Annual vs. Single-Trip Travel Insurance Calculator

Traveling more than once this year? Find out whether an annual travel insurance policy saves you money — or costs more than buying per trip.

Step 1 — Your Trips This Year

Add each trip you're planning or have already taken this year. The calculator estimates the single-trip policy cost for each and compares the total against an annual policy.

Step 2 — Annual Policy Cost

Enter the annual policy premium you've been quoted, or let the calculator estimate based on typical market rates. Annual multi-trip policies typically run $300–$600 for a single traveler.

$
total cost for 12-month coverage
from your policy terms
Step 3 — Coverage Type

What type of coverage are you comparing? This affects how single-trip premiums are estimated.

applies to single-trip estimates
international adds medical coverage value
Step 4 — Premium Credit Cards You Hold (Optional)

Select any premium cards you carry and use for travel. Their built-in coverage reduces what you actually need to buy — the calculator will adjust its recommendation accordingly.

Chase Sapphire Reserve $10,000/person, $20,000/trip cancellation • Trip delay after 6 hrs • Baggage up to $3,000 • No emergency medical coverage abroad
American Express Platinum $10,000/trip cancellation total • Trip delay after 6 hrs • Baggage up to $3,000 • No emergency medical coverage abroad • Full trip must be charged to card
Your Results
Single-Trip Total
—
across all trips
Annual Policy Cost
—
12-month coverage
Your Savings
—
choosing the better option
Trip-by-Trip Cost Breakdown
Trip Trip Cost Non-Refundable Trip Length Est. Single-Trip Premium Annual Policy Covers?
Total Single-Trip Cost — —
Break-Even Trip Count

See how the math shifts as you add more trips. Your annual policy cost stays flat — the single-trip cost grows with each trip.

Number of Trips Single-Trip Total Annual Policy Savings Better Option
Things to Know

Compare Annual Travel Insurance Quotes

Squaremouth lets you filter specifically for annual multi-trip policies and compare premiums across 30+ insurers side by side.

Compare Annual Policies on Squaremouth →

Single-trip premium estimates are based on industry averages (4–6% of non-refundable costs for standard coverage, 9–12% for CFAR, 5–8% for comprehensive) and are for planning purposes only. Actual premiums vary by insurer, traveler age, destination, and policy terms. Always get a quote before purchasing. MilePro.com earns affiliate compensation from links on this page.