Holidays on Anna Maria Island: My Insider Guide

Updated: June 2026

The holiday season on Anna Maria Island is magical. Whether you are visiting for Christmas or ringing in the New Year, the island delivers festive events, parades, light displays, twinkling decorations, fireworks, and candlelit church services that make the season feel genuinely special in a way only a small beach town can. Below is a comprehensive guide to Christmas and New Year events on and around Anna Maria Island. Exact dates will be added as they are published.

For the full picture of where to eat during your holiday visit, my Dining on Anna Maria Island: My Insider Guide covers every craving across the island.

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Holiday Events

Enjoy a jolly good time on and around Anna Maria Island, where the season shines bright with festive events, sparkling holiday decor, and lively island charm. Stroll beneath trees glowing with hundreds of twinkling lights, browse local shops that stay open late, and soak up the warmth of island-style holiday cheer.

Christmas on Bridge Street

• November 22nd · 2025
• 2:00 PM to 8:00 PM
• 101 Bridge Street · Bradenton Beach

Experience the magic of Christmas on Bridge Street with a dazzling tree lighting ceremony that brings the island to life. Stroll beneath twinkling lights, enjoy festive decor, seasonal treats, live music, and special offers from local merchants. Bring the whole family for a night of holiday cheer and a special visit from Santa Claus.

Light Up Longboat

• November 22nd · 2025
• 5:00 PM to 7:00 PM
• Karon Family Pavilion · Town Center Green · 600 Bay Isles Road · Longboat Key

A festive event to kick off the holiday season with a tree lighting ceremony, live music, special appearances by Santa and Mickey and Minnie, local eats, merchandise and gift card sales, and raffle giveaways. The Rotary Club of Longboat Key will be collecting unwrapped children’s gifts.

North Pole Express

• November 28, 29, 30 and December 3 -7, 10-14, 17-22 · 2025
• 4:45 PM
• The Florida Railroad Museum · 12210 83^rd Street East · Parrish 

All aboard for a magical holiday adventure from Parrish to the North Pole. The journey begins with a train ride where festive music and cheerful anticipation fill the air. Upon arrival, guests step off at the special North Pole station where Santa greets every child for a memorable visit. Enjoy holiday entertainment, cozy campfires, and hot chocolate and cookies throughout the evening.

Mistletoe Market

• November 29th & 30th · 2025
• 10:00 AM to 5:00 PM
• City Field · 6001 Marina Drive · Holmes Beach

Step into the magic of the Mistletoe Market, where holiday spirit meets island charm. Browse booths filled with handcrafted gifts, local art, and festive treats perfect for everyone on your list. Enjoy cheerful music, twinkling lights, and plenty of holiday joy at this seasonal event on Anna Maria Island.

Holmes Beach Holiday Open House & Tree Lighting

• December 6th · 2025
• 5:00 PM to 8:00 PM
• AMI Chamber Lot

Local shops stay open late, welcoming visitors with festive treats, cheerful caroling, and a warm sense of community. An evening filled with holiday sparkle and island charm to kick off the season.

Lester Family Fun Day

• December 6th · 2025
• 10:30 AM to 2:00 PM
• The Center of Anna Maria Island · 407 Magnolia Avenue
• Golf Ball Drop Raffle at 2:00 PM · $50 per ball or 3 for $100

One of the island’s most beloved annual traditions, this heartwarming event brings together locals and visitors for a day of old-fashioned fun filled with laughter, music, and holiday cheer. Pony rides, inflatables, cookie decorating, and crafts make it a great stop for families. Live music from DJ Freeze, performances by the Manatee High School Drum Line, and a visit from Santa at noon round out the afternoon. Classic food favorites are available on site, and the Golf Ball Drop Raffle at 2:00 PM adds a fun finale when a helicopter drops numbered golf balls for a chance to win.

Winter Wonderland

• December 6th · 2025
• 5:00 PM to 8:00 PM
• Old Main Street · Bradenton

Step into the magic of Winter Wonderland in Downtown Bradenton. Meet Santa and Mrs. Claus for a photo, brave the snow slide, and capture festive photos with holiday-themed vignettes. Snow falls throughout the evening while performances on the Winter Wonderland Main Stage and roaming entertainers delight visitors in the streets. Free winter carnival games, local vendors, and food trucks round out a perfect family outing.

Christmas on Bridge Street

• TBA
• 3:00 PM to 8:00 PM
• Pier Circle on Bridge Street · Bradenton Beach

Santa and his sleigh join the crowd for live music, face painting, and an outdoor screening of timeless Christmas classics.

Jingle Jeeps

• TBA
• City Hall Field · Holmes Beach
• Anna Maria Island Longboat Key St. Armands Circle

The route runs from AMI on Manatee, turning south at Publix onto Gulf of Mexico Drive through Bradenton Beach, stopping briefly at Coquina Beach, then continuing south through Longboat Key and through St. Armands Circle.

Old Florida Christmas

• December 13th · 2025
• 10:00 AM to 3:00 PM
• Manatee Village Historical Park · 1404 Manatee Avenue East · Bradenton

Celebrate the season with local vendors, food trucks, family-friendly activities, and live entertainment that capture the spirit of the holidays. The park will be decorated in Victorian and Florida pioneer style, offering a charming glimpse into past holiday traditions.

