MIAMI BEACH, Fla.—The big auction houses capped the fall art season with $1.1 billion in sales in New York two weeks ago, but collectors must still have a few blank walls left. How to tell? At least 77,000 people are expected this week at Art Basel in Miami Beach, a contemporary fair that is the year’s last art-buying hurrah.

Since the auctions just tested values for blue-chip artists like Pablo Picasso, the stakes and atmosphere at this fair, which opened Wednesday and runs through Sunday, are somewhat more relaxed. It’s commonplace to see billionaires and museum directors wearing flip-flops as they navigate the warren of 269 gallery booths in the Miami Beach Convention Center. Amid the $2.5 billion worth of works that insurer AXA Art estimates is on offer, the goal is to make an artistic discovery and reap the rewards before everyone else does.

Beyond the main fair, a playful vibe also imbues the 25 satellite art fairs—a record tally—that have set up shop around the city. Artist duo Jen Catron and Paul Outlaw intend to critique the profusion of satellite displays by swimming around in a 3,000-gallon, makeshift bowl of cereal located outside the Satellite Art Show, according to organizers. Over at the beachfront fair called Untitled, artists Rirkrit Tiravanija and Tomas Vu plan to operate a pop-up surf shop during Art Basel week. The store will be outfitted with 15 surfboards inscribed with Beatles lyrics as well as a shower shaped like a water tower where participants can rinse off after hitting the waves.

Elsewhere, other artists are offering aromatherapy sessions and free tattoos. At Wednesday’s VIP preview, attendees included actress Charlotte Gainsbourg, directors Brett Ratner and Yi Zhou, as well as collectors Jean Pigozzi, Dasha Zhukova and Maja Hoffmann. And on Friday, Madonna shows up to host a charity auction at Argentine collector Alan Faena’s new cultural center, Faena Forum.

No amount of glitz can mask the fact that the global art market has been sluggish. But Noah Horowitz, Americas director for Art Basel, said he thinks the November auctions gave the market a new floor. “We feel like a baseline has now been established, and we expect collectors to feel more confident,” Mr. Horowitz said. “Challenging environments also tend to bring out the strongest art.”

Some dealers brought artists who seem safe bets in good markets or bad. New York dealer Emmanuel Di Donna displayed $40 million worth of modern masters, including Spanish artist Joan Miró’s 1976 “Painting,” a portrait of what appears to be a gaping monster and a nude woman. The Spanish painter gave the work to his compatriot and fellow artist, Eduardo Chillida. Mr. Di Donna was offering it for $12 million. The dealer was asking $8 million for “The Explanation,” a 1952 René Magritte depicting a wine bottle morphing into a carrot.

Galerie Gmurzynska, of Switzerland, hired a pair of art-world heavyweights—Picasso’s son, Claude, and curator Norman Rosenthal—to design the slant-walled booth and choose the display of works by Kazimir Malevich and other members of the 20th-century Russian avant-garde.

Some dealers brought lesser-known artists, betting on the fair’s reputation for transforming young or overlooked creators into international stars. A few highlights:

HOWARDENA PINDELL

This 73-year-old abstract expressionist from Philadelphia makes art using an everyday hole punch, puncturing canvases over and over until the dots clump amid bright splashes of paint. During the 1970s, Ms. Pindell spent her days working as a curator at the Museum of Modern Art and her nights painting. New York’s Garth Greenan Gallery has brought three of her untitled, 7-foot-wide abstracts from 1972-73 to the fair, angling for a market reappraisal before her retrospective at Chicago’s Museum of Contemporary Art planned for 2018.

–Kelly Crow

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