Introducing ThinkInsurance: Travel Insurance Built into Your Booking Engine

The context: why travel insurance, and why now?

At ThinkGrowth, we shared that a lot of last year’s work has been focused on two themes: simplifying operations and increasing conversions in your booking engine. Those themes are what led to the new front desk dashboard, the redesigned housekeeping and task system, dynamic messaging templates, ThinkAccounting, ThinkPayments, and now, ThinkInsurance.

For years, properties have been telling our team some version of the same story:

• “Our cancellation policy is clear, but we still end up making exceptions.”
• “Guests are used to insurance on flights and cruises; they expect something similar from us.”
• “I want to protect my revenue without feeling like I’m arguing with people on the phone.”

Travel insurance isn’t a new concept, of course. What’s new here is the way it’s being integrated directly into your booking flow and operations, in a way that feels natural for both guests and staff.

What is ThinkInsurance?

ThinkInsurance is the name we’re using internally for our integration with TravelSafe, a well‑established travel insurance provider. When you enable it, your guests see an option to add trip protection as part of their online booking, both on ThinkWeb sites and the standard ThinkReservations booking engine.

Behind the scenes, TravelSafe handles:

• Determining whether the guest is eligible (based on their state/region and dates)
• Displaying the correct plan details and pricing
• Emailing the guest their insurance confirmation and policy wording
• Processing and adjudicating any claims

Your role is deliberately simpler: you keep your existing cancellation policies, see which guests purchased coverage, and point those guests to TravelSafe when they need to file a claim.

How it appears to your guests

Once ThinkInsurance is enabled in your PMS:

1. A guest starts an online reservation as usual.
2. After they enter their state or region, the system checks whether travel insurance is available for that location and their dates.
3. If they’re eligible, they see a clearly labeled section in the booking flow, such as:
   Add Travel Protection? LodgingSafe Prestige – [Premium Amount]
   What’s covered: Trip Cancellation (100% of trip cost), Trip Interruption (150%), Travel Delay, Baggage, Emergency Medical, Accidental Death & Dismemberment, and more.
4. Links to Policy Wording, Product Information, and Terms & Conditions are displayed so the guest can read the fine print before they decide.
5. The guest chooses either Yes, add protection or No thanks, then continues to confirm.

There are a few important nuances here:

• Guests in certain states or regions may not see the offer at all if trip insurance is not permitted there.
• Same‑day reservations are typically not eligible, so the offer will be hidden in those scenarios as well.
• Guests can generally purchase up to the day before departure. For “Cancel For Any Reason” (CFAR) benefits, they need to purchase within 21 days of their initial payment.
• From their perspective, this looks very similar to what they’re used to when they book flights or cruises online—which subtly signals professionalism and modernity without you having to build a custom integration of your own.

How it works for your team

One of the concerns we heard repeatedly in our planning meeting was very practical: “What exactly is my front desk supposed to say when someone calls and says, ‘I bought travel insurance’?

To make sure your staff isn’t left guessing, ThinkInsurance is designed to tie back into ThinkReservations:

• Reservation visibility. When a guest purchases travel insurance during booking, that information is associated with their reservation, including the claim number they’ll need when contacting TravelSafe. Your team can quickly verify, “Yes, I see you purchased travel insurance for this stay.”
• Clear division of responsibility. You maintain your normal cancellation policy. If the cancellation falls inside the non‑refundable window, your staff can explain the policy and then direct the guest to TravelSafe with their claim number and contact details.
• 14‑day free look. Guests have a 14‑day period in which they can cancel the insurance itself for a refund, as long as they haven’t started travel or filed a claim. This is handled by TravelSafe, but it’s helpful for your team to know the rule of thumb when questions come up.

This structure is intentional. You’re not put in the position of deciding what’s “covered” or negotiating on behalf of an insurer. Instead, you gain a straightforward way to support your policies and your guests at the same time.

Pricing: what you should know (but don’t have to calculate)

TravelSafe calculates premiums based on the cost of the covered trip. At the time of writing:

• The premium is 8.18% of the room cost,
• with a minimum premium of $41

These numbers are displayed to the guest right in the booking flow. You don’t quote or collect the premium separately; it’s processed as part of the online reservation according to the integration rules.

Guests who want broader CFAR coverage need to purchase within 21 days of their initial deposit or payment. After that window, they can still buy standard travel protection (subject to eligibility), usually up to the day before arrival.

