Best Travel Insurance for 2027: 5 Smart Picks for Every Kind of Trip
Disclosure: Travel Report is reader-supported. Some links in this guide are affiliate links, which means we may earn a commission if you buy through them, at no extra cost to you. Right now we earn from InsureMyTrip only; the other options are included because they're genuinely useful, and we'll say so if that changes. Insurance terms change, so always read the policy wording before you buy.
You booked the flights, the rooms and maybe a non-refundable lantern-festival ticket. Then a fever, a canceled connection or a lost bag threatens to wreck it all. Travel insurance won't stop that from happening, but the right plan can stop it from costing you the whole trip.
The catch is that "travel insurance" covers very different products: comprehensive trip plans, travel medical plans, adventure plans and annual plans. Below are five picks for 2027, what each is best at, and how to choose in about five minutes.
Quick answer: the best travel insurance for 2027
- Best overall way to shop: InsureMyTrip. Compare plans from roughly 20 insurers side by side, with licensed agents and claims advocates behind you.
- Best for claims backup: Squaremouth. A comparison marketplace whose Zero Complaint Guarantee lets licensed adjusters mediate a denied claim.
- Best for long trips and digital nomads: SafetyWing. Subscription-style travel medical cover you can start while already abroad.
- Best for adventure travelers: World Nomads. Trip-based plans that list 250+ covered activities for US travelers.
- Best annual plan for frequent travelers: Allianz Travel AllTrips. One policy for a year of trips (each up to 45 days on AllTrips Prime).
Comparison table
Affiliate disclosure: we may earn a commission from links in this table (currently InsureMyTrip only).
| Pick | What it is | Best for | Standout feature | Watch out for | Link |
|---|---|---|---|---|---|
| InsureMyTrip | Comparison marketplace (since 2000) | Most US travelers comparing comprehensive plans | Anytime Advocates help with claims and appeals; carries insurers like Travel Guard and Nationwide | The insurer, not the site, decides and pays claims | Compare quotes |
| Squaremouth | Comparison marketplace | Travelers who want extra claims backup | Zero Complaint Guarantee: licensed adjusters review and mediate denied claims | Mediation isn't a payout guarantee | Compare plans |
| SafetyWing Nomad Insurance Essential | Travel medical, billed every 4 weeks | Long trips, remote workers, buying while abroad | $62.72 per 4 weeks for ages 18–39 (listed price, Nov 2026); no deductible on Essential | Not a cancellation plan; US coverage is an extra; no pre-existing conditions | Get a quote |
| World Nomads | Trip-based travel insurance | Hikers, divers, skiers and active trips | 250+ activities listed for US plans; Explorer tier covers higher-risk activities and altitudes | You can't upgrade Standard to Explorer mid-trip | See plans |
| Allianz Travel AllTrips Prime | Annual multi-trip plan | People taking 2–3+ trips a year | Covers unlimited trips in 365 days (max 45 days each); $3,000 cancellation/interruption per year | Cancellation limit is per year, not per trip | See annual plans |
Prices and benefits checked Nov 10, 2026 from each company's own pages where available. Quotes vary by age, state, trip cost and dates.
1. InsureMyTrip: best overall way to shop
InsureMyTrip isn't an insurer. It's a comparison marketplace, running since 2000, that shows plans from about 20 insurance companies (the count varies by trip and over time) so you can line them up by price and coverage. That matters because the "best" plan for a $6,000 family trip to Vienna is rarely the best plan for a two-week solo trek.
Why we like it - Side-by-side quotes filtered to plans you're eligible for, with add-ons like Cancel For Any Reason where available. - Licensed agents in all 50 states, at no extra cost, before, during and after your trip. - Anytime Advocates, part of its customer care team, can help you follow a claim and start an appeal if it's denied.
Keep in mind: you file claims with the insurer named on your policy, and that insurer makes the final decision.
Best for: most US leisure travelers who want to compare comprehensive trip plans in one place.
Compare travel insurance quotes on InsureMyTrip
2. Squaremouth: best for claims backup
Squaremouth is another comparison marketplace. Its headline perk is the Zero Complaint Guarantee: if your claim is denied and you believe it was unfair, its licensed claims adjusters review the case and mediate with the insurer. If the complaint isn't resolved to Squaremouth's satisfaction, it says it will remove that insurer from its site. It also says it only offers policies from insurers rated "Good" or higher by A.M. Best.
Keep in mind: it isn't a way to file a claim, and it doesn't guarantee a payout. Squaremouth only processes claims for its own Tin Leg brand.
Best for: travelers who want a second set of eyes if a claim goes sideways.
3. SafetyWing: best for long trips and digital nomads
SafetyWing's Nomad Insurance Essential is travel medical insurance you can buy before you leave or while you're already traveling. It's listed at $62.72 per 4 weeks for ages 18–39 (Nov 2026; higher for older age bands), covers stays of up to 364 days at a time, and SafetyWing's help center says the Essential plan has no deductible.
What it covers: new, unexpected medical issues abroad (hospital stays, surgery, medication), emergency evacuation, plus some lost-luggage and travel-delay benefits, and up to 30 days of medical coverage in your home country.
