Three kinds of insurance matter on a bike tour: coverage for the money you'd lose if you cancel, coverage for you if you crash, and coverage for your bike. You won't always need all three.
Start with cancellation. If you're flying to a bike tour, buy a policy. If you're driving to one in the US and the tour gives you a full refund up to a cutoff date, you don't need cancellation coverage at all. What decides it is how much money you'd lose if you had to cancel, and the date you'd start losing it.
I run our trips and I ride every mile of them. I set our refund policy, and I've read plenty of other tour companies' policies and insurers' terms. Here's how I'd work it out for any guided trip, ours included.
Start with the tour company's refund policy
Travel insurance pays you back for money you can't get back any other way. So the first question isn't which policy to buy. It's how much of the trip is refundable, and until when.
Ask the tour company two things before you book. What do I get back if I cancel? And does that change depending on the date? A lot of operators use a sliding scale: you lose the deposit first, then a percentage of the trip, then all of it, and some add an admin fee on top.
Ours has one date. Every booking has a non-refundable date, and it's in your confirmation email and on your booking page. Cancel before it and you get back everything you've paid, deposit included. Cancel on or after it and you get nothing back. There's no fee and no sliding scale.
Add up what you'd actually lose
Write down every cost you can't get back, and the date each one stops being refundable:
- The tour, from the operator's refund cutoff onward.
- Your flights. Read the fare rules. Some fares come back as a credit with the airline rather than cash. Check whether a basic economy fare allows any changes at all.
- Any hotel nights you booked yourself before or after the trip on a prepaid rate.
That total is your number. If losing that amount wouldn't bother you, you don't need cancellation coverage. If it would, you do.
What trip cancellation insurance covers, and what it doesn't
Standard trip cancellation pays you back when you cancel for a reason the policy lists. The usual ones are you or a close family member getting sick or injured, or a death in the family. It doesn't pay because you changed your mind, work got busy, or you didn't get the training in.
Two things to check before you buy:
- Read the exclusions list for the word cycling. A policy that excludes it won't help you on a bike tour.
- Read how it treats a pre-existing condition. Policies that cover one set a short window after your first trip payment for you to buy in. If you've got a knee problem, a heart condition or anything else you see a doctor about, buy early.
Is Cancel For Any Reason worth it?
Cancel For Any Reason, or CFAR, is an add-on to a standard policy. It pays out when your reason isn't on the list, including just deciding not to go. Here's how it works with most insurers:
- You buy it within about 10 to 21 days of your first trip payment.
- You have to insure the full prepaid, non-refundable cost of the trip.
- You cancel at least 48 hours before you leave.
- It pays back 50% to 75%, not all of it.
- It adds roughly 40% to 60% to the price of the policy.
On a trip with a steep sliding scale, CFAR is worth pricing. On a trip like ours, where you get everything back up to the non-refundable date, you'd be paying extra mostly to cover the weeks between that date and the start. Work out what those weeks put at risk and decide from that number.
Your own health insurance pays first
On a trip in the US, your own health insurance is what pays if you crash. We don't provide health coverage, so check one thing on your plan before you go: how it treats care in another state. If your plan has a local network, find out what it pays at a hospital outside it.
If you're on Original Medicare, it covers you in every US state. It doesn't cover you outside the US, and a lot of private plans cover little or nothing abroad either. That's the main reason a policy with emergency medical coverage matters more on an international trip than a domestic one.
What about getting home after an injury? Say you break a collarbone on day two. You'll need to change your flight, get yourself home with one working arm, and get your bike home too. A policy with trip interruption and medical transport benefits pays for that part.
The prices and coverage in the rest of this post are what each company listed in October 2026. They can change, so check the company's own page before you buy.
USA Cycling's 365 Insurance
This is one I've looked at for myself. USA Cycling sells an add-on called 365 Insurance for $365 a year. You need a membership first, and the cheapest one, the non-racing fan membership, is $40 a year on auto-renewal, so the total comes to about $405 a year.
It pays up to $50,000 per accident, with no deductible, when you're hurt riding a bike: a training ride, a group ride, a gran fondo or your commute, anywhere in the world. A race counts only if USA Cycling sanctions it. It's secondary to your health plan, so it pays what your own plan leaves you owing, your deductible and out-of-pocket costs, up to that limit. If you don't have health insurance, it covers up to the $50,000 on its own.
Read the conditions before you count on it. You need emergency room treatment within 72 hours of the crash, it doesn't cover your bike, and an e-bike has to be under 750 watts. The details are on USA Cycling's 365 Insurance page.
Most travel policies cover your bike badly
Baggage coverage on a standard travel policy has a limit for everything you've packed, and a lower limit for any single item. Some policies leave sports equipment out entirely. Neither one is designed for a road bike that cost thousands of dollars. If you're flying with it, I went through what the airlines charge in how much it costs to fly with your bike.
So sort your bike's coverage separately:
- Ask your homeowners or renters insurer whether your bike is covered away from home, and up to what amount. Some policies cover it, some cap it low, and some need it listed on its own.
- Look at a specialist bicycle policy. These cover crash damage and theft, and many cover the bike while you travel.
- Ask the tour company whether its insurance covers your bike while it's in its support vehicle or at a bike shop. Don't assume it does.
Bike insurance through USA Cycling
USA Cycling's bike insurance partner is BikeInsure, underwritten by Great American Insurance Company. It covers crash damage, and theft if you add it:
- Plans start around $16 a month for damage only, or $20 a month with theft. A $5,000 bike on its casual riding plan, with theft, is about $21 a month.
- The deductible is $150 per claim, and it pays what it costs to replace the bike, with nothing taken off for its age.
- The casual riding plan covers you in the US and Canada. The race plan covers you anywhere.
- If you fly with your bike, it has to be in a hard case to be covered, and theft while an airline or shipping company has it isn't covered.
USA Cycling members get a discount, though BikeInsure's site doesn't say how much. It's at bikeinsure.com.
Velosurance, underwritten by Markel, is another option. It starts at about $100 a year, you pick your own deductible, and USA Cycling members get 10% off. You can add worldwide coverage for a single trip, which covers a bike an airline loses or damages. It's at velosurance.com.
Where to compare travel insurance policies
These sites put policies from many insurers side by side, so you can check the cycling exclusion and the price in one place:
- InsureMyTrip compares about 20 insurers and has licensed agents you can ask.
- Squaremouth compares more than 20 insurers and has an adventure and sports category.
- TravelInsurance.com compares plans from insurers including Seven Corners and Trawick.
So, do you need it?
If you're driving to a trip in the US and you'd cancel before the refund cutoff if you were going to cancel at all, you don't need cancellation coverage. Check your health plan for out-of-state care, check your bike's coverage, and you're done.
If you're flying, buy a policy that covers your flights and the trip from the refund cutoff onward. Make sure cycling isn't excluded, and buy it soon after your first payment.
If your bike is worth more than a travel policy's single-item limit, cover it on its own.
If you ride a lot, look at USA Cycling's 365 Insurance for what your health plan would leave you owing after a crash.
We don't sell insurance and we don't take a commission from anyone named here. Every trip we're running, with its dates, is on our trips page.