I've had my 1966 Ford Galaxie 500 for about 3 years now.  Since the day I purchased it from a guy in Massachusetts, it's been insured by Hagerty.

Hagerty was one of the top rated insurers when I Googled it initially.  I was also able to use them through my local Allstate agent so they got it all setup for me which was nice.  I opted for their Hagerty Driver's Club on top of my normal premium.  This in my opinion added so much more for only about $70 per year.

My total premium for a year is $250, this assumes the car is worth $12,000.  It covers $100,000 per person and $300,000 per accident for bodily injury.  $100,000 for property damage.  $20,000 for personal injury per person, and it's $100,000/$300,000 for both uninsured and underinsured motorists.  This is all with zero deductible.

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What I like about them most is that every time I have called they are incredibly polite and helpful.  Their Driver's Club add-on includes roadside assistance with unlimited calls and guaranteed flatbed towing within 20 miles, and up to $100 for emergency services like lockouts, battery jumps, and even tire changes.  I've had to use the roadside a couple of times, once to move it in the winter, and the other because I knocked a hole in my oil pan.  Both times, they didn't question anything, and made sure they had me taken care of before leaving the line.  It's the only classic car insurer that I've dealt with but it's the only one I'm going to with what you get for the price.  Who do you insure your classic ride through?