Old Town Trolley Holiday Lights & Sights Tours
Multiple nightly tours begin at Mallory Square and convey caroling passengers through magically decorated streets and neighborhoods.
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Conch Tour Train Holiday Sights and Festive Nights Tours
Multiple nightly tours depart from Key West High School and convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.
Holiday Jazz in the Gardens
The Gardens Hotel at 526 Angela street welcomes holiday-goers to festive outdoor jazz in its famous garden, with a full cash bar on site and a 20% Christmas discount on bottled wine and bubbly.
Christmas Day Brunch Aboard Schooner America 2.0
A 2.5 hour Christmas Day Brunch with complimentary mimosas, Bloody Mary’s, wine, beer, soft drinks, and H2o. Brunch includes spiraled ham, bagels and pastries, meats and cheeses, smoked salmon, crudités, and other delicious holiday treats.
Key West Waterfront Winter Wonderland
The Coffee Butler Amphitheater at Truman Waterfront Park will welcome revelers of all ages to a holiday wonderland with beautiful lighting displays, an ice skating rink, rides, attractions, music and more. Closed Christmas Eve and Christmas Day.
Key West Waterfront Winter Wonderland
The Coffee Butler Amphitheater at Truman Waterfront Park will welcome revelers of all ages to a holiday wonderland with beautiful lighting displays, an ice skating rink, rides, attractions, music and more. Closed Christmas Eve and Christmas Day.
Key West Waterfront Winter Wonderland
The Coffee Butler Amphitheater at Truman Waterfront Park will welcome revelers of all ages to a holiday wonderland with beautiful lighting displays, an ice skating rink, rides, attractions, music and more. Closed Christmas Eve and Christmas Day.
City of Key West Menorah Lighting Ceremony
Bayview Park 1300 White Street, Key West, FL, United States5:00pm at Bayview Park, 1300 White Street.
Key West New Year’s Eve Celebrations
For your midnight toast, chose between an array of uniquely Key West New Year’s Eve Celebrations, including the world-famous Red High Heel Drop at the Bourbon St. Pub; the annual “Conch Shell Drop” at Sloppy Joe’s Bar on Duval St.; the “Lowering of the Pirate Wench at Midnight” at Schooner Wharf Bar and Galley and more.