Hello, dear readers! In this issue:

• Derisking your travel

• Travel safety tips most don’t know 

• Are your meds legal in other countries?

Derisking Your Travel

This week’s feature is by guest contributor Jason, an expert on both travel and risk. More about him at the end of the article.

The thirst for travel has never been higher among older adults. At the same time, factors of aging and recent geopolitical trends make travel risks a real concern. We’ve enlisted the help of an expert to give you solid, actionable advice for enjoying travel while mitigating risk.

1. Don’t put all your money in one place

A gentle reminder that money disappears faster than you think, especially when it’s all in one pocket.

If your wallet or purse disappears – whether you lost it or someone helped it disappear – you don’t want your entire trip disappearing with it. 

The fix is simple, and it’s amazing how many of us don’t do it: split your resources. Carry your primary wallet/purse as usual, but keep a backup credit card and some emergency cash in a separate place. That might be your luggage, your hotel safe, or even a different bag. 

This isn’t about paranoia, it’s about basic resilience. I’ve seen travelers go from completely stuck to completely fine just because they had a backup card tucked away. Same problem, totally different outcome. One person is canceling their trip. The other is ordering an umbrella drink and figuring out the next steps. Don’t let a single point of failure end your trip. I admit I’ve failed to follow my own advice here multiple times, thinking “it won’t happen to me,” but travel enough and it eventually will.

2. Back up what actually matters (not your whole life)

Eat like a local, live like a local… just don’t assume your stomach can, too.

Travel comes with friction. Bags get delayed. Things get misplaced. Occasionally, stuff just vanishes into the void. So the question isn’t “how do I prevent that entirely?”  because you won’t. The question is: what can I absolutely not function without?

For most people, that list is pretty short:

• Prescription medication

• Glasses, contact lenses, or other assistive devices

• Essential documents such as your passport

Those are the things worth duplicating or planning around. 

What’s not on that list? Your third backup phone. Your second laptop. Your “just in case” tablet. I know people who travel like they’re opening a small electronics store, and it’s completely unnecessary. 

• If your laptop dies, you log into the cloud on a new one. 

• If your phone breaks, you replace it. 

• Be thoughtful about redundancy where it matters, but don’t confuse preparation with overpacking. 

PRO TIP: Always store a PDF copy in the cloud of your passport and other critical docs. That way, if it decides to wander off, you at least have something to show the police or other officials in the meantime.

3. Tell someone where you are (but don’t tell the Internet)

There’s a sweet spot between being completely off-grid and broadcasting your every move to the world. When you’re doing something even slightly higher risk – remote hiking, long solo drives, unfamiliar areas at night – tell someone you trust where you’re going and when you expect to be back. 

• Build in a little buffer so they don’t panic if things run late, but make sure someone has a general sense of your plan. 

• At the same time, resist the urge to post everything in real time, especially in places where security is less predictable. Not everyone following you has good intentions, and you don’t need to make it easy for anyone to track your movements. 

• Share the story later. Experience it fully in the moment. A little bit of discretion goes a long way.

4. Safety in numbers… but not a traveling circus

There’s truth to the idea that two heads are better than one. Traveling with a companion can make decision-making sharper, provide a second set of eyes, and generally reduce risk. But there’s a tipping point. 

As groups get larger, they become more visible, less flexible, and frankly more chaotic. You’re more likely to stand out, more likely to attract attention, and almost guaranteed to have at least one person making questionable decisions that affect everyone else. Large groups can also become easier targets. They’re predictable, they move more slowly, and they often signal “tourist” from a mile away. Smaller groups, or even pairs, tend to move more intentionally. They blend in better, adapt faster, and keep a tighter awareness of their surroundings. Travel like a team, not an entire traveling circus.

5. Go where the locals go (with eyes open)

Street markets = flavor, culture, and sometimes a reminder that your stomach has a different passport.

Crowds are magnets: for energy, for culture…and for pickpockets. Stay alert!

