Best Travel Insurance in New York for 2026

The Cancel for Any Reason (CFAR) Situation in New York

Let’s start with the elephant in the room: Cancel for Any Reason coverage. CFAR is the holy grail of travel insurance flexibility. It lets you cancel your trip for literally any reason (cold feet, bad vibes, your favorite show dropped a new season, and you’d rather stay home) and get back 50% to 75% of your prepaid, nonrefundable costs. It’s extremely popular, especially post-pandemic, when everyone realized how quickly travel plans can fall apart.

Here’s the thing: for years, CFAR was flat-out unavailable to New York residents. The New York Department of Financial Services (DFS) ruled that CFAR doesn’t technically qualify as insurance under state law because canceling a trip “for any reason” doesn’t depend on a “fortuitous event.” In insurance-speak, a fortuitous event is something that happens by chance or accident, something outside your control. If you can decide to cancel because you feel like it, there’s no fortuity involved.

In March 2020, the DFS issued an Insurance Circular Letter that slightly revised this stance. Now, CFAR benefits CAN be sold in New York under certain conditions. Insurers can offer it if it’s “necessarily or properly incidental” to their travel insurance business, and it must be sold as a separate, standalone contract from the standard insurance policy. Non-insurers (such as travel agencies) can also offer CFAR benefits if they’re not sold as insurance products.

What does this mean for you in practice? It means CFAR availability in New York is still limited compared to other states. Many major insurance providers simply don’t offer CFAR policies to New York residents because structuring the product in compliance is more complicated and expensive. When you do find CFAR coverage available, the terms and structure may differ from what’s offered in other states.

Winter Weather: Why Travel Delay Coverage Is Non-Negotiable for New Yorkers

If you’ve flown out of JFK, LaGuardia, or Newark during the winter months, you already know the drill: winter storms in the Northeast cause some of the most significant flight disruptions in the entire country. We’re talking hundreds of cancellations, multi-hour delays, ground stops, and the kind of chaos that leaves people stranded in terminals overnight.

In late December 2025 alone, a single winter storm caused over 400 cancellations across New York-area airports, with JFK logging more than 300 cancellations and 100 delays in a single day. Flights were delayed an average of two hours, and some passengers reported being stuck on the tarmac for three hours or more. This isn’t unusual. It happens multiple times each winter.

Here’s the thing about weather-related cancellations: airlines are NOT required to provide you with hotel accommodations, meals, or additional services when weather is the cause. The Department of Transportation considers weather to be outside an airline’s control. Sure, you can get a refund for a cancelled flight, but that doesn’t help when you’re stuck in Queens at 11 PM trying to figure out where to sleep.

This is where travel delay coverage becomes essential for New York travelers. Look for policies that offer at least $150 to $200 per day for delays of 6 to 12 hours or more, and make sure meals, accommodations, and essential items are covered. Given our airport situation, you should prioritize policies with lower delay thresholds (e.g., 6 hours vs. 12) and higher daily limits.

You’re Flying from America’s Biggest International Gateway

JFK is the largest international gateway in the United States. It offers nonstop flights to over 125 international airports worldwide. It’s the number one airport for flights to Europe, Africa, and the Middle East, and it’s second only to Miami for flights to the Caribbean, Central America, and South America. London Heathrow, Paris CDG, and Rome are among the top international routes.

What does this mean for your travel insurance needs? If you’re a New Yorker, there’s a good chance you’re flying internationally. And international trips require different coverage than a quick domestic hop.

What International Travelers from New York Should Prioritize

Caribbean Bound? Here’s What to Watch For

The Caribbean is one of the most popular destinations for New York travelers, and for good reason. It’s relatively close (3 to 5-hour flights), the weather is excellent, and there are direct flights from JFK to seemingly every island. But Caribbean travel comes with some specific insurance considerations you should know about.

Hurricane Season: If you’re traveling to the Caribbean between June and November, you’re traveling during hurricane season. Standard trip cancellation coverage typically covers hurricanes that force you to cancel. Still, there’s often a catch: the hurricane needs to be officially named or declared before you depart for coverage to kick in. If you want the flexibility to cancel because a storm is forming and you’re nervous, you’ll need CFAR coverage (which, as we discussed, is tricky in New York).

Cruise Coverage: New York is a significant departure point for cruises, especially during the warmer months. If you’re cruising, make sure your policy covers cruise-specific scenarios, such as missed port departures, itinerary changes, and cruise line financial default. Not all policies are created equal when it comes to cruises.

Practical Tips for Shopping for Travel Insurance in New York

Given the regulatory quirks of buying travel insurance in New York, here’s how to approach the process:

1. Use comparison sites, but verify availability. Sites like Squaremouth, InsureMyTrip, and TravelInsurance.com let you compare policies, but make sure to enter your state of residence correctly. Some policies that appear in search results may not actually be available to New York residents, especially for CFAR coverage.
2. Read the policy documents, not just the marketing. New York insurance regulations are strict about what insurers can and can’t say. The actual policy documents will tell you exactly what’s covered. Don’t rely on summary pages or marketing materials.
3. Buy within the window. Most policies with the best benefits (including pre-existing condition waivers and, when available, CFAR) require you to purchase within 14 to 21 days of your initial trip deposit. Don’t wait until the last minute.
4. Take advantage of the free look period. New York requires insurers to offer a free look period (typically 10 to 14 days) during which you can review the policy and receive a full refund if it doesn’t meet your needs. Use this time actually to read the policy.
5. Consider annual policies if you travel frequently. If you take multiple trips per year, a yearly travel insurance policy might offer better value and simplify things. Just make sure it covers the types of trips you typically take.
6. Contact DFS if you have issues. The New York Department of Financial Services has a consumer hotline (800-342-3736) and will help if you have complaints about a travel insurance policy or provider. They take consumer protection seriously.

The Bottom Line for New York Travelers

Yes, buying travel insurance in New York is more complicated than in other states. The CFAR restrictions are frustrating, especially in an era when trip flexibility feels more critical than ever. But the core protections (medical coverage, trip cancellation for covered reasons, travel delay coverage, and baggage protection) are all still available and still valuable.

Given that you’re likely flying out of one of the busiest and most weather-impacted airport systems in the country, and probably taking international trips to places where your regular health insurance doesn’t cover you, travel insurance isn’t just a nice-to-have. It’s a swisefinancial decision.

The goal isn’t to find perfect coverage (it doesn’t exist). The goal is to find coverage that protects you from the financial disasters that could actually happen on your specific trip. For New Yorkers, that means prioritizing robust travel delay coverage, solid international medical protection, and carefully reading the fine print when it comes to cancellation flexibility.

Safe travels, and may your flights be on time and your connections smooth. (But just in case they’re not, you’ll be covered.)

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