I've Been to 24 Countries.
Here's What I've Learned About Travel Insurance.
Know your cancellation options
Standard policies only cover specific reasons. "Cancel for Any Reason" costs more but covers everything.
Get medical evacuation
An air ambulance from Bermuda to the US can cost $50K+. Remote islands mean expensive evacuations.
Compare before you buy
Prices vary wildly for identical coverage. I've seen 2x differences between providers.
Your vacation is an investment—flights, hotels, tours, cruise deposits. Travel insurance protects that investment when the unexpected happens.
Our Exclusive Travel Insurance Partner
Squaremouth
Compare 40+ travel insurance providers in one place.
This is an affiliate link—using it supports our agency at no extra cost to you.
You'll be redirected to Squaremouth.com to compare quotes and purchase.
Whether you're flying out of Charleston (CRW), Columbus (CMH), Cincinnati (CVG), or Pittsburgh (PIT)—I've helped folks from across the Ohio Valley find the right coverage.
Buy Within 14-21 Days of Booking
Most "Cancel for Any Reason" policies and pre-existing condition waivers are only available if you purchase within 14-21 days of your first trip deposit. Wait longer and you lose these options entirely.
Same Trip. Different Prices. Different Coverage.
Real quotes for a $7,500 trip—prices vary because benefits vary
Budget
IMG iTravelInsured
$350
$100K medical
$500K evacuation
Mid-Range
Tin Leg Gold
$589
$500K medical
$500K evacuation
Premium
Seven Corners Choice
$788
$500K medical
$1M evacuation
The right policy depends on your trip. Adventure travel abroad? You might want higher evacuation limits. Weekend beach trip? Basic coverage may be plenty. Comparing lets you choose—not guess.
Claim #1
Hurricane Evacuation: $6,500 Saved
Back around 2015, I booked a $6,500 beach house for a multi-family vacation—we were splitting it with relatives. Days before we were supposed to leave, a hurricane triggered a mandatory evacuation order.
Because I'd purchased a policy through Squaremouth, I was able to cancel and file a claim. I was fully reimbursed—every dollar. They even covered the airline ticket change fees and my prepaid luggage costs.
That's how I discovered Squaremouth, and why I recommend them to anyone planning a trip.
Claim #2
Work Emergency: $1,176 Saved
In January 2019, my son Jay (an owner at our agency) and his wife Hannah had an Orlando trip planned. Three days before departure, Hannah's employer revoked her vacation—a partner at the CPA firm had a family medical emergency during busy season, and they needed all hands on deck.
They had to rebook their flights through Allegiant Air. The travel insurance covered $1,176 in rebooking and change fees.
This is why "covered reasons" matter—work emergencies are often included. (Claim filed February 2019)
I've since traveled to 24 countries across 4 continents—and I never leave without coverage.
What Could Have Happened
Real trips. Real risks. Here's what travel insurance would have covered.
Stelvio Pass, Italy
48 hairpin turns • 9,045 ft elevation
A motorcycle accident on these steep Alpine switchbacks could mean an air ambulance to Munich or Milan. If the worst happened, repatriation costs to bring remains home can exceed $20,000.
Coverage needed: Emergency Medical Evacuation ($100K-$1M) + Repatriation of Remains
Neuschwanstein Castle, Bavaria
The castle that inspired Disney
Your flight from JFK to Munich is delayed. You miss your connection to your motorcycle tour start in Füssen. Last-minute rebooking, hotel for the night, catching up to your group—costs add up fast.
Coverage needed: Travel Delay + Missed Connection benefits
Eagle's Nest (Kehlsteinhaus)
6,017 ft • Berchtesgaden Alps
Icy walkways at 6,000 feet. A bad fall, broken hip, and suddenly you need helicopter evacuation to a trauma center. Your US health insurance? Zero coverage abroad.
Coverage needed: Emergency Medical ($100K+) + Medical Evacuation
New River Gorge, West Virginia
America's newest National Park
You arrive and your cabin rental had a fire—it's uninhabitable. Bridge Day weekend, everything's booked. Now you're scrambling for lodging at peak-season prices.
Coverage needed: Trip Interruption + Additional Accommodation expenses
Tail of the Dragon, Tennessee
318 curves in 11 miles • Deals Gap
Hurricane flooding devastated parts of Tennessee in recent years. Imagine booking a week-long motorcycle trip, cabins, guided tours—then watching the news as flash floods close every road in the area. Without travel insurance, you're out thousands.
