Travel insurance protects your vacation investment from cancellations, medical emergencies, and trip interruptions. Learn why buying coverage immediately after booking is critical and what your credit card won’t cover.
Let me tell you about the call no travel advisor wants to make.
Last year, I had to tell a client that the $48,000 they’d spent on their dream Italy trip—flights, hotels, private tours, everything—was gone. Not delayed. Not postponed. Gone.
Why? A family medical emergency two weeks before departure. No travel insurance.
I’ve been in this industry long enough to have these conversations more times than I want to count. And every single time, the response is the same: “I didn’t think it would happen to me.”
Here’s the thing: none of us do.
The Real Cost of Skipping Travel Insurance
Travel insurance isn’t about pessimism. It’s about protection. When you book a luxury vacation—whether that’s $5,000 or $50,000—you’re making a significant financial investment. You wouldn’t buy a house without homeowners insurance or drive without auto insurance, so why would you risk thousands on unprotected travel?
We’ve seen clients lose their entire investment because of:
- Sudden illness or injury (theirs or a family member’s)
- Unexpected work obligations that can’t be rescheduled
- Natural disasters affecting their destination
- Airline bankruptcies or tour operator closures
The truth? Life happens. And when it does, travel insurance is the difference between losing everything and getting your money back.
When You Buy Matters Just as Much as What You Buy
Here’s what most people don’t know: when you purchase travel insurance is just as critical as buying it in the first place.
Buy Within 14-21 Days of Your Initial Deposit
Most travel insurance companies offer important benefits ONLY if you purchase within 14-21 days of making your first trip payment:
Pre-Existing Medical Condition Waiver
If you or a family member has a pre-existing medical condition (diabetes, heart condition, cancer history, etc.), you need this waiver. Without it, any claim related to that condition will be denied. To qualify, you must:
- Purchase insurance within the specified time frame (usually 14-21 days of initial deposit)
- Be medically able to travel at the time of purchase
- Insure 100% of your prepaid, non-refundable trip costs
Financial Default Coverage
This protects you if your airline, cruise line, tour operator, or hotel goes bankrupt before your trip. We’ve seen this happen with airlines, boutique hotels, and even major tour companies. If you don’t buy early, this coverage typically isn’t included.
Cancel for Any Reason (CFAR) Upgrade
Some policies offer “Cancel for Any Reason” upgrades that let you cancel for literally any reason and receive 50-75% reimbursement. This must be purchased within 14-21 days of initial deposit and costs about 40-50% more than standard coverage—but the flexibility can be worth it.
Bottom line: Don’t wait until closer to your trip to “see if you need it.” By then, you’ve lost access to critical protections.
Not All Travel Insurance Policies Are Created Equal
This is where it gets complicated—and where working with a travel advisor who knows insurance inside and out becomes invaluable.
Every travel insurance company has different:
- Coverage limits
- Exclusions
- Claim processes
- Definition of covered reasons for cancellation
- Medical coverage amounts
- Emergency evacuation provisions
You need to read the fine print. And let’s be honest—most people don’t.
That’s why we only work with vetted, reputable travel insurance providers we trust. We’ve seen the claims process firsthand. We know which companies actually pay out without hassle and which ones make you jump through hoops.
Why Your Credit Card Coverage Probably Isn’t Enough
“But my credit card offers travel protection!”
Yes, it might. But here’s what it probably doesn’t cover:
❌ Trip Cancellation – Most credit cards only offer trip interruption or delay coverage, not cancellation
❌ Future Travel Credits – If an airline gives you a credit instead of a refund, your credit card won’t reimburse you
❌ Pre-Existing Conditions – Credit card coverage rarely includes medical condition waivers
❌ “Cancel for Any Reason” – This doesn’t exist with credit card coverage
❌ Comprehensive Medical Coverage Abroad – Credit card coverage is usually minimal
❌ Emergency Medical Evacuation – Can cost $100,000+ out of pocket without proper coverage
Credit card travel benefits can be useful for things like lost luggage or trip delays, but they’re not a substitute for comprehensive travel insurance.
The companies we work with provide full reimbursement—not travel credits, not vouchers, actual money back in your account. That’s the difference.
What Good Travel Insurance Actually Covers
Comprehensive travel insurance protects your investment with coverage for:
Trip Cancellation
Reimburses prepaid, non-refundable expenses if you need to cancel for covered reasons (illness, injury, death in family, jury duty, job loss, natural disasters, etc.)
