Island Holiday Events + Activities in the Florida Keys

Celebrate Thanksgiving at Kindler with an elevated holiday special featuring truffle-infused Turkey Ballotine, decadent sides, and a beautifully spiced poached pear finale, with the regular Kindler menu also available for those craving a classic favorite.

Celebrate Thanksgiving at Amara Cay with a classic island-style feast at ReelCatch, featuring roast turkey, all the holiday favorites, and cranberry-mango chutney, or head to Tiki Bar for festive jerk turkey sliders and sweet potato wedges.

Sip into the holiday spirit at Amara Cay from November 28 through December 31 with a festive lineup of holiday cocktails and happy hour bites. Enjoy seasonal favorites like the Cranberry Moscow Mule, Candy Cane Tini, Amara Coquito, and Jack Frost, paired with Sunset Small Bites including Cranberry-Brie Mini Quesadillas, Wings in “Paradise,” Shrimp Po’ Boy Sliders, and more. Come for the cocktails, stay for the bites, and celebrate the season island-style!

11/26 | 6pm – 9pm |​ Music at Tiki Bar

11/26 | 11am-12pm | Turkey Rice Crispy Treat Decorating​ | Lighthouse Tiki

11/26 | 2pm-3pm | Turkey Scavenger Hunt​ | Lighthouse Beach

Nov 26 | 10:00am – 11:00am | Turkey Rice Krispy Treat Decorating | Sidecar​

Nov 26 | 2:00 PM – 3:00 PM​ | Turkey Scavenger Hunt​ | Recreation Tiki

Nov 26th | 10:30 AM – 11:30 AM ​| Turkey Rice Krispy Treat Decorating | Paradise Tiki​

​Nov 26th | 1:00 PM – 2:00 PM ​| Turkey Scavenger Hunt​ | Recreation Tiki ​

Nov 26th | 3:00 PM – 4:00PM​ | Turkey Bowl​ | Paradise Beach

Nov 26th | Turkey Sandwich Thanksgiving Special | Tiki Bar

Nov 26th | 6pm-9pm | Live Music | Tiki Bar

Celebrate Christmas at ReelCatch at Amara Cay Resort with a festive island-inspired feast featuring Spiny Lobster Bisque with Tio Pepe, Lobster Toast, and Herb-Crusted Prime Rib served with garlic mashed potatoes, grilled asparagus, horseradish cream, Merlot reduction, and warm popovers. Finish the evening with a decadent Barbancourt Rum Cake with Tropical Fruit Krema for the perfect sweet finale. $75++ per person — a delicious way to make your Christmas celebration extra special.

Celebrate Christmas Eve at Kindler at Three Waters with an elevated holiday dinner featuring a beautifully curated cheese and charcuterie board, tender 72-hour braised short ribs with butternut squash purée and red wine jus, and a decadent carrot cake finale with Biscoff, salted butterscotch, and mascarpone cream. The regular Kindler menu will also be available, making it easy for everyone to enjoy their holiday favorites. Gather around the table and make Christmas Eve one to remember.

Set sail into the holiday spirit aboard the Rum Runner every Friday evening in December for the Jingle & Mingle Karaoke Cruise—a festive night of island views, holiday cheer, and singing your favorite tunes on the water!

Dec 24^th- Dec 31^st | Signature Holiday Drink 

Dec 24th​ | 10:00am-11:00am​ | Ornament Craft​ | Sidecar​

Dec 24^th | 2:00pm-3:00pm​ | Holiday Trivia | Sidecar

Dec 25^th | Live Music | Sidecar

Dec 25^th | 2:00pm – 3:00pm | Holiday Slime Craft | Sidecar

Dec 4^th – 12^th | Menorah Lighting 6pm | Lobby

Dec 4^th – 12^th | Dreidel Game | Lobby

Dec 21st: Snowman Sand building Contest 2pm | Lighthouse Beach​

Dec 22nd: Candy Cane Hunt 2pm | Lighthouse Beach​

Dec 23rd: Holiday Trivia 2pm | Tiki Bar​

Dec 24th: Ornament Workshop 2pm | Lighthouse Beach

Dec 24th: Letters to Santa 9a-5p Recreation Hut and Front Desk 5p – 10p​

Dec 24th: Cookies & Milk 4p – 8p​ | Lobby ​

Dec 25th: Santa and Grinch with picture opportunity 8:30am-9:30am | Lighthouse Beach

