Seabound Journeys · The Showdown

Faye vs. Freely

Two app-native carriers, one plan each, and a decision you can finish in ten minutes. Faye will not sell you more than $250,000 of medical cover at any price, because there is no higher tier to buy. Freely will sell you $500,000 and a million dollars of evacuation, and will not sell you cancel-for-any-reason at all. Two refusals. Pick the one you can live with.

Faye
A fixed price list with three good numbers on it, one benefit almost nothing else carries, and no way to buy your way past any of it.
One plan · $250,000 medical · $500,000 medical evacuationPlus $100,000 for non-medical emergency evacuationWaiver and CFAR both gated at 14 days
VS
Freely
The strongest limits in the series, sold by the day rather than by the trip, by a company that will not price a change of mind at all.
Essentials Plan · $500,000 medical · $1,000,000 evacuationAdventure cover bought by the day, not the fortnightCancel for any reason: not offered, at any price
Compared August 2026 · Limits, windows and plan structures change — verify for your policy
The One-Question Test
One question decides this one.

Neither company will sell you everything. Which missing thing would you rather do without?

01

The story that explains everything

Most comparisons are decided by what a carrier hands you. This one is decided by what each carrier will not sell you, at any price, to anybody.

Money buys you a great deal from both of these companies. It does not buy you everything.

Faye and Freely arrived from the same direction at almost the same moment. Faye launched in 2022 with venture funding and a team drawn from Allianz and Lemonade, then built the product the way a software company would: one plan, an app, digital claims. Freely launched in 2020, app-first rather than adapted to an app afterwards, and neither asks you to decode tiers whose names sound like sizes.

Then you reach the point where you would normally spend a little more to fix whatever the plan does not do, and both companies stop taking your order. Faye's emergency medical limit is up to $250,000 and it is fixed — no higher tier, no medical upgrade, so a traveller who wants more cannot buy it at any price. Freely publishes the numbers that traveller wishes he had: $500,000 of medical, $1,000,000 of evacuation, as standard. And Freely sells no cancel-for-any-reason, at any price.

Those are not the same kind of refusal, and the difference between them is the whole decision. Faye declines to go higher on a figure most sailings never test. Freely declines to sell the benefit built for the way cruises are actually bought — six to twelve months ahead, against deposits that do not come back. In the ordinary week, both plans are fine. In the week where something goes wrong, they fail in opposite directions.

Neither refusal is an oversight; both follow from selling a single product, because a plan with nothing above it cannot be upsold, which is exactly what makes it simple to buy and impossible to adjust. The tier ranges everybody complains about exist so that somebody can be sold the bigger one. Take the tiers away and that goes too.

One plan eachYou ask for moreThe answer is no
02

The quick verdict

Sixty seconds, no hedging. Read both columns, because the reason to choose one carrier here is usually printed in the other's list.

Faye, if…

  • You have deposits down on a sailing a year out and want cancel-for-any-reason at 75%, priced by one review at about a quarter on top
  • The itinerary carries political, security or disaster exposure: $100,000 of non-medical emergency evacuation
  • Up to $250,000 of medical is enough for the cruise you booked, which for a mainstream Caribbean week it is
  • You want a missed-connection benefit at all — it triggers after a covered three-hour delay
  • You are still inside fourteen days of your first trip payment

Freely, if…

  • A catastrophic medical event is what you are insuring against: $500,000 of medical and $1,000,000 of evacuation, both standard
  • Your cancellation exposure is small or already spent — nothing left to recover, nothing lost to the missing upgrade
  • The itinerary has a dive day and a glacier hike, and you would rather cover the Tuesday than the fortnight
  • You want one group behind everything: Zurich American underwrites, Cover-More sells, and Cover-More is Zurich
  • You would use 24/7 in-app telehealth at sea, where a video call can beat a ship's clinic
03

Everything here has a price except the two things that do not

These are the two most alike products in the series — one plan each, an app each, no tier puzzle in either. The scorecard still splits four–four, because what each withholds is different in kind.

