$15,400

When some families head to Sarasota for a vacation, they not only rent a lavish beachfront home; they also hire the same kind of five-star meal service you’d find at an ultra-luxury resort. Sarasota’s Innovative Dining, headed by chef Jeremy Hammond-Chambers, regularly does such catering, providing the vacationers breakfast, lunch, dinner and a full open cocktail bar all day long, for anywhere from 10 to 30 people—sometimes more—for a week or more. Cost: $250-$275 per day, per person. For a family of eight, that works out to about $15,400 a week.

$394,000

It wasn’t the design, fabric or beauty that made a recent auction item one of the most expensive chairs ever sold. It was the magical provenance. The simple oak chair was the one J.K. Rowling sat in as she wrote her famed Harry Potter books. Gerald Gray, owner of Sarasota’s AutoKontrol USA, paid $29,000 for the chair on eBay in 2009. It proved to be a good investment, bringing $394,000 when Gray sold it at auction earlier this year.

$2 million

The richest little lap dog in the world was a longtime Sarasota resident. Trouble, a white Maltese that belonged to New York hotel heiress Leona Helmsley, inherited $12 million when her owner died. A judge later knocked that down to a paltry $2 million, but it was still enough for Trouble to live in luxury at Sarasota’s Helmsley Sandcastle Hotel, with $8,000 worth of grooming each year and her own full-time security guard, before passing away in 2011 at the age of 12.

$14.5 million

Can you put a price tag on fulfilling the dream of owning your own private island? Mark Pentecost, founder and CEO of Palmetto-based It Works!, a global distributor of beauty and nutrition products, did exactly that last summer when he and his wife bought Little Bokeelia Island for $14.5 million. He says he’ll use the 104-acre island near Charlotte Harbor as a family and corporate retreat.

$8,950

In July, four Sarasota couples enjoyed the foodie trip of a lifetime with celebrity chef Roy Yamaguchi of Roy’s Restaurants. Offered by Admiral Travel, the experience included a tour of Tokyo’s Tsukiji Market, the largest wholesale seafood market in the world, with a sushi-making lesson by a sushi master. The cost? $8,950 per person.

$600,000

Jeweler Tina Little has sold many exquisite pieces to local customers at her Queens’ Wreath Jewels, including a ring set with a rare pink diamond priced at $600,000. But the splurge that stands out in her memory was a diamond necklace by Italian jewelry house Zydo. A male customer had stopped into the shop just to say hello, and she pointed out the necklace, which was priced at $100,000. “Can you imagine the woman who would wear this piece?” she asked him. He agreed it was beautiful and lamented that he didn’t have a woman like that in his life right now. A few minutes later, though, he picked up the necklace and said, “I’m going to buy it, anyway. If the right woman comes along, I’ll put it around her neck. If not, I’ll leave it to my son.” Two years later, says Little, “I went to his wedding and the bride was wearing it.”

$800,000

High fliers like a little leg room. They get plenty when they charter a BBJ—Boeing business jet—through Paramount Business Jets for $12,000 an hour. A converted 737 airliner that can accommodate 19 passengers in regal comfort, the BBJ has two bedrooms, two full baths, a luxurious stateroom, multiple flat-screen TVs and a full range of high-tech business services. A company sales rep says customers range from entertainers and executives to private families and have included a number of Sarasotans. A Florida dad chartered one for two weeks over this year’s spring break to fly his brood to a Caribbean island, at a cost of $800,000—and that’s not counting concierge and dining services.

$900

Tennis Hall of Famer Nick Bollettieri, founder of what’s now IMG Academy in Bradenton, coached Andre Agassi, Monica Seles and many more pros to tournament titles. Now in his 80s and as vital as ever, he’s still sought after by rising young stars, whose parents shell out $900 a session for private lessons with the legendary guru.

$1 million

The outrageous landscapes Lucas Congdon of Lucas Lagoons creates for Southwest Floridians on TV’s Insane Pools have shot the show to No. 1 on Animal Planet. A typical client might spend $500,000 to $1 million or more for a lazy-river pool with Tennessee rock grottos, water walls, sound and light shows, fire features, spa, outdoor kitchen and a jungle of landscaping. Congdon is currently working on his biggest project yet, for a Miami couple with five kids. At $2.2 million, it includes a sleek rooftop outdoor living space with day beds and other seating, water feature and outdoor kitchen; and a ground-floor pool area, with a monumental meandering pool, a hot tub the size of most pools, grottos galore, a beach, another outdoor kitchen and every other embellishment Congdon’s feverish imagination can dream up.

$34,000

Fired up by the cause, the competition, and, let’s be honest, some cocktails as well, folks at nonprofit galas can bid astonishing amounts on live auction items. Sarasota socialites have paid thousands for a quilt their kids’ classroom has stitched together, $20,000 and up for catered dinners for a group, and way more than that for trips to Paris or the Oscars. But even jaded gala-goers quieted down when, at the Sarasota Museum of Art’s “Big Bash” in January 2014, a single bottle of wine—six liters of 2000 Chateau Petrus—was sold for $34,000 to Robert and Mimi Eisenbeis. Mimi looked surprised by the bid, but turns out Robert knew what he was doing, reselling the bottle for a tidy profit a few months later in New York.