The most common mistake travelers make when googling “Progressive Travel Insurance” is assuming Flo will be the one handling their claim if their luggage goes missing in Lisbon. In reality, Progressive acts more like a high-end concierge than a direct insurer for travel. They’ve partnered with InsureMyTrip, a comparison engine that effectively “shops” the market for you. This means when you buy through the Progressive portal, you aren’t getting a Progressive-branded policy—you’re getting a curated selection from giants like IMG, Trawick, or Seven Corners. This is actually a major advantage for you, provided you know which levers to pull.
Because Progressive doesn’t underwrite these policies themselves, they have the flexibility to offer you a massive range of plans. Whether you’re a 22-year-old backpacker looking for a “bare-bones” medical plan or a 70-year-old retiree on a luxury Rhine River cruise, the platform adapts. However, this flexibility comes with a “Paperwork Penalty.” Since your policy might be with one company and your payment processed through another, knowing exactly who to call when a flight gets canceled is the difference between a refund and a headache.
The “InsureMyTrip” Factor: How Progressive Actually Works
When you click the “Travel” tab on the Progressive website, you are essentially entering a specialized portal of InsureMyTrip. As of now, this is a strategic partnership designed to leverage Progressive’s massive user base.
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The Advantage: You get to compare multiple quotes in one place, but with the added “brand trust” of Progressive’s customer service backing.
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The Discount: If you are an existing Progressive auto or home policyholder, you might see “Loyalty” pricing or easier integration, though travel insurance isn’t typically “bundled” in the traditional sense for a multi-policy discount.
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The Variety: You can find everything from Single-Trip Comprehensive to Annual Multi-Trip and even International Medical-only plans.
Comparison of Plan Types Offered Through Progressive
| Plan Type | Best For… | Key Feature |
| Comprehensive | Standard Vacations | Trip Cancellation, Medical, and Luggage. |
| Travel Medical | Digital Nomads / Expats | High medical limits, low/no cancellation cover. |
| Annual Multi-Trip | Frequent Flyers | Covers all trips in a 365-day period for one price. |
| Group Plans | 10+ Travelers | Discounted rates for mission trips or large families. |
The “Primary vs. Secondary” Medical Debate
One of the biggest “gotchas” in travel insurance is the medical coverage type. Many travelers don’t realize that “Secondary” coverage (which is common on cheaper plans found through the Progressive portal) requires you to file a claim with your home health insurance first.
If you are a Medicare recipient, this is a nightmare because Medicare almost never covers you abroad. You’ll be forced to wait for a Medicare denial letter before the travel insurance pays a cent.
Editor’s Tip: Always filter for “Primary Medical” coverage if you can afford the extra $10–$20. It allows the travel insurer to pay the hospital directly, skipping the home-insurance bureaucracy. This is especially vital if you’re traveling to countries with high healthcare costs like Singapore or Switzerland.
Cost Analysis: What You’ll Actually Pay
Travel insurance costs are strictly regulated by state laws, so you won’t necessarily find a “cheaper” version of an IMG plan on Progressive than you would elsewhere. However, the selection Progressive shows you is curated for value.
Estimated Pricing Matrix (Based on Current Market Data)
| Trip Cost | Traveler Age | Approx. Premium (Comprehensive) | % of Trip Cost |
| $2,500 | 30 | $95 – $115 | 4% |
| **$5,000** | 45 | $210 – $260 | 5% |
| **$10,000** | 65 | $650 – $820 | 7-8% |
Rates vary wildly based on destination (cruises are more expensive to insure) and state of residence.
Cancel For Any Reason (CFAR): The 21-Day Rule
If you want the ultimate flexibility—the ability to wake up and decide you just “don’t feel like going”—you need CFAR. While Progressive’s partner plans offer this, it is highly time-sensitive.
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The Window: You usually must buy your policy within 14 to 21 days of making your very first trip deposit.
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The Coverage: Most CFAR add-ons reimburse 50% to 75% of your non-refundable costs.
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The Catch: You must insure 100% of your pre-paid trip costs to qualify. You can’t just insure the flight and expect CFAR to work.
Pros and Cons of Booking via Progressive
| Pros | Cons |
| Trusted Platform: Backed by Progressive and InsureMyTrip’s 20+ years of data. | Third-Party Claims: You don’t file the claim with Flo; you file with the underwriter (e.g., Trawick). |
| Huge Selection: Access to 20+ different insurance providers in one quote. | Portal Confusion: Can be overwhelming for first-time buyers who don’t know the lingo. |
| Free Wifi/Perks: Some plans specifically offer “Concierge” services for rebooking flights. | State Limitations: Certain high-end benefits like CFAR are not available to NY or WA residents. |
Expert FAQ: Real Answers for Real Travelers
Q: Is Progressive travel insurance just white-labeled?
A: Exactly. It’s a partnership with InsureMyTrip. You are buying policies from other companies through Progressive’s “storefront.”
Q: Can I bundle this with my car insurance for a discount?
A: Not directly. Unlike home and auto, travel insurance is usually a standalone product. You won’t see a “Multi-Policy” discount on your Progressive dashboard for this.
Q: Does it cover COVID-19?
A: Yes, most comprehensive plans offered through the portal treat COVID-19 like any other unforeseen illness.
Q: What if I have a pre-existing condition?
A: You must look for plans that offer a “Pre-existing Condition Waiver.” To get this, you usually need to buy the insurance within 14-21 days of your initial trip payment.
Q: Does it cover my pet if I’m traveling with them?
A: Some plans on the portal include “Pet Medical” or “Pet Return” benefits if you are hospitalized and your pet needs to be sent home.
Q: Can I buy it after I’ve already left?
A: Generally, no. Most plans require you to be at your “Primary Residence” at the time of purchase.
Q: How do I file a claim?
A: You must contact the actual insurance provider listed on your policy certificate (e.g., Berkshire Hathaway or IMG). Don’t call the Progressive auto-claims line!
Q: Does it cover cruises?
A: Yes, but make sure to select a plan that has “Missed Connection” and “Itinerary Change” coverage, which are specific to cruise travelers.
Actionable Next Step
Locate Your First Receipt: Before you get a quote, find the exact date you made your first payment (even a $50 deposit). If you are within the 14-day window, prioritize a plan with a Pre-existing Condition Waiver. If you are past 30 days, focus on a “Basic Medical” plan, as most “Cancel for Any Reason” options will no longer be available to you.
