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10 Outdoor Events to Ring In the Holiday Season 

Between collections of artist-decorated trees and a parade of illuminated yachts, these holiday festivities are sure to spread good cheer.

BY November 23, 2020

The holidays have quickly snuck up on us after a rather wayward year, but it would be amiss to complain about the upcoming season of joy. It seems the Southwest Florida community feels the same way, having debuted a robust calendar of events with socially-distant guidelines in place, so you and yours can stay safe and have fun with the festivities throughout our tropical wonderland.


Christmas on the Farm at M&M Farms 

If shopping vintage, repurposed or handmade items sounds tempting, then you might want to consider dropping by the Christmas on the Farm sale at M&M Farms in Fort Myers on Dec. 4-5. The property welcomes dozens of local vendors who offer specialty goods that are perfect for gifting (or just adding to your own collection at home), as well as homemade tea and lemonade to sip as you meander through the booths. 


Holiday Nights at Calusa Nature Center and Planetarium

For a quieter holiday celebration that highlights our surroundings, head to Calusa Nature Center and Planetarium on weekend nights from Dec. 11-20 for Holiday Nights. The nature trails will be aglow with soft lights, and visitors are invited to roast marshmallows on the campfire. 


14th Annual Festival of Trees at Sidney and Berne Davis Art Center

The 2020 Festival of Trees at Sidney and Berne Davis Art Center offers four days of holiday festivities, including a raffle and the annual wreath lighting with the mayor from Dec. 3-6. A collection of trees decorated by local business will be available for viewing throughout the weekend, and patrons can stick around on Friday night for live music from the Beatles tribute group, The Nowhere Band.


Christmas Boat Parade on Naples Bay 

Although you have the length of Naples Bay to settle in, we recommend grabbing a spot early. A parade of privately-owned boats captivate as they cruise along the bay, wrapped in thousands of lights for the Christmas Boat Parade on Dec. 12. Expect a dazzling lightshow as this year’s theme is “All that Glitters.”


Holiday Nights at Edison and Ford Winter Estates

History tells us that the Edison family loved celebrating Christmas, so it’s safe to say that they would be giddy at the site of Edison and Ford Winter Estates during its 45th annual Holiday Nights. The Mysore Fig tree on the Ford lawn will be the site of the official tree lighting on Nov. 27. On each night through Jan. 3, see the historic homes and property illuminated with light show displays, and enjoy live Christmas music on select days. 


Trees and Teas Festival 

Take part in the inaugural Trees and Teas Festival on Fifth Avenue South from Dec. 4-19. Presented by The Naples Players, the festival features special artist-designed trees along the avenue, with carols performed by members of the theater. The Naples Spice and Tea Exchange has partnered up for the event to offer an assortment of its luxurious teas so you can sip while you stroll.


Night Lights in the Garden at Naples Botanical Garden

Take in the magic of Naples Botanical Garden during its Night Lights event on select evenings, starting Nov. 27 through Jan. 3. The pathways and various trees throughout the Garden are set aglow by millions of colorful lights, and the enchanting occasion is emphasized by the simultaneous exhibition of artist Steve Tobin’s soaring sculptures throughout the property. Read more: 6 Things to Experience at Night Lights in the Garden.


47th Annual Christmas on Fifth Avenue South
Fifth Avenue South’s beloved Christmas on 5th returns this year on Dec. 4 and 5. Celebrate the season during the festive weekend full of music and delectable treats. Scheduled activities include live music, a skating rink, a live Nativity and an appearance by Santa Claus. Several restaurants will also offer expanded outdoor dining right on the avenue.

2020 Festival of Lights at the Promenade at Bonita Bay

Don’t forget to give back this season by donating a new, unwrapped gift to the Children’s Network of Southwest Florida during the 2020 Festival of Lights at Promenade at Bonita Bay. As a thank you, children and families can capture a free photo with Santa, enjoy live music and take part in holiday crafts throughout the plaza following the lighting of the Promenade Christmas tree. 


Christmas at Farmer Mike’s

Farmer Mike’s U Pick is spreading holiday cheer Friday and Saturday nights, Dec. 11- 19. Families can enjoy story time with Santa, a 3-acre light walk, hayrides, sledding and a screening of The Polar Express. Bring home the holiday spirit with Christmas trees for purchase.


Photo by YinYang/Getty Images

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