Coverage needed: Trip Cancellation for weather/natural disaster
Countries I've Visited
Europe
- Germany
- Austria
- Spain
- Italy
- France
- Switzerland
- England
- Wales
- Netherlands
- Belgium
- Luxembourg
- Andorra
Caribbean & Atlantic
- Bermuda
- Bahamas
- Curaçao
- Aruba
- Bonaire
- Virgin Islands
Americas
- Canada
- Mexico
- Costa Rica
- Belize
Africa & Asia
- Morocco
- Japan
What Travel Insurance Covers
Trip Cancellation
Covered reasons include illness, injury, death of traveler or family member, job loss, jury duty, natural disasters, and more. Cancel for Any Reason (CFAR) upgrades available.
Emergency Medical
Your domestic health insurance often provides zero coverage internationally. Travel medical insurance covers doctor visits, hospital stays, prescriptions, and emergency dental.
Emergency Evacuation
Medical evacuations can cost $50,000-$250,000+. Coverage includes air ambulance, medical escort, and transportation to the nearest adequate medical facility or home.
Lost & Delayed Baggage
Coverage for personal belongings, essential items if bags are delayed, and replacement of necessities. Higher limits available for expensive items.
Travel Delays
Reimburses meals, accommodations, and transportation when flights are delayed or cancelled. Coverage kicks in after a specified delay period (typically 6-12 hours).
24/7 Assistance
Access to travel assistance hotlines for medical referrals, emergency cash advances, translation services, legal referrals, and help with lost documents.
Insurance Tips From My Travels
Different trips need different coverage. Here's what I've learned matters most for popular destinations.
Europe
My top three: Germany, Austria, and Spain. I'll always go back to these places.
- Medical coverage is essential. Your US health insurance won't cover you.
- Multi-country trips: Check that coverage applies everywhere you're going.
- Motorcycle touring? Verify adventure sports coverage.
Caribbean & Mexico
From the ABC islands (Aruba, Bonaire, Curaçao) to the Bahamas and Virgin Islands.
- Hurricane season: Trip interruption coverage is worth it June-November.
- Medical evacuation: Critical for island destinations far from major hospitals.
- Diving/snorkeling: Check coverage for water activities.
Adventure Travel
Motorcycle tours, hiking, adventure sports—what I look for in coverage.
- Read the exclusions. "Adventure sports" means different things to different insurers.
- Higher medical limits: Adventure injuries can be expensive to treat.
- Trip delay: Remote locations mean longer delays when things go wrong.
Want to Ride Abroad?
I've done multiple motorcycle tours through the Alps with Edelweiss Bike Travel—the gold standard for guided tours in Europe. If you're thinking about riding the Stelvio Pass, the Dolomites, or anywhere else in Europe, I can't recommend them highly enough.
Just remember: adventure travel insurance is essential for motorcycle touring abroad. Make sure your policy covers it.
Visit Edelweiss Bike TravelFrequently Asked Questions
How much does travel insurance cost?
Typically 4-10% of your total trip cost, depending on coverage level, traveler age, and destination. A $5,000 trip might cost $200-500 to insure.
What is "Cancel for Any Reason" coverage?
CFAR is optional coverage that lets you cancel for any reason—cold feet, schedule conflicts, anything. It reimburses 50-75% of non-refundable costs, but must be purchased within 14-21 days of your initial deposit.
Does my credit card provide travel insurance?
Some premium cards offer limited protection, but it's usually far less comprehensive than standalone policies. Credit card coverage often excludes medical emergencies, has low limits, and requires paying with that specific card.
Are pre-existing conditions covered?
Many policies offer pre-existing condition waivers if you purchase within 14-21 days of your first trip deposit. Without the waiver, they're typically excluded.
What's NOT covered?
Common exclusions: pre-existing conditions (unless waived), high-risk activities without add-on coverage, travel to countries under State Department advisories, and claims related to alcohol or drug use.
Ready to Protect Your Next Adventure?
Whether you're cruising the Caribbean, touring Europe, or planning something off the beaten path—get the coverage that fits your trip. Compare 40+ providers in 60 seconds.
We're happy to help you understand your options.
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