Don’t get too fancy. Head to edgier, trendier, neighborhoods. And definitely stay on time.

These are a few of the tricks cities are deploying in their all-out effort to woo Amazon.com Inc.’s new headquarters, a move the online retailer says could bring nearly 50,000 jobs and more than $5 billion in investment over nearly two decades. Amazon executives have quietly visited more than half of the cities on its list of 20 finalists, which are vying to host what it calls HQ2, according to people familiar with the matter. The visits, which started in recent weeks, have included Dallas, Chicago, Indianapolis and the metropolitan Washington, D.C., area.

Amazon hasn’t provided much guidance on what it expects from the site visits. It has asked for breakout sessions on education and talent, plus visits to the sites it is considering, all within a strict time frame of two days, max. The rest is up to local officials.

As a result, officials of candidate cities are scrutinizing the company’s business practices to concoct the perfect 48-hour-or-less-visit that could win over Amazon.

Details of the visits are scarce. Amazon, which has said it plans to announce the winning suitor later this year, has advised HQ2 candidates to keep this phase private. And city officials are loath to spill any tricks that could give their rivals a leg up.

Still, people familiar with the visits paint a picture of whirlwind trips with Amazon’s small economic-development team. Led by Holly Sullivan, it dives into data provided by the cities—such as the ACT and SAT scores of local high-school students—and asks a lot of probing questions regarding how much talent Amazon can attract.

Municipal officials said that while Amazon has some of the quirky features of a hotshot technology company—it allows employees to bring thousands of dogs to its Seattle campus and gives out free bananas at two campus stands—it doesn’t offer many of the other trappings associated with working at a tech giant, such as free meals.

Amazon is “a frugal-ass company,” said one city official working to win the project. “They’re making a 100-year decision…. All of the extra fluffy stuff is fluff.”

So, many cities are nixing the fancy hotels, dinners at the governor’s mansion, private planes and small gifts—all typical core aspects of a traditional site visit, according to people familiar with the matter. “We were concerned that if we went over the top, it would push them away,” said a person involved in one site visit.

Instead, they are attempting to be creative by bringing in university officials, younger people and professionals who can speak to talent and growth in the area. Officials are adding visits to trendier neighborhoods to highlight the draw for younger employees. And cities have even ferried Amazon executives around by bicycle and boat as modes of transportation.

“Amazon is working with each HQ2 candidate city to dive deeper on their proposals and share additional information about the company’s plans,” an Amazon spokesman said in a written statement. The spokesman confirmed site visits were taking place.

A few of Amazon’s desires are crystallizing, some of the people said. The company appears to be leaning toward a more urban site, despite requesting proposals that included sites in the suburbs. It also wants to come to a city prepared to handle the company’s growth and the influx of high-paid employees. In its home base of Seattle, Amazon has faced criticism for contributing to traffic and higher housing costs.

“They believe there is no American city that can provide for all their needs,” said the person involved in a site visit. Another person said the company expects to have to compromise no matter which location it selects. Amazon has also placed particular emphasis on the tech talent pipeline: how much already exists locally, and how much Amazon can attract from around North America and the rest of the world.

Some cities are offering financial incentives. New Jersey and the city of Newark have offered a package valued at $7 billion, while Maryland—where Amazon is considering a location in Montgomery County—has put $5 billion on the table.

In the past, cities have become creative to attract or retain a coveted company. To try to keep JetBlue Airways Corp. based in New York, the city’s economic-development corporation did its research. Officials found out the company hosted regular softball tournaments, so they specifically pitched the airline on a location near a field. City and state officials also worked out a joint deal offering JetBlue co-branding rights to the “I (heart shape) NY” logo as well as the slogan, “JetBlue, New York’s Hometown Airline”—something that helped seal the deal.

Washington, D.C., might have a leg up, having already hosted Amazon Chief Executive Jeff Bezos for visits when he considered acquiring the Washington Post, which he now owns. Mr. Bezos also purchased the former Textile Museum in Washington’s Kalorama neighborhood for $23 million in 2016 and is currently turning it into a private residence.