The zoo. Wrigley Field. Deep-dish pizza. Getting rerouted through Chicago with a family of four doesn’t sound all that bad — except when it adds up to thousands of dollars because your home airport is closed for a week due to extreme weather. It’s what happened to Stan Sandberg during Hurricane Sandy. He was inspired by that experience and another to help co-found insurance comparison website TravelInsurance.com.
“I took my family on a trip to Costa Rica, and the bag with the bathing suits, flip flops and SPF for the kids was missing. If you don’t have coverage for delayed luggage, it can cost you the hundreds of dollars it cost us to replace those things at a small local store, and the stress of not getting reimbursed can pierce that ‘vacation bubble.’”
Enter TravelInsurance.com
, which includes a simple form with all of the ages of up to 10 travelers, date and duration of trip, and destination, and then quotes are aggregated with various coverages and prices.
Sandberg said not only is it easy to use, but meets a growing demand. “We’ve seen a lot of new customers come to market. With terrorism in Barcelona and Paris, and places you never expected it before, that’s covered as a standard reason for cancellation,” he said. “Car insurance spent millions to develop consumer-friendly brands but we haven’t really seen that in travel insurance. For the cost of a meal on your vacation, you can get interruption medical coverage and most comprehensive plans also come with emergency evacuation.”
Whether you’re planning on zipping down a ski hill or just chilling on a beach when your kid gets water in their ear and has to visit a local health clinic (which also happened to Sandberg’s son), medical coverage, lost-luggage claims or delays can all add up to stress and dollar signs, he says. Plans typically start at about 4 percent of the total trip cost.

Photo: Conejota | Dreamstime
Good news for families with kids? The younger the person insured, the less it costs. But for those bringing along Grandma or Granddad on that heritage trip to Israel, it’s worth a bigger investment, since Medicare doesn’t cover anyone overseas. And if you think your travel credit card will cover unexpected challenges, they’re not all created equal, says Sandberg. “That secondary coverage is subject to deductibles so if you have a medical claim, you’re required to make it with your existing health insurance first and then file paperwork for anything that’s not covered. It’ a lot of homework on the consumer’s end.”
Sandberg’s other tips for buying travel insurance:
Buy travel insurance quickly after booking a trip, so there’s pre-departure coverage (like trip cancellation coverage). Pre-existing conditions are often only covered if insurance is purchased within 14 days of booking a trip, as well.
Don’t buy trip insurance directly through the company offering the trip, since a “refund” may be offered in the form of a credit on a future trip, versus cash back.
Keep copies of trip insurance coverage and emergency numbers on hand at all times — not locked in a safe with your passport in a hotel.
Read This Next
#WhereverFamily
Insta FeedDestinations
Sep 2, 2026Look Past the Traditional Classroom with Scott Dunn’s Back-to-School Itineraries
Parents looking to provide their kids with hands-on learning experiences going beyond textbooks by visiting unique destinations with family-centric approaches will find that and more with Scott Dunn's private, expert-led itineraries. These experiences provide lessons the classroom cannot.
Sponsored Content
Best of Both Worlds
Enjoy the best of both worlds when you fly with TAP Air Portugal thanks to the Portugal Stopover program. With the program, TAP passengers, whether traveling for business, leisure or both, can stop in Portugal for up to 10 days at no additional airfare on the way to their final destination. What does this mean for travelers wishing to explore by both land and sea? It means after flying to Portugal with TAP and experiencing the country in an entirely new way, travelers can then embark on scenic river and ocean cruises from Portugal’s port cities, or fly with TAP to another European destination.
Destinations / North America
Sep 2, 2026Visit an Old-Fashioned County Fair in Maine
Celebrate autumn with a family trip to a traditional New England county fair. These annual celebrations of agriculture and country life are filled with sights and activities for the whole family to enjoy, from admiring prize pumpkins and meeting live animals to witnessing horse shows, listening to country music and dancing, and doing craft demonstrations. Most fairs also have carnival rides and hands-on activities for kids.
Destinations / Europe
Sep 2, 2026A Brand-New, World-Class Aquarium Coming to Dublin, Ireland
A groundbreaking new marine attraction, OceanÈire, was recently announced in Dublin, Ireland, promising to redefine family entertainment, marine research and conservation in Ireland. While a debut date and specific location has yet to be revealed, OceanÉire already unveiled several details of the multimillion-dollar aquarium.
Sponsored Content
GET TO KNOW TAP FORBIZ
Unlock flexible, refined business travel with TAP Air Portugal’s program, TAP FORBIZ. Developed for small, medium and large Companies, with options for corporate events, TAP FORBIZ offers exclusive advantages adapted to each type of business.
Hotels
Sep 1, 2026Hyatt Regency Maui Resort and Spa to Welcome Return of Elf on the Shelf This Holiday Season
The magic of Christmas quickly approaches as summer comes to a close, and families can experience the holiday season in a unique way this year.
ShareThis