Why You Shouldn’t Skip Travel Insurance (Real Stories + Expert Advice)

Planning a trip is one of my favorite parts of what I do.

Whether it’s a romantic honeymoon, a long-awaited family vacation, a cruise, or a destination wedding surrounded by everyone you love, there is so much excitement that goes into choosing the destination, the resort, the flights, and all the little details that make the trip special.

But after nearly a decade in this industry, I’ve learned something very important:

You can plan everything perfectly… and still have things go wrong.

Winter storms. Flight delays. Medical emergencies. Missed connections. Illness right before departure.

These are not rare situations. They happen every single season.

And this is exactly where travel insurance becomes less of an “extra” and more of a true safety net.

Travel insurance is what protects your investment when life happens. It’s what stands between you and losing thousands of dollars if you can’t travel, if your trip is delayed, or if you need help while you’re away from home.

I’ve seen firsthand how much of a difference it makes.

I once worked with clients who decided to skip insurance to save a little money. A few days before their trip, one of them became ill and their doctor advised them not to travel. Because they didn’t have coverage, they lost almost the entire cost of their vacation. No refund. No credit. Just a very expensive and heartbreaking lesson.

On the other hand, I had a couple traveling in the winter who did purchase insurance. A snowstorm caused them to miss their connection on the way to their cruise. They needed an overnight hotel stay, new flights, and meals while they waited. Their insurance covered those unexpected expenses. Instead of worrying about the cost, they were able to focus on getting to their vacation and still enjoy their trip.

Those experiences are why I am such a strong believer in travel insurance.

It’s not about expecting something to go wrong. It’s about being prepared if it does.

Because the truth is, your vacation is an investment (of money, time, and memories). And protecting that investment is one of the smartest travel decisions you can make.

So let’s talk about why you shouldn’t skip it, what it actually covers, and how to choose the right policy for your trip.

“But Travel Insurance Is Too Expensive…”

This is the number one objection I hear, and I get it. When you’re already spending thousands on a vacation, honeymoon, or destination wedding, adding another $100-300 for insurance feels like a lot.

But here’s the reality check:

That $200 insurance policy? It can protect a $5,000+ trip investment.

Without it, one unexpected event (illness, weather delay, family emergency, lost luggage) could cost you everything.

Let me break down the math:

• Average trip cost for a couple: $4,000-$8,000
• Average travel insurance cost: $150-$400 (about 5-8% of trip cost)
• Cost of losing your entire trip: 100% of what you paid

When you look at it that way, insurance isn’t expensive. Losing your entire trip because you didn’t have it? That’s expensive.

“My Credit Card Covers Travel…”

I hear this one a lot too. And yes, some premium credit cards do offer travel protections.

But here’s what most people don’t realize:

Credit card coverage is usually limited and comes with restrictions:

• Often only covers trip delays, not cancellations
• May require you to book the entire trip on that card
• Doesn’t typically cover pre-existing medical conditions
• Won’t cover you if you get sick and can’t travel
• Has much lower coverage limits than a dedicated travel insurance policy

Your credit card might cover:

• Lost luggage (with low limits, like $500-$1,000)
• Travel delays (partial reimbursement)
• Rental car damage (primary or secondary coverage)

Your credit card won’t typically cover:

• Trip cancellation for illness
• Medical emergencies abroad
• Emergency medical evacuation
• Trip interruption for family emergencies
• Comprehensive baggage loss/delay
• “Cancel for any reason” protection

If your trip costs $6,000 and your credit card only covers $1,000 in baggage loss, that’s a problem. Read the fine print carefully, and consider whether it’s truly enough coverage.

“My Health Insurance Covers Me Everywhere…”

This is a dangerous assumption, especially if you’re traveling internationally.

Here’s the truth:

Medicare does NOT cover medical expenses outside the United States. If you or your travel companions are on Medicare and you need medical care abroad, you’re paying out of pocket. Medical emergencies overseas can cost tens of thousands of dollars.

Employer health insurance often has limited or no international coverage. Some plans cover emergency care abroad, but many don’t. And even if they do, you might need to pay upfront and get reimbursed later, which can be financially devastating.

What happens if you need emergency medical evacuation? Air ambulance services can cost $50,000-$100,000+. Most health insurance plans don’t cover this at all.

Travel insurance fills these gaps with:

• Emergency medical coverage abroad
• Emergency medical evacuation and repatriation
• 24/7 assistance services to help you find care
• Coverage that works anywhere in the world

Don’t gamble with your health coverage when you’re thousands of miles from home.

What Travel Insurance Actually Covers (And Why It Matters)

Let me walk you through what a good travel insurance policy actually includes:

1. Trip Cancellation Coverage

What it covers: If you need to cancel your trip before you leave due to a covered reason (illness, injury, death of a family member, natural disaster, etc.), you get reimbursed for your non-refundable expenses.

Why it matters: Honeymoons, destination weddings, and all-inclusive vacations often require deposits months in advance. If something happens and you can’t go, you don’t want to lose thousands of dollars.

Real example: Remember that couple who got sick before departure and lost their entire trip cost? Trip cancellation coverage would have saved them.

