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Key West: America's Caribbean Island

A tropical paradise with fabulous weather, exotic plants and flowers that grow wild, sunsets famous for their beauty and a historic district larger than most any city in America… there’s something for everyone in Key West.

Historic sites, charming shops, great art galleries and quiet beaches provide a wealth of entertainment. Key West nightlife is exciting with world class restaurants, lively bars, shows, and theatres. Best of all, everything is within walking or biking distance from the Almond Tree Inn! 

Key West is also known for its never-ending events! There always seems to be something going on within the island. Scroll down or click here to view the Key West Calendar of Events (anchor link down to section).

Here are some of our top picks, just to name a few! Ask the front desk for more recommendations to fit your style.

Key West Attractions & Museums: 

Key West Activities & Tours

Key West Restaurants & Bars (there’s plenty, but here are a few right out our doors):

Key West Calendar of Events

Event calendar courtesy of fla-keys.com
The Tourism & Development Council of the Florida Keys

Events in The Florida Keys for December, 2016
Year: Month: 
November 28 to December 18,  in Key West
Florida Residents Save at Ripley's Believe It or Not! Odditorium
Florida residents can enjoy half-price tickets to Ripley's Believe It or Not! Key West Odditorium. Residents will need to show a local photo ID in order to receive the discount. All adults in the party will need to have proof of residency in order to receive the discount. the Odditorium is located at 108 Duval St.
Contact: 407-345-0501
Email: kasinski@ripleys.com

December 03 to December 31,  in Key West
Key West Holiday Fest
Each year a wide range of seasonal celebrations takes place throughout Key West during the month of December. Events include the lighting of the Harbor Walk of Lights, tours of historic decorated inns, a holiday parade and much more.

December 10 to December 18,  in Key West
Nutcracker Key West
Inspired by the unique and colorful environment of the Florida Keys, Clara and her young Prince encounter enchanted landscapes complete with snowy egrets on shimmering salt ponds, a wicked Rooster-King, an exquisite Sea-Star Fairy, and "underwater" sequences of almost unimaginable beauty. Local children, adults and community leaders are cast alongside a nationally-cast corps de ballet in this spectacularly crafted semi-annual production of a beloved classic. Shows held Dec. 10-11 & Dec. 14-18 at the Tennessee Williams Theatre. Purchase tickets online.
Contact: Box office 305-295-7676

December 11,  in Key West
Christmas on the Sheriff's Animal Farm
From 1-3 p.m., kids and adults can visit the furry, fluffy and feathered residents of the Animal Farm and petting zoo 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. The Sheriff's Animal Farm is open the second and fourth Sundays of the month.
Contact: 305-293-7300

December 14,  in Key West
NEW DATE: Schooner Wharf Bar Annual Lighted Boat Parade
Lighted and decorated vessels from rowboats to tall ships proceed around Key West's Historic Seaport and harbor areas. Parade is scheduled to begin at 8 p.m. Holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport.
Contact: 305-292-3302

December 16,  in Key West
Holiday Historic Inn Tours
Enjoy an enchanted evening of decorated inns and a sampling of holiday treats and cheer at each property. From 6-8 p.m., tours are self guided. Participants are welcome to bike or use their own transportation. Call the Lodging Association for tickets.
Contact: 305-296-4959

December 18,  in Key West
Key West Theater presents: Edwin McCain with Nick Norman
McCain's innate ability to write and perform songs that somehow every listener claims as their own has made him one of the most enduring and downright likable entertainers of our generation. Nick Norman is truly the man with a golden voice; a talented singer/songwriter who delights his audiences with soulful and inspirational performances.
Contact: 305-985-0433
Email: info@thekeywesttheater.com