Trip Interruption
Covers you if you have to cut your trip short and return home early for covered reasons
Medical Expenses
Pays for emergency medical and dental care while traveling (your regular health insurance often doesn’t cover international travel)
Emergency Medical Evacuation
Covers transportation to the nearest adequate medical facility or back home—can easily cost $50,000-$150,000 without insurance
Travel Delays
Reimburses meals and accommodations if your trip is delayed for covered reasons
Baggage Loss/Delay
Covers lost, stolen, or damaged luggage and reimburses necessary purchases if bags are delayed
24/7 Assistance Services
Access to emergency help anywhere in the world
Real Stories, Real Protection
Client Story 1: The Medical Emergency
A couple booked a $32,000 African safari six months in advance. Three weeks before departure, the husband had a heart attack. Because they purchased comprehensive travel insurance within 14 days of their deposit, they received full reimbursement—including the pre-existing condition waiver for his previous heart issues. Total recovered: $32,000.
Client Story 2: The Hurricane
A family’s $25,000 Caribbean vacation was cancelled due to a hurricane hitting their resort. Their travel insurance covered the full cancellation, plus additional expenses to rebook at a different resort. Without insurance, they would have been stuck with resort credits they couldn’t use for over a year.
Client Story 3: The Tour Operator Bankruptcy
When a boutique tour company unexpectedly went bankrupt two months before a client’s $55,000 custom Europe trip, their financial default coverage kicked in. They received a full refund and we rebooked them with a different operator. Without insurance purchased within the initial time window, that money would have been gone.
How to Purchase Travel Insurance the Right Way
1. Buy within 14-21 days of your initial trip deposit
Don’t wait. As soon as you make your first payment, purchase insurance.
2. Insure 100% of your non-refundable trip costs
Include flights, hotels, tours, transfers—everything prepaid and non-refundable.
3. Read the policy documents carefully
Understand what’s covered, what’s excluded, and what the claim process requires.
4. Consider “Cancel for Any Reason” if you want maximum flexibility
Worth the extra cost if your plans might change.
5. Work with a travel advisor who partners with reputable insurance companies
We handle the complexity so you don’t have to.
Ready to Protect Your Travel Investment?
Whether you’re booking through us or on your own, don’t skip travel insurance.
Get a travel insurance quote here →
We’ve partnered with trusted providers who offer comprehensive coverage, straightforward claims processes, and actual customer service when you need it most.
Work With Us
At Bagshaw Travel, we don’t just book your trip—we protect it. Every client itinerary we design includes guidance on the right insurance coverage for their specific journey. We’ve reviewed hundreds of policies, filed claims on behalf of clients, and know exactly which providers deliver on their promises.
Because when life happens (and it will), you should be worrying about your family, your health, or whatever emergency arose—not whether you’re about to lose thousands of dollars.
Ready to plan your next journey with peace of mind? Contact us today.
About Bagshaw Travel
Bagshaw Travel is a Virtuoso-affiliated luxury travel advisory specializing in bespoke journeys, wellness retreats, and Latin America travel. We believe every detail matters—including protecting your investment with comprehensive travel insurance.
Frequently Asked Questions About Travel Insurance
Q: Is travel insurance really necessary for domestic trips?
A: Yes. Medical emergencies, flight cancellations, and trip interruptions happen domestically too. If you’ve prepaid non-refundable expenses, you should protect them.
Q: What if I’m healthy and don’t have pre-existing conditions?
A: You still need the pre-existing condition waiver to cover family members who might have conditions. Plus, unexpected illnesses or injuries can happen to anyone.
Q: Can I buy travel insurance after I’ve already booked?
A: Yes, but you’ll miss out on critical benefits like pre-existing condition waivers and financial default coverage if you don’t buy within 14-21 days of your initial deposit.
Q: How much does travel insurance cost?
A: Typically 4-10% of your total trip cost, depending on your age, trip length, destination, and coverage level. A small price for protecting thousands of dollars.
Q: What counts as a “covered reason” for cancellation?
A: Covered reasons typically include: illness/injury/death of you or immediate family, severe weather, jury duty, job loss (under specific circumstances), home emergencies, travel supplier financial default, and more. Each policy lists specific covered reasons—read carefully.
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