2. Trip Interruption Coverage

What it covers: If you have to cut your trip short and come home early due to a covered reason, insurance reimburses you for the unused portion of your trip plus the cost of getting home.

Why it matters: Family emergencies happen. If you need to fly home suddenly, you’re looking at last-minute flights (expensive!) plus losing the vacation days you already paid for.

3. Travel Delay Coverage

What it covers: If your trip is delayed for a covered reason (weather, mechanical issues, etc.), insurance reimburses you for additional expenses like hotels, meals, and transportation.

Why it matters: Remember the couple whose winter storm delayed their cruise departure? This coverage paid for their hotel, meals, and rebooking. Without it, they would have been out hundreds of dollars, plus stressed about the cost.

Important note: If your flight is delayed or canceled due to weather, the airline is NOT obligated to help you. Weather is considered an “act of God,” and you’re on your own for hotels and meals.

4. Emergency Medical and Dental Coverage

What it covers: Medical emergencies while traveling, including doctor visits, hospital stays, prescriptions, and emergency dental care.

Why it matters: If you’re traveling internationally and need medical care, costs can be astronomical. And as I mentioned earlier, Medicare doesn’t cover you outside the U.S.

5. Emergency Medical Evacuation

What it covers: If you need to be transported to a medical facility or evacuated back home due to a serious medical emergency.

Why it matters: Air ambulance and medical evacuation can cost $50,000-$100,000+. This is coverage you hope you never need, but if you do, it’s literally life-saving.

6. Baggage Loss/Delay Protection

What it covers: Reimbursement if your luggage is lost, stolen, damaged, or delayed.

Why it matters: Imagine your wedding dress or suit is lost on the way to your destination wedding. Or your luggage is delayed and you’re stuck without clothes and toiletries for days. Insurance covers the cost of replacing essential items so you’re not stuck.

7. 24/7 Emergency Assistance

What it covers: Access to a team that can help with medical emergencies, lost passports, emergency cash transfers, translation services, and more.

Why it matters: When you’re in a foreign country dealing with an emergency, having someone who can help you navigate the situation in real-time is invaluable.

Cancel for Any Reason (CFAR) Coverage

Some policies offer an upgrade called “Cancel for Any Reason” coverage.

Standard travel insurance only covers cancellations for specific reasons listed in the policy (illness, injury, natural disasters, etc.).

CFAR coverage lets you cancel for literally any reason and get back 50-75% of your trip cost.

When it makes sense:

• You’re booking far in advance and circumstances might change
• You’re nervous about work obligations or other commitments
• You want maximum flexibility

The catch:

• It costs more (usually adds 40-50% to your premium)
• You typically need to purchase it within 14-21 days of making your initial trip deposit
• You usually only get back 50-75% of costs, not 100%

It’s not for everyone, but for high-stakes trips like destination weddings or once-in-a-lifetime honeymoons, it can be worth it.

When Should You Buy Travel Insurance?
The short answer: As soon as you make your first trip payment.

Here’s why:

✔️ Many policies have time-sensitive benefits. For example, pre-existing medical condition waivers and CFAR coverage often require you to purchase within 14-21 days of your initial deposit.

✔️ The sooner you buy, the sooner you’re covered. If something happens between booking and departure, you’re protected.

✔️ Waiting means you might miss out on coverage for events that occur before you purchase the policy.

Don’t wait until a few weeks before your trip. Buy it when you book.

How to Choose the Right Travel Insurance

With so many providers out there, how do you choose?

Here are my top recommendations based on years of experience:

Allianz Global

• Comprehensive coverage for single trips and multi-trip plans
• Rental car coverage available
• Policies start as low as $23
• Great for budget-conscious travelers who still want solid protection

Travel Insured

• High limits for medical expenses and trip interruption
• Ideal for longer trips or those with significant financial investments
• Robust coverage options

How to decide:

Work with your travel advisor (hi, that’s me!) to assess the risks specific to your trip and choose a plan that fits your budget and needs. I help my clients navigate the options and find the right coverage every single day.

Real Talk: Is Travel Insurance Worth It?

Here’s how I think about it:

Travel insurance isn’t about whether something will go wrong. It’s about whether you can afford for something to go wrong without it.

If losing $5,000-$10,000 wouldn’t be a financial burden for you, and you’re comfortable taking that risk, then maybe you skip it.

But for most people? That’s a lot of money to gamble with.

I’ve seen too many clients devastated by losing their entire trip investment because they didn’t have coverage. And I’ve seen just as many clients relieved and grateful when their insurance saved them thousands of dollars during an emergency.

The peace of mind alone is worth it. Knowing that if something happens, you’re covered? That’s priceless.

Don’t Leave Home Without It

Whether you’re planning a romantic honeymoon, a destination wedding, a family vacation, or a long-awaited cruise, travel insurance is one of the smartest investments you can make.

It’s not just about protecting your money. It’s about protecting your peace of mind so you can actually enjoy your trip, knowing you’re covered no matter what happens.

Ready to plan your next trip with the right protections in place?

Schedule a complimentary consultation with me, and I’ll help you choose the perfect travel insurance policy for your needs. Let’s make sure your dream vacation stays a dream, not a financial nightmare.

Safe travels! ✈️