Use your credit card’s trip protection benefits, not just your primary travel insurance policy.
The Special Forces Unit That Backs Up Your Army
Your main travel insurance is your army; it’s designed for the big, heavy fighting. But your premium credit card often has a secret, elite special forces unit of its own. This “trip protection” can be the perfect backup. It might have a better rental car policy or cover smaller, more specific delays that your main policy doesn’t. When you have a problem, don’t just call the army; you must also call in your special forces. Using them together gives you the most complete protection on the battlefield.
Stop just cancelling your trip. Do get a doctor’s note specifically stating you are “unfit to travel,” instead.
The Legal Affidavit, Not a Casual Sick Note
Telling your insurer, “My doctor said I’m sick,” is like whispering a rumor. It’s weak and easy to ignore. A formal letter from your doctor that uses the magic words “unfit to travel” is a legal affidavit. It is your doctor’s sworn, expert testimony that your medical condition makes the physical act of traveling impossible or dangerous. This transforms your claim from a vague complaint into a powerful, medically-backed argument that the insurance company is required to take seriously.
Stop accepting a denial because you cancelled due to a travel warning. Do check for “Cancel For Any Reason” coverage, instead.
The Master Key That Opens Any Lock
Standard trip insurance is like a key that only opens one specific lock—the one labeled “medical emergency” or “jury duty.” If your reason isn’t on that approved list, the door stays shut. A “Cancel For Any Reason” (CFAR) policy is the master key. It allows you to unlock the door and get a significant portion of your money back for almost any reason, whether it’s a new government travel warning or simply your own fear and anxiety. It is the ultimate key to freedom and flexibility.
The #1 secret for getting a pet insurance claim paid is a full veterinary history submitted before the first claim.
The Pre-Purchase Inspection for Your Pet’s Health
When you buy a used car, a smart buyer first gets an inspection report to prove the car is in good shape. Submitting your pet’s full medical history to the insurer before you ever file a claim is that pre-purchase inspection. It creates a baseline record that shows your pet was healthy when you bought the policy. This makes it much harder for them to later claim that a new injury is actually an “undisclosed pre-existing condition.” You are proving the car was sound before you ever drove it off the lot.
I’m just going to say it: The term “pre-existing condition” in pet insurance is intentionally broad and vague.
The Giant, Blurry “No Trespassing” Sign
The “pre-existing condition” clause in a pet insurance policy is like a giant, blurry “No Trespassing” sign that the insurer can move around your property wherever they want. Did your dog have a limp in its left leg two years ago? They will use that to deny a claim for arthritis in its right leg today. The term is deliberately vague, allowing them to connect unrelated issues across time to protect their financial interests. It is the single most powerful and frequently used weapon in their arsenal.
The reason your trip interruption claim was denied is because you didn’t get proof of the delay from the airline.
Your Word vs. Their Official Confession
Telling your travel insurer that the airline delayed your flight is just your personal testimony. The airline can deny it, creating a “he said, she said” standoff. To win, you need their official confession. You must go to the gate agent and ask for a printed statement on airline letterhead that documents the reason for and the length of the delay. This piece of paper is the airline’s signed confession, an undeniable piece of evidence that proves your claim and forces the insurer to pay.
If you’re still buying travel insurance from the airline’s website, you’re losing access to better, more comprehensive policies.
The Vending Machine vs. the Supermarket
Buying travel insurance from the airline’s pop-up window during checkout is like buying dinner from a vending machine. It’s convenient, but the selection is tiny, the quality is questionable, and the price is high. Using an independent comparison website is like walking into a giant supermarket. You can compare dozens of different “meals” from different brands, read the ingredients (the coverages), and choose the high-quality, comprehensive policy that is the perfect fit for your trip and your budget.
The biggest lie you’ve been told is that your travel medical insurance will pay the foreign hospital directly.
The ATM, Not the Credit Card
You believe your travel medical policy is like a credit card that you can hand to a foreign hospital to pay your bill. It is not. It is an ATM. In almost all cases, you are required to pay the hospital’s bill yourself, out of your own pocket. You then submit the receipts to the insurance company, who will reimburse you later. It is a reimbursement policy. Thinking they will pay upfront is a catastrophic misunderstanding that can leave you stranded in a foreign country with a massive, unexpected bill.
I wish I knew about the “foreseeable event” exclusion before I booked a trip during hurricane season.
