Here is an updated list to our original post of festive fun in Key West!
The Florida Keys and Key West offer an array of festive fun during the holiday season. From holiday events, lighted boat parades, and more… Key West is just the place to enjoy the festive spirit. Parrot Key Resort will also get you in a jolly mood with our lighted Christmas tree and exterior festive light decorations.
Parrot Key Resort offers great family accommodation options during the holidays with up to 3-bedroom options to choose from. View our accommodation options here or enjoy a range of festive activity below, in and around Key West!
Festive Holiday Events Around Key West
Image by Florida Keys News Bureau
Now through Sunday, Dec. 22
Holiday Photos with a Dolphin at Dolphin Research Center (Marathon)
At Dolphin Research Center, mile marker (MM) 59 bayside on Grassy Key, visitors who participate in the Meet the Dolphin program also can pose with the dolphins for a holiday photo. Visitors can bring their holiday-themed props to pose with, and DRC’s experienced photographers will shoot the pictures using high-resolution digital cameras. The program is offered several times each day on a walk-in basis and costs $25 per person in addition to general admission prices. The photos are supplied on a flash drive for $20 for one person or $35 for multiple people in the same shot. Group size is limited to four people. Contact: 305-289-1121 or www.dolphins.org
Wednesday, Nov. 27, 6 p.m.
Key West Holiday Fest (Key West)
The harbor walk along the Historic Seaport at the Key West Bight, stretching from Greene Street to Grinnell Street, is to be festively lit from rooftops to the sea for the holiday season. Celebrate with holiday events, browse at local shops and galleries and relax at waterfront restaurants and watering holes. This and other seaport festivities are part of the inaugural Key West Holiday Fest. Contact: www.KeyWestChristmas.org or www.KeyWestHolidayFest.com
Sunday, Dec. 1, 8 p.m.
“The Messiah” (Key West)
As many as 90 singers from around the Florida Keys participate in the annual performance of George Frideric Handel’s holiday masterpiece. Directed by Dean Walters, the 31st consecutive production is to be staged at Key West United Methodist Church at the corner of Eaton and Simonton streets, and admission is free. Contact: 305-296-2392
Friday, Dec. 6, 8 p.m.
Keys Chorale 2013 Holiday Concert (Key West)
The Keys Chorale will present a holiday concert at the Key West United Methodist Church, corner of Eaton and Simonton streets. Tickets are $20 for general admission. Contact: 305-849-1474 or www.keystix.com
Saturday, Dec. 7, 7 p.m.
Key West Holiday Parade (Key West)
The island city shows its holiday spirit with this annual hometown parade. Featuring marching groups and motorized and nonmotorized floats, the festive procession traditionally draws entries from churches, civic organizations, businesses and neighborhood and school groups. Starting at Truman Avenue and White Street, it proceeds down Truman to Duval, where it takes a right and continues on to Eaton Street. Contact: 305-809-3881 or visit www.keywestcity.com
Saturday, Dec. 14, 10 a.m. to 4 p.m.
Big Pine & Lower Keys Island Art Festival (Big Pine Key)
Experience the joys of art and music, and find some unique holiday gifts, at this festival held on the wooded grounds of the Lower Keys Chamber of Commerce, MM 31 oceanside. Family fun highlights include live music by favorite local entertainers, exhibits and booths featuring the original work of artists and artisans, raffles and vendors offering food and beverages. Parking and admission are free. Contact:305-872-2411 or www.lowerkeyschamber.com
Saturday, Dec. 14, 7 p.m.
Lower Keys Lighted Boat Parade (Lower Keys)
All boats are welcome to participate in this favorite Lower Keys holiday event sponsored by the Lower Keys Rotary Club. Santa and Mrs. Claus are expected to arrive and hand out candy to the kids. Best viewing spots include the Old Wooden Bridge Guest Cottages & Marina, No Name Key Bridge and Big Pine Community Park, all off U.S. Highway 1 at MM 31. Contact: Steve at 305-923-5370 or email@example.com
Saturday, Dec. 14, 8 p.m.
Schooner Wharf Bar & Galley Lighted Boat Parade (Key West)
Festively decorated kayaks, fishing craft and schooners are to glitter in Key West’s Historic Seaport during the 23rd annual Schooner Wharf Bar Lighted Boat Parade. The Gerald Adams Elementary School Steel Your Heart Band kicks off the festivities at 6 p.m. singing holiday favorites, followed by popular family band The Doerfels. Spectators can view the dozens of participating vessels from resorts, bars and restaurants in and around the Historic Seaport. Contact: 305-292-3302 or www.schoonerwharf.com
Sunday, Dec. 15, 1-3 p.m.
Christmas on the Farm 2013 (Stock Island, Key West)
Kids and adults can visit the furry, fluffy and feathered residents of the Animal Farm and get a photo taken with Santa. The Monroe County Sheriff’s Office Animal Farm is situated at the county’s detention center just outside Key West at 5501 College Road. This event is free and open to the public. Contact: Jeanne Selander at 305-293-7300 or www.keysso.net/miscellaneous/animal_park.htm
Sunday, Dec. 15, 3 p.m.
Southernmost Christmas Tree Celebration (Key West)
Holiday revelers enjoy free conch chowder and then board Conch Tour Trains to proceed to the continental United States’ Southernmost Point to set up the southernmost Christmas tree at sunset overlooking the Atlantic Ocean. The event is an annual community thank-you party presented by the Monroe Association for ReMAR Cable Citizens. The fun starts at 1401 Seminary St. Contact: 305-294-9526
Friday and Saturday, Dec. 27-28, 4-7 p.m.
54th Annual Key West House & Garden Tours (Key West)
Presented by the Old Island Restoration Foundation, the annual self-guided tours showcase festively dressed Key West homes and gardens. Tickets are $30 and proceeds benefit the Old Island Restoration Foundation’s museums, collection and education, grant and scholarship programs. Contact: 305-294-9501 or www.oirf.org
New Year’s Eve
The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval Street.
Tuesday, Dec. 31, 12 p.m.
Annual Key West Dachshund Walk (Key West)
The procession of pooches begins at noon at the corner of Whitehead and Fleming streets in Key West’s historic downtown. The walking route, deliberately kept brief to cater to the dachshunds’ short legs, includes a portion of the downtown area and a block of Duval Street. Many dogs wear offbeat costumes or accessories. Contact: firstname.lastname@example.org
Tuesday, Dec. 31, just before midnight
Key West New Year’s Eve Celebrations (Key West)
The Southernmost City celebrates New Year’s Eve with a “conch shell drop” at Sloppy Joe’s Bar, 201 Duval St.; the descent of a super-sized red high-heel shoe carrying drag queen Sushi at the Bourbon St. Pub/New Orleans House complex, 724 Duval St.; the splash of a huge replica Key lime wedge into a massive margarita glass at Ocean Key Resort’s Sunset Pier and the descent of a pirate wench from atop a tall ship’s mast in the island city’s Historic Seaport. Contact: 305-296-2388, ext. 121, for the conch shell drop; 305-293-9800 for the high-heel drop; 305-295-7005 for the Key lime splash and 305-292-3302 for the descent of the pirate wench
Image by Florida Keys News Bureau