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Would the current owners consider sailing it back with/for you? You might even make that part of the negotiations for purchase. In addition to relocating the boat, that's a great way to get the "pass down" from the prior owner, on all the quirks and systems, etc.

I did the same with my boat, though it was only a 25 mile trip. But the seller appreciated the chance to take one last sail, and we had a nice trip.
 

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This is a 3 day trip. You can get it done for $250 a day from Niceville plus expenses plus return flight cost. You could also just motor it yourself through the ICW all the way to Slidell. The mast on a Hunter 31 is less than 50' so you would be able to clear the one 50' bridge along that route which is at Fort Walton at the western side of Choctahatchee bay. The only down side to taking the ditch would be that you would miss some very nice cruising grounds on the outside from Niceville to Pensacola although Santa Rosa Sound is one of the nicer sections of the ICW should you decide to take that route.
 

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As a delivery captain I require that the owner submit me to the insurance company as an authorized vessel operator and I believe this is a common solution to the vessel insurance issue
That is how it's commonly done and there is occasionally a small added fee, for a defined trip, during a defined window. Understand, however, being added as an operator only means the owner's policy will pay the owner's covered losses, while you are operating the vessel. That does not mean it protects the non-owner operator.

For example, say the delivery skipper rams another boat. The owner gets their boat fixed on the insurance company's dime, along with coverage for any liability that is accrued to them, perhaps for damage to the other boat. However, the other damaged vessel can still sue the operator directly, who is not covered. Not to mention, the owner's insurance company has the legal right to pursue the party that caused their loss (ie subrogate the claim). In order for the new operator to have coverage under the policy, they must be added as an additional insured party, not just an authorized operator. Additional insureds are harder to do temporarily and cost more. As an owner, I typically have only added the skipper as an operator and doubt they've fully understood they're not the ones that are covered.
 

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I wonder what you guys end up buying. I've been following your posts and very excited for you. good luck!
 
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