You Can’t Buy Fire Insurance When the House Is Already Smoking
The “foreseeable event” exclusion is the rule that says you can’t buy insurance for a disaster that is already happening. Booking a trip to Florida a week after a hurricane has been named and is on the news is like trying to buy fire insurance when you can already smell the smoke in your house. The event was “foreseeable,” and the insurer will deny your claim because you willingly and knowingly walked into a danger that was already in progress.
99% of people make this one mistake with pet insurance: not understanding the waiting period for specific conditions.
The Probationary Period for Your Pet’s Knees
Your pet insurance policy is not fully active on day one. It has a “waiting period,” which is like a probationary period at a new job where your full benefits haven’t kicked in yet. There might be a 14-day wait for illnesses, but a much longer, 6-month wait for specific orthopedic issues like knee or hip problems. If your pet has a knee injury during that specific waiting period, it will not be covered. You must know exactly when each type of coverage becomes fully active.
Use your event cancellation insurance, not just losing your deposits when a venue cancels on you.
The Safety Net for Your Big Day’s Big Deposits
Planning a major event like a wedding is like walking a financial high wire. You make huge, non-refundable deposits to the venue, the caterer, and the photographer. But what if the venue has a fire a week before your wedding? Event cancellation insurance is the safety net that catches you. It will reimburse you for all your lost deposits, allowing you to rebook your event without suffering a catastrophic financial loss. It is the essential protection for the most expensive day of your life.
Stop accepting a denial for a “bilateral condition” in pet insurance. Do get your vet to state the conditions are unrelated, instead.
The Tale of Two Knees
A “bilateral condition” is a tricky exclusion. If your pet has a diagnosed problem in its left knee, the insurer will automatically label any future problem in the right knee as the same pre-existing condition. It’s like saying a flat tire on the left side of your car means the right tire was also always bad. You must fight this. Get your veterinarian to write a specific report arguing that the new injury is a separate, traumatic event, not a continuation of the old problem.
Stop thinking your lost luggage claim is limited to the airline’s low payout. Do use your travel insurance for the real value, instead.
The Small Change vs. the Full Bank Account
The airline’s liability for your lost luggage is like the small amount of petty cash a company might give you for a minor inconvenience. It is a tiny, legally capped amount that comes nowhere near the real value of your belongings. Your travel insurance policy, on the other hand, is the full bank account. It is designed to pay you for the actual, replacement cost value of the expensive camera, the new clothes, and the other valuables that were inside your bag.
The #1 hack for a successful travel medical claim is to contact the insurer’s 24/7 assistance line before seeking treatment.
The 911 Dispatcher for Your Medical Emergency Abroad
Your travel insurance policy is not just an insurance card; it is a 24/7 emergency response service. The assistance line is the 911 dispatcher. Before you go to a local clinic, you must call them. They will act as your advocate, telling you which hospital is in their network, arranging for payment, and coordinating your care. Calling this number first is the single most important step. It’s the difference between having a powerful ally on your side versus trying to navigate a foreign medical system all by yourself.
I’m just going to say it: Wedding insurance is one of the most valuable and underutilized niche policies.
The Fire Extinguisher for the Most Expensive Day of Your Life
A wedding is a massive, one-day financial investment, with dozens of moving parts and vendors. It is an incredibly fragile and expensive event. Not buying wedding insurance is like building a beautiful, expensive house and not installing a single fire extinguisher. For a tiny fraction of the total cost, this policy protects your huge deposits from a vendor bankruptcy, extreme weather, or a sudden illness. It is the one, simple tool that can save your entire investment from going up in smoke.
The reason your pet’s treatment was denied is because it was classified as “preventative” instead of “diagnostic.”
The Oil Change vs. the “Check Engine” Light
An insurer sees two types of vet visits. “Preventative” care is a routine oil change—a regular check-up to keep things running. This is usually not covered. “Diagnostic” care is when the “check engine” light comes on—your pet is showing symptoms, and the vet is running tests to find the problem. This is usually covered. Insurers will often try to classify a visit for a new problem as “routine” to avoid paying. You must prove the check engine light was on.
If you’re still not taking photos of your rental car before you drive it, you’re losing your defense against a damage claim.
