Updated: October 2026
Christmas on Anna Maria Island is a small-town affair. The island lights its trees on Bridge Street and in Holmes Beach, Santa rides through town on a pirate ship, and a lighted boat parade passes the marina, all in a beach town where December afternoons often reach the 70s. This guide covers the tree lightings, parades, markets and church services on and around the island, plus a few mainland events worth the short drive.
Dates and times below reflect 2026 announcements where venues have published them. Events still waiting on 2026 details are are listed with TBA and information is updated as it arrives. For where to eat during your visit, see my Dining on Anna Maria Island: My Insider Guide.
Planning Tips
- Book early · Island rentals for Christmas week fill far in advance and popular events such as the North Pole Express sell out.
- Arrive early for evening events · Parking on Bridge Street and Pine Avenue is limited once the crowds gather.
- Pack layers · Days are usually mild but evenings by the water can drop into the 50s.
- Bring a lawn chair · For parades and outdoor events comfort is important.
Christmas Events on Anna Maria Island by Date
Christmas on Bridge Street
- November 21 · 2026
- 2:00 PM to 8:00 PM
- 101 Bridge Street · Bradenton Beach
The island’s Christmas season opens with the tree lighting on Bridge Street. Santa visits, local merchants offer specials, and live music and seasonal treats fill the street until evening. For restaurants and shops along the street, see Bridge Street on Anna Maria Island: My Insider Guide.
Light Up Longboat
- November 21 · 2026
- 5:00 PM to 7:00 PM
- Karon Family Pavilion · Town Center Green · 600 Bay Isles Road · Longboat Key
Longboat Key starts the season with a tree lighting, live music, local food, raffle giveaways, and gift card and merchandise sales. Santa appears along with Mickey and Minnie. The Rotary Club of Longboat Key collects unwrapped children’s gifts at the event.
North Pole Express
- November 27, 28, 29 and December 2 -6, 9-13, 16-22 · 2026
- Departures · 5:15 PM and 7:15 PM
- The Florida Railroad Museum · 12210 83rd Street East · Parrish
This is a short drive from the island and worth the trip for families with young children. A vintage train carries guests from Parrish to a North Pole set up on a grassy field. The ride takes about 45 minutes each way, and guests spend roughly two and a half hours at the North Pole. The full evening lasts about three hours and 45 minutes.
Every ticket includes the round-trip ride, a private visit with Santa, a gift for every child, unlimited cookies and hot chocolate, campfires, storytelling, model train displays, reindeer food and access to the toy tent. S’mores kits and extra food are sold on site.
Seating comes in four levels. Coach Class uses open-air cars and is the most affordable. Excursion Class adds assigned seats, and some cars are enclosed. First Class has assigned seats in climate-controlled cars, with snacks and drinks on the ride. A Private Caboose holds up to 16 guests.
A couple of practical notes: arrive 45 to 60 minutes before departure and book everyone in your party on one reservation so you are seated together.
Privateers Christmas Parade
- TBA
- 10:00 AM
- Coquina Beach in Bradenton Beach to Bayfront Park in Anna Maria
The parade features the Privateers’ famous pirate ship float, festive floats, classic cars, and local groups decked out in holiday gear. Locals and visitors line the streets to cheer and collect candy and beads tossed from the floats.
Anna Maria Island Jeep Christmas Parade
- December 4 to 6 · 2026
This weekend of holiday events collects canned goods to stock the shelves of the Manatee County Food Bank. It opens Friday with a meet and greet, continues Saturday with a lighted Jeep convoy, and ends Sunday with a scavenger hunt. Bring canned goods to take part.
Mistletoe Market
- December 5 & 6 · 2026
- 10:00 AM to 5:00 PM
- City Field · 6001 Marina Drive · Holmes Beach
Booths fill City Field with handcrafted gifts, local art and seasonal treats, with music playing throughout the weekend. It is a good stop for holiday shopping before the evening events begin.
Christmas Tree Lighting and Holiday Open House
- December 5 · 2026
- 5:00 PM to 8:00 PM
- AMI Chamber Lot · Holmes Beach
Holmes Beach shops stay open late with treats, caroling and holiday sales. The tree is typically lit around 6:00 PM.
Lester Family Fun Day
- December 5 · 2026
- 10:30 AM to 2:00 PM
- The Center of Anna Maria Island · 407 Magnolia Avenue
This longtime island tradition at The Center offers pony rides, inflatables, cookie decorating and crafts. DJ Freeze provides the music, the Manatee High School Drum Line performs, and Santa visits at noon. Duffy’s Tavern, Anna Maria Oyster Bar, and Small Town Creamery sell food on site.
The day ends at 2:00 PM with a helicopter golf ball drop, a 50/50 raffle in which the ball landing closest to the flag wins. Balls cost $50 each or three for $100 and benefit The Center’s community programs. For more ideas, see Things to Do with Kids on Anna Maria Island: My Insider Guide.