If that sounds like a lot to memorize, that’s exactly why we’ve documented the details in our support article and rely on TravelSafe’s own product information and terms for the fine print.

How ThinkInsurance interacts with your cancellation policies

This is probably the most important conceptual piece.

ThinkInsurance is not a replacement for your cancellation policies. It sits alongside them:

• Your cancellation policy defines what happens to the reservation if a guest cancels at different times or under different circumstances.
• Travel insurance defines what happens to the guest’s financial loss when those cancellations (or other covered events) occur.

In practice, that might look like:

• Your policy states that cancellations within 14 days are fully non‑refundable.
• A guest cancels 5 days before arrival due to a covered medical reason.
• You can keep the revenue per your policy.
• The guest can file a claim with TravelSafe to be reimbursed for their loss, subject to the policy terms.

Of course, you can always choose to make exceptions—it is hospitality, after all. But you’re no longer backed into a corner where your only options are “lose the revenue” or “lose the relationship.”

Several people on our team, including Allison Bruen (Director of Customer Success), specifically pushed to highlight this in the rollout communications: properties should feel excited about travel insurance because it helps them enforce the policies they already have, not because it forces them into new ones.

Enabling, disabling, and controlling ThinkInsurance

ThinkInsurance is available to all ThinkReservations customers and is controlled directly in your PMS settings.

To manage it:

1. Log in to your PMS account.
2. Go to Settings.
3. Click Travel Insurance in the left‑hand menu.
4. Choose one of:
   • Enable Now – turns travel insurance on for your booking engine.
   • Opt Out – disables it.

You can change this setting at any time. There’s no long‑term lock‑in; if you test it for a few months and decide it doesn’t align with your brand, you can turn it off, and vice versa.

Because the feature is deeply integrated and doesn’t require custom setup per property, we are enabling ThinkInsurance by default for all customers on January 14, with the opt‑out path clearly documented and linked in our email and in‑app messages.

Frequently Asked Questions

Is this only for ThinkWeb customers? No. Travel insurance is offered through the online booking engine itself, so it’s available to both ThinkWeb and non‑ThinkWeb sites using the ThinkReservations booking engine.

Can guests buy insurance on phone reservations? Right now, ThinkInsurance is focused on online reservations, where we can present all of the required disclosures and links in a clear, compliant way. In our internal planning, we discussed future options like sending a secure payment link so phone‑booking guests can add insurance themselves, but that’s not the first version we’re rolling out.

How does a guest cancel their insurance if they change their mind? TravelSafe offers a 14‑day “free look” period. During that time, a guest can request a refund of their insurance premium, provided they haven’t started their trip or filed a claim. They can contact TravelSafe using the email or phone details in their confirmation. Our team has tested this and confirmed that requesting a cancellation via email works as expected.

What if a guest says they bought insurance, but we don’t see it? First, check the reservation in ThinkReservations to see whether travel insurance is listed and whether a claim number appears. If it isn’t there, guests should refer to their TravelSafe confirmation email. In some rare edge cases (for example, a guest buying insurance independently through another channel), you may not see it tied to the reservation in your PMS, and they’ll need to work directly with TravelSafe to confirm their coverage.

Will this change how we account for revenue? Your room revenue and cancellation revenue follow your existing policies and remain in ThinkReservations as usual. Travel insurance premiums and any claim payouts are handled through TravelSafe’s systems. If you are using ThinkAccounting, your accountant can help you interpret any reports related to this and make sure your financials stay clean and comparable over time.

Do we have to explain coverage details to guests? No. That’s intentionally TravelSafe’s role. Your responsibility is to explain your property policies clearly, confirm whether a guest purchased travel insurance, and provide or confirm their claim details. All specific coverage questions (what’s included, what’s excluded, how a claim is decided) should be directed to TravelSafe using the contact information in the guest’s confirmation.

Travel plans will always change. Storms roll in, kids get sick, flights are missed. What ThinkInsurance offers is not a magic shield against all of that, but a more professional, more sustainable way to handle it—for you and for your guests.

And that, in the bigger picture of ThinkGrowth and where the platform is headed, is exactly the kind of change we’re trying to make: use technology to quietly do more of the hard work in the background, so the conversations at your front desk can stay focused on hospitality instead of friction.​