Celebrate the magic of the holiday season near Gracewater at Sarasota! With our ideal location, you’ll be just minutes away from the area’s best festivities. From parades and markets to concerts and holiday-themed activities, there’s something for everyone. Here’s your local guide to December’s most exciting events.
Christmas Carol Trolley: Letters to Santa
December 1–23 | Various Times
Discover Sarasota Tours, 1826 4th St, Sarasota
Hop aboard this festive trolley for a holiday lights tour and musical performance featuring carols, stories, and jokes for the whole family. Guests can enjoy holiday drinks and browse the Trolley Cottage Gift Shop before the adventure begins.
Sip & Shop Downtown Sarasota
December 6 | 4:00 PM – 7:00 PM
Downtown Sarasota, Main Street
Stroll downtown Sarasota for an evening of boutique shopping, live music, and wine tastings. Visit art galleries, meet shop owners, and enjoy the festive atmosphere.
Holiday Night of Lights at St. Armands Circle
December 6 | 6:00 PM – 9:00 PM
St. Armands Circle
Kick off the holiday season with a tree lighting ceremony, live holiday music, and a Christmas carol sing-along. Santa himself will make a special appearance.
Light Up the Night at Selby Five Points Park
December 6 | 7:00 PM – 10:00 PM
Selby Five Points Park, Downtown Sarasota
Experience the charm of Sarasota with live music, festive decorations, and the lighting of a holiday tree. Snap a photo in the inflatable snow globe!
Sarasota Holiday Parade
December 7 | 7:00 PM – 8:30 PM
Downtown Sarasota, Main Street
This annual tradition brings holiday cheer to Sarasota’s downtown streets with floats, music, and dazzling displays.
Taste of the Bay
December 15 | 12:00 PM – 3:00 PM
The Bay Park, 1055 Blvd of the Arts, Sarasota
Sample dishes from locally-owned restaurants while enjoying live music and scenic views at this outdoor food festival. Tickets are available for purchase at the event.
Selby Gardens: Lights in Bloom®
December 16–31 | 6:00 PM – 9:00 PM
Marie Selby Botanical Gardens, 900 S. Palm Ave, Sarasota
Stroll through a mesmerizing display of over two million lights at this beloved holiday event. Enjoy live music, food, and activities for all ages in the stunning gardens.
Photos with Santa at Gracewater
December 21 | 10:00 AM – 1:00 PM
Gracewater at Sarasota, Sales Center
Skip the mall lines and bring your family to Gracewater for Photos with Santa! Capture cherished holiday memories in a relaxed setting, just in time for Christmas.
Call our Sales Manager or visit our social media for more information
Breakfast with the Sharks
December 28 | 8:00 AM – 9:30 AM
Mote Marine Laboratory & Aquarium, 1600 Ken Thompson Parkway
Start your day with a light breakfast while learning about Mote’s sharks and their cutting-edge research. A guided tour follows the feeding session.
New Year’s Eve Pineapple Drop
December 31 | 1:00 PM – 1:30 AM
Downtown Sarasota, Main Street & Lemon Ave
Ring in the New Year with carnival rides, live music, and the iconic Pineapple Drop countdown followed by fireworks over Sarasota Bay.
New Year’s Eve at Perspective Rooftop Bar
December 31 | 8:00 PM – 1:00 AM
Art Ovation Hotel, 1255 N Palm Ave, Sarasota
Party 80’s style at this rooftop celebration featuring live music, a buffet, party favors, and a champagne toast at midnight. VIP packages available for a premium experience.
Living at Gracewater means having Sarasota’s best events at your doorstep. Whether you're exploring holiday markets, enjoying family-friendly activities, or ringing in the New Year at an elegant soirée, Gracewater is the perfect place to call home.
Enjoy the season, and don’t forget to follow us for more local updates!
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