Faye's refusal is about size. The limits are the limits, and Faye's own materials ask you to read the product as a fixed price list rather than a menu. It will still sell you plenty around the edges: extreme sports cover for skydiving or bungee jumping, rental car damage, vacation rental damage, and a pet package listed at $2,500 for pet medical expenses plus smaller sums for kennelling. Not one of them raises the medical or evacuation figure by a dollar. Faye sells the periphery and keeps the middle.

Freely's refusal is about a reason. It will sell you the strongest limits on this site as standard, adventure cover metered down to a single day, and pre-existing condition cover as an optional benefit with its own terms. What it will not sell, at any figure, is the right to cancel for a reason nobody wrote down — a benefit every other carrier reviewed here offers somewhere, which makes the absence a decision rather than an accident.

Put it plainly and the page collapses into one line. Faye caps how much it will pay. Freely caps why it will pay. A cap on the amount is a number you can hold against your own itinerary and judge in a minute. A cap on the reasons stays invisible until the day you need one that is not listed.

One possibility worth naming before the evidence stacks up: neither refusal may touch you. Book six weeks out, pay in full, sail the western Caribbean, come home. Insurance is bought for the other week.

04

Two price lists, and what is actually printed on each

Four headline entries decide most of this booking, and Freely takes two by a distance. Of the two Faye takes, one is not a number at all.

Emergency medical: Faye publishes up to $250,000, which clears the working floor this site uses for international cruising and which cannot be moved. Freely publishes up to $500,000 of emergency medical and dental, included in the bundle rather than reserved for a tier you have to find. Twice the number, in a product of identical shape.

Evacuation: Faye carries up to $500,000 for emergency medical evacuation, described in its own FAQ as covering air ambulance where a condition is acute, severe or life-threatening and adequate treatment is not available locally. Freely carries up to $1,000,000 of evacuation and repatriation. Both are multiples of the usual $250,000 minimum, and the gap counts most where the nearest hospital is a helicopter ride away.

Non-medical emergency evacuation: here the direction reverses. Faye includes up to $100,000, kept separate from the medical figure, covering transport from a place of danger to a place of safety after a natural disaster or a political or security emergency. Very little else in this series includes it, and the Freely materials reviewed here name no equivalent.

Cancel for any reason: Faye sells it as a paid add-on at 75%, cancel at least 48 hours before departure, buy within 14 days of your first trip payment. Freely does not sell it at a higher price, on request, or on a plan you have yet to find. The fourth line of its price list is blank.

Faye's one plan, in full

  • Up to $250,000 emergency medical — fixed, no upgrade path
  • Up to $500,000 medical evacuation, air ambulance named
  • Up to $100,000 non-medical emergency evacuation
  • CFAR at 75%, paid add-on, cancel 48 hours out
  • No interrupt-for-any-reason, at any price

The Freely Essentials Plan, in full

  • Up to $500,000 emergency medical and dental, included
  • Up to $1,000,000 evacuation and repatriation, included
  • Accidental death, belongings and interruption
  • Pre-existing condition cover as an optional benefit, own terms
  • No CFAR and no IFAR, at any price
Round 1 — the call

Freely on the limits, by a factor of two. Faye on the line Freely leaves blank, and on the line almost nobody else prints. Which pair matters depends on whether your money is at risk before departure or after it.

05

Faye's whole offer fits on one page, and there is no second page

One plan, six published lines, and no version that costs more. That is the best thing about the product and its only real limitation.

There is no tier to choose and no upgrade path for either figure that matters, which is why Faye's guide asks you to read the product as a fixed price list. Nothing sits above it.

The trade arrives immediately, because those medical and evacuation figures are the top of the product rather than a starting point. For a Caribbean week that is fine. For a Greenland expedition it is the first question to sit with and probably the last, because willingness to pay changes nothing.

The $100,000 for non-medical emergency evacuation is the line worth stopping on. A company that will not sell a dollar more of hospital cover at any price includes a hundred thousand dollars for getting you out of a country that has stopped working.

