Do You Really Need Travel Insurance?(Yes. Here’s Why.)

Let me tell you about a phone call I never want to receive.

It goes something like this: someone I’ve booked reaches out from the airport, or worse, from a destination. A flight cancelled. A missed connection that cost them a full day at the resort. A medical situation that came out of nowhere. Lost luggage with everything in it.

And then the question I dread most: “DeShawn, I know I declined travel insurance. What do I do?”

I have been planning travel for nine years. I have seen the full range of what can go wrong on a trip and I have seen the difference between clients who were protected and clients who were not. That difference is significant. Sometimes it is thousands of dollars. Sometimes it is someone stranded in a foreign hospital trying to figure out how to pay for care that their domestic insurance will not cover.

Travel insurance is not a luxury. It is not a formality. It is one of the most important things you can add to any trip you take. And I want to tell you exactly why.

Your Domestic Health Insurance Does Not Travel With You

This is the part that surprises most people. They assume that because they have good health insurance at home, they are covered everywhere they go. They are not.

Most US employer-sponsored health plans offer little to no coverage outside the country. Medicare does not cover medical expenses abroad at all in most situations. Even plans that claim international coverage often operate as secondary coverage, meaning you pay out of pocket first, submit for reimbursement later, and hope the claim is approved.

Now imagine this: you are on your dream trip in Jamaica. You slip on wet tile near the pool and fracture your wrist. You need X-rays, a doctor, possibly a specialist. You are taken to a local clinic or hospital. The first question they ask is not “how are you feeling”, it’s “how are you paying?”

Without travel medical insurance, you are writing a check. With travel medical insurance, you make a phone call.

Medical costs in the US are expensive but, abroad can be staggering. A single night in a hospital in the Caribbean can cost several thousand dollars. Surgery or specialist care can reach tens of thousands. And if your condition requires medical evacuation such as being airlifted to a more advanced facility or transported back home that bill alone can exceed $100,000 without coverage.

Travel insurance fills the gap your domestic plan leaves open. It covers emergency medical treatment, hospitalization, prescription medications related to a covered illness or injury, and emergency dental care. The best plans provide primary coverage, meaning they pay first without requiring you to get a denial from your domestic insurer before they step in.

What Travel Insurance Actually Covers

Beyond medical, travel insurance is a comprehensive protection plan for everything that can go wrong before and during your trip. Here is what a good policy actually covers:

Trip cancellation and interruption

If you have to cancel before departure because of a serious illness, a family emergency, a hurricane forcing mandatory evacuation, an unexpected job loss, or dozens of other covered reasons,travel insurance reimburses your prepaid, non-refundable costs. If something forces you to cut your trip short after you’ve already left, trip interruption coverage picks up the additional transportation costs to get you home and reimburses the unused portion of your trip.

Emergency medical evacuation

If the local medical facility cannot provide the level of care you need, emergency evacuation coverage pays to transport you to a facility that can including back home if necessary. Premium plans cover transport to the hospital of your choice rather than simply the closest available facility. This distinction matters enormously if you’re facing a serious diagnosis in an unfamiliar country.

Trip delays and missed connections

A flight delayed more than six hours triggers coverage for meals and accommodations. A missed connection that causes you to lose a day at your resort is covered. These seem like minor inconveniences, but they add up quickly at airport hotels and restaurants. Travel insurance means you are not absorbing those costs alone.

Lost, stolen, or delayed baggage

Airlines lose bags. It happens on the best carriers in the world. Travel insurance reimburses you for lost or stolen personal belongings and covers emergency purchases such as clothes, toiletries, essentials. When your bag is delayed 12 or more hours on the outbound journey. Nobody should spend the first day of their vacation in the same outfit and undergarments they traveled in.

The Most Important Thing Most People Get Wrong

Here it is: timing.

Most people think about travel insurance when they’re packing. That is too late, not to purchase insurance at all, but to unlock the full benefits of your policy.

For a pre-existing conditions waiver to apply, most policies require that you purchase your plan within 14 to 21 days of making your initial trip deposit. If you have a medical condition that could affect your travel and you wait until two weeks before departure to buy insurance, that condition may not be covered.

The same applies to cancel-for-any-reason coverage — the most flexible protection available. This benefit requires early purchase.

My advice to every client I book: buy your travel insurance the same week you book your trip. Not the same month. The same week. The cost is the same either way, but your coverage is significantly stronger when you act early.

Plans I Recommend For Single Trip Insurance — And How to Get a Quote

I recommend Arch RoamRight to my clients because their plans consistently deliver on what they promise. Here is a quick overview of the four plans available through my personalized portal:

Plan	Best for
Pro Plan	Shorter trips up to 90 days. Up to $15K trip cost, $25K medical, $500K evacuation. Great value entry point.
Pro Plus Plan	Most travelers. Up to $50K trip cost, $100K medical, $1M evacuation. One child under 18 included free. Cancel for Work Reasons included.
CancelFlex Plan	Maximum flexibility. Everything in Pro Plus plus the ability to cancel for any reason and recover 75% of non-refundable costs.
On Trip Plus Plan	Already traveling or booking last minute. Can be purchased up to the day before departure. Starting at $41.

You can explore all four plans and get a personalized quote directly through my portal: partner.roamright.com?agencycode=YouCanTravelToo&agentid=DShepard. If you have questions about which plan is right for your specific trip, reach out to me directly and I’ll help you choose.

Annual Travel Insurance

Personally, I purchase an annual travel insurance plan. This plan covers all of my trips that are more than 100 miles from home. I've only had to use it once and it was just the coverage I needed. I do purchase single trip insurance for some high-dollar trips but most of the time, my annual plan is more than sufficient. If interested in a quote for annual travel insurance, you can reach out to me directly.

The Bottom Line

Every trip I book, a Jamaica group getaway, a Sandals honeymoon, a European adventure, I have the same conversation with every traveler: please protect your investment.

The cost of travel insurance is small relative to the cost of a trip. The cost of not having it, when something goes wrong, can be devastating, financially, emotionally, and practically. I’ve seen both sides of this equation up close. The peace of mind that comes with knowing you are covered is worth every penny.

You work hard for your vacations. You plan them carefully. You dream about them. Protect them the same way you plan them intentionally and early.

And if you ever have questions about coverage, costs, or which plan makes the most sense for your upcoming trip, I am always here.

Dee Shepard is the owner of You Can Travel Too.

She helps couples, families and groups plan memorable vacations and milestone celebrations.