Enjoy the Florida Keys and Key West this Holiday Season!

Enjoy the Florida Keys and Key West this Holiday Season!
17 Nov 2017

It’s always been a dream of mine to drive the The Overseas Highway in the Florida Keys. Starting in downtown Miami, and cruising the 160 miles to Key West, at the tip of the Florida Keys. Rollin in a 5.0, with the rag top down so my hair can blow. Wait… where have I heard that before?

Although I have visited Florida a couple of times, I have never been to the southern tip of Florida. Farthest south I have been in Florida is Anna Maria Island (just north of Sarasota) on our family vacation last summer.

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Events in the Florida Keys

For Canadians wanting to escape the colder weather, and enjoy some Florida sunshine, now is the time. There is so much going on in the Florida Keys and Key West, from now until the end of the year. Here is just a taste of the events.

florida keys pier

Key West Holiday Fest

Location: Key West
Dates: November 22nd – December 31st
Each year during the holiday season, a wide range of celebrations takes place throughout Key West. Highlights include the lighting of the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade. Visit keywestholidayfest.com.

Lighting of the Key West “Harbor Walk of Lights”

Location: Key West
Date: November 22nd
The eagerly awaited pre-Thanksgiving event is to begin at 6 pm at Greene and Elizabeth streets, with the lighting of a holiday tree made from plastic foam trap floats, a nautically decorated fresh pine Christmas tree and a lobster trap tree along the Key West Historic Seaport’s Harbor Walk. The Harbor Walk is lit nightly through New Year’s Eve. Visit keywestchristmas.org.

Big Pine & Lower Keys Island Art Festival

Location: Big Pine Key
Date: November 25th
Held outdoors in a relaxed natural setting, the event features a creative range of holiday and Keys crafts. The art fair takes place from 9 a.m. to 2 p.m. on the grounds of the Lower Keys Chamber of Commerce at mile marker 31 oceanside. Visit lowerkeyschamber.com or call 305-872-2411.

Zonta’s Festival of Trees

Location: Marathon
Dates: November 29th – December 2nd
The annual Festival of Trees is to take place at the Florida Keys Country Club at 4000 Sombrero Blvd. Holiday trees are festively decorated and displayed by members of the Zonta Club of Marathon, a humanitarian service organization. Visitors and residents can bid to purchase the decorated trees. Visit zontaclubofmarathon.org or call Charlotte Quinn at 305-393-9501.

Florida Keys Holiday Festival

Location: Islamorada
Date: December 1st
Frolic in a 30-ton magical mountain of snow at Founders Park at mile marker 87 from 4-10pm, watch the ceremonial lighting of a 35-foot-tall tree or bid on a one-of-a-kind Keys-designed creation during the popular ornament auction. Inspired by the Burl Ives song, “Silver and Gold,” a themed parade is to usher in Santa Claus amid food, drink, music and kids’ activities. A Santa Paws canine competition for dogs and owners awards the best doggone holiday attire. Visit islamoradachamber.com or call 305-664-4503.

florida keys from plane

Light Up Key Largo

Location: Key Largo
Date: December 2nd
Sponsored by the Key Largo Chamber of Commerce, holiday happenings with live music, decorations, food and drinks are to spark the seasonal spirit. The annual tree lighting and related activities are to be held at the Murray E. Nelson Government Center and Key Largo Cultural Center, mile marker 102, from 5-9pm. Eggnog, caroling and an appearance by Santa and Mrs. Claus are virtually guaranteed to put everyone in a festive mood. Visit keylargochamber.org or call 305-451-1414.

Key West City Hometown Holiday Parade

Location: Key West
Date: December 2nd
Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and nonmotorized floats and lively community participation. Catching tossed candy is a highlight for kids. The route begins at Bayview Park and the best viewing spots are along Duval Street and Truman Avenue. Call 305-809-3881.

Pet Photos with Santa

Location: Marathon
Date: December 6th
Scheduled from 4-8pm at Keys Animal Hospital, the event supports the medical and special needs for the shelter animals at Florida Keys SPCA campus in Marathon. Cost of photos is free, although contributions of pet food, toys, beds or financial donations are welcome. Call 305-743-DOGS (6250).