Then the fourteen days. Faye gates both the pre-existing condition waiver and the cancel-for-any-reason upgrade at 14 days from your first trip payment, where much of the market allows 21; its own guide records that as the joint-tightest window this series has found. You must also be medically able to travel when you buy. Book a year ahead and a fortnight passes without ceremony. This is the one refusal here you can defeat by being early.

A further condition sits behind that upgrade, and it only bites people who plan well. One review flags that buying cancel-for-any-reason blocks you from increasing your insured trip cost afterwards, so excursions added in March and flights booked in June may sit outside the cover. The response is slightly absurd and completely correct: estimate your total trip cost generously rather than accurately.

The rest behaves as the headline suggests. Base cover already includes non-extreme activities — Faye names surfing, hiking and snorkelling — while paid add-ons handle extreme sports, rental cars, vacation rentals and pets. Missed connection triggers after a covered delay of more than three hours, the right shape for a cruise, though Faye's FAQ puts the amount at up to $500 and a 2023 review at $200 per person.

Round 2 — the call

Faye, on everything except the number people quote at you. Simplicity, the non-medical evacuation benefit and a cheap cancel-for-any-reason upgrade are real advantages. The fourteen-day window is the thing most likely to cost you the policy you wanted.

06

Freely will sell you a Tuesday. It will not sell you a change of mind.

The most rational structure in the series sits beside the most consequential omission in it, inside the same plan.

Start with the part nobody else offers. The bundled Essentials Plan runs the whole trip, and adventure and extreme activities sit outside it, as they do everywhere. What Freely adds is Daily Boosts: cover you switch on for particular days rather than the whole booking. Sea days need nothing. The dive in Cozumel gets a boost for that day, the quiet port day after it gets none, the glacier hike in Alaska gets one of its own.

On a two-week sailing the physical risk is rarely spread evenly across the fortnight. It sits in two afternoons. Every other carrier here asks you to buy adventure cover for the whole trip or go without it. Freely lets you buy it for the Tuesday.

Whether it saves you money is a different question, and one this page cannot answer. Freely quotes rather than publishing rate tables, so any figure you have read elsewhere is a sample rather than a rate.

Now the blank space. Freely sells no cancel-for-any-reason at any price, on any plan, and every other carrier reviewed on this site offers it somewhere. Cruises are booked six to twelve months out against non-refundable deposits, the precise situation the benefit was invented for. Book eleven months ahead, then need to cancel for a reason that is not on the covered list, and this policy does nothing. Not a reduced payout. Nothing.

That is a fair trade in the abstract and a bad one for this way of travelling. A policy without cancel-for-any-reason is not worse in general; it is a worse fit for a purchase you commit to a year before you make it.

One more thing to read before assuming. Freely offers pre-existing medical condition cover as an optional benefit with its own terms, rather than the standard waiver most of this market runs on a 14-to-21-day clock.

And one refusal both companies share, which the scorecard below records as a tie at the bottom of the scale. Neither sells interrupt-for-any-reason, so once you have left the pier, both respond to the reasons printed in the policy and to nothing else.

Round 3 — the call

Freely on structure, comprehensively. Daily Boosts are the most intelligent thing any carrier here has built. None of it touches the missing upgrade, because a benefit that does not exist cannot be outweighed by one that does.

07

An A+ and an F, and they are not about the same company

Search Faye and you will find both grades, and both are real. They measure different things about different entities, and the confusion is itself the finding.

Faye is a brand rather than an insurer, which is where the tangle starts. Its policies are underwritten by United States Fire Insurance Company, part of Crum & Forster, with Great American also named on its plans. AM Best upgraded Crum & Forster members to A+ (Superior) on 28 August 2025, and that grade answers exactly one question — can the company pay what it owes — on which Faye is in good order.

The F is a different measurement, of a different entity, by a different organisation. A 2025 review found the Faye brand entity, Zenner Insurance Services, carrying an F rating from the Better Business Bureau, which grades complaint handling and business history rather than solvency. A strong balance sheet and a poor complaint record coexist routinely. It is also a report of a grade that moves.

What neither number establishes is how often Faye pays claims. Nothing published does.

