A Look Inside the Sunshine State’s Most Festive Cities

While the holidays are often synonymous with glistening snow, piping hot cocoa and roaring fires, many opt to enjoy the cozy season in a setting less snowy and more sandy. Across Florida, small towns and big cities transform into warm winter wonderlands to help locals and visitors alike immerse themselves in the holiday spirit. After all, the holidays are meant to be filled with thanks, family, friends and relaxation – a cocktail best served on the rocks under the warm Florida sun.  

From an award-winning holiday light display to a real life Polar Express to vibrant boat parades, a visit to any of these cities is sure to leave you feeling festive in Florida.  

St. Augustine 

The award-winning Nights of Lights in St. Augustine will return for its 28th year this winter. Beginning the week before Thanksgiving and lasting through January, the historic town illuminates with more than three million dazzling lights strung throughout the streets – a spectacle earning acclaim as one of the best light displays in the world by National Geographic. Visitors can hop aboard a trolley or train donning magical viewing glasses and billowing Christmas carols while escorated through the town. Guests can also view the lights by boat, getting an added view of the lights reflecting off water, or by foot for a sparkling stroll throughout the city. Tour operators stand ready to guide guests on a memorable journey each holiday season.  

The Palm Beaches 

The Palm Beaches – comprising West Palm Beach, Boca Raton, Jupiter and more – come alive each holiday season to create a North Pole in South Florida. The cities debut a number of festive events, from lights shows and parades to the performing arts and visits from Santa. In West Palm Beach, guests can experience a nightly snowfall and light show at the Wishing Tree in the city’s square, experience a drive-thru light show spanning more than a mile at Okeeheelee Park or see the wonder of lights illuminating the Palm Beach Zoo and Mounts Botanical Garden of Palm Beach. Spanning from Palm Beach to Jupiter, experience a holiday boat parade in early December, complete with decked-out boats and a rousing fireworks display. Heading indoors, experience holiday shows including The Nutcracker and seasonal symphony shows across the area. For a multi-stop holiday experience, The Palm Beaches offer festive fun for the whole family.  

Pensacola

Named one of the top holiday events in the state, Pensacola’s annual Winterfest celebration transforms the iconic downtown streets into a true winter wonderland with 500,000 white lights illuminating the streets, live performances, trolley tours and cascades of replicated falling snow. The annual event kicks off the day after Thanksgiving and runs through Christmas Eve. Guests can take photos with Santa – and even the Grinch – during various themed tours that run throughout the season. Fans of the Polar Express, A Christmas Carol and more can become immersed in their favorite holiday tales during Winterfest in Pensacola each season. Aside from Winterfest, Pensacola also hosts seasonal events and parades – including a lighted boat parade with fireworks. One can’t-miss parade in particular, traveling from Via de Luna to Casino Beach, will welcome Santa to the beach town during the Surfing Santa parade.  

Sarasota 

For a season that’s truly merry and bright, visit Sarasota this winter. With rows of beautifully decorated homes and several bright focal points throughout the city, visitors can enjoy immersive twinkling lights throughout the town. Visit Marie Selby Botanical Gardens to walk among flower plants by day and the “Lights in Bloom” event by night. More than 2 million lights ignite the gardens through tunnels, gardens and technicolor butterflies and dragonflies. Continue to the University Town Center, perfect for finishing holiday shopping before its giant Christmas tree serves as the focal point for holiday fun. Enjoy ice skating, “snow” tubing, carousel rides or a horse-drawn carriage for a festive evening.  

Tallahassee 

Home to Florida State University, the city of Tallahassee comes alive with holiday cheer even when students return home for the holidays. Kick off the season and jump start your shopping with the annual Hearth & Soul holiday window reveal in mid-November. Throughout December, a number of holiday events are ready to be enjoyed - enjoy hot cider and cookies, a silent auction and tours of beautifully decorated homes at Camellia Christmas, celebrate the Winter Festival’s lights, music and arts in Downtown Tallahassee, shop one of the region's largest craft shows during Market Days and the Florida Fairgrounds, or catch the Tallahassee Ballet’s Nutcracker performance to celebrate the sweetness of the season.  

Fort Myers 

The boat parades continue in Fort Myers, with floating events taking place on various waterways throughout December. Donning both nautical and holiday themes, the parades are a feat for both boaters and spectators alike to enjoy a warm-weather take on the holidays. Indoors, the Burroughs Home & Gardens adorns the building with elegant period decor including multiple trees, garlands and lavishly decorated interiors. For even more holiday fun, visit Fort Myers’ Festival of the Trees, an event inviting the community to decorate trees in exuberant themes and colors. Often representing hobbies or interests of their decorator, the trees are put to a vote and a winner is selected each year.  

Tampa Bay 

The holiday celebrations take to the water each year in Tampa Bay, with the annual Tampa Riverwalk Lighted Boat Parade cruising along the Riverwalk. Hosted in mid-December, the event welcomes hundreds of decorated boats to participate, ushered in by a 35-foot LED Christmas tree that floats the river all season. Twinkling light exhibits can be enjoyed at the Lowry Park Zoo, Florida Botanical Gardens and Largo Central Park. Transport in time at the Henry B. Plant Museum, which transforms from a museum to a Victorian-era Christmas home complete with 14 decorated rooms with period-specific greenery, Christmas trees, toys and ornaments. Lastly, the famed Busch Gardens amusement park transforms into Christmas Town each year – the ultimate holiday extravaganza – with more than a million lights, shopping, shows, visits from Santa and characters from iconic films.  

Key West 

Spending the holidays at the southernmost point of the United States may have you feeling far from the North Pole, but Key West transforms into holiday towns fit for even Santa himself. Parades are plenty throughout the season, with a lighted boat parade, classic car show and a traditional holiday parade all taking place each December. The city also hosts tours of its historic inns, where the quaint bed and breakfasts transform with Christmas charm. For the most immersive experience, hop aboard the Holiday Lights and Sights trolley tour, complete with cookies and cider. For a true departure from the traditional snowy sights, hop aboard the Ultimate Christmas Adventure by Fury Water Adventures for a full day of watersports and a holiday meal served on a catamaran.  

Head South this winter to experience all the holiday magic that unfolds throughout the state of Florida. No matter which city you’re spending the holidays in, we hope the season is filled with warmth, joy and peace. Safe travels and happy holidays!