Christmas in Cortez

• December 13th · 2025
• 12:00 PM to 3:00 PM
• Florida Maritime Museum · Cortez

Free activities including a bounce house, holiday crafts, lawn games, and visits with Santa inside the Cortez Cultural Center. A fun, festive afternoon for the whole family in the historic fishing village of Cortez.

A Night Before Christmas

• December 13th · 2025
• 4:00 PM to 8:00 PM
• GT Bray Park · 5502 33^rd Avenue Drive West · Bradenton

Santa and Mrs. Claus on hand for professional photos, a snow slide, foam zone, inflatables, face painting, crafts, and a petting zoo. A vendor marketplace and food trucks round out a festive, family-friendly evening. Entry is free with a new unwrapped toy donation per family for Toys for Tots.

Manatee River Holiday Boat Parade

• December 13th · 2025
• 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

The county’s largest holiday event of the year. A fleet of festively decorated vessels cruises the river competing for cash prizes while thousands of locals and visitors line the shores to soak up the holiday magic.

Winter Nights Under the Lights

• December 18th to 21st · 2025
• 6:00 to 9:00 PM
• Palma Sola Botanical Park · 9800 17th Avenue NW · Bradenton 

The park sparkles with holiday lights as live festive music fills the air. Meet Santa and Mrs. Claus, enjoy food trucks, hot cocoa, coffee, and cider. Shop for holiday gifts inside the Galleria building and vote for your favorite Christmas tree decorated by local elementary students. Admission is free with donations welcome and unwrapped toys for Toys for Tots encouraged.

Privateers Christmas Parade

• Cancelled · 2025
• 10:00 AM
• Coquina Beach in Bradenton Beach to Bayfront Park in Anna Maria in Bradenton Beach

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.

Christmas Holiday Walk

• December 12th · 2025
• 5:00 PM to 9:00 PM
• Pine Avenue · Anna Maria

Local businesses offer holiday treats, warm beverages, and seasonal sales during an open house along Pine Avenue. Enjoy Christmas carols while Santa Claus greets children and poses for photos.

Santa in the Park

• TBA
• City Pier Park · Anna Maria

Santa spreads joy with goody bags for children.

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Christmas Services

AMI offers several churches which host Christmas Eve and Christmas Day services.

CrossPointe Fellowship

• Location · 8605 Gulf Drive · Holmes Beach
• Christmas Eve Candlelight Service · blending contemporary worship music with traditional elements

Episcopal Church of the Annunciation

• Location · 4408 Gulf Drive · Holmes Beach
• Christmas Eve Service · service with music, Holy Communion, and candlelight
• Christmas Day Service · traditional service

Roser Memorial Community Church

• Location · 512 Pine Avenue · Anna Maria
• Christmas Eve Candlelight Service · service with carols, scripture readings, and a message of hope
• Christmas Day Service · service with hymns

St. Bernard Catholic Church

• Location · 248 South Harbor Drive · Holmes Beach
• Christmas Eve Mass · Midnight Mass · 4:00 PM and 6:00 PM
• Christmas Day Mass · 8:30 AM, 10:30 AM, and noon

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New Year

For a lively New Year’s Eve celebration, head to Bridge Street in Bradenton Beach for its famous Oyster Drop. Restaurants and bars across the island provide live music, specials, and entertainment to ring in the new year. For Christmas dining specifically, my Christmas Dining on Anna Maria Island: My Insider Guide covers where to eat during the holiday season.

• Daiquiri Deck · Rockin’ Rooftop NYE Party · 8:00 PM to 12:00 AM · happy hour 3:00 PM to close ·  champagne toast at midnight · live music · $20 buffet
• Drift-In · New Year’s Eve Countdown Celebration · live music
• Bamboo Island Bar · New Year’s Eve Party · five course dinner for $100
• Freckled Fin is hosting its annual New Year’s Eve Bash from 9:00 PM to 1:00 AM with live music. They will offer a complimentary toast at midnight and VIP tables are available for purchase.
• Mademoiselle Paris French Restaurant · An elegant multi-course New Year’s Eve dining experience. Check their website for this year’s menu and reservations.
• Rossi Park · Downtown Bradenton · Ring in the New Year under the stars with live music, food, drinks, and local vendors along the beautiful Manatee River. A festive, family-friendly atmosphere starting at 9:00 PM.
• Pier 22 · Located on the Manatee River in downtown Bradenton, just a short drive off AMI. New Year’s Eve celebration with buffet, open bar, DJ, photo booth, and live countdown.

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Coastal Close

Anna Maria Island does the holidays the way it does everything else: unhurried, warm, and with a little salt air thrown in for good measure. Whether you are here for the tree lightings, the boat parade, a candlelit church service, or just a cold drink on Bridge Street as the clock strikes midnight, the island has a way of making the season feel exactly right. For everything you need to plan your holiday meals on the island, my downloadable Anna Maria Island Restaurant Guide on Etsy is the place to start.

— izzy