Panama Canal Question

Well, who do you think will be the one held in jail until the damage you create is paid for?

There is no specific requirement for insurance. You are responsible for any damage to the locks and either a deposit is made or a bond through a line of credit. Typically pleasure boats just make a deposit and it's promptly returned.

First time, I wouldn't pass through without using a local agent. Several great ones available.

Now as to taking the job, hasn't the owner already told you all you need to know about them and their level of responsibility? You really want to be the front man to it? The one on site to be held responsible while they attempt to reach the owner? Such an owner is also they type to do other things half-way such as repairs and maintenance and even including paying you. Well, you already know what you're getting into if you do it.

Old junky boat in bad shape and know it all old man owning it.

Umbrella only extends to things covered by other policies and typically requires them being mentioned. For instance ours would cover any items not fully covered by our Marine Insurance.

I'm not an insurance expert, and, according to GEICO, neither are you. According to GEICO, what I've highlighted above is NOT true. Here's what GEICO says about umbrella insurance:

"Umbrella insurance provides coverage beyond the limits of your other insurance policies, or for claims that may not be covered by liability policies. Umbrella insurance generally provides liability coverage for:

• 
  
  • Injuries
  • Damage to property
  • Certain lawsuits
  • Personal liability situations"

Be careful of the advice you give. The "know it all old man" (your words) may have everything covered insurance-wise.

I will stick to my answer. While umbrella policies may cover some things not insured, such as libel or slander or false arrest, in most areas of liability it is an "excess" policy and covers excess over other policies. I said "typically" and typically if you have no marine liability insurance then it will not cover marine claims unless it has a specific rider saying it does. Geico further states

1. Umbrella insurance may provide coverage when your homeowners, auto, and boat insurance policies limits are exhausted.
2. Umbrella insurance provides coverage for claims that may be excluded by other liability policies including claims like false arrest, libel, slander, and liability coverage on rental units you own.

It's the first of those two points that marine insurance fits under. From another site about what umbrella policies do not cover. "Boats are another common area of exclusions. Some companies cover certain sizes or types of watercraft only, while others don’t cover them at all unless you have an existing boat insurance policy."

From Farmer's, "Umbrella insurance provides additional liability coverage — over and above the limits on your auto and other personal liability policies." Their standard policy only covers your primary residence, two motorized vehicles, small sailboats and motorboats under 50 hp and everything else is optional.

From Forbes, "Umbrella insurance provides “excess liability insurance” (meaning additional coverage) beyond the liability insurance already in your auto, homeowners and/or watercraft insurance policies. It’s for expensive situations where medical bills or repairs exceed your “base” auto, home or boat policies." and also from Forbes, "Umbrella insurance kicks in when your “base” liability limits have been reached." Then they add areas that umbrella generally covers in addition and those areas are:

-Libel, defamation or slander. For example, if you post something defamatory about someone else to a website, you could be sued.
-False arrest, imprisonment or detention
-Malicious prosecution
-Wrongful eviction or entry
-Invasion of privacy

I've had an umbrella policy for 20 years and it's very specific including mention of it's exclusions. I've had many discussions of umbrella policies with insurance experts, both risk management professionals and brokers, and they've always made it clear that the umbrella was limited.

Umbrella does differ from strict "excess" policies as they often have "follow form" clauses and umbrella policies typically do not so if a basic policy excludes something, an umbrella may still cover it. When an umbrella covers starting with dollar one as I've mentioned above or as a special rider then it's referred to as "drop down." Like most forms of insurance the policies may widely vary, but my advice to the OP remains the same, that just because someone claims they have an umbrella policy does not mean they're covered for marine insurance. Clearly I haven't seen the man's policy but I do have a thorough understanding of how umbrella policies generally work and until I did see it, I wouldn't even consider running his boat.

Umbrella policies are actually quite inexpensive for the limits they generally have and the only reason they can be is that all normal claims are covered by other policies. What you've quoted from Geico is a very general web statement but not reflective of this situation. Similarly, the quotes I've posted are general and not like clauses pulled from actual policies. Even umbrella policies though have exclusions like all other policies.

Grand Cayman is only about a 540 nm trip from Key West and then 300 nm or so from there to Jamaica. We crossed from Jamaica to Isla Bastimentos which is about 650 nm. The only caution is that once you leave Key West on that swing, you're completely on your own.

Freebird. What is the flag state of the boat?

I believe you are not interpreting this correctly. Olderboater is correct, the umbrella only covers if it is listed in an existing policy. I just went through this with my insurance. In a very simplistic example, you cannot cover one car with a policy then get an umbrella and assume you can have 10 cars and they are all covered under your umbrella. An umbrella provides additional or supplemental liability of your base coverage but you have to primary coverage in place first.

Well, knowing it's flag state is important. As to running those long legs, you can shorten the route to Cancun by doing 340 nm legs to Cancun and then Cancun to Cayman. You can shorten the trip out of Jamaica by going to Honduras about 360 nm or so. Regardless, Grand Cayman and Jamaica add a lot of miles. Now they're both still worth it if you have time. You can go to Jamaica by first cruising the Eastern Caribbean and coming from there, cutting through between Cuba and Haiti, not a path I'd recommend today.