front desk will tell you where you want to be.
5. Is there a better fare or rate?
Most travel providers automatically offer the lowest price available, but sometimes an agent misses a better deal. A little probing can provide good results. For example, I was planning a trip from Orange County, California, to New York and was offered a coach rate exceeding $1,000; on further review, I found that a first class ticket was available for $795. And I have often picked up hotel rooms with better views — or free breakfast or spa services being offered on a midweek special — that the booking agent overlooked. Simply asking can pay handsome rewards.
6. Should I take a different route?
Later this month I have a trip to Mendoza, Argentina. My regular route would take me first to Buenos Aires then on a short flight to Mendoza. However, when I tried to book this route using my first class upgrades, all the available upgrades were gone. After trying unsuccessfully for a few days to get an upgrade, I inquired about flying through Santiago, Chile. Not only did I get the upgrades, I saved more than $400.
7. Where do you recommend I visit?
Key any city into Google and what do you get? An endless list of ads and tour operators pitching their goods. A better idea is to ask your local hotel agent where he would go if he were exploring the city on a budget. Specifying “budget” has a triple benefit: You will price out of the tourist traps; you will likely get an authentic local experience; and you will save money.
8. Can you leave the seat next to me open?
Airplane cabins are tight quarters; if the seat next to you is open, you gain a little elbowroom. On a return flight from Panama recently, I mentioned to the gate agent that I would be grateful if he could keep the seat next to me open. Just before the plane left the gate, the agent came aboard to seat a non-revenue passenger. The passenger pointed to my empty seat, but the gate agent just kept going, escorting her to another open seat a few rows back. Asking doesn’t always work, but when it does, it sure is nice to spread out.
9. If I pay a small premium, can I get an upgrade?
This is a good question for hotels. It works with airlines, too, but with hotels you can find yourself scoring a suite for pennies on the dollar just by offering to pay a nominal upgrade fee.
10. Can I get a complimentary upgrade?
The Holy Grail of penny-pinching luxury travel is getting a free upgrade. It happens — usually just by asking. I was rerouted a few months back onto a flight on American Airlines, an airline I had flown only once before. I asked the agent for a first class upgrade, and lo and behold, she printed me a boarding pass for 6B.
This is not a comprehensive list of questions, but it should get you on your way. The key is to just think ahead and dare to ask questions. Nothing ventured, nothing gained.
Joel Widzer is an expert on loyalty and frequent flier programs. He is the author of "The Penny Pincher's Passport to Luxury Travel," a guidebook on traveling in high style at budget-friendly prices. or . Want to sound off about one of his columns? Try visiting .