Freely's arrangement is the tidier one, and tidiness is worth something. Zurich American Insurance Company underwrites the US policies, provided through the licensed agency Cover-More, Inc., which is itself a Zurich company. Brand, agency and insurer sit inside one group, which is one fewer party to chase when a claim goes sideways.

Both structures illustrate the same unglamorous fact. Faye is the fourth name in this series running at least partly through the same underwriting company — Seven Corners and IMG are two of the others, and Crum & Forster owns Travel Insured International outright, which is four consumer brands and one balance sheet. Zurich is the second name here behind two consumer brands, since it also underwrites newer Travelex policies. A shopper comparing brand names is very often comparing two marketing departments.

The last thing they share is youth. Faye launched in 2022 and Freely in 2020, so the buying experience at each is the cleanest here and the record to judge either one on is the shortest.

Round 4 — the call

A tie, and a well-documented one. Both sit behind serious underwriters and both say who they are. Read the rating at the source, and read each grade next to what it measures.

08

The showdown scorecard

Same scale, every category that decides this booking. Fit scores — not quality scores. Both are judged on the whole product, because in both cases the whole product is one plan — nothing cheaper to mark down, nothing dearer to reward.

Seabound Showdown Scorecard
FayeFreely

Every score is Seabound's judgement, not an insurer's figure. A benefit that cannot be bought at any price is scored as an absence rather than a low number, because that is what it is.

Emergency medical limitFy 8Fr 10
Up to $250,000 against up to $500,000, both standard. Faye clears the working floor, and is held back only because the figure is fixed there.
Evacuation limitFy 9Fr 10
Up to $500,000 of medical evacuation against up to $1,000,000, both multiples of the $250,000 usually called a sensible minimum. Freely has more of it.
Non-medical evacuationFy 9Fr 4
Faye's clearest win. Up to $100,000 for disaster, unrest and security emergencies. The Freely materials name no equivalent.
Cancel for any reasonFy 8Fr 1
The widest gap on the board. Faye pays 75%, cancel 48 hours out, at a price one review put near a quarter on top. Freely sells none.
Pre-existing conditionsFy 5Fr 5
Tied, for opposite reasons. Faye runs a real waiver on a 14-day clock, the joint-tightest here. Freely runs optional cover with its own terms.
FlexibilityFy 4Fr 10
Fixed limits, no IFAR, and a CFAR condition that reportedly blocks raising your insured trip cost — against Daily Boosts, which nothing else here offers.
SimplicityFy 9Fr 8
Both are one plan, no tier to decode, no state-renamed twin. Freely loses a point on quote-based pricing.
Cruise-specific benefitsFy 6Fr 5
Neither builds a cruise product. Faye at least carries missed connection after a three-hour delay; Freely names none.
Who stands behind itFy 7Fr 8
United States Fire, part of Crum & Forster, at A+ (Superior) since August 2025. Freely edges it: Zurich underwrites, and Cover-More is Zurich too.
Interrupt for any reasonFy 2Fr 2
The row where both refuse the same thing. Neither sells IFAR, so once you have sailed both answer to the listed reasons.
Rows wonFaye 4Tied 2Freely 4

Four rows each is the most genuinely even result this series has produced, and the two ties are the tell. Both are rows where a benefit is missing or restructured, not rows where the companies agree on a strong number. Neither sells interrupt-for-any-reason. Neither runs a pre-existing arrangement you can lean on without reading it. The board is level because these products are equally good and equally incomplete, in places that do not overlap.

09

Now the honest part

The things that complicate everything above, including the parts that undercut this page's own conclusion.

The strongest argument against this page is that most people never cancel. On the published numbers Freely wins outright: double the medical, double the evacuation, both standard, in a product just as easy to buy. The missing upgrade costs you nothing until the day you want to cancel for a reason nobody wrote down, and for most bookings that day never comes.

Neither source guide publishes a price, and neither does this one. Freely quotes rather than publishing rate tables, and Faye's cancel-for-any-reason pricing rests on one review's estimate. Anybody telling you which is cheaper without quoting both is guessing.

