The city of Anna Maria’s annual Holiday Walk along Pine Avenue is back.
And businesses along the roadway are ready for the festivities.
Pine Avenue will be closed to traffic 5-9 p.m. Friday, Dec. 12, for the 2025 Holiday Walk, which did not happen last year since the city was still recovering from hurricanes Helene and Milton.
The event turns Pine Avenue into a festive walking-only zone, allowing people to stroll the corridor and visit its businesses, many of which will stay open and celebrate the night by providing special offerings to the public.
Multiple business owners and managers along the roadway told The Islander Dec. 5 that they are excited for the event’s return.
“We always love the holiday walk. It’s a lot of fun,” Lauren Collins, owner of Island Charms, 218C Pine Ave., said. “I think everybody’s very happy to have it back. After the hurricanes, there was just so much work to do and none of the businesses and locals got to do their normal holiday festivities.”
Collins said her boutique reopened last December after nearly three months of post-storm recovery efforts and, while the first months back were slow, business has since rebounded back to where it had been in years past.
Now, she is excited to celebrate the return of the Holiday Walk by keeping the store open and serving complimentary sangria and treats to visitors.
“I think everybody’s looking forward to it,” Collins said.
Other business owners, such as Tara Obrien, owner of Pineapple Marketplace, 425 Pine Ave., share Collins’ eagerness to get the festivities started.
“We’re ready,” Obrien said. “We’re ramped up and ready to go.”
The Pineapple Marketplace has traditionally worked in tandem with its next-door business, Beach Bums Recreational Rentals & Gift Shop, 427 Pine Ave., during Holiday Walks.
While Beach Bums hands out free hamburgers and hot dogs, Pineapple Marketplace provides tables to sit at, live music to enjoy and complimentary drink samples for eventgoers.
Obrien said that tradition would return with this year’s Holiday Walk, with the marketplace serving complimentary margarita samples to people over the age of 21.
Rebecca Preston, owner of the Shiny Fish Emporium, 306 Pine Ave., said her boutique will bring back its tradition of serving eventgoers “drunken hot chocolate,” an alcoholic version of the hot beverage, along with homemade cookies and treats.
Additionally, the store will hold giveaways for children.
“This has always been a big highlight of the year for us,” Preston said. “It’s such a sweet event.
For the Chocolate Emporium, 216C Pine Ave., this year’s Holiday Walk may be the start of its own tradition.
The business opened in August and has so far received “outstanding support” from the community, according to manager Liv Baker.
Baker said that, after getting a taste of what a crowded Pine Avenue is like during Bayfest earlier this year, she was looking forward to the business’ first Holiday Walk.
“We’re so excited,” she said. “We were here for Bayfest and we had the best time. … We’re very lucky to be on a street that hosts so many different events.”
Baker said the store will remain open for the event and staff will take to the street and hand out free samples of chocolate, taffy and other candies to eventgoers.
For some people, like Kelly Kary, owner of the Olive Oil Outpost, 401 Pine Ave., their excitement for the event is mixed with some anxiety.
Kary said the store will provide complimentary “libations and snacks” to visitors during the event, but declined to detail the offerings since she did not want to drum up more “craziness” than usual.
“I hate to say what I’m going to hand out because I’ll be stampeded again,” she said. “The lines get long enough as it is.”
Despite the madness, Kary said the event helps drum up business by increasing exposure and getting people in the holiday spirit.
“It’s a lot to prepare for … but it is great,” she said. “In the past years, it has always helped quite a bit.”
Many people are just happy to see the return of a beloved community event — and the community that makes it happen.
“It’s just great to see everyone get together, especially after last year,” Ben Sato, owner of gRub Tropical BBQ, 415 Pine Ave., said. “It’s great to get back to normal things like that.”
Sato said his restaurant, which is having its best year yet, will be open for the event and provide complimentary frosés — slushy cocktails made from rosé wine — to visitors aged 21 or over.
Hannah Adams, general manager of Poppo’s Taqueria, 212C Pine Ave., said last year’s storms may have made the community and its local businesses even more tight-knit.
“It feels like the community has come together really well and it seems like the hurricanes kind of made us stronger,” she said. “It’s one of those things that we’re not going to forget about, but we’re definitely coming together more now.”
According to Adams, Poppo’s will remain open during the event, but the business would also share a tent outside with 3 Daughters Brewing out of St. Petersburg.
They will provide complimentary mini crunch wraps, as well as beer and cider samples, to eventgoers from the tent.
Preston said the Holiday Walk is an opportunity to give back to the community that kept so many local businesses afloat through last year’s struggles.
“It sounds kind of corny, but it’s kind of like a hug to the community. Like, thank you so much and we’re just so happy the island is celebrating again. It feels like everything is OK again,” she said.
Additional offerings
Elsewhere on Pine Avenue, people attending the Holiday Walk can enjoy:
- A visit with Santa Claus at the Anna Maria Island Historical Society Museum, 402 Pine Ave.;
- Complimentary spiked eggnog and sweet treats at the Anna Maria General Store, 503 Pine Ave.;
- Complimentary champagne and oysters outside of Duncan Real Estate, 310 Pine Ave.;
- Complimentary gingersnap cookies at Hometown Desserts, 507 Pine Ave.