Jake Holehouse from HH Insurance Group is a marine insurance specialist who helps boaters understand the complexities of boat insurance coverage, particularly hurricane damage claims, liability protection, and policy optimization. In this episode, Jake reveals how Florida's building code reforms are actually leading to insurance rate decreases despite major storms, why most boaters have massive coverage gaps they don't know about (including offshore limits and Bahamas exclusions), and the specific policy endorsements hidden on page 30 that can turn a $250 electronics deductible into a $60,000 out-of-pocket nightmare. If you own a boat, charter a boat, or trailer anywhere beyond your home waters, the gaps Jake exposes will change how you think about your coverage.
Are Florida boat insurance rates going up after the 2024 hurricanes?
Despite Hurricanes Helene and Milton hitting Florida within thirteen days, Jake Holehouse explains that Florida insurance rates are actually showing resilience due to building code reforms passed after the 2004-2005 hurricane seasons. Without the 2024 storms, Florida would have seen 15-20% rate decreases on homeowners insurance, and newer construction with fortified roofs and hurricane shutters is proving significantly more survivable than older homes.
Who is Jake Holehouse?
Jake Holehouse is from HH Insurance Group, a marine insurance specialist company. He grew up in the insurance business working with his father, studied insurance and entrepreneurship in college including earning a master's degree, worked for a large insurance carrier, and now runs the family agency specializing in marine and property insurance for boat owners, charter captains, and boat dealerships.
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Why Florida's Building Code Is Changing the Insurance Game
Jake breaks down something most people don't realize: the brutal 2004-2005 hurricane seasons actually forced Florida to implement building code reforms that are now protecting homes and boats in ways that simply didn't exist before. He describes driving through the Florida Keys after Hurricane Irma and seeing a pattern—newer houses with intact roofs standing next to older houses with roofs completely torn off. The difference wasn't luck. It was engineering. Jake explains how these newer constructions with fortified roofs can withstand storms where residents can move back in hours after a storm instead of months, and how insurance carriers are now factoring this resilience into their pricing models. The most surprising reveal? Florida was heading toward 15-20% rate decreases before the 2024 storms hit. The full explanation of Florida's insurance market transformation starts at 09:53.
The Coverage Gaps Hiding in Your Boat Policy
Tom opens up about his own insurance wake-up call: he thought his policy covered everything, but when HH Insurance reviewed it, they found major exclusions—no Bahamas coverage, offshore limits he didn't know existed, and unclear protection if he just pulled his boat out and stored it somewhere during a storm. Jake reveals that many Florida-based policies don't cover beyond 75 miles offshore, and some carriers have dropped that to 20 or 25 miles. Even more alarming: many boaters don't know their policy requires a haul-out 72 hours before a hurricane watch or warning, and if they don't execute that plan, they're not covered. Jake shares how one boat owner thought he had full coverage, only to discover his policy excluded The Bahamas entirely—a devastating surprise for someone who regularly crosses to the islands. The offshore and navigation territory breakdown starts at 48:37.
Hear Jake explain the specific policy exclusions that catch most boaters by surprise
The $60,000 Deductible You Didn't Know You Had
This story will make your stomach drop. Jake walks through a real claim scenario: a boater had two Garmin screens stolen. He looked at his policy and saw a $250 electronics deductible—seemed reasonable. But when he filed the claim, the carrier pointed to page 30 of his policy, where a theft endorsement modified that $250 deductible to 10% of the boat's value. On a $600,000 boat, that's a $60,000 deductible. The boater went from thinking he had full coverage to realizing he had essentially no coverage for the theft. Jake emphasizes that endorsements—those additions buried deep in your policy documents—are often more important than the base policy language because they can completely transform your coverage. He also reveals that what used to be a $300,000 boat is now a $600,000 boat due to inflation, meaning those percentage-based deductibles have doubled in real dollars. The theft endorsement horror story starts at 55:53.
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SubscribeCharter Captains and the Media Exclusion Trap
If you're a charter captain filming content for YouTube, Instagram, or any social platform, this section is critical. Jake describes how he's worked with TV show hosts who had policies with total business use exclusions—and filming for profit qualified as business use, meaning they had zero coverage while shooting their shows. The line between recreational filming and commercial media is blurry, and Jake explains how that gray area can destroy your coverage. He breaks down when you need specific crew coverage (anytime you have a mate or someone dedicated to filming), when you cross into media exclusion territory (when a film crew comes aboard or content creation becomes structured), and how named operator provisions work on commercial policies. Tom shares his own experience running professional redfish tournaments while also chartering—trailering his boat to Texas, fishing outside his coverage zone, and having gaps he didn't even realize existed. The charter captain and media coverage discussion starts at 41:10.