The “Before” Photo That Proves Your Innocence
When you rent a car, you are borrowing someone else’s expensive property. Before you ever get in, you must be a detective documenting the “scene of the crime.” Walk around the car and take detailed photos of every single scratch, dent, and ding you can find. This creates a time-stamped, “before” picture. When you return the car and they try to blame you for a pre-existing scratch, you will have the undeniable photographic evidence that proves the damage was already there.
The biggest lie you’ve been told is that all pet insurance policies cover exam fees.
The Doctor’s Bill vs. the Prescription Cost
Imagine your health insurance covered the cost of your medicine, but not the cost of the doctor’s visit to get the prescription. This is how many pet insurance policies work. They will reimburse you for the cost of the X-rays and the treatment for your dog’s broken leg, but they will not cover the initial “exam fee” from the vet who diagnosed the problem. It is a frustrating and common gap in coverage that can add hundreds of dollars to your out-of-pocket costs.
I wish I knew that I needed to get a police report for a stolen item to be covered by my travel insurance.
The Official Witness to Your Stolen Property
Telling your insurance company your passport was stolen is just a story. A police report is the official, third-party verification that a crime actually occurred. Without it, your claim is just your word against a world of potential fraud. Most policies make a police report a mandatory requirement for any theft claim. You must treat it as the first and most critical piece of evidence you need to collect, the official witness that proves your story is true.
99% of travelers make this one mistake: they don’t realize their policy excludes sports and adventure activities.
The Tourist Policy vs. the Explorer Policy
Your standard travel insurance policy is designed for a tourist. It covers you for walking around Paris and visiting museums. It is not designed for an explorer. If you are going skiing, scuba diving, or even on a strenuous mountain hike, you have crossed a line into “adventure activities,” which are almost always excluded. For these, you must buy a special explorer’s policy with an “adventure sports” rider. Don’t make the mistake of bringing a tourist’s map into a jungle.
Use a detailed timeline of events to prove your trip was “interrupted,” not just “inconvenienced.”
The Domino Effect That Caused a Catastrophe
A flight delay is an “inconvenience.” But a “trip interruption” is a chain reaction of dominoes. Your timeline must prove this. “8 AM: Flight delayed (See airline notice). 2 PM: Missed connecting flight (See boarding pass). 6 PM: Arrived too late for cruise ship departure (See cruise itinerary).” This detailed timeline proves the delay wasn’t just an inconvenience; it was the first domino that set off a catastrophic chain reaction, causing you to miss a significant, pre-paid portion of your trip.
Stop accepting a denial for your pet’s dental cleaning. Do have your vet document the medical necessity for extractions, instead.
The Teeth Polishing vs. the Oral Surgery
A “dental cleaning” for your pet is a routine, preventative procedure, like getting your teeth polished, and it is almost never covered. But if your vet discovers that a diseased tooth needs to be pulled, the procedure is no longer a simple cleaning. It has become a medically necessary oral surgery. You must have your vet carefully document that the purpose of the procedure was the diagnosis and treatment of a dental disease, which required extractions. This transforms it from a cosmetic issue into a covered surgery.
Stop letting them deny your claim because a close family member wasn’t on the policy. Do check the definition of “family member” in the policy, instead.
The Policy’s Dictionary vs. Your Family Tree
You cancel your trip because your grandmother is gravely ill. The insurer denies the claim, saying she wasn’t traveling with you. This is a trick. You must open the policy and find the “Definitions” section, their official dictionary. Look up “Family Member.” A good policy will include a broad definition that covers non-traveling relatives like grandparents, siblings, and even aunts or uncles. Your claim is not about who was on the ticket; it’s about who is on the list in their dictionary.
The #1 secret to cell phone insurance is that the deductible is often close to the cost of the repair.
The Insurance That Costs the Same as the Cure
You pay $15 a month for your cell phone insurance. You crack your screen, and you feel smart for being covered. But then you file a claim and discover the deductible is $200. You call a local repair shop and find out they can fix your screen for $250. The “insurance” has only saved you $50 after you’ve already spent hundreds on premiums. The high deductible is the secret that makes the policy almost useless for the most common types of damage.
I’m just going to say it: The “free” travel insurance that comes with your credit card has major gaps in coverage.
The Free Sample That Won’t Feed You in a Famine
The “free” travel insurance that comes with your credit card is a free sample. It’s a taste of protection that is designed to make you feel secure. But if you get into a real, catastrophic travel emergency—a serious medical event in a foreign country—you will discover that your free sample is not a full meal. It has low limits, huge exclusions, and very little real-world assistance. It is a wonderful perk for minor inconveniences, but it is not a substitute for a real, comprehensive travel insurance policy.
