Buying guide

Insuring a five- or six-figure trip: Cancel For Any Reason, the pre-existing condition waiver, and medical evacuation

Updated October 27, 2026 · Written by the Only for the Wealthy editors · General information, not legal or financial advice

A trip planned a year ahead, with deposits to match, deserves protection chosen as carefully as the suite. Here is what the regulators, the statutes, and the policy documents actually say about travel insurance, Cancel For Any Reason, and medical cover abroad.

We don’t sell, quote, or arrange insurance, and we don’t book travel. Only for the Wealthy is a publisher, and this is general information, not insurance, legal, or medical advice. Every travel policy is its own contract, and the certificate and fulfillment materials you are actually issued always govern. We are not affiliated with any insurer, card network, or government agency named here, and we earn nothing from them.

Why the protection deserves the same care as the itinerary

The trips that matter most tend to be the ones with the most money paid up front: the expedition cruise booked a year ahead, the private villa with a nonrefundable deposit, the safari lodges that want final payment months before you land. More travelers are protecting those payments. The U.S. Travel Insurance Association’s 2022–2024 market study, conducted by Willis Towers Watson, found that U.S. travelers spent $5.56 billion on travel insurance in 2024, up 46% from $3.81 billion in 2019. The total trip value protected rose from $49 billion in 2019 to $68.04 billion in 2024, and trip cancellation and interruption packages made up about 94.7% of consumer spending [1]. The NAIC, the organization of state insurance regulators, cites the same study on its travel insurance page, last updated April 1, 2026 [2].

The trouble is that “travel insurance” is a label, not a promise. A plan bought at checkout may bundle real insurance with services that aren’t insurance at all. The card in your wallet may cover only the airfare. Cancel For Any Reason may pay back part of the trip, not all of it. Here is what the regulators and the policy documents actually say, so the protection is as considered as the trip itself.

First, know what you are buying: a travel protection plan has three parts

Illinois adopted a Travel Insurance Act in 2021, built on the NAIC’s model law. The NAIC reports that, as of April 2026, 38 states have enacted that model [2]. The Illinois definitions are a clear map of what a plan can contain [4]:

Component	What it is	Is it insurance?
Travel insurance	Coverage for personal risks of planned travel: trip cancellation or interruption, lost baggage, damage to accommodations or rental vehicles, sickness or injury during travel, emergency evacuation, and repatriation of remains [4].	Yes. It is regulated by the state insurance department [2][4].
Cancellation fee waiver	An agreement with the travel supplier to waive some or all of its own nonrefundable cancellation fees [4].	No. The statute says so in as many words [4].
Travel assistance services	Services like security advisories, medical referrals, case monitoring, transport coordination, document replacement, lost-luggage help, and concierge services, where you are not indemnified for a loss [4].	No. They “are not insurance and are not related to insurance” [4].

The NAIC adds the practical point: even when these products are sold together as one package, only the insurance has the oversight of state insurance departments [2]. Illinois lets a plan be sold for one price, but only if it discloses before purchase which of the three parts it includes, lets you get more information about the features and pricing of each, and sets them out separately in the fulfillment materials with contact details for whoever provides the non-insurance parts [6]. If a supplier’s “protection” turns out to be only a cancellation fee waiver, its value depends entirely on that supplier staying in business and keeping its word.

The protections the law already gives you as a buyer

Illinois’s sales-practice section is short, and every line is useful to a buyer [7]:

A free look. Unless you have started the covered trip or filed a claim, you may cancel for a full refund of the plan price until at least 15 days after the fulfillment materials are mailed to you, or 10 days after they are delivered any other way, including email [7]. The NAIC model contains the same 15- and 10-day periods [17]. Use the window: read the certificate in full while you can still walk away.
The brochure must match the policy. Sales, advertising, and marketing materials must be consistent with the policy forms, endorsements, rate filings, and certificates [7].
Pre-existing condition terms must be disclosed. If a policy excludes pre-existing conditions, you must be given information and a chance to learn more about the exclusion before you buy, and again in the fulfillment materials [7]. The NAIC’s examination standard for regulators goes further: examiners check that buyers were told whether the exclusion can be waived, under what circumstances, and whether coverage for pre-existing conditions can be purchased [8].
Primary or secondary must be stated. The insurer must disclose in the policy documents and fulfillment materials whether the coverage is primary or secondary to your other coverage [7]. Secondary coverage pays only after your other plans do, so this one word shapes every claim.
No pre-checked boxes. No one may sell travel insurance by negative option or opt-out, such as a box already ticked at checkout that you must uncheck [7].
No “free” blanket coverage, and no illusory policies. Marketing blanket travel insurance as free is an unfair trade practice, and so is selling a policy that could never pay a claim for anyone it covers [7].