This conversation goes deeper than most insurance discussions ever do.
Jake answers every question boaters should be asking but usually don't know to ask.
Key Takeaways
- Florida's building code reforms after 2004-2005 are proving so effective that insurance carriers were heading toward 15-20% rate decreases before the 2024 storms—a resilience story most people don't know about
- Many boat policies cap offshore coverage at 75 miles or less, exclude The Bahamas entirely, and require specific haul-out plans 72 hours before a hurricane—gaps most boaters discover only after filing a claim
- Policy endorsements buried on page 30 can transform a $250 deductible into a $60,000 deductible—making them more important than your base policy language
- Charter captains filming content for social media or YouTube may be operating under a business use exclusion without knowing it, potentially voiding all coverage
- Trailering your boat to tournaments or distant fishing locations often puts you outside your policy's coverage territory unless specifically added—a gap many tournament anglers and traveling captains have no idea exists
- Jake grew up in the insurance business, earned a master's degree in insurance and entrepreneurship, worked for a major carrier, and now runs HH Insurance Group specializing in marine coverage
- Uninsured boater coverage protects you when someone without insurance damages your boat or injures you—a provision many boaters don't carry despite the risk
Final Thoughts from Tom
This conversation with Jake changed how I think about boat insurance. I thought I had good coverage until we started working with HH Insurance Group, and they found gaps I didn't even know existed—offshore limits, Bahamas exclusions, unclear haul-out requirements. I was operating under assumptions that could have cost me everything.
What I appreciate most about Jake is that he doesn't just sell policies—he educates. He walks you through what you're actually covered for and, more importantly, what you're not covered for. That honesty is rare. Most agents just want to close the sale and move on. Jake wants you to understand your policy before you sign it, which is exactly how it should work.
If you own a boat, charter a boat, or trailer anywhere beyond your home marina, this episode will make you pull out your policy and start asking questions. And if you can't answer those questions confidently, it's time to call Jake's team. Don't wait until you file a claim to find out you're not covered. Listen to this whole episode—it might save you tens of thousands of dollars.
Frequently Asked Questions
What is the National Flood Insurance Program and how much coverage does it provide?
The National Flood Insurance Program (NFIP) is the primary underwriter for most flood insurance policies in the United States, though it appears under various company names like Wright Flood Insurance or Allstate. The maximum coverage limit available through NFIP is $250,000, which can leave significant gaps for homeowners with properties valued above that amount, and the program typically doesn't include coverage for temporary living expenses during repairs.
Do boat insurance policies cover damage in The Bahamas?
Many Florida-based boat insurance policies do not automatically cover The Bahamas unless specifically added to the policy. Jake Holehouse explains that this is a common coverage gap, particularly for Miami-based boaters who frequently cross to The Bahamas, and the exclusion must be specifically removed through policy modification.
What is a boat insurance haul-out requirement?
A haul-out requirement is policy language that requires boat owners to remove their boat from the water and secure it in an approved location when a hurricane watch or warning is issued, typically 72 hours before the storm. Many policies require the boat to be hauled off lifts, placed on a trailer, and stored according to specific guidelines—either with an approved hurricane plan or 25 miles inland—and failure to comply can result in denied claims.
How far offshore does standard boat insurance cover?
Most standard boat insurance policies from carriers like Progressive cover up to 75 miles offshore, though some carriers have reduced that to 20 or 25 miles. Boaters who plan to travel farther offshore need to specifically request extended coverage territory, which must be added to the policy before departure or the claim may be denied.
What liability coverage do charter boat captains need?
Charter boat captains typically need between $300,000 and $500,000 in liability coverage at minimum, with many opting for $1 million in coverage through their boat policy. For higher liability limits, charter captains can purchase an umbrella policy that provides excess coverage beyond the base policy limits, protecting against catastrophic injury claims that could otherwise result in personal financial liability.
Related Episodes
Essential coverage gaps and policy requirements for anyone who owns or operates a boat
Haul-out strategies and storm preparation that Jake references throughout this conversation
Critical information for captains running charter businesses and dealing with commercial coverage
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About this Guest
Jake Holehouse
Jake Holehouse is from HH Insurance Group, where he specializes in marine insurance for boat owners, charter captains, and boat dealerships. He grew up working in his father's insurance agency, studied insurance and entrepreneurship in college earning a master's degree, gained experience working for a large insurance carrier, and now runs the family agency with a focus on educating customers about coverage gaps and policy optimization. Jake is passionate about fishing, boating, and helping marine customers understand the complex world of boat insurance. Contact HH Insurance Group at (727) 498-5551 or visit hhinsgroup.com.
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