The reason your event liability claim was denied is because of an alcohol-related exclusion.
The Designated Driver Who Goes Home if You Break the Rules
Your event liability policy is your designated driver for the party. But it comes with very strict rules. If you serve alcohol to a minor, or to someone who is obviously intoxicated, or if you don’t use a licensed bartender as required, you have broken the rules. The policy’s “liquor liability” exclusion means your designated driver has just gone home. You are now personally on the hook for any accident or injury that occurs, with no insurance to protect you.
If you’re still throwing away your receipts while on vacation, you’re losing your ability to claim for delayed baggage expenses.
The Paper Trail That Proves Your Emergency Shopping Spree
Your luggage is delayed for 24 hours. Your policy says you can buy “essential items” until it arrives. But you can’t just tell them you spent $300. You need to produce the paper trail that proves it. The receipts for the new toothbrush, the change of clothes, and the toiletries are the hard evidence. Each receipt is a single breadcrumb on the trail of your expenses. Without them, you have no proof, and the insurer has no obligation to reimburse you for your emergency shopping spree.
The biggest lie you’ve been told is that you can’t appeal a pet insurance denial.
Their Financial Decision, Not a Final Medical Opinion
When a pet insurance company denies your claim, it can feel like a final, authoritative medical verdict. It is not. They are not your veterinarian. They are a financial services company that has made a business decision based on their interpretation of a contract. You absolutely have the right to appeal that business decision. By providing more evidence from your vet and a clear argument, you are not questioning their medical expertise; you are challenging their financial calculation.
I wish I knew about the “Change of Mind” exclusion in event insurance before the bride got cold feet.
The Insurance for a Hurricane, Not a Change of Heart
Wedding insurance is a powerful tool designed to protect you from unforeseeable disasters—a hurricane that floods your venue, a caterer that goes bankrupt, or a close relative who has a medical emergency. It is a safety net for external events. But it has a giant hole in it called the “change of mind” exclusion. It will not cover any losses that occur because the bride or groom has a change of heart and decides to call off the wedding. That is a risk no insurance company is willing to take.
99% of people make this one mistake: they buy travel insurance after a major storm has already been named.
You Cannot Buy a Lifeboat After the Ship Has Already Hit the Iceberg
Travel insurance is designed to protect you from unforeseen events. The moment a winter storm or a hurricane is officially named by the weather service, it is no longer unforeseen. It is a known, active event. It is the iceberg that the ship has already hit. If you buy your policy after that moment, the “foreseeable event” exclusion will kick in, and you will have no coverage for any delays or cancellations caused by that storm. You have bought a lifeboat that is already full.
Use your policy’s “trip delay” benefits for meals and hotels, not just waiting at the airport.
The Expense Account for Your Forced Layover
A long flight delay doesn’t just mean you have to wait; it means you incur extra costs. Your “trip delay” coverage is the secret expense account for this forced layover. After a certain number of hours, it will reimburse you for the reasonable cost of your meals, your drinks, and even a hotel room if the delay is overnight. Don’t just sit in a miserable airport chair and spend your own money. Open your policy, check the rules, and start using the expense account you already paid for.
Stop accepting a pet insurance denial for a “hereditary condition.” Do check if your policy covers them after a waiting period, instead.
The Pre-Existing Condition You Are Born With
A “hereditary condition” is a pre-existing condition that is written into your pet’s genetic code, like hip dysplasia in a Labrador. Many policies used to exclude these entirely. But the market is changing. Now, many of the best policies will cover these conditions, as long as the pet showed no signs of the issue before the policy started and a specific (and often long) waiting period has passed. Don’t accept a denial; check to see if your modern policy has evolved to cover these common issues.
Stop abandoning your trip without authorization. Do get approval from the insurer to return home early, instead.
The Doctor’s Note That Discharges You from Your Vacation
If you get sick on your trip, you can’t just decide to fly home and expect the insurer to pay. You must treat them like your doctor at a hospital. You must call their 24/7 assistance line and get officially “discharged” from your vacation. Their medical team will review your case and give you the formal authorization to cut your trip short. If you leave without their approval, they will deny your trip interruption claim for abandoning the trip without a doctor’s permission.
