The Ferrari: you can pick up one of the early 80s 308s or a mondial, even one with less than 50k, for about $30,000. The sticker price itself is actually not to bad when you compare it to the price of a new SUV. However, the full ownership cost is going to be a lot more. My brother has an 86 Lambourgini Countach, and that thing is broken down half the time. Not like he can take it to his local garage, either. Plus, for most of us, $30K is still way too much to pay for a "play car" that won't be useful for picking the kids up from soccer practice. If you broaden your imagination enough, and can accept just a red Italian sports car, then why not try an Alfa Romeo Spyder Veloce from the late 70s through early 80s. Drivable ones can be had for$3,000, maybe even less. And they are simple enough to work on yourself.
The surfski - a new fiberglass surfski like Magnum's runs $3,000 to $5,000. If you're going to be really into the sport, that's really not to bad. If you live on the West Coast, you can probably find used ones, too, but if not, you will likely have a hard time finding used or new. Plus, surfskis are very tippy, can be frustrating to learn to ride. A plastic sit-on-top kayak is easy to use the first time you try (though get a little training for safety sake) and new ones can be found at sporting goods stores throughout the country for as low as $200. Though I recommend spending a little more, as the short cheap kayaks can be frustratingly slow. One I can recommend personally is the Ocean Kayak Frenzy. New they are under $500, but they are so popular used ones are widely available for even cheaper. Hobie and Wilderness Systems also make good, widely available kayaks, with the lower end (but still fun to paddle) models being similar in price.
As far as Magnum's Colt M1911A1 goes, if you are into firearms, that is really easy to get on the cheap. The real thing is widely available and not that expensive, and lots of gun companies like Taurus make perfectly serviceable knockoffs.
Update:
While we can't all live in Hawaii, or even on the ocean, there are steps you can take to "Magnify" your house. If your wife doesn't mind, or you have a "man-cave", you can certainly decorate it in a tropical or tiki theme - a lot of rattan and bamboo, wooden masks on the wall, etc.
I'm fortunate in that my wife shares my eclectic decorating tastes. I have traveled a lot in Mexico, Africa, Europe and Japan and have brought home folk art, so our living room has an old school globetrotting adventurer look, wooden masks, carvings, a Maasai spear, etc., kind of like the Adventurer's Club on Pleasure Island in Downtown Disney in Orlando, if you've ever been there. It is certainly a place that Higgins would be comfortable in. I also inherited two chinese chests as end tables and a chinese coffee table from my grandmother, so that has informed our style in that room.
If you don't already have the stuff I have but want to go for that look, hit Pier One and Cost Plus World Market.
Indoor plants like Neanthabella palms can lend a tropical flair.
Then in the backyard, go with tropical landscaping. I am on the Gulf Coast, so I can do a lot of tropicals - bananas, ginger, philodendron, hibiscus, bird of paradise, canna lilies, etc.
If you live in a colder climate, there are a lot of "tropical looking" plants that can survive freezing, like canna lilies, some hibiscus, and rose of sharon, even chinese windmill palms do really well in cold climates. You can also keep more tender tropical plants in pots, and bring them inside during the winter. I do that with my pygmy date palm and plumeria (the plant Hawaiians use the flowers of to make leis).
If you have a swimming pool, that is a great way to have a tropical resort feel in your backyard. I don't but I did put in a 150 gallon pond that really adds to the feel of the backyard, especially in the summer when the water lily is in bloom. I also keep small, colorful native fish that I catch nearby, like sailfin mollies, golden topminnows, and orangespotted sunfish, as well as small crayfish.
Of course, I don't recommend this for everyone, but if you were really hardcore, you could choose your house to fit your Magnum lifestyle. There are a lot of mid 1960s ranch-style houses out there which had an Asian flair. Here are two examples in different neighborhoods of Houston.
midcentury modern 2 by mmyers1976
Midcentury modern by mmyers1976
