Your Travel Questions Answered
Ask Jesse, The Thrifty Senior Traveler
Welcome to Our Travel Q&A
Welcome to the place where Jesse attempts to answer questions posed by some very savvy travelers.
And believe me, they ask good questions.
After years of traveling, I've learned that there are always things I don't know — and usually, someone else has already thought of the question I should have asked.
So this page is where we tackle the questions that come up before, during and sometimes after a trip.
Some will be about saving money. Some will be about destinations. Others may involve travel insurance, solo travel, senior discounts, hotels, airlines or those little travel headaches that nobody tells you about until you're already dealing with them.
I'll give you my best answer based on my own experiences, research and, when necessary, a little digging.
And if I don't know the answer? I'll say so.
Because being a savvy traveler doesn't mean knowing everything. It means knowing what questions to ask — and where to look for the answers.
So, let's get started. What travel question is on your mind?
Write your text here...
Question: “How Should I Pack My Prescription Medications?”
Jesse's Answer: The U.S. Centers for Disease Control and Prevention (CDC) recommends keeping prescription medications in their original, clearly labeled containers.
That's especially important when traveling internationally. The U.S. State Department also warns that medications commonly prescribed or sold over the counter in the United States — including some ADHD medications, sleep aids and pain relievers — may be illegal or restricted in other countries. Some destinations may require special documentation or permits.
Before traveling internationally, check with the embassy or consulate of the country you're visiting to find out whether your medications are permitted and whether any special requirements apply.
My recommendation: Always pack prescription medications in your carry-on luggage — never in checked baggage. If your checked bag decides to take a separate vacation, your medications won't be going with it.
I also recommend carrying a printed list of your medications using their generic names, since brand names can vary from country to country.
Don't Forget a Doctor's Letter for injectable medications, medical devices or controlled substances explaining why you need the medication or device.
Thrifty Senior Traveler Tip: I also like to carry a few extra days' supply whenever possible. Flights get canceled, connections get missed and, occasionally, vacations last longer than planned.
Question: “How Active Is a Particular Trip?”
Jesse's Answer: This is a question I strongly recommend asking before booking any organized tour.
Phrases such as “moderate activity” or “light walking” can be notoriously vague. What one tour company considers a leisurely day may feel like an endurance test to someone else.
Senior travelers, in particular, don't want to discover after arriving that their vacation involves climbing steep staircases, navigating uneven cobblestone streets, standing for hours or walking far more than they expected.
My recommendation: Don't simply ask whether a trip is “active.” Ask specific questions.
For example:
How many hours of walking or standing are involved on a typical day?
Are early-morning departures required?
How much free time or downtime is built into the itinerary?
Are there particularly demanding days that involve significantly more walking than others?
Ask About Terrain and Accessibility. The amount of walking is only part of the story.
Ask about the actual terrain and physical challenges you may encounter. Will you need to climb high steps to get on and off tour buses? Are there cobblestone streets, steep hills or uneven walking surfaces? Will you be visiting historic sites that have lots of stairs and no elevators?
And don't forget to ask about your luggage. Find out whether baggage handling is provided between buses, trains and hotel rooms — or whether you'll be expected to manage your own bags.
Thrifty Senior Traveler Tip: The more specific your questions, the fewer surprises you'll encounter. A great trip should stretch your horizons — not your knees.
Question: “Should I Buy Travel Insurance?”
Jesse's Answer: My favorite answer to this question is probably the least satisfying one: It depends.
I've purchased travel insurance for some trips and skipped it for others. The decision depends on where I'm going, how much money I have at risk and what would happen financially if I had to cancel.
But for older travelers, there is one issue I believe deserves special attention: What Happens If You Have a Medical Emergency?
If you're traveling internationally, don't assume your regular health insurance — or Medicare — will take care of you if you become seriously ill or injured. Medical treatment abroad can be expensive. And if you need emergency medical evacuation, the cost can be enormous.
That's why, when considering travel insurance, I look carefully at:
Emergency medical coverage
Emergency medical evacuation coverage
Trip cancellation and interruption coverage
Coverage for pre-existing medical conditions
The policy's exclusions and limitations
Don't Automatically Insure Everything: Here's another important point: You may not need to insure every dollar of every trip. If you're taking a relatively inexpensive domestic trip and could afford to lose the money, expensive travel insurance may not make sense.
But if you've put thousands of dollars into a nonrefundable overseas vacation, cruise or tour, the calculation can be very different.
My recommendation: Before buying a policy, ask yourself one simple question:
“If something goes wrong, how much money could I afford to lose?”
Then look at what protection you may already have through your health insurance, credit cards or the travel company before paying for additional coverage.
Thrifty Senior Traveler Tip: The cheapest policy isn't necessarily the best value. And the most expensive policy isn't necessarily the best one either. Read what the policy actually covers — especially the exclusions.
For a more detailed look at when travel insurance may, or may not, make sense, see my article: When Is Travel Insurance Worth It?
Written by Jesse Slome, The Thrifty Senior Traveler
Originally published August 18, 2026 | Last updated August 118 2026
Question: “How Much Money Should I Carry When Traveling Overseas?”
Jesse's Answer: My short answer? Probably less than you think. Basically it depends on the country visited.
Today, inmost countries, credit cards work. I only withdraw additional cash from an ATM as needed.
For my last four trips (which were tours so most expenses were covered):
Iceland (only credit cards).
Argentina/Antarctica (Only credit cards).
India (only credit cards).
South Africa, Zimbabwe, Zambia and Botswana (only credit cards).
Visa and Mastercard are accepted everywhere, even for small charges in supermarkets, McDonalds, even on buses for fares.
Carrying a large amount of cash can create an entirely new travel problem: What happens if it gets lost or stolen?
I generally travel with: two primary credit cards (including one that has no foreign exchange fees). An ATM/debit card for withdrawing cash if and when necessary. A small amount of U.S. dollars for emergencies (usually between $200 and $300 dollars). If I don't need it, I use it for tips for my Overseas Adventure Travel trip director.
I also notify the credit card companies and the bank (ATM card issuer) that I will be traveling abroad,
Thrifty Senior Traveler Tips
First: Check online before you leave to see how widely credit cards are accepted in the country you're visiting. Don't assume that what worked on your last trip will work everywhere.
Second: I make a photocopy of the front and back of each credit and ATM card. I put the copies inside a plastic sleeve and tuck it under the zippered lining of my suitcase. If two of us are traveling, I put my copy into her suitcase and visa versa. If my wallet disappears, I still have the information I need to contact the card companies.
Third: I never keep all my money, cards and backup cards in the same wallet. Even on my last trip to Iceland — a place that seemed about as safe as you could imagine — someone on my tour was pickpocketed and lost his wallet.