Dec 25th: Christmas Cookie Decorating 11am | Lighthouse Tiki​

Dec 26th: Green Foam Party 11am | Lighthouse Beach

Dec 27th: Reindeer Games 2pm | Lighthouse Beach

Dec 4^th – 12^th | Menorah Lighting | Starbucks

Dec 23rd | 10:30am-11:30am | Cookie Decorating ​​| Sunrise Tiki

Dec 24th​ | 10:30am-11:30am​ | Make Holiday Slime​ | Sunrise Tiki

Dec 24^th | 2:00pm-3:00pm​ | Candy Cane Hunt​| Sunrise Beach ​

Dec 25^th | 10:00am-11:00am | Santa Claus + Grinch | Entire Property

Dec 25^th | 6:30pm - 7:30pm | Neon Foam Party | Sunrise Beach

Sip into the holiday spirit at Tiki Bar from December 24–31 with a festive lineup of seasonal cocktails, including the Christmas Mojito, Holiday Rum Punch, Peppermint Espresso Martini, Tropical Eggnog, and Frozen Candy Cane Colada. Whether you’re craving something tropical, creamy, or perfectly peppermint, there’s a holiday cocktail waiting to make your celebration a little merrier.

Treat yourself to a little holiday sweetness at Lucky Twist at Three Waters Resort from December 24–31 with festive specialty milkshakes and frozen treats. Choose from the Grinch Shake, Candy Cane Crunch Shake, Gingerbread Cookie Shake, Peppermint Hot Chocolate Float, or Christmas Cookie Sundae, all topped off with holiday-themed waffle cones and festive toppings. The perfect sweet stop for a little extra holiday cheer!

Ring in 2027 at Kindler with an indulgent six-course New Year’s Eve prix fixe dinner featuring elevated favorites like Spicy Yellowfin Tuna, Beef Carpaccio Caesar Salad, Butternut Squash Bisque, Spanish Octopus, and your choice of Fillet Oscar or Grilled Atlantic Salmon. End the evening on a sweet note with a decadent Black Forest Torte or Coconut & Lemongrass Panna Cotta. A truly memorable way to savor the final night of 2026 and welcome the new year in style.

Ring in 2026 in unforgettable style at Toast at The Top, an exclusive New Year’s Eve rooftop experience at Little Limon overlooking the coast. From 9 PM–1 AM, enjoy a premium open bar, live music under the stars, gourmet late-night bites, and a sparkling midnight toast—all paired with panoramic ocean views and a front-row seat to the resort’s spectacular fireworks show. Limited to just 35 adult guests, this intimate rooftop celebration is the perfect way to welcome the new year above it all.

This New Year’s Eve, let the tides of time take you somewhere unforgettable. Ring in the new year at the exclusive All That Glitters New Year's Eve Party at Tiki Bar Backyard — complete with a live band, DJ, and a dazzling fireworks show at midnight.

Dec 31 | 12pm – 3pm | Steelband | Pool 

Live Band 6 – 9p – DJ 9p – 1a with Champagne Toast at Midnight ​

Jan 1 | 7am - 4pm | Bloody Mary and Mimosa Special $22 |​ Reel Catch and Tiki Bar

Jan 1 | 11am | New Years Olympics​ | Lighthouse Beach

Join us at Amara Cay for an elevated five-course dinner featuring a delicious lineup of seasonal flavors and island-inspired ingredients. Start with Amara Oysters Rockefeller and roasted pumpkin bisque, followed by a fire-roasted cherry salad, before enjoying the star of the evening: grilled filet Oscar with spiny lobster, jumbo asparagus, crispy fingerlings, hollandaise and cabernet reduction. Finish on a sweet note with coconut bread pudding and Irish cream sauce. $125 per person, plus 7.5% tax and 20% gratuity.