Lighted Bike Rides

Key West: December 6th
Key Largo: December 9th
Marathon: December 10th
Three lighted bike rides are held in the Keys to benefit Wesley House, a family service organization, and its toy drive. Families and individuals decorate and light their bikes for the evening rides. Registration is one new unwrapped toy. Email clare.hiller@wesleyhouse.org or call 305-809-5000.

florida keys beach

Inaugural Southernmost Spirits Festival

Location: Key West
Dates: December 8th to 10th
Enjoy a cocktail, culinary and cultural extravaganza celebrated in Key West. Appealing to industry insiders, consumer cocktail and culinary lovers alike, the event is to encompass product innovation, education and a good time filled with entertainment, camaraderie, tastings, celebrity bartender competitions and fun. Visit southernmostspiritsfest.com.

I Love Stock Island

Location: Stock Island
Dates: December 8th to 10th
The family-friendly festival is to blend culinary events, live music, history and art studio tours, a lively community party, watersports offerings and other immersive experiences that showcase the island and its eclectic working waterfront. A boat parade, “Taste of Stock Island,” “Discover Stock Island” excursions, “StockFest,” the Stock Rock & Roll Bike Ride and more highlight the area’s seafaring tradition, culinary riches and vibrant creative enterprises. Visit ilovestockisland.org.

Lighted Boat Parades

Locations: Stock Island, Key West, Key Largo & Key Colony Beach
Dates: December 8th to 10th
Decorated and lighted boats are to cruise Florida Keys waters. For details about the Stock Island Lighted Boat Parade (December 8) through community marinas, visit ilovestockisland.org. For more on the Schooner Wharf Lighted Boat Parade (December 9) that travels around Key West’s Historic Seaport and harbor areas, visit schoonerwharf.com. For the Key Largo Boat Parade (December 9) on Blackwater Sound around mile marker 104, visit keylargoboatparade.com. For the Key Colony Beach Boat Parade (December 10) visit kcbca.org/boatparade.htm.

Holiday Historic Inn Tours

Location: Key West
Dates: December 8th and 15th
Two evenings of tours include trolley transportation between several participating inns, each decorated for the holidays. Treats and libations are offered at each inn. Event-goers also can provide their own transportation or bicycle to the inns. Contact the Lodging Association of the Florida Keys and Key West to purchase tickets, priced at $30 per person. Visit keywestholidayfest.com or call 305-296-4959.

Keys Community Concert Band Holiday Concert

Location: Key Largo
Date: December 9th
The family-friendly free-admission event, themed “Not So Frozen,” offers traditional and pops music performed by the Keys Community Concert Band, singalongs, stories and Santa as well as a children’s ballet troupe performance. The concert is to be held at the Murray Nelson Government & Cultural Center, mile marker 102. Visit keyscommunityconcertband.org.

florida keys sunset

Fourth Annual Parade of Paws and Holiday Bazaar

Location: Key West
Date: December 9th
The pet parade at Higgs Beach Dog Park supports the Florida Keys SPCA’s animal care fund. Pets’ humans gather funding pledges from family and friends. Top earners win bragging rights for the titles of king, queen, prince, princess, duke or duchess for their treasured companions. Four-legged creatures and owners can mingle, take photos with Santa and enjoy entertainment, food and crafts from 10am to 2pm Visit fkspca.org or call 305-294-4857.

Christmas on the Sheriff’s Animal Farm

Location: Key West
Date: December 10th
Children 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 located at the county’s detention center just northeast of Key West at 5501 College Road. It’s open on the second and fourth Sundays of each month. Call 305-293-7300.

A Holiday Concert at Marathon Community Theatre

Location: Marathon
Dates: December 15th and 16th
Shows are slated to ring in the holiday cheer at 7pm both evenings at the theater, located at 5101 Overseas Highway. Tickets are on sale online at marathontheater.org or call 305-743-0994.