December 20 to December 30,  in Key West
Randy Roberts LIVE!
Female impersonator extraordinaire brings a one man, all live tribute to some famous and infamous women of stage and screen. A Key West tradition for 18 years. Join Randy for an evening with "Bette Midler", "Cher", and Randy's signature lounge act. Hilarious comedy, gorgeous costumes, and voice that never fails to thrill! Open your eyes and mind and let yourself go with Randy Roberts LIVE! The NY Times calls him "Delicious ,..at the top of his game, ...truly talented", and you'll call yourself lucky to catch Randy Roberts LIVE! Visit website for show dates.
Contact: 305-296-6706
Email: bookings@randyroberts.net

December 20 to December 24,  in Key West
Fringe Theater presents: A Very Lillian Baxter Christmas
Feeling the tropical island holiday blues? We've got just the antidote! It's 1970 and Lillian Baxter is staging her comeback with a Christmas show. Oy Vey! Tinsel flies in this very entertaining "one woman" show. Written by and starring John Vessels as Lillian Baxter with Jay Schwandt on piano. "This is an extreme dose of whatever it is your holiday spirit is missing!" Performances at 7 p.m., at Little Room Jazz Club at 821 Duval Street.
Contact: 305-731-0581

December 21,  in Key West
Inaugural Holiday Concert & Bazaar at Custom House Museum
The event, from 5-9 p.m., will feature Key West's finest artisans, musicians and choirs, along with a spectacular holiday light show. Browse hundreds of unique gift options while enjoying the music, food and libations on and around the island's architectural crown jewel, with eggnog to lift the frazzled 'final shopping days' spirits and Santa on hand for last minute requests and 'selfie' photos. Open and free to the public.
Contact: 305-295-6616
Email: scowles@kwahs.org

December 27 to December 28,  in Key West
57th Annual Key West House & Garden Tours
Presented by the Old Island Restoration Foundation, the annual self-guided tours showcase festively dressed Key West homes and gardens. December tours are from 4-7 p.m., both evenings. Transportation between homes is NOT included. Tickets are $30. Proceeds benefit the Old Island Restoration Foundation's museums, collection and education, grant and scholarship programs.
Contact: 305-294-9501

December 31,  in Key West
New Year's Eve: Conch Shell Drop at Sloppy Joe's
The arrival of 2017 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Thousands of spectators gather on Duval for the annual gala, emceed by a rooftop host starting at 10 p.m. and featuring dancing in the street and a countdown to midnight recorded on a huge clock.

December 31,  in Key West
New Year's Eve: Pirate Wench Drop at Schooner Wharf
For piratical partiers, a New Year's Eve salute to Key West's rowdy seafaring roots is scheduled at the island's Historic Seaport. At midnight, a winsome pirate wench is to descend from the top of the mast of the tall ship America 2.0 as cannon blasts welcome 2017. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.

December 31,  in Key West
New Year's Eve on the Pier: Featuring a Key Lime Wedge "Drop"
At the Ocean Key Resort & Spa, 0 Duval St. on Key West Harbor, plans call for a huge replica of a Key lime wedge to splash down into a larger-than-life margarita glass as crowds welcome 2017 on the property's Sunset Pier. The free event features live entertainment by local favorites the E'Claires and Happy Dog, followed by the Robert Albury Band.
Contact: 305-296-7701

December 31,  in Key West
Key West Dachshund Walk
Frost-free Key West becomes a "wiener wonderland" when about 200 dachshunds and their owners take a noontime New Year's Eve stroll through the island's picturesque downtown. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets.
Email: keywestdachshundwalk@gmail.com

December 31,  in Key West
New Year's Eve Shoe Drop Celebration
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 St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.
Email: schroedkw@aol.com

December 31,  in Key West
New Year's Eve Dockside Bash on Schooner America 2.0
Enjoy a front-row seat for the famous "Lowering of the Wench" at Schooner Wharf Bar! This special adults-only event features complimentary beer, wine, champagne, well drinks, soda, and water and delicious hot and cold hors d' oeuvres! From 9:30 PM- 12:30 AM; tickets for purchase.
Contact: 646-772-4880
Email: heather@classicharborline.com