The #1 hack for fighting a travel insurance denial is to file a complaint with the U.S. Travel Insurance Association.
The Better Business Bureau for Your Bad Trip
The U.S. Travel Insurance Association (UStiA) is the official industry group for travel insurers. They are like the Better Business Bureau for your vacation. If you have a legitimate claim that is being unfairly denied, filing a formal complaint with UStiA is a powerful escalation. It gets your case in front of the industry’s watchdogs, and no company wants to have a record of unresolved complaints with their own governing body. It is a free, effective tool that can get a stubborn insurer to take another look.
I’m just going to say it: Most identity theft insurance is a waste of money.
The “Helper” Who Just Fills Out Paperwork You Could Do Yourself
Identity theft insurance gives you the false impression that it will pay you back for the money that was stolen. It does not. The vast majority of these policies are just “restoration” services. They are a helper who will get on the phone for you and fill out the paperwork to fix your credit. While this is a hassle, it is work you can do yourself for free. And most of the monitoring services they offer can now be gotten for free from your bank or credit bureaus.
The reason your claim was denied is because you traveled to a country with a “Do Not Travel” advisory.
The Giant “Road Closed” Sign from the Government
Before you travel, you must check the U.S. State Department’s official travel advisories. If a country is listed as a Level 4: “Do Not Travel,” it is the equivalent of a giant, official “Road Closed” sign. If you choose to ignore that warning and travel there anyway, your insurance company will deny any claim that arises from that trip. You have deliberately and knowingly driven past the barricades into a known danger zone, and in doing so, you have voided your coverage.
If you’re still not getting an itemized bill from the foreign clinic, you’re losing your proof for reimbursement.
The Grocery Bill That Just Says “Food: $500”
To get reimbursed for a foreign medical bill, you need a proper receipt. A bill that just says “Medical Services: $5,000” is like a grocery bill that just says “Food: $500.” The insurer has no idea what they are paying for. You must insist on an itemized bill that lists every single procedure, every test, and every medication. This detailed invoice is the proof they need to see what they are paying for and to process your reimbursement correctly.
The biggest lie you’ve been told is that your rental car insurance waiver covers loss of use fees.
The Insurance for the Dent, Not for the Lost Time
The Collision Damage Waiver (CDW) you buy from the rental car company is great insurance for the physical damage to the car. It pays for the dent in the door. But it has a huge hole in it. It does not cover the “loss of use” fees that the rental company will charge you. This is a fee for the income they lost while the car was in the shop being repaired. It can add up to hundreds of dollars, and it is a nasty surprise that your waiver almost never covers.
I wish I knew that I needed to provide the original purchase receipts for items in my lost luggage.
The Price Tag That Proves the Value of Your Treasure
When your luggage is lost, you are making a claim for the treasure that was inside. But the insurer needs proof that your treasure was real. They will ask for the original purchase receipts for the most expensive items, like your camera or your new laptop. Without these receipts, they have no way to verify the age or the true value of what you lost. They will be forced to give you a lower, depreciated value based on a guess, not the hard proof of a price tag.
This one small action of reading the definition of “covered reason” will change how you buy travel insurance forever.
The Short List of Keys That Will Actually Open the Door
The travel insurance policy you bought is a locked door. The “Covered Reasons” section of the policy is the small, specific list of the only keys that will open that door. People assume the door will open for any logical reason, but it will not. If your specific reason for cancelling—”my dog is sick,” “I’m afraid of a protest”—is not on that exact list, the door will remain locked. Reading this one, short list before you buy is the only way to know what you are truly protected from.
Use a medical translation service to ensure your doctor’s notes are understood by the insurer, not just submitting them in a foreign language.
A Blurry Photo vs. a High-Definition Image
Submitting your medical records to your insurer in a foreign language is like submitting a blurry, out-of-focus photograph as your only evidence. It’s useless. They cannot read it, and they will deny your claim. You must use a professional medical translation service to turn that blurry photo into a crystal-clear, high-definition image. The translated documents, certified for accuracy, become the undeniable, easy-to-understand proof that your claim is valid, and gives them no excuse to deny it for confusion.
Stop accepting a denial for your pet’s prescription food. Do get a letter of medical necessity from your vet, instead.
