What travel insurance coverage is worth buying and what you can skip!

I know, I know – last week we talked about booking holiday travel, and now I’m hitting you with an entire newsletter about travel insurance. Not exactly the most exciting topic, right?

But here’s the thing: if you’re booking Thanksgiving or Christmas travel right now (and you should be), this is exactly the right time to understand what travel insurance actually does and whether you need it. With the government shutdown creating uncertainty and holiday travel prices climbing daily, the decisions you make this week about protecting your trips could save you thousands of dollars – or a massive headache – down the road.

So bear with me for a few minutes. I promise to make this as painless as possible and give you the straight truth about what’s worth buying and what you can skip. Think of this as your travel insurance review course – everything you need to know, nothing you don’t.

Let’s dive in.

When do you need travel insurance? (The honest answer)

Travel insurance isn’t always necessary, but it’s absolutely worth the cost in certain situations – and in some countries, it’s actually required. Here’s when you should seriously consider it, when it’s mandatory, and when you can probably skip it.

Travel Insurance May Be Required by Local Laws

Some countries now mandate travel insurance for entry. According to Elliott.org, these destinations require proof of coverage at the border:

• Cuba – Must have medical coverage
• Ecuador – Requires health insurance for all visitors
• Thailand – Required for certain visa types
• Turkey – Mandatory for some visa categories
• United Arab Emirates – Required for tourist visas
• Schengen Area countries (26 European nations) – Requires minimum €30,000 medical coverage for visa applicants

Check your destination’s entry requirements before booking. You may need to purchase insurance and provide proof at customs and immigration before leaving the airport.

Here’s when 50+ travelers should have travel insurance

1. Your trip is expensive and/or nonrefundable. Insurance protects that investment if you’ve prepaid $5,000+ for flights, hotels, tours, or cruises that won’t be refunded if you cancel. 

Real-world example: You book an $8,000 European river cruise six months in advance, then break your ankle two weeks before departure. Navigating the ship’s stairs and gangplanks would be impossible, and you’d miss all the shore excursions. Trip cancellation insurance reimburses your prepaid costs.

Review how trip cancellation coverage works.

2. You’re traveling internationally. Your US health insurance likely doesn’t cover medical care abroad, and Medicare definitely doesn’t. International travel insurance provides medical coverage and emergency evacuation. 

Real-world example: You have a heart attack while touring Italy. Emergency medical treatment and evacuation back to the US costs $150,000+ without insurance – your policy covers it.Review how emergency medical and evacuation/repatriation coverage works.

3. You have pre-existing medical conditions. If you or a traveling companion has health issues that could flare up, you need coverage that includes pre-existing conditions (usually requires buying within 14-21 days of your first trip payment). 

Real-world example: Your spouse’s chronic condition worsens unexpectedly, forcing you to cancel your anniversary trip. Without pre-existing condition coverage, you lose everything.

Review how pre-existing medical coverage works.

4. You’re traveling during uncertain times. Government shutdowns, hurricane season, political instability, or family health concerns make trip interruption more likely. 

Real-world example: Your elderly parent falls ill the day before your departure. Trip cancellation insurance lets you cancel and recover your costs to stay home and help.

Review how cancel for any reason coverage works.

5. Your trip involves multiple connections or tight timelines. Complex itineraries with cruises, tours, or events that can’t be rescheduled benefit from trip delay and interruption coverage. 

Real-world example: Your flight to Lisbon is delayed, causing you to miss your cruise departure. Trip interruption insurance covers the cost of catching up to the ship at the next port.

Travel insurance is about protecting yourself from financial loss you can’t afford to absorb. Ask yourself: “If I had to cancel this trip tomorrow or faced a medical emergency abroad, could I handle the cost?” If the answer is no, buy the insurance.

Here’s when you could probably skip travel Insurance

• When your trip is inexpensive and/or close to home. A weekend road trip or short domestic flight with minimal prepaid costs doesn’t warrant insurance – you can absorb the loss if something goes wrong.
• Everything is refundable or flexible. If your flights, hotels, and activities can be canceled or changed without penalties, you don’t need cancellation coverage.
• You have excellent credit card travel benefits. Some premium travel credit cards include trip cancellation, interruption, and delay coverage. Check your benefits guide – you might already be covered up to a limit (check the limits!).