When the plan is offered by the cruise line, tour company, or booking site itself, Illinois law adds another rule. The travel retailer must make written materials available that identify the insurer, explain that buying the insurance isn’t required to buy anything else, and explain that an unlicensed retailer may describe the coverage and price but isn’t qualified to answer technical questions about the terms or evaluate your existing coverage [5]. Its unlicensed staff may not interpret the policy’s technical terms, advise you about your existing insurance, or hold themselves out as insurance experts [5]. If you have a real question about how a clause applies to you, ask a licensed agent or the insurer in writing.

Trip cancellation: covered reasons, not every reason

Standard trip cancellation and interruption coverage reimburses prepaid, nonrefundable trip costs when you cancel or cut a trip short for a reason the policy lists [2][3]. The NAIC’s June 16, 2026 consumer guide gives typical covered reasons: you or a travel companion become sick or injured and a doctor says you aren’t fit to travel; a family member at home is hospitalized or dies; severe weather or a problem with your airline, train, or cruise line disrupts the trip; a natural disaster strikes your home or destination; or you are required to serve on a jury or testify in court [3].

The same guide lists the common exclusions: pre-existing health conditions, pandemics, civil and political unrest at the destination, pregnancy and childbirth, and activities the insurer considers hazardous, such as bungee jumping, backcountry skiing, and snowboarding [3]. It also gives the timing rule that matters most in hurricane season: if you wait until a storm has been named, your policy likely won’t cover claims related to it [3]. Buy early, ideally when you make the first payment you couldn’t afford to lose.

Maryland’s insurance regulator adds two practical cautions. Check the refund policies on your prepaid bookings and the terms of the insurance you already hold before you buy, and know that some suppliers refund cancellations made months ahead but not days ahead [15]. Those two facts decide how much of the trip is genuinely at risk, and therefore how much you need to insure.

Cancel For Any Reason: real flexibility, with conditions

Cancel For Any Reason, or CFAR, is the upgrade most discerning travelers ask about. The NAIC describes it plainly [2][3]:

It is usually an add-on to a standard trip cancellation policy, and the reason you cancel doesn’t matter [3].
It reimburses only part of the trip cost, not the full amount. The NAIC’s topic page puts the typical partial refund at 50% to 75% [2][3].
It usually must be bought within a set period after you book [3].
You are generally required to insure all of your prepaid, nonrefundable trip costs to qualify [3].
There is usually a set cancellation window; the NAIC notes CFAR typically requires you to cancel 48 hours or more before departure [2][3].
It costs more than a standard policy, and the NAIC observes that the more expensive the trip, the more the add-on costs [2][3].

Read CFAR as a decision about the share of the trip you are willing to forfeit. If a covered reason applies, the standard cancellation benefit is usually the better claim. CFAR is for everything else: a change of heart, a business conflict, a destination that no longer feels right. Before you buy, find four things in the actual certificate: the purchase deadline, the percentage reimbursed, the latest point at which you may cancel, and whether every prepaid cost has to be insured.

Your card’s trip benefit may be narrower than you think

The NAIC tells travelers to check whether their credit card’s trip cancellation coverage is enough for them [3]. The standard terms for Visa Infinite’s Trip Cancellation and Interruption benefit, effective April 15, 2025, show why that check matters on a large trip [9]:

It pays up to $2,000 per insured person, and only for nonrefundable common carrier tickets, such as airline, cruise, rail, or bus fares, paid with the covered card or its rewards program [9]. Villa rentals, lodges, and private guides are not common carrier tickets.
You must charge the entire cost of the trip to the card [9].
The covered reasons are narrow: death, accidental injury, disease, or physical illness of you or an immediate family member, verified by a physician and preventing travel; or the carrier’s default due to financial insolvency [9].
Pre-existing conditions are excluded, defined as an injury, disease, or illness that occurred or manifested in the 60 days before the initial deposit or booking date [9].
You should notify the benefit administrator within 20 days, or as soon as reasonably possible, and you will need the itinerary, billing statement, proof of the nonrefundable amount and cancellation, and the supplier’s cancellation policy [9].

Individual issuers can and do offer richer terms than these network defaults, so read your own card’s benefit guide rather than assuming. A card benefit can be a pleasant layer under a proper policy. On a trip measured in five or six figures, it is rarely a substitute for one.

Medical care and evacuation abroad: the gap Medicare leaves

This is the part of travel protection that can matter far more than the trip cost. The State Department is blunt: the U.S. government does not pay medical costs for U.S. citizens traveling abroad, and Medicare and Medicaid do not pay for medical care outside the United States. It recommends buying travel health insurance before the trip and strongly recommends medical evacuation insurance for areas with higher risk or limited medical care [13]. It also notes that most health plans won’t pay for a special medical evacuation by air ambulance back to the United States, which it says can cost from $20,000 to $200,000 depending on where you are and your condition [14].

