Key West Christmas, 2020

Traditionally, Christmas time in Key West offers many celebrations in addition to beautiful surroundings. In the year of Covid, many of these celebrations have been cancelled. But that does not mean that there will be nothing to do on the island; there is still so much to enjoy along with a few holiday events to check out!

key west Christmas lights
Beautifully lit island B&B. Enjoy the Christmas Holiday in Key West!

Everyday Including Key West Christmas Day Activities

Dream Catcher Charters offers private fishing, snorkeling, and sightseeing charters for the whole family to enjoy everyday including Christmas! Call Island Genn to reserve your charter and enjoy an amazing day on the water here in Key West! Availability is limited. – 305-292-7212.

Key West Christmas Themed Events

ANNUAL HOLIDAY ARTISAN MARKET – All Day Online market with local artists! View at 11/27/2020 thru 12/24/2020.

MARC annual Christmas Tree Sale Lot – 1401 Seminary Street. Hours 9AM-7:45PM daily. Poinsettias, wreaths, garland, holiday accessories, ornaments, and great local gifts! New Shipments arrive 12/1 and 12/8! Contact Becki Balcer at 305.294.9526 ext. 25. 11/27/2020 thru 12/24/20 (or until all trees are sold)!!

Key West Garden Club Holiday Lighting Party12/1/20 from 9:30am to 2pm at Fort West Martello Tower at Higgs Beach, 1100 Atlantic Ave, 305-294-3210. The Key West Garden Club is decorating historic Fort East Martello for the holidays, and much of it will be visible at night when walking or driving by. Admission to the Fort grounds is free; donations cheerfully accepted. Masking and social distancing required. or

Key West Holiday Movie Challenge Launch – Christmas Community Chorus in the 35th annual performance.  Online Filmmaking Competition + Screening, The Studios of Key West – Thursday, December 3 at 7pm EST – Virtual. Virtual Screening: Saturday, December 19 thru Dec 26, 2020. What would Love Actually sound like with a Conch accent? What if It’s a Wonderful Life’s George Bailey grew up in Key West instead of Bedford Falls? Participants have one long weekend to reimagine their favorite Christmas movies with a Key West twist. The challenge is open to filmmakers of all levels—even first timers. All entries are eligible for random door prizes, and People’s Choice awards will be given in two categories: short film and mini challenge

Old Town Trolley Holiday Lights & Sights Tours – No need to gas-up the snowblower this year if you’re planning a holiday escape to the Conch Republic! Here, ‘Christmas chill’ means rockin’ your flops and kicking back island-style and one of the best ways to do that is hopping a ride on Old Town Trolley’s Holiday Lights & Sights Tour! The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition. 12/04/2020 thru 12/23/2020 from 6:30pm & 7:15pm, No tours offered December 5, 2020* Phone 305-296-6688 | Web

Conch Tour Train Holiday Lights Tours – It won’t get cold and it will not snow, but the festive lights have the city aglow. Join the Conch Tour Train for their annual holiday lights tour of the island. All aboard for an hour tour that takes you to all of the island’s most elaborately decorated houses, buildings and neighborhoods and caroling. 12/04/2020 thru 12/23/2020 from 6:30pm and 7:15pm., *No tours available December 5, 12 or 17. Subject to change. Departs from: Key West High School, 2100 Flagler Avenue. Phone 305-294-5161.

MARC House Holiday Open House12/6/20 from 11AM-2PM at 1401 Seminary Street, featuring new art by June Klausing and our ReMARCable Clients. Light refreshments, Holiday music, and great gift ideas! Contact Becki Balcer at 305.294.9526 ext. 25 or email

The ReMARCable Tabletop Christmas Tree and Wreath Auction12/9/20 from 7pm to 9pm at Margaritaville Resort LIMITED SOCIALLY DISTANCING SEATING AVAILABLE. Also, there will be a private zoom room for the auction. Contact Becki Balcer at 305.294.9526 ext. 25 or

Holiday Clearance Blowout! Conch Farm Yard Sale – 12/11/20 from 11am until 4pm at the Conch Republic Seafood Company. Huge retail clearance blowout featuring shirts from past few seasons with a Conch Farm Yard Sale! Mostly women’s and children’s but ALL SHIRTS AND ALL CHILDREN’S CLOTHES ARE ONLY $10.00! All sizes, colors, and shapes from long sleeve, short sleeve, tanks, bathing suits, jackets and much, much more! 