Faye's own materials contradict themselves on a benefit this page has repeated twice. Missed connection is up to $500 in Faye's FAQ and $200 per person in a 2023 review, and nobody has reconciled them. Read every other number here as the up to amount it says it is.

The F rating deserves less weight than it will get. It is a 2025 third-party report of a grade that moves, against the brand entity rather than the insurer, measuring complaint handling rather than solvency. It will still be the most memorable thing here for some readers, because a letter grade is easier to hold than a structure.

And the scorecard flatters the idea that these are different products. Ten rows, four–four, two ties: it reads like a close contest between rivals, when structurally they are nearly the same thing — one plan, an app, digital claims, no tiers, a young company, a serious underwriter, no interrupt-for-any-reason. Strip out the two refusals and most of the rest is a coin toss dressed up in gauges.

10

The flagship duel

Neither company has a flagship in the usual sense, which is rather the point of both. Where a carrier spends, and where it refuses to, is the clearest statement it makes about you.

◆ Faye's only plan

The one plan

No tier name, because there is nothing to distinguish it from

Up to $250,000 of emergency medical and up to $500,000 of medical evacuation, plus a separate $100,000 for non-medical emergency evacuation. Cancel-for-any-reason at 75% as a paid add-on, no IFAR, and both the waiver and the upgrade gated at 14 days.

The pricing tellFaye prices the change of mind cheaply and the limits not at all. One review put the CFAR upgrade near a quarter on top of the premium where much of the market charges half again — while the same company will not sell a dollar of extra medical cover at any figure. It sells flexibility about whether you go, none about what happens once you have gone.
◆ Freely's only plan

The Freely Essentials Plan

Everything bundled · adventure cover metered by the day

Up to $500,000 of emergency medical and dental and up to $1,000,000 of evacuation and repatriation, both included rather than upgraded to. Accidental death and disability, belongings and trip interruption bundled alongside, pre-existing condition cover optional, and Daily Boosts for the days you dive.

The pricing tellFreely spends everything on the two limits that cover catastrophe and nothing at all on the benefit that covers regret. It will meter adventure cover down to a single Tuesday and will not price a change of mind at all. That is a company built around what happens to you, sold into a market that mostly claims for what happens at home.
11

Head to head, on paper

Every figure is an up to amount, taken from each carrier's published materials and verified July 2026. Limits vary by state; the policy issued to you governs.

FayeFreely
Plan structureOne plan, no tiers, no upgrade pathOne bundled Essentials Plan, plus Daily Boosts
Emergency medicalUp to $250,000 — fixed at any priceUp to $500,000 medical and dental, included
EvacuationUp to $500,000 medical evacuation; air ambulance namedUp to $1,000,000 evacuation and repatriation
Non-medical evacuationUp to $100,000, separate from the medical figureNo equivalent named in the materials reviewed
Cancel for any reason75%, paid add-on; buy within 14 days, cancel 48+ hours outNot offered at any price, on any plan
Interrupt for any reasonNot offeredNot offered; interruption for listed reasons
Pre-existing conditionsWaiver gated at 14 days from your first trip paymentOptional cover with its own terms, not a waiver
Adventure coverPaid add-on for extreme sports; base covers snorkellingDaily Boost — bought for the day you dive, ski or climb
Missed connectionFAQ says up to $500 after a three-hour delay; a 2023 review says $200 eachNone named in the materials reviewed
UnderwriterUnited States Fire Insurance Company, part of Crum & Forster; Great American also namedZurich American Insurance Company, through Cover-More, Inc., itself a Zurich company
Ratings on the recordAM Best A+ (Superior) for Crum & Forster members, 28 August 2025; a 2025 review found brand entity Zenner Insurance Services at F with the BBBCheck the rating at AM Best rather than on a reseller page
12

Who should actually pick which

Faye
Booked eleven months out, deposit already gone

This is the booking cancel-for-any-reason was invented for, and Freely does not sell it. Faye pays 75% if you cancel at least 48 hours before departure. Buy within 14 days of that first payment, and estimate your trip cost generously rather than accurately.