Winter Wonderland
- December 5 · 2026
- 5:00 PM to 8:00 PM
- Old Main Street · Bradenton
In past years, Santa and Mrs. Claus have posed for photos, snow has fallen through the evening, and a snow slide, carnival games, performances, vendors and food trucks have filled the street.
Old Florida Christmas
- December 12 · 2026
- 10:00 AM to 2:00 PM
- Manatee Village Historical Park · 1404 Manatee Avenue East · Bradenton
The park is decorated in Victorian and Florida pioneer style. Local vendors, food trucks, family activities and live entertainment round out the day.
Christmas in Cortez
- December 12 · 2026
- 12:00 PM to 3:00 PM
- Florida Maritime Museum · Cortez
This free event in the historic fishing village includes a bounce house, holiday crafts and lawn games. Children can visit Santa inside the Cortez Cultural Center. To explore the village before or after the event, see The Historic Cortez Fishing Village: My Insider Guide.
A Night Before Christmas
- December 12 · 2026
- 4:00 PM to 8:00 PM
- GT Bray Park · 5502 33rd Avenue Drive West · Bradenton
Santa and Mrs. Claus pose for professional photos, and the park offers a snow slide, foam zone, inflatables, face painting, crafts and a petting zoo. A vendor marketplace and food trucks are on site. Entry is free with one new, unwrapped toy per family for Toys for Tots.
Pine Avenue Holiday Walk
- December 12 · 2026
- 5:00 PM to 9:00 PM
- Pine Avenue · Anna Maria
Pine Avenue businesses open their doors with holiday treats, warm drinks and seasonal sales while carolers sing and Santa greets children for photos. For where to shop and eat along the street, see Pine Avenue on Anna Maria Island: My Insider Guide.
Manatee River Holiday Boat Parade
- December 12 · 2026
- Bradenton · along the Manatee River · between the De Soto and Green Bridges
Estimated Viewing Timeline
- 5:30 PM · Staging begins at Shaw Point
- 6:15 – 7:30 PM · Bradenton Yacht Club (Private Members Club)
- 7:15 – 8:15 PM · Riverhouse Waterfront Restaurant
- 7:30 – 8:30 PM · Pier 22 Restaurant /Twin Dolphin
Decorated boats compete for cash prizes while thousands of spectators line the shore. Estimated viewing times:
Winter Nights Under the Lights
- December 17 to 20 · 2026
- 6:00 to 9:00 PM
- Palma Sola Botanical Park · 9800 17th Avenue NW · Bradenton
The park glows with holiday lights while live music plays. Visitors meet Santa and Mrs. Claus, buy food truck fare, hot cocoa, coffee and cider, shop in the Galleria building and vote for a favorite Christmas tree decorated by local elementary students. Admission is free. Donations and unwrapped toys for Toys for Tots are welcome.
Christmas Church Services on Anna Maria Island
The island has five churches that hold Christmas services. Churches usually confirm their Christmas schedules in early December, so call ahead.
CrossPointe Fellowship
- 8605 Gulf Drive · Holmes Beach
- 941-778-0719
- Christmas Eve Candlelight Service · blending contemporary worship music with traditional elements
Episcopal Church of the Annunciation
- 4408 Gulf Drive · Holmes Beach
- 941-778-1638
- Christmas Eve Service · service with music, Holy Communion, and candlelight
- Christmas Day Service · traditional service
Harvey Memorial Community Church
- 300 Church Avenue · Bradenton Beach ·
- 941-779-1912
- Christmas Eve Service
Roser Memorial Community Church
- 512 Pine Avenue · Anna Maria
- 941-778-0414
- Christmas Eve Candlelight Service · service with carols and scripture readings
- Christmas Day Service · service with hymns
St. Bernard Catholic Church
- 248 South Harbor Drive · Holmes Beach
- 941-778-4769
- Christmas Eve Mass · 4:00 PM and 6:00 PM
- Christmas Day Mass · 8:30 AM, 10:30 AM, and noon
Let Someone Else Handle the Decor
Visitors and vacation rental owners who want a decorated home without doing the work have two island options. My Beach Concierge offers a Holiday Concierge service that styles Christmas trees, holiday decor and seasonal touches. Sandy Toes Picnics runs Island Elves, a Christmas concierge service. Both book up early in the season, so reach out for pricing and availability.
Want more real-time tips and honest answers about Anna Maria Island? Join Anna Maria Island Insider, my Facebook group built on one simple rule: real, helpful answers only. Join the group.
Coastal Close
Anna Maria Island does the holidays the way it does everything else, unhurried and with a little salt air. A tree lighting on Bridge Street, a pirate ship rolling down Gulf Drive, a candlelight service on Pine Avenue or an evening watching the boat parade all feel like the island at its best. For where to eat on Christmas Eve and Christmas Day, see Christmas Dining on Anna Maria Island: My Insider Guide. For a downloadable list of where to eat year-round, my downloadable Anna Maria Island Restaurant Guide on Etsy is the place to start.
— izzy