Keep in mind: it's not a trip-cancellation plan, US coverage is a paid add-on, and Essential doesn't cover pre-existing conditions, maternity or cancer treatment. Adventure sports is an add-on.
Best for: long trips, slow travel, remote workers and anyone who forgot to buy coverage before leaving.
4. World Nomads: best for adventure travelers
World Nomads sells trip-based travel insurance with medical, belongings and pre-trip cancellation benefits, and it's known for activity coverage. For US travelers it lists more than 250 covered activities across its plans, from snorkeling and safari tours on the Standard plan to higher-risk activities and higher altitude limits (up to 6,500 meters for some activities) on Explorer.
Keep in mind: pick the right plan up front. World Nomads says you can't upgrade from Standard to Explorer mid-trip, and some activities have altitude or guide requirements. Check your activity on its list before you buy.
Best for: hikers, divers, skiers and anyone whose itinerary includes the word "trek."
Check World Nomads activity coverage
5. Allianz Travel AllTrips: best annual plan
If you take several trips a year, an annual plan can be simpler than buying a policy every time. Allianz AllTrips Prime covers unlimited trips during a 365-day period, with each trip up to 45 days. Allianz lists $3,000 trip cancellation and $3,000 trip interruption per insured per year, $20,000 emergency medical and $100,000 emergency medical transportation per trip, plus baggage, travel delay and rental-car damage coverage (rental-car cover isn't available to residents of KS, TX and NY).
Need bigger limits? AllTrips Premier offers trip cancellation tiers up to $15,000 per policy per year, covers trips up to 90 days, and can cover a whole household.
Keep in mind: the cancellation limit is shared across the whole year, so one expensive trip can use most of it.
Best for: frequent travelers taking two or more shorter trips a year.
How to choose travel insurance in 5 minutes
- Decide what you're protecting. Prepaid, non-refundable costs (flights, festival tickets, hotel deposits) point to a comprehensive plan with trip cancellation. Medical bills abroad point to travel medical coverage. Most international trips need medical coverage either way.
- Check what you already have. Some credit cards include trip delay or cancellation benefits, and your health plan may cover little or nothing abroad. Medicare generally doesn't cover care outside the US.
- Buy early if you want Cancel For Any Reason. CFAR is an optional upgrade that typically reimburses part of your trip cost (often 50–75%) and usually must be added within a short window after your first trip deposit. Read the exact rules in your policy.
- Match the plan to the trip. Long or open-ended trip: travel medical (SafetyWing). Adventure-heavy: World Nomads. Several trips a year: an annual plan. Everything else: compare comprehensive plans on InsureMyTrip.
- Read the exclusions. Pre-existing conditions, activities, alcohol-related incidents and "known events" like a named storm are common gaps.
FAQ
Is travel insurance worth it in 2027?
It's most worth it when you've prepaid non-refundable costs you couldn't afford to lose, or when you're traveling somewhere your health insurance won't cover you. A single overseas hospital stay or medical evacuation can cost far more than a policy.
What does travel insurance usually cover?
Comprehensive plans typically include trip cancellation and interruption, emergency medical, medical evacuation, travel delay and baggage benefits. Travel medical plans focus on medical care and evacuation and usually don't cover cancellation. Limits and covered reasons vary by plan.
Does Medicare cover me when I travel abroad?
Generally no. Medicare.gov says Medicare usually doesn't cover health care or supplies you get outside the US, with only rare exceptions. Some Medigap plans include limited foreign travel emergency coverage, so check yours.
What is Cancel For Any Reason (CFAR) coverage?
An optional upgrade that lets you cancel for reasons a standard policy won't cover and get part of your prepaid, non-refundable costs back, typically 50–75%. It usually has to be bought soon after your first trip payment and costs extra.
Can I buy travel insurance after I've left home?
Some plans allow it. SafetyWing, for example, lets you start coverage while you're already traveling. Most comprehensive plans with cancellation benefits must be bought before you depart.
Is it cheaper to buy from a comparison site?
Travel insurance rates are generally filed with state regulators, so the same plan typically costs the same whether you buy from the insurer or a comparison site. Comparison sites help you find a cheaper or better-fitting plan, not a discount on the same one.
Plan the trip, then protect it
Before you buy a policy, know what your trip actually costs and where you're going. Get a free trip preview at www.travelreport.ai: tell us your destination and dates, and we'll show you a personalized plan in minutes.
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Disclosure: We may earn a commission when you buy through links on this page, at no extra cost to you. This guide is general information, not insurance advice. Coverage depends on your policy wording, state of residence and personal situation.
Sources checked Nov 10, 2026: insuremytrip.com; squaremouth.com/about/guarantee and /about/customer-service; safetywing.com/nomad-insurance and SafetyWing Help Center ("Nomad Insurance Essential: Does it have a deductible?"); worldnomads.com (US activities list; Standard vs Explorer); allianztravelinsurance.com (AllTrips Prime; AllTrips Prime vs Premier); medicare.gov/coverage/travel-outside-the-u.s.