What 50+ Travelers Actually Need in a Policy

When choosing travel insurance, the goal isn’t finding the most expensive policy – it’s finding the right coverage at the lowest cost. Paying more doesn’t always mean getting better protection. Here’s what to prioritize.

1. Weather Coverage

This is one of the most common reasons trips get canceled or delayed, yet not all policies cover weather-related issues equally. Make sure your policy explicitly covers:

• Trip cancellation due to severe weather at your destination
• Delays caused by weather that prevent you from reaching your departure point
• Hurricanes, snowstorms, and other natural disasters

Weather coverage protects you when Mother Nature disrupts your plans – which happens more often than you’d think in all seasons.

2. Primary Medical Coverage

Primary (not secondary) medical coverage is critical and makes filing claims 100 times easier. Here’s why: Primary coverage pays first, without requiring you to file through your health insurance (which can take lots of time). 

Primary medical coverage means faster reimbursement, less paperwork, and no coordination between multiple insurance companies. For international travel where your US health insurance won’t apply, primary coverage is essential.

3. Cancel for Any Reason (CFAR) Coverage

CFAR has become very popular because it gives you maximum flexibility – you can cancel for literally any reason and get 50-75% of your trip cost back. This includes reasons not covered by standard policies like:

• Work stress or schedule changes
• Anxiety about traveling
• Simply changing your mind
• Concerns about your destination

Expect to pay 5-10% of your total trip cost to insure it with CFAR. For a $5,000 trip, that’s $250-$500. 

CFAR is worth considering if you’re booking far in advance, traveling during uncertain times, or want complete peace of mind. 

When Do You Need Pre-Existing Medical Condition Coverage?

Many travelers 50+ have pre-existing conditions – high blood pressure, diabetes, heart conditions, or other chronic issues. Standard policies always exclude these, but you can get coverage if you:

• Purchase insurance within 14-21 days of your first trip payment
• Meet the policy’s requirements (usually being medically able to travel when you buy)

Without pre-existing condition coverage, any claim related to your existing health issues will be denied. This is non-negotiable for most travelers in this age group.

How Much Medical Coverage Do You Need?

Medical care abroad can be expensive, and evacuation costs can exceed $100,000. Adequate coverage limits ensure you’re protected in worst-case scenarios.

You’ll want higher medical coverage limits for international travel. Look for:

• Minimum $100,000 in medical coverage
• Unlimited or high-limit emergency medical evacuation (at least $100,000)

Note: Emergency medical evacuation should be separate from regular medical coverage with a high limit. This coverage gets you to proper medical care when local facilities aren’t adequate—essential when traveling to remote areas (like cruise ships) or developing countries.

New Ways Travel Insurance is Helping Travelers

Modern travel insurance providers do more than reimburse canceled trips—they provide real-time assistance that can prevent disasters before they happen.

• 24/7 Emergency Assistance – Comprehensive policies include round-the-clock concierge services that can locate English-speaking doctors, pharmacies, emergency evacuations, help with lost passports, and arrange emergency cash transfers. This is a lifeline when you’re dealing with a crisis abroad.
• Flight Rebooking Help – When flights are canceled, your insurance assistance team may be able to find and book alternative flights faster than you can while standing in a chaotic airport line. Some policies cover the cost difference if replacement flights are more expensive.
• Prescription Replacement – Lost your medications? Your travel insurance assistance team can locate pharmacies, coordinate with your home doctor for refills, and arrange emergency prescription replacements – invaluable for travelers who take daily medications.
• Real-Time Travel Alerts – Some travel insurance companies now offer their own apps, which can send proactive alerts about severe weather, political unrest, health advisories, and transportation disruptions at your destination, giving you time to adjust plans before problems escalate.

What to Look for in the Fine Print

Before purchasing a plan, check:

• Covered reasons list: What specific situations trigger coverage?
• Coverage limits: Are they adequate for your trip cost and destination?
• Exclusions: What’s NOT covered? (Pre-existing conditions, certain activities like skiing, etc.)
• Deductibles: Do you pay anything out of pocket before coverage kicks in?
• Claims process: How do you file? What documentation is required?

The best travel insurance balances comprehensive coverage with reasonable cost. Focus on weather coverage, primary medical coverage, and consider CFAR for maximum flexibility. Add pre-existing condition coverage and adequate limits for your specific trip. Don’t pay for bells and whistles you don’t need – but don’t skimp on the essentials that could cost you thousands.