5 Festive Holiday Events to Enjoy Near Compass Hotel Naples This December

Escape to the holidays at Compass Hotel Naples, where December 2025 brings sparkling lights, coastal traditions, and festive events just a short drive from your suite. Naples transforms this time of year—palm trees glow with twinkle lights, waterfront parades glide across the bay, and historic streets come alive with Old Florida charm. If you're planning a seasonal getaway filled with music, parades, and holiday magic, here are five must-see celebrations happening throughout the month. Event details may vary year to year, so be sure to confirm exact dates, times, and pricing on each official event website before finalizing your plans.

Christmas Walk & Tree Lighting on 5th Avenue South 
December 5th &6th
Kick off the holiday season in Downtown Naples during the annual Christmas Walk & Tree Lighting on 5th Avenue South, a beloved tradition that typically takes place on the first Friday of December. The avenue transforms into a winter wonderland of twinkling lights, live entertainment, festive shopping, and seasonal bites. The highlight of the evening, of course, is the official tree-lighting ceremony along one of the city’s most iconic streets.

From Compass Hotel Naples, 5th Avenue South is just 5 miles, or a convenient 10–15 minute drive. Arrive early to find parking or opt for rideshare to make the evening even more relaxed. Then stroll the avenue, enjoy the live music, and take in Naples’ magical kickoff to December. For confirmed 2025 dates, times, and activity details, visit the official 5th Avenue South events calendar.

Naples Christmas Parade
December 9th
A classic Naples tradition, the Naples Christmas Parade brings illuminated floats, marching bands, local organizations, and plenty of holiday cheer to downtown streets. The parade begins at 6:30 pm and draws families from all over Southwest Florida.

The parade route is also about 5-6 miles from Compass Hotel Naples, usually a 10–15 minute drive. Plan to arrive at least an hour early to secure a great viewing spot and enjoy time exploring nearby cafés and shops before the parade begins.

For the official parade date, route map, and logistical updates for December 2025, check the City of Naples parks and recreation events page.

Christmas Boat Parade on Naples Bay
December 13th
For a uniquely coastal celebration, don’t miss the Christmas Boat Parade on Naples Bay. This waterfront event features boats decked out in sparkling lights gliding across the bay—an unforgettable holiday experience with a tropical twist. The parade is typically scheduled for a Saturday evening in mid-December, beginning just after sunset and lasting one to two hours.

Guests at Compass Hotel Naples can reach the Naples Bay viewing areas—Tin City or Bayview Park—in 10–15 minutes by car. Many waterfront restaurants offer prime viewing and festive prix-fixe menus, so consider pairing the parade with dinner for a memorable night out.

Holiday Pops with the Naples Philharmonic at Artis–Naples
December 18th-21st
If your ideal holiday includes live music, seasonal classics, and a stunning performance venue, the Holiday Pops concerts at Artis–Naples are a must. This beloved series typically runs over a long December weekend and features festive orchestral arrangements, carols, and even sing-along moments performed by the renowned Naples Philharmonic.

Artis–Naples is conveniently located 1 mile from Compass Hotel Naples, usually a 5 minute drive. Many guests choose to make a full evening of it by enjoying dinner at nearby restaurants before or after the show.

For 2025 performance dates, seating options, and ticket purchases, visit the official Artis–Naples website.

Christmas at Palm Cottage
December 2nd-24th
Step back into Old Florida charm at Christmas at Palm Cottage, Naples’ oldest surviving home, beautifully decorated for the holidays. Hosted by the Naples Historical Society, this event typically includes guided or self-guided tours offered on select afternoons and evenings throughout December. Visitors can explore period-style décor, local history, and timeless seasonal traditions.

Palm Cottage sits just 6 miles from Compass Hotel Naples, making it an easy 15-minute drive. Its location near the beach, Third Street South, and 5th Avenue South makes it a perfect addition to a day of shopping, dining, and holiday exploring.

Plan Your Holiday Getaway at Compass Hotel Naples

December is one of the most magical times to experience Naples—sunny skies, festive celebrations, and unforgettable coastal charm. Whether you’re here for twinkling lights downtown, music by the Philharmonic, or the beauty of boats gliding across the bay, Compass Hotel Naples puts you close to it all.

Stay tuned for more local guides, insider tips, and seasonal highlights to help you make the most of your time in paradise.