Artisan Market, A Holiday “Shop Local” Edition

Location: Key West
Date: December 17th
Browse the vibrant open-air bazaar filled with Keys artists, authors, chef-made cuisine, craftspeople and performers. Admission is free and the market, located at 1111 Eaton St., is open to the public from 10am to 2pm. Visit facebook.com/KeyWestArtisanMarket.

Third Thursday Art Walk

Location: Islamorada
December 21st:
Showcasing the area’s fine arts, music and culinary nuances, the Morada Way Arts & Cultural District features national and local artisans who are showcased in galleries at Morada Way between mile markers 81 and 82, as well as beer tastings and live music, from 6-9pm. Admission is free to this great pre-holiday celebration. Art Walk is held the third Thursday of each month. Visit moradaway.org.

florida keys bridge

Second Annual Custom House Holiday Concert & Bazaar

Location: Key West
Date: December 21st
The Key West Art & Historical Society is to host this second annual event at the historic Custom House Museum, 281 Front St. Highlights of the evening gathering are to include performances by musicians and choirs, local artisans showcasing their wares, a light show and “selfies” with Santa. Visit kwahs.org or call 305-295-6616.

58th Annual Key West House Tours

Location: Key West
Dates: December 27th to 28th
Self-guided tours of unique Key West homes and gardens, festively dressed for the holidays, are to be presented by the Old Island Restoration Foundation. Tickets are $35 each. Proceeds benefit the foundation’s museum and programs. Visit oirf.org or call 305-294-9501.

Annual Key West Dachshund Walk

Location: Key West
Date: December 31st
As many as 200 dachshunds, many of them costumed, participate in this noontime “wiener wonderland” stroll. Canines and their people meander through the island’s picturesque downtown during the beloved, much photographed walk. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets. Visit their Facebook page.

New Year’s Eve “Drops” in the Southernmost City

Location: Key West
Date: December 31st
Ring in the new year with a “conch shell drop” at Sloppy Joe’s Bar, 201 Duval Street; 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 Street; the lowering of a pirate wench from atop a tall ship’s mast at the Schooner Wharf Bar, 202 William Street; or at the Ocean Key Resort & Spa, at 0 Duval Street, watch as a huge replica of a Key lime wedge splashes down into a larger-than-life margarita glass.

New Year’s Eve Fireworks on Blackwater Sound

Location: Key Largo
Date: December 31st
The backcountry bay is the setting for the annual New Year’s Eve fireworks extravaganza hosted by Sundowners, Jimmy Johnson’s Big Chill, Señor Frijoles, Cactus Jack’s, Gus’s Grille at the Marriott Key Largo Beach Resort and the Caribbean Club, all located around mile markers 103-104. Visit keylargofireworks.com.

New Year’s Eve Midnight Fireworks

Location: Islamorada
Date: December 31st
Morada Bay Beach Café at mile marker 81.6 bayside is to host a large beach party with live music, a beach barbecue, signature cocktails, performers and fireworks.

florida keys palm tree reflection in water

For more information, please check out the Florida Keys events calendar.

Big Daddy

If you would like me to review your product, service, restaurant, or travel destination, please send me an email at craig@bigdaddykreativ.ca or tweet me at @BigDaddyKreativ


Craig Silva

Craig is a husband, a father, team leader, senior youth group coordinator, designer, brander, community builder, volunteer, blogger, and social media manager. Craig likes to go camping, travel, go on road trips, watch movies, read with his girls, build stuff, operate the grill, and play bass guitar. In June 2017, PR firm Cision identified Craig as one of Canada’s top 10 most popular male bloggers in the parents and family space. Known as Big Daddy Kreativ, his blog specializes in travel, lifestyle, food, automotive, events, parenting, movies, tech, recipes, health, pets, reviews, and giveaways.


  1. Great post/list, Craig! The Florida Keys is one of my favourite destinations. I was terribly concerned when the recent hurricane hit the area. I sure am glad to hear that things are getting back to normal in the area. One of the things the Keys need most is for the tourists to come visit. I hope to get back there one day soon. I hope you also get to knock this destination off your bucket list!

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