#10 Most EMBARRASSING Travel Questions

"You're going to think this question is so stupid," a recent travel companion of mine told me over the phone, before we went on a trip to the Caribbean. "You're going to laugh." I promised her I would do neither, and wondered what she could possibly think was so humiliating that she was afraid to ask me. "After I get off my connecting flight," she began slowly, "do I have to pick up my luggage before I get on the plane to Aruba?" Think the answer is obvious? Not so fast!

Recently, American Airlines announced that it would no longer "through check" bags to a final destination if separate tickets on an airline not affiliated with American are presented at check-in. So if she had been flying two different airlines, she would have had to grab that bag. (Other airlines like Delta and Frontier also have this policy.) In this case, though, I assured her the airline would make sure her suitcase got to Aruba, no need for her to intervene. And I definitely didn't laugh!

It just goes to show you: "The rules change," says Sally Watkins, travel agent at Century Travel and Cruises in Austin, Texas. Because even seasoned travelers can use a brush-up, we asked travel experts to share questions people have been embarrassed to ask them, along with their no-nonsense answers. What you learn might surprise you.

When my miles expire, can I get them back?

Sometimes, yes—even if you feel foolish for asking or for letting them lapse to begin with. "People feel really guilty about letting them expire," says travel expert Brian Kelly, better known as The Points Guy . "Most airlines will charge you to get them back, if at all. Or some airlines, like US Airways, are more lenient than others."

Other airlines, Kelly says, will give your miles back to you for free if you do something for them, like sign up for one of their credit cards or do another "certain qualifying activity."

"In general, it never hurts to ask, so don't feel guilty," Kelly says. "Always ask the airline or credit card company. But it's not always worth it to pay the price. Always make sure you'll get more value than what you pay for them."

Can I flirt or sweet-talk my way into an upgrade on a flight?

First-class upgrades are more difficult to score than, for example, being moved to a seat with more legroom in coach, Kelly says. That said, never underestimate the power of that great equalizer: chocolate. (Yes, really!)

"Gate agents at the airport get berated all day long, and being nice and bribing them, whether it's a box of chocolates or just being super-sweet, you'd be surprised how much that still [counts for]. They have a lot of say. Gate agents are in control of who gets what seats. There are processes, and if coach is oversold and there are some business-class seats, they can still absolutely move whomever they'd like up front."

The takeaway? It doesn't hurt to try. "You never know," Kelly says. "Go into any situation with an open mind. A simple candy bar to a gate agent could potentially get you first-class upgrade, and if not first, one of the best seats in coach. A small gesture can still go a long way even in 2014."

Do I check my luggage on the train?

Unfortunately, no—not in these post-Victorian times, says Watkins, who says she is sheepishly asked this question a lot.

"The days of porters in the rail station are gone, unless you pay for a private service," she says. "Otherwise, you are responsible for getting your luggage to your correct train car, and getting it up whatever little steps there are, and putting it on the luggage rack."

She offers this step-by-step advice to people who are lugging their things across Europe, especially:

"At the end of each car, there will be shelves to put your luggage," she says. "Some trains have overhead racks for luggage; some trains have seats that are back to back, leaving a triangle in between, where they can slip a suitcase. It all depends on how that particular train is configured. I recommend that if they have smaller bags, in particular, when the train stops at a station, they might want to go back and lurk around the luggage rack. I used to never worry about that, but there have been reports that, when the train makes a quick stop, some guys jump on and grab a bag and take off, and then the train leaves. I've never had it happen to anyone, but I have read that."

How much should I tip?

Whether you're signing the bill in a restaurant, taking a sightseeing tour, or trying to score discounted tickets to a hot Broadway show via your hotel concierge, his one's a toughie, and the answers you'll hear often depend on whom you're traveling with.