Hey Lykkers! Ready to spice up your portfolio beyond stocks and bonds? We don’t blame you. Alternative investments like classic cars or private vineyards can be thrilling—both financially and personally.

But before you get swept up in the romance of owning a rare collectible or a slice of paradise, let’s talk about the less glamorous but absolutely critical side of the equation: insurance.

These aren’t assets you can just add to your existing policies. They come with unique risks that demand special protection.

Here’s a look at 6 "alternative" investments that require special insurance before you buy, so your passion project doesn’t turn into a financial pitfall.

That vintage Porsche isn’t just a car—it’s a moving piece of art. Standard auto insurance won’t cover its agreed value, specialized repairs, or the fact that it’s often stored, not driven. You’ll need a stated-value or agreed-value policy from a specialty insurer.

"The classic vehicle marketplace behaves differently than the new or used car market does. Classic vehicles are an emotional purchase," explains Hagerty, a leader in collector vehicle insurance. Without proper coverage, a minor fender-bender could mean a total loss on your investment.

2. Fine Art & Sculptures

Whether it’s a contemporary painting or a Renaissance sketch, art is vulnerable to damage, theft, and market shifts. A fine art floater or inland marine policy is essential. It should cover transit, restoration, and market value—not just purchase price.

Ensure your policy covers every step from auction house to your climate-controlled wall.

3. Private Aircraft

A plane isn’t a luxury car with wings; it’s a complex liability. Insurance must cover hull (physical damage), liability for passengers and ground damage, and even "avionics" equipment.

4. Rare Watches & Jewelry

A Patek Philippe on your wrist or a diamond necklace in a safe is a magnet for theft, loss, or accidental damage. Standard jewelry coverage under homeowners insurance has low sub-limits (often $1,500-$5,000).

You need scheduled personal property coverage with worldwide protection and no deductible. Remember, the market for rare watches has exploded—make sure your coverage has too.

5. Vacation & Rental Properties (Abroad)

Buying a villa in Italy or a cabin in the Rockies? Your standard policy won’t cross borders or cover frequent guest turnovers. You need dwelling-fire or specialized landlord policies that include liability for short-term rentals, local catastrophe risks (like wildfires or floods), and emergency assistance.

Don’t assume your U.S. insurer has you covered abroad.

6. Digital Assets (Cryptocurrency & NFTs)

Your Bitcoin and Bored Ape exist on the blockchain, but the risks are very real: exchange hacks, device theft, and "sim-swapping" to access your wallet. Traditional insurance doesn’t touch this.

You need cyber insurance or specialized digital asset custody insurance. Some crypto exchanges offer limited coverage, but for large holdings, "cold storage" solutions with third-party insurance are becoming the gold standard. Remember: If you lose your private key, not even insurance can bring it back—so secure it first, insure it second.

Diversifying into alternative investments is smart, Lykkers—but protecting them is smarter. Each of these assets tells a story, and the right insurance policy ensures that story doesn’t have an unexpected, costly ending. Always get the policy before the purchase, and work with a broker who specializes in these unique fields.

Which alternative asset is calling your name? Share below—and let us know if you’ve already insured it!