Winter in the Florida Keys

Leave the cold weather behind for warm-weather cruising in the Florida Keys.
Fort Zachary Taylor State Park
Fort Zachary Taylor State Park is on the southern edge of Key West. It’s the southernmost state park in the United States. Susanne Pommer/Shutterstock

When it comes to making memories and celebrating good times, it’s tough to think of anyplace better than the Florida Keys. These islands are known for kicking back and relaxing all year round—and during the winter holidays, they take the fun to a Frosty-worthy level.

No, there’s no snow here; typical temperatures during December are in the mid- to high 70s. But that doesn’t stop merry-makers from Key Largo all the way down to Key West from getting their Santa on. The island attitude blends with the holiday spirit like a finely mixed cocktail of joy.

Arguably, the event that best epitomizes this spirit within the boating community is the annual Schooner Wharf Lighted Boat Parade on Key West. This will mark the 31st year of the event, on December 11, starting at the Historic Seaport and continuing past the Schooner Wharf Bar for judging.

All kinds of boats, from kayaks to schooners, typically participate, with a backdrop of island musicians belting out holiday tunes and other fan favorites. Never heard “Santa Claus Is Coming to Town” played by a steel-drum band? Well, then, you’re in for a treat.

Boaters who participate in this parade often go for the gusto with their decorations. In recent years, boaters have decked out their decks with giant inflated characters, glistening mermaids and fish, fake forests full of twinkling white lights, “dolphins” pulling Santa’s toy-filled sleigh, and a Rudolph so big that it filled the entire bow of a U.S. Coast Guard boat. Real, full-size Christmas trees are sometimes set up in cockpits for paradegoers to peruse along the docks, and boaters, of course, lend their own musical signature to their displays, sometimes with competing speaker setups.

Yes, there are some other lighted boat parades in Florida, but Key West, as with so many things, always puts its own spin on the fun. As they say at Schooner Wharf, “We don’t need snow to make our holidays bright.”  

Hawks Cay

This resort destination on Duck Key, in the Middle Keys, has a marina and fuel dock for boats up to 110 feet length overall. Holiday packages are available this winter, when you can go ashore for a few nights and celebrate the most wonderful time of the year. Santa’s Workshop is open for making Christmas ornaments.   gingerbread houses are available for decorating. Mrs. Claus hosts story time with hot chocolate. Carolers will come by a villa or hotel room and spread some holiday cheer for guests who sign up in advance. Elf tuck-ins are available for the kids, with Santa’s elves stopping by to offer a bedtime story and gift.

The Big Meal

Want to get out of the galley on Christmas Day? You can do it in Key West, where numerous restaurants are taking reservations for the holiday.   

  • Prime Steakhouse at Conch Harbor Marina pairs steaks with local favorites such as lobster and Key lime pie.   
  • LaTeDa on Duval Street serves up freshly caught fish, crabcakes, caramelized duck and more.   
  • Four Marlins on Simonton Street is decorated like a 1930s fishing lodge. It offers main courses of fish, ribs, lobster ravioli and risotto with jumbo shrimp.   
  • Grand Cafe on Duval Street is known for its wine list, which is 35 pages long. Favorite dishes include seafood pasta and steak frites.