Original Medicare, in most cases, pays nothing abroad. Medicare.gov says you pay all costs in most cases, with narrow exceptions such as certain care on a cruise ship that is in a U.S. port or within 6 hours of one, and rare cases where a foreign hospital is closer than the nearest U.S. hospital that can treat you. Medicare drug plans don’t cover prescriptions bought outside the U.S. [10].
Some Medigap plans help, within limits. Medigap Plans C, D, F, G, M, and N include a foreign travel emergency benefit at 80%, while Plans A, B, K, and L don’t [11]. Maine’s insurance bureau sets out the standard terms: 80% of billed charges for medically necessary emergency care abroad, only if the emergency begins during the first 60 days of a trip, after a $250 calendar-year deductible, with a $50,000 lifetime maximum [12]. That is a backstop, not a plan for a serious illness on an extended voyage.
Your employer or private health plan may or may not travel with you. The State Department’s advice is to call your insurer and ask whether it covers emergency and routine care abroad, and whether it pays providers directly [13].

The State Department’s checklist is the right one to take to any policy: it should be valid in every country you plan to visit, cover the full length of the trip, include emergency medical care and medical transportation back to the United States, cover travel and lodging expenses, address all current medical conditions for you and your family, include the activities you plan to do, and offer a 24-hour help line [13]. The NAIC adds two questions for travel medical coverage: whether you need the insurer’s approval before getting care, and whether pre-existing conditions are excluded [3]. For voyages to remote regions, our luxury and expedition cruise guide covers the cruise line’s own obligations.

Baggage, watches, and jewelry

Travel baggage coverage is usually secondary, and the NAIC points out that your homeowners policy or credit card may already cover some of the same losses [2]. Maryland’s regulator warns that baggage coverage often limits or excludes items such as electronics and jewelry, and that it generally doesn’t cover items lost or damaged by an airline [15]. The NAIC’s advice is to check with your homeowners insurer, and to consider a rider for expensive items such as fine jewelry [3]. For a fine watch or a significant piece, a scheduled homeowners endorsement is usually the more serious answer than a travel plan’s baggage limit; our guide to insuring a fine watch or jewelry explains how a schedule works, and our customs guide covers crossing borders with it.

Buying it well: the order of operations

Price the risk first. Add up what you have paid or will owe that you can’t get back, using each supplier’s written cancellation schedule [15]. That is the figure trip cancellation protects.
Inventory what you already have. Your card’s benefit guide, your health plan’s overseas terms, Medigap if you have it, and your homeowners policy [3][10][15].
Buy early. CFAR usually must be bought within a set period after you book, and a storm that has already been named is likely too late [3]. If a pre-existing condition waiver matters to you, ask what its conditions are before the first deposit, since the seller must tell you whether and when the exclusion can be waived [7][8].
Insist on the full certificate before paying. Online sellers may show a short summary as long as you can reach the full policy electronically [7]. Read the full policy, not the summary.
Confirm the insurer, not just the brand. A plan sold by a travel company must identify the insurer and its contact information [5]. Your state insurance department can confirm the insurer is licensed and can answer questions about travel insurance [3][15].
Use the free look. You have at least 10 days after electronic delivery, or 15 after mailed delivery, to cancel for a full refund if you haven’t started the trip or filed a claim [7].

If you need to claim

Notify the insurer or benefit administrator as soon as you know you must cancel or return; the Visa terms, for example, ask for notice within 20 days or as soon as reasonably possible [9].
Cancel with every supplier promptly, in writing, and keep confirmation that each booking was cancelled [9].
Get the physician’s statement or other proof of the reason you cancelled at the time, not weeks later [9].
Keep the itinerary, receipts, statements showing how you paid, any credit vouchers you were offered, and each supplier’s cancellation policy [9].
Abroad, call the plan’s 24-hour assistance line before a major treatment or transport decision whenever you safely can [3][13].
If a claim in Illinois stalls or is denied without a clear reason, you can file a complaint with the Illinois Department of Insurance [16]. Elsewhere, start with your own state’s insurance department [3].

If the supplier itself has failed, the cancellation fee waiver it sold you may be worth nothing, which is why the insurance and payment-method protections matter. Our guide to credit card dispute rights explains what a card issuer owes you when a merchant doesn’t deliver.

The discerning traveler’s checklist

You know your total nonrefundable exposure, supplier by supplier.
You know which parts of any plan are insurance, which are a cancellation fee waiver, and which are assistance services.
You read your card’s trip benefit and know its limit, what it covers, and its pre-existing condition rule.
You know whether your health coverage works abroad, and whether it includes evacuation home.
If you want CFAR, you bought it within its deadline, insured every prepaid cost, and noted the percentage and the cancellation cutoff.
The fulfillment materials say whether the coverage is primary or secondary, and you read how pre-existing conditions are treated.
Fine watches and jewelry are covered by a schedule, not a baggage limit.
The 24-hour assistance number and policy number are saved on your phone and with someone at home.
You read the full certificate inside the free-look window.