2025 Renovation

As The Temperature Drops, Things Are Just Heating Up in Naples

Can you believe another year is already coming to a close? In a blink, the winter holidays will be here! This most wonderful time of the year is full of equally wonderful things to do, both as part of the Olde Cypress social calendar and around town in lovely Naples. We're looking forward to a November filled with gratitude and great food, and a December that's jam-packed with joy and celebration. Below are some jolly ways to get in the spirit of the season so we invite you to mark your calendars with the activities that seem most merry.

 

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Club Happening Highlights  

You know that your favorite country club of Naples never misses an opportunity to get decked out and celebrate together so we do it big for the holidays at The Club at Olde Cypress! We've compiled a few of our favorite events and you can check out the full calendar here.

 

November

8th: Welcome Back Event "50's Theme"

23rd: Tennis Bubbles and Brunch

28th: Thanksgiving Buffet

 

December

13th: Holiday Dinner Dance

14th: Brunch with Santa

26th: Menorah Lighting Dinner

31st: New Year's Eve Celebration

 


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Grand Illuminations 

Whether you're ready to kick off your holiday shopping or just kick back and soak in the magic of the season, Grand Illuminations at The Village Shops On Venetian Bay has something for everyone. On November 23, the whole family can find entertainment and awe from 5-8pm at this immersive event that's billed as "nothing short of a magical holiday experience." 

 


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Christmas on Third

If you're in the mood for more shopping and cheer, take a stroll down "Third Street South, Naples' historic and iconic downtown shopping and dining district." Now in its impressive 47th season, Christmas on Third is "a month-long calendar of events for all ages." Taking place from November 28 through December 24 this year, Christmas on Third has all sorts of seasonal fun – from nightly snowfall to pet photos with Santa. 

 

 

Johnsonville Night Lights in the Garden 

For something a little quieter and just as magical, head to the Naples Botanical Garden between November 29 and December 10 for Night Lights in the Garden. "This beloved annual tradition" lets you stroll through the tropical fauna decked out in thousands of lights for a "seasonal staple that is distinctly Southwest Florida." Like the golf courses in Naples FL, this is a nature-lover's paradise! A good way to find a bit of peace among the holiday bustle, perhaps.

 

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The Nutcracker & Holiday Pops 


You may know Artis—Naples as the premier destination for the visual and performing arts in Southwest Florida. So who better to put on the holiday classic, The Nutcracker? Performances will be on November 30 and December 1 so snag a ticket before they're gone! Equally delightful is the Holiday Pops show. This "program of beloved holiday tunes" will be performed by the Naples Philharmonic Chorus and Naples Philharmonic Youth Chorus on December 19 and December 22. Get ready to sing along!

 

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Christmas Island Style 

Every year, Marco Island goes all out for the holidays with Christmas Island Style - a full calendar of "various events [to] bring…joy to attendees." One of the highlights is the Marco Island Annual Christmas Boat Parade, happening this year on December 21 at 6pm. Find your favorite spot and let the mirth come to you! How wonderfully South Florida is that?