Ultimate Event Guide for the Holidays on Anna Maria Island

The holiday season on Anna Maria Island is magical. Whether you’re visiting for Christmas or the New Year, the island offers a variety of holiday events, parades, light displays, celebrations, fireworks, and Christmas church services.

Below is a comprehensive list of Christmas and New Year events on Anna Maria Island. Exact dates will be added as published.

Enjoy a jolly good time on and around Anna Maria Island, where the season shines bright with festive events, sparkling holiday décor, 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.

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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 décor, seasonal treats, live music, and special offers from local merchants. Bring the whole family for a night of holiday cheer — and don’t miss a special visit from Santa Claus himself!

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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. There will be a tree lighting ceremony, live music, special appearances by Santa and Micky & Minnie, local eats, merchandise & gift card sales, and raffle giveaways. The Rotary Club of Longboat Key will be collecting unwrapped children’s gifts.

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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 3.5-hour magical holiday adventure from Parrish to the North Pole! The journey begins with a 35-minute train ride, where festive music and cheerful anticipation fill the air. Upon arrival, guests step off at the special North Pole station, where Santa himself greets every child for a memorable visit. Enjoy a wonderland of holiday entertainment, cozy campfires, and endless hot chocolate and cookies, all included in your visit. Additional food and beverages are also available for purchase as you soak up the spirit of the season at this unforgettable Christmas experience.

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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 can’t-miss seasonal event on Anna Maria Island.

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Holmes Beach Holiday Open House & Tree Lighting

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

Celebrate the season at the Holmes Beach Holiday Open House and Tree Lighting! Local shops stay open late, welcoming visitors with festive treats, cheerful caroling, and a warm sense of community. Enjoy an evening filled with holiday sparkle, island charm, and the joy of coming together to kick off the season.

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Lester Family Fun Day

• December 6th · 2025
• 10:30 AM to 2:00 PM
• The Center of Anna Maria Island · 407 Magnolia Avenue

Join us for one of the island’s most beloved annual traditions — the Lester Family Fun Day. This heartwarming event brings together locals and visitors for a day of old-fashioned fun at old-fashioned prices, filled with laughter, music, and holiday cheer. From pony rides and inflatables to cookie decorating and crafts, there’s something for everyone — especially the young and the young at heart. Don’t miss live tunes from DJ Freeze, performances by the Manatee High School Drum Line, and of course, a special visit from Santa at noon with small gifts for the kids!

After working up an appetite, enjoy classic favorites like Duffy’s burgers, AMOB hot dogs, chips, soda, and sweet treats from Small Town Creamery. Be sure to stick around for the thrilling Golf Ball Drop Raffle at 2 PM, when a helicopter drops numbered golf balls for a chance to win big — $50 per ball or 3 for $100! It’s a day of family fun, community spirit, and holiday magic you won’t want to miss on Anna Maria Island.

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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 and share your holiday wishes, brave the snow slide, and capture festive photos with holiday-themed vignettes. Watch in awe as snow falls magically throughout the evening while enjoying performances on the Winter Wonderland Main Stage and roaming entertainers delighting visitors in the streets.

Have fun at the free winter carnival, playing games like snowball toss and ice fishing to win prizes. Browse local vendors for unique holiday gifts, treats, and festive food and beverages, making it a perfect outing for the whole family.

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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.

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Jingle Jeeps

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

Route is 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 then through St. Armands Circle.

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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 at An Old Florida Christmas! Enjoy a festive day filled with local vendors, delicious food trucks, family-friendly activities, and live entertainment that capture the spirit of the holidays. Be sure to stop by the Whistle Stop Gift Shop for unique gifts and holiday treasures.

The park will be beautifully decorated in Victorian and Florida pioneer style, offering a charming glimpse into past holiday traditions. Browse holiday crafts, enjoy festive treats, and soak up a day of fun for all ages in true island holiday style.

Christmas in Cortez

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

Celebrate the season at Christmas in Cortez! Enjoy free activities including a bounce house, make-and-take holiday crafts, lawn games, and more — perfect for families with young children, though visitors of all ages are welcome.

While the museum will be closed for structural rehabilitation, don’t miss free visits with Santa inside the Cortez Cultural Center, courtesy of the Cortez Village Historical Society. It’s a fun, festive day filled with holiday cheer for the whole family!

A Night Before Christmas

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

Get into the holiday spirit at the annual A Night Before Christmas event. Santa and Mrs. Claus will be on hand for professional photos with the kids, which you can download for free. Families can enjoy a variety of fun activities, including a snow slide, foam zone, inflatables, face painting, crafts, and a petting zoo.

Don’t miss the “Shop Local” Vendor Marketplace in the parking lot, along with food and dessert trucks for tasty treats. Entry is FREE, though organizers kindly request a new, unwrapped toy donation per family for Toys for Tots. It’s a festive, family-friendly day full of holiday cheer!

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

Get ready for the Manatee River Holiday Boat Parade, the county’s largest holiday event of the year! A dazzling fleet of festively decorated vessels cruises the river, competing for cash prizes and the coveted winning title. Thousands of locals and visitors line the shores to soak up the holiday magic, enjoy the lights, and celebrate the season in true island style.

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 

Experience the magic of Winter Nights Under the Lights at Palma Sola! The park will sparkle with holiday lights as live festive music fills the air. Meet Santa & Mrs. Claus, enjoy a variety of food trucks with seating, and sip on hot cocoa, coffee, or cider.

Shop for holiday gifts inside the Galleria building and vote for your favorite Christmas tree decorated by local elementary students. Admission is free, though donations are welcome to support the park and future events — and don’t forget to bring unwrapped toys for Toys for Tots!

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Privateers Christmas Parade

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

Get ready for the Privateers Christmas Parade 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, while kids delight in seeing Santa ride through the parade.

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Christmas Holiday Walk

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

The evening begins with an open house where local businesses offer holiday treats, warm beverages, and seasonal sales. Stroll along Pine Avenue and enjoy Christmas carols while Santa Claus greets children and poses for photos.

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Santa in the Park

• TBA
• City Pier Park · Anna Maria

Santa spreads joy with goody bags for children.

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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

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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

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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

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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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For a lively New Year’s Eve celebration, try Bridge Street in Bradenton Beach for its Oyster Drop. Restaurants and bars provide live music, specials, and entertainment.

• 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.

Celebrate New Year’s Eve at Mademoiselle Paris French Restaurant with an elegant five-course experience featuring an amuse-bouche of brie gougère, followed by a creamy lobster bisque infused with truffle oil, parmesan, and croutons. Enjoy a second course mini burger à la française with caramelized onions and secret French sauce before choosing your main course: seared salmon in champagne wine with Parisian potatoes and sautéed spinach, or classic Coq au Vin Provençal with red wine–braised chicken, baby carrots, and pearl onions. Finish the night with a raspberry crème brûlée topped with fresh berries and a caramelized sugar crust—all for $99.

Ring in the New Year under the stars at Rossi Park in Downtown Bradenton with live music, food, drinks, and local vendors. The festivities begin at 9:00 PM with an energetic performance by the Derek Lersch Band, plus tasty bites from local food trucks and unique finds from artisan vendors. Celebrate 2026 along the beautiful Manatee River in a festive, family-friendly atmosphere.

Just a short drive off AMI and located on the Manatee River in downtown Bradenton, New Year’s Eve Celebration at Pier 22 offers a buffet, open bar, DJ, photo booth, and live countdown.

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Until next time…

· izzy