Freely
Alaska or the Galapagos, with a dive day and a hike

Up to $500,000 of medical and up to $1,000,000 of evacuation, the headroom you want when the nearest hospital is a helicopter ride from the ship. Then Daily Boosts, so adventure cover is bought for the two afternoons carrying the risk.

Freely
Paid in full, sailing in six weeks

Nothing left to recover means nothing lost to the missing upgrade, and the argument against Freely evaporates. What remains is the strongest pair of limits on this site — and pre-existing terms to read against your own quote first.

Faye
A repositioning through somewhere politically uncertain

Faye's $100,000 for non-medical emergency evacuation covers transport from a place of danger to a place of safety after a disaster or a security emergency, and very little else here includes it at all. On that itinerary it outweighs the medical gap.

13

Quick answers

Which one has the better medical and evacuation limits?

Freely, by a factor of two on both. It bundles up to $500,000 of emergency medical and dental and up to $1,000,000 of evacuation and repatriation as standard, where Faye publishes up to $250,000 of medical and up to $500,000 of medical evacuation. Faye's figures still clear the working floor this site uses for international cruising, and Faye carries one limit Freely does not: up to $100,000 of non-medical evacuation.

Does Freely really sell no cancel-for-any-reason?

None at any price, on any plan. Every other carrier reviewed on this site offers cancel-for-any-reason somewhere in its range, and cruises are typically booked six to twelve months ahead against non-refundable deposits. That is exactly the situation the benefit exists for. If your reason for cancelling is not on the covered list, nothing here reimburses you.

Can I buy a higher medical limit from Faye?

No. There is one plan, no higher tier and no medical upgrade, so a traveller who wants more than $250,000 of cover cannot buy it at any price. The paid add-ons cover extreme sports, rental car damage, vacation rental damage and pets, and none of them raises the medical or evacuation figure. Note also that both the waiver and the cancel-for-any-reason upgrade are gated at 14 days from your first trip payment.

What is a Daily Boost?

Cover you switch on for particular days rather than the whole trip. Adventure and extreme activities sit outside the bundled Essentials Plan, so if you dive in Cozumel on Tuesday and hike a glacier on Friday, you boost those two days instead of paying across the fortnight. The bundled cover runs throughout regardless, and nothing else in this series prices cover by the day.

Faye's underwriter is rated A+ but I have seen an F. Which is it?

Both, because they measure different things about different entities. AM Best rates financial strength, and Faye's policies are underwritten by United States Fire Insurance Company, part of Crum & Forster, whose members were upgraded to A+ (Superior) on 28 August 2025. The Better Business Bureau rates complaint handling, and a 2025 review found the Faye brand entity, Zenner Insurance Services, holding an F there. Check the listing yourself, since these grades move.

14

The verdict — an honest fork, not a tie

One caps how much it will pay. The other caps why.

Faye

The one you can still cancel

Cancel-for-any-reason at 75%, priced unusually well, plus $100,000 of non-medical emergency evacuation that very little else here carries. Buy it when your money is at risk before you sail — inside fourteen days of the first payment.

VS
Freely

The one that pays when it goes wrong

Up to $500,000 of medical and up to $1,000,000 of evacuation as standard, adventure cover metered down to a single day, one group behind everything. Buy it when your money is at risk after you sail rather than before.

Neither of these carriers is better than the other, and here that is not a hedge — the question has no answer. The one worth asking is where your money is actually exposed. Cash committed before departure points at Faye. A body a long way from a hospital points at Freely. Fourteen days from your first payment decides whether Faye is on the table at all.

15

Still torn?

Tell us what is already paid for, and where the ship goes.

What you would lose if you cancelled, how far the itinerary gets from care, and which deadline bites first.

Faye or Freely for us?Do I actually need cancel-for-any-reason?Is $250,000 of medical enough for my cruise?How many days do I have left to buy?What is a Daily Boost worth?

Seabound Journeys is an independent travel advisory and does not sell insurance · answers are general information, not advice about your policy.

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