Top 10 Places to Visit During the Holidays in Naples, FL in 2025–26

In many ways, Naples’s holiday season reflects the city’s personality: refined, welcoming, and full of character. Each event, from the glittering streets of downtown to the serene cruises along the bay, offers an experience rooted in local tradition and sophistication. The celebrations of 2025–26 promise to be vibrant, offering countless ways to enjoy the city’s natural beauty and festive charm.

Third Street South captures the essence of Naples during the holidays with its signature event, Christmas on Third. Taking place in late November, this celebration transforms the historic shopping district into a festive wonderland with twinkling lights, live music, and a towering Christmas tree in the courtyard. Visitors stroll past designer boutiques and restaurants as snowfall machines create a wintry atmosphere unique to coastal Florida.

Live entertainment, jazz ensembles, and seasonal performers contribute to the charm. Shoppers can enjoy extended store hours and exclusive holiday collections, while cafés along the street offer outdoor dining beneath canopies of lights. The area remains beautifully illuminated throughout December, making it a must-visit destination for Naples holiday events.

Each winter, Lights in the Garden at the Naples Botanical Garden offers an extraordinary visual experience. The event combines art, light, and landscape design, transforming the garden’s tropical and subtropical plant collections into a radiant holiday display. Pathways are lined with illuminated sculptures and colorful installations, encouraging visitors to explore every corner of the 170-acre property.

Live music performances and seasonal treats enhance the evening experience. Many guests make it an annual tradition, returning to see the evolving light installations. The event also showcases sustainable design elements, aligning with the garden’s environmental mission while offering one of the most striking nighttime attractions in Naples.

The Naples Christmas Parade, a long-standing local tradition, takes over Fifth Avenue South in early December. Featuring elaborate floats, marching bands, and community organizations, the parade draws large crowds to the heart of downtown. The procession celebrates the season with performances, decorated vehicles, and a grand finale that typically includes a visit from Santa Claus.

The parade highlights Naples’s sense of community pride and coastal elegance. Restaurants and cafés along the route fill quickly, offering prime viewing for diners who want to experience the event in comfort. The combination of classic holiday pageantry and local participation makes this one of the most cherished Naples holiday events.

Fifth Avenue South, the city’s premier downtown boulevard, hosts its annual Tree Lighting and Holiday Stroll as a centerpiece of Naples’s holiday calendar. The event begins with the lighting of an enormous Christmas tree, followed by live entertainment, dance performances, and open-air festivities that stretch the length of the avenue.

Boutiques and galleries extend their hours, creating a relaxed and lively environment for shopping and dining. The atmosphere blends luxury and leisure, with visitors exploring art galleries, jewelers, and fine restaurants. The stroll reflects Naples’s signature blend of sophistication and seasonal warmth.

For those seeking a festive evening surrounded by wildlife, Holiday Lights Spectacular at the Naples Zoo offers a unique setting. The zoo’s walkways glow with illuminated animal displays, lanterns, and themed light shows synchronized to music. Visitors can enjoy hot cocoa, holiday snacks, and appearances by costumed characters throughout the event.

The Naples Zoo’s tropical landscaping and lakeside paths provide a distinctive backdrop for the holiday season. Its emphasis on conservation and community involvement makes it a meaningful stop for anyone exploring Naples during the holidays.

At The Village Shops on Venetian Bay, shoppers and diners experience one of the most scenic holiday displays in Naples. The Mediterranean-inspired waterfront complex features boutiques and fine restaurants overlooking the bay, illuminated by thousands of lights. The annual Holiday on the Bay event includes live music, boat parades, and carolers who stroll along the promenade.

As evening sets in, the reflections of the lights across the water create a tranquil yet celebratory mood. Luxury boutiques present seasonal collections, while waterfront dining venues provide an elegant view of the festivities. This destination combines coastal luxury with the magic of the season, making it one of Naples’s most refined holiday experiences.

Music lovers will find the Naples Philharmonic’s Holiday Pops an essential part of the season. Held at Artis–Naples, this annual performance blends classical orchestration with popular holiday music in a dynamic showcase of local and national talent. The venue’s acoustics and design elevate the concert experience, making it one of the premier cultural Naples holiday events.

Beyond the Holiday Pops, Artis–Naples hosts additional performances throughout December, including choral ensembles and ballet productions. The Philharmonic’s contribution to the holiday season underscores Naples’s standing as a cultural center of Southwest Florida, attracting audiences who appreciate artistry and elegance.

The Naples Princess, a luxury yacht offering sightseeing and dining cruises, hosts special holiday sailings each December. Guests can experience Naples Bay and Port Royal while enjoying gourmet meals and panoramic views of waterfront homes illuminated with festive décor. The sunset cruises are particularly popular, offering striking views as twilight colors reflect off the bay.

The yacht’s comfortable decks and attentive service make the evening sophisticated and relaxing. The combination of luxury dining and scenic beauty captures the refined spirit of Naples’s coastal lifestyle during the holidays.

During the holiday season, the Third Street South Farmers Market adds festive touches to its usual weekend lineup. Seasonal décor, holiday music, and specialty vendors create a celebratory atmosphere. Shoppers find artisan foods, handmade crafts, and locally produced goods that make thoughtful gifts.

This market also reflects Naples’s emphasis on community and quality. Many visitors enjoy breakfast at nearby cafés before browsing the stalls. Its combination of fresh ingredients, craftsmanship, and festive energy makes it a standout destination during the season.

Naples Bay hosts the annual Christmas Boat Parade in mid-December, where decorated vessels travel a set route and gather at Naples City Dock. The route begins at dusk and runs from around 6:15 p.m. to 8:30 p.m., offering waterfront viewing at multiple restaurants and parks.

Guests may view the parade from the dock, Pinchers Tin City, Riverwalk Restaurant, or Kelly’s Fish House. This illuminated water parade blends maritime tradition with holiday cheer, making it a standout in the city’s calendar of Naples holiday events.

If you’re inspired by the vibrant lifestyle, stunning scenery, and exclusive properties that define Naples, now is the perfect time to explore your options. The Whitcomb Group combines market expertise with a personalized approach to help you find a home that fits your vision. Whether you’re searching for a waterfront estate, a golf course retreat, or a downtown condo close to seasonal events, our team ensures every step of the process is seamless.

If you're considering relocating to Naples or simply want to learn more about the area, reach out to The Whitcomb Group today. Let their expertise help you find the property that meets your needs and exceeds your expectations.