The Food That Is Actually Medicine
An insurer will deny a claim for prescription pet food, saying, “We don’t cover food.” This is a word game. You must reframe the argument. Have your veterinarian write a formal letter of medical necessity that states the food is not “food” in the traditional sense; it is a “medical treatment in the form of food,” prescribed to treat a specific, diagnosed illness. This letter is the expert testimony that proves they are not paying for your pet’s dinner; they are paying for its medicine.
Stop thinking you can’t get a refund if the event is postponed. Do check your policy’s specific language on postponement vs. cancellation, instead.
The Rain Delay vs. the Forfeit
A postponed event is a rain delay in a baseball game. A cancelled event is a forfeit. Your event insurance policy has different rules for each. For a postponement, the policy may not pay you back for your tickets immediately. It may require you to wait to see if you can attend on the rescheduled date. You must read the specific language in your policy to know if you are entitled to a refund for a simple rain delay, or only for a full forfeit of the game.
The #1 secret for a successful emergency medical evacuation claim is to let the insurer arrange the transport.
The 911 Operator Dispatches Their Own Ambulance
If you are seriously ill in a remote location, your policy may pay to have you medically evacuated. But you cannot just call your own helicopter. You must call the insurer’s 24/7 assistance line. They are the 911 operator, and they have their own, pre-approved network of air ambulances. If you arrange your own transport, they will likely refuse to pay, claiming it was too expensive or medically unnecessary. You must let their dispatcher send their own ambulance to the scene.
I’m just going to say it: The per-article limits on baggage insurance are ridiculously low.
The Tiny Safe Inside the Big Suitcase
Your baggage insurance says it covers you for $2,500. This sounds great. But buried in the fine print is a “per-article” limit, which is a tiny, locked safe inside your big suitcase. It will say that they will not pay more than $250 for any single item. So when your $1,500 laptop and your $1,000 camera are stolen, you are not going to get $2,500. You are going to get $250 for the laptop and $250 for the camera.
The reason your claim was denied is because your “illness” was considered a normal symptom of pregnancy.
The “Illness” vs. the “Condition”
Travel insurance covers you if you have to cancel because of a sudden, unforeseen “illness.” But a normal, healthy pregnancy is not considered an illness; it is a “condition.” The common, expected symptoms of that condition, like morning sickness, are not a valid reason for cancellation. However, if you develop a serious, unexpected complication of the pregnancy that a doctor deems makes you unfit to travel, that complication can then be classified as a covered illness.
If you’re still not keeping your original boarding passes, you’re losing your proof of travel.
The Ticket Stub That Proves You Were at the Show
Your e-ticket or itinerary proves you bought a ticket to the show. But your original boarding pass is the torn ticket stub that proves you were actually in your seat when the show started. For many claims, especially trip interruption or delay, the insurer will demand a copy of your boarding passes. It is their way of verifying that you actually took the flight you are claiming was delayed. Without that stub, you have no proof you were even there.
The biggest lie you’ve been told is that your policy covers you if the travel company goes bankrupt.
The Financial Default Is Not an Accident
A travel company going out of business feels like an unforeseen disaster. But in the world of insurance, it is a “financial default,” and it is specifically excluded from almost all standard travel insurance policies. It is not considered an “accident” or a “covered peril.” To be protected from your tour operator or cruise line going bankrupt, you must buy a more expensive policy that specifically includes an upgrade for “financial default” or “supplier bankruptcy.”
I wish I knew to buy a policy that covers pre-existing conditions with a “waiver.”
The Golden Ticket That Erases the Past
The “pre-existing condition” exclusion is the biggest monster in any travel insurance policy. But there is a secret golden ticket that can make it disappear. If you buy your policy within a short window of time (usually 14-21 days) after making your first trip payment, many policies will grant you a “pre-existing condition waiver.” This is the ultimate upgrade. It means the company agrees to waive the exclusion, and you are now covered for any unforeseen flare-up of your chronic condition.
99% of people make this one mistake: they don’t buy their travel insurance within the 14-21 day window after their first trip payment.
The Magic Window for the Best Benefits
When you put down the deposit for your big trip, a secret, magic window opens. This window usually lasts for only 14 to 21 days. If you buy your travel insurance inside this window, you are eligible for the policy’s best and most powerful benefits, like the “pre-existing condition waiver” and “Cancel For Any Reason” coverage. If you wait and buy your policy after that window has closed, those golden tickets are no longer available. You are left with a basic, less powerful policy.