Tampa's Downtown on Ice: Even in Florida, you can get in the holiday spirit by skating on an outdoor rink in the park. Each 90-minute session includes skate rental. The rink is open through Jan. 3. 4 p.m., Curtis Hixon Park, 600 N Ashley Drive, Tampa. $12. (813) 966-5505.
TobyMac: The Christian pop superstar brings his blend of hip-hop and rock along with openers, Britt Nicole, Colton Dixon and Hollyn. 7:30 p.m., University of South Florida Sun Dome, 4202 E Fowler Ave., Tampa. $25-$75. (813) 974-3004.
Florida Orchestra Pops: Curtis Stigers Celebrates Sinatra: It's a 100th birthday celebration of Frank Sinatra with such beloved hits as Come Fly with Me, The Best is Yet to Come, among others. 8 p.m., Ferguson Hall at the Straz Center for the Performing Arts, 1010 N MacInnes Place, Tampa. $15-$45. (727) 892-3331.
Gulfport Fall Fest: Gulfport's large family festival with live entertainment, games, face painting, midway rides, food and drink. 5 p.m., Most Holy Name of Jesus Church Maria Center, 5800 15th Ave. S, Gulfport. Free (food and rides additional). (727) 347-9989.
Have Mercy: The indie-rock band brings a trio of openers including, Transit, SoMoS and Microwave. 7 p.m., The Orpheum, 1915 E Seventh Ave., Ybor City. $13-$15. (813) 248-9500.
Wine, Women and Shoes: The event centered around the art of wine and shoe pairing is a walk-around wine tasting and boutique shopping experience featuring a high energy fashion show, auction and live entertainment. 6:30 p.m., Renaissance Tampa Hotel International Plaza, 4200 Jim Walter Blvd., Tampa. $125, $175 VIP. (813) 367-5437, ext. 5.
Damon Fowler Group CD Release Party: The monster roots, rock, blues and sacred steel player returns with his band to celebrate his most recent recording, Sounds of Home. 8 p.m., Palladium Theater, 253 Fifth Ave. N, St. Petersburg. $20-$30. (727) 822-3590.
Wizards of Winter: The Yuletide progressive metal ensemble featuring former members of Trans-Siberian Orchestra presents a holiday themed concert. 8 p.m., Capitol Theatre, 405 Cleveland St., Clearwater. $34.50-$49.50. (727) 791-7400.
Heather McDonald: The comic and bestselling author wrote for and appeared frequently on Chelsea Lately. 8 and 10:30 p.m., Improv Comedy Theater, 1600 E Eighth Ave., Tampa. (813) 864-4000.
KIDS AND FAMILY
Parents' Night Out: Parents can drop off their children in grades VPK through 3 to play at the museum while they have some quiet time together. Registration is required. 6 p.m., Great Explorations Children's Museum, 1925 Fourth St. N, St. Petersburg. $35, $25 members. (727) 821-8992.
Guy's Big Bite, 8 p.m., Food Network. Guy Fieri and some of his chef pals whip up a Thanksgiving feast that's bigger and better than ever. The menu includes turkey meatballs with fire-roasted green chile.
MORE TO EXPLORE
Find more holiday fun and shopping at tampabay.com/things-to-do.