There’s a reason certain places show up in every guidebook. They’re famous, accessible, and designed to handle large volumes of visitors. They’re also predictable. And anything predictable (big chain hotels, major tourist restaurants, packed festivals, iconic attractions) can become a natural focal point not just for travelers, but for people looking to take advantage of them. 

This doesn’t mean you should avoid these places entirely. Some are absolutely worth seeing. But it does mean you should approach them with awareness. 

• Balance them out by spending time where locals actually live their lives. 

• Stay in neighborhoods that aren’t built exclusively for visitors. 

• Eat at places that aren’t optimized for tourists. 

• Explore beyond the obvious. You’ll often find that not only do you feel more grounded and less targeted, you also have a far richer experience. 

One small reality check: your immune system is not local. That incredible street food spot might be perfectly normal for residents and a full-blown adventure for you. Ease into it. Your stomach will thank you.

The Bottom Line

Derisking your travel isn’t about wrapping yourself in bubble wrap or eliminating every unknown. It’s about making a series of small, smart decisions that compound in your favor. So when something inevitably goes wrong, it’s not catastrophic, it’s just an inconvenience. You’re still moving. Still exploring. Still saying yes. And that’s the whole point.

About Jason

Jason is a 25-year veteran of the World Bank and in the small club of a few hundred people who have visited every country on Earth (yes, even the ones you’re questioning). His newsletter, 196Stories, tells the tales of his extraordinary visits to 196 countries. Consider subscribing if you enjoy that sort of content!

Bonus tips for our readers

Jason’s fantastic advice applies to everyone. We decided to research a few extra tips, especially relevant to older adults.

Master your medication before you go

• Carry a written list of all medications, dosages, and your doctor's contact information, as this can be essential if you need to replace a prescription or seek emergency care on the road. If any of your medications require syringes or other medical paraphernalia, carry a doctor's note clearly explaining what you have and why, especially when traveling by air.

• Bring more medication than you think you'll need. At a minimum, a few extra days' supply to account for unexpected travel delays or that tablet that accidentally falls down the drain.

• Always keep your medications in your carry-on bag, not in checked luggage, in case bags are lost or delayed. 

PRO TIP: Jason added that if you are traveling internationally, also check the legality of your medications. As he says, “that Xanax that calms your anxiety at home can land you in prison in Singapore.” Check your medications

Thwart the thieves

Older travelers are well-known targets for pickpockets and petty theft, particularly in tourist-heavy areas.

• One proven tactic is carrying a "dummy" wallet containing a small amount of cash and no critical cards. If a pickpocket succeeds, the damage will be minimal. 

• Keep your actual ID, credit cards, and larger sums in a travel pouch or hidden pocket designed for travelers.

• Anti-theft gear has advanced considerably. Slash-resistant travel bags with locking zippers, stainless steel wire-mesh portable safes, and pickpocket-proof clothing with deep interior magnetic pockets are all practical investments for frequent travelers.

Plan for health insurance

This is important and often overlooked: Medicare does not cover most medical costs outside the United States except for a handful of exceptions.

This gap is serious. A medical evacuation from a foreign country can cost tens of thousands of dollars out of pocket without insurance, so consider purchasing a dedicated travel medical insurance policy before any international trip. Look for plans that offer at least $100,000 in medical coverage, $500,000+ in emergency evacuation coverage, and coverage for the "acute onset of pre-existing conditions.”

Keep your blood flowing

Long-haul flights of four hours or more are associated with a 2-to-4-fold increase in blood clot risk, and flights of eight hours or longer carry the greatest danger.

Simple advice here: move. 

• On flights, get up and walk the aisle every hour or two. 

• On road trips, build in frequent stops to stretch your legs. 

• Wearing compression socks – ideally after confirming with your doctor that they are appropriate for your circulation – can meaningfully improve blood flow. 

• Avoid crossing your legs while seated, wear loose-fitting clothing, and stay well-hydrated, as dehydration is an additional DVT risk factor at altitude.

Quick-reference checklist