Ring in the Season with Key West’s Merriest Events

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Lighted Boat Parade. Credit: Carol Tedesco_KeyWestHolidayFest.com.

One of the most popular winter destinations comes alive, just a month after the conclusion of Fantasy Fest, for holiday themed parties, tours, and rides in a place that lives for celebrating a good time. Here are three of the most visually spectacular and fun events to ring in the season in Key West.

Lighted Boat Parade

While sunsets dominate the seaside attractions on the Gulf, the Historic Seaport and Bight Marina dazzle with a colorful nighttime display of lighted boats for its annual parade. Yachts, schooners, whalers, patrol boats, and the odd floating tiki hut don Christmas lights and holiday decorations while cruising along the coast and past Schooner Wharf Bar. Spectators line the harbor and neighboring bars and restaurants to view the procession for what is one of the most “Keys-y” attractions all season. For those looking to get in on the festivities, several charters and water sport companies offer ticketed sails that allow passengers to watch the parade from out on the water. Takes place Dec. 14 at 8 p.m.

Annual Holiday Parade

This family-friendly and inclusive affair is perhaps rivaled only by the annual parades that take place during Fantasy Fest. In this case, however, Santa replaces sexy, and gratuitous beads are replaced by candy thrown for the children who tightly line the Holiday Parade route, which features dozens of entries. Decorated conch trains, Christmas convertibles, and boats in tow riddled with holly and cheer help make this a must-see event of the holiday season. The duration also lends itself better to watchers, who usually have enough time to wander around various vantage points or grab dinner with a view. Takes place Dec. 7 starting at Truman Avenue.

Lighted Conch Train Tour

A staple sight through the month of December, lighted conch trains snake their way through the island’s neighborhoods for a tour of homes that put on Charlie Brown tributes, great blasts of snow, and adult treats and beverages. While you can rent and arrange your own train or trolley, it is far easier to purchase tickets from one of the many organizations (typically nonprofit) or bars that host annual rides. This fun night out is especially great for group outings and provides an already thought-out map of the brightest homes and displays. Tours are complete with narrations from your conductor, who points out the merriment along the way.

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