Key West Artisan Market: Fill the Pantry SOS Edition12/13/20 from 10am to 3pm at Higgs Beach, Indigenous Park. The focus is on fresh, locally sourced food offered by our growers and makers. Share the bounty with the SOS Foundation by bringing canned goods and donations to help the SOS Callahan Community Kitchen fill their pantries to provide meals and snacks for our community’s underserved children. Free entry, free parking. Please BYOB (bring your own bags). Contact: Sean Krikorian at 305-294-7994 or

Firefly’s Festive Holiday Brunch & Gift Drive – 12/13/20 from 10am to 3pm at 223 Petronia St. Is your Ugly Sweater feeling neglected this year? Do you have a fantastic Christmas dress waiting in the wings? Got a glorious onesie that shows off your holiday package? Don your holiday “best” and join us for a socially-distanced, festive holiday brunch! Want a free split of Maschio Prosecco to go with your brunch? All you have to do is bring an unwrapped, new gift to support our community. All donations will go to the FKOC to help our local homeless families celebrate the holidays. While all gifts are appreciated, our friends at FKOC say that the area of greatest need is actually for the adults, especially women, that they have in their program. They are overworked, overstressed, and often overlooked during the holiday season. We are looking for gifts to bring them some holiday cheer. Some suggestions might be a pedicure kit, a shaving kit, nice slippers or socks, or candy. Use your imagination and bring something to make someone smile. Festive attire is strongly encouraged. Make your reservations now on Yelp, Open Table, or call 305-849-0104! Seating is limited and reservations are recommended. Here’s some fine print! You’ll receive a split of Prosecco with your brunch during this event if you bring a new, unwrapped, appropriate gift— use your judgement! You are welcome to bring as many gifts as you would like, but the complimentary prosecco will be limited to one per person. As always, masks are required upon arrival, while moving around the restaurant, and while anyone is standing at your table, including our staff members. Thank you for helping to keep us safe!

Light the Menorah – 12/13/20 at 5:30pm. Virtual event presented on teh City of Key West Facebook page.

Holiday Gift Show – Collections Key West Gallery12/13/20 – 12/14/20 from 11am until 4pm at 6810 Front Street, Stock Island. Also by appt., Tel: 305-923-4778 E-mail:

Key West Artisan Market “Shop Local for the Holidays” 12/20/20 from 10am to 3pm at Higgs Beach, Indigenous Park. The show will be stocked with keys-made items perfect for gift giving this holiday season. Free entry, free parking. Please BYOB (bring your own bags). Contact Sean Krikorian at 305-294-7994 or

Conch Republic Seafood Holiday Classic Car Show – 12/20/20 from 11am until 3pm. See classic cars from a variety of eras at the official show of the Florida Keys Southernmost Car Club and choose a People’s Choice winner. At the Conch Republic Seafood Company parking lot, at the corner of Greene and Elizabeth Streets. Attendees are asked to bring an unwrapped toy for the Monroe County Domestic Abuse Shelter.

Jazz Brunch with Santa – 12/20/20 from 11am until 3pm at Four Marlins. Enjoy brunch and take photos with Santa by the holiday sand sculpture. Call 305-293-6250 for reservations.

Christmas Eve Mass at The Basilica of St. Mary Star of the Sea12/24/20 at 1010 Windsor Lane. 5pm vigil mass in the Basilica; 5pm vigil mass in the Stations Garden.

Christmas Midnight Mass at St. Paul’s Episcopal Church. 12/24/20 from 10:30pm until 12/25/20 12:30am. 401 Duval Street.

Christmas Day Mass at The Basilica of St. Mary Star of the Sea 12/25/20 at 1010 Windsor Lane. 7:30am vigil mass in the Basilica; 7:30am vigil mass in the Stations Garden. 9am vigil mass in the Basilica; 9am vigil mass in the Stations Garden. 10:30am vigil mass in the Basilica; 10:30am vigil mass in the Stations Garden. Noon Spanish mass in the Basilica; Noon Spanish mass in the Stations Garden.

Fury’s Key West Christmas Ultimate Adventure – 12/25/20 from 10am until 4pm. A six-hour voyage on a Fury catamaran with activities including snorkeling, parasailing, jet-skiing, banana boat ride, fun at a water park with aqua slide, action climbing tower and water trampoline, plus beverages, and breakfast and lunch featuring a special holiday-themed menu. Call Island Genn to reserve your seats and enjoy an amazing day on the water here in Key West! Availability is limited. – 305-292-7212.

Key West Artisan Market12/27/20 from 10am to 3pm at Higgs Beach, Indigenous Park. The artists will be stocked with keys-made items perfect to treat yourself to the gift you… Contact: Sean Krikorian at 305-294-7994 or

Holiday Jazz Brunch – 12/27/20 from 11am until 3pm at Four Marlins. Enjoy brunch with special holiday inspired features. $65 per person includes all you can eat small plates as well as bottomless bloody Marys and mimosas. Call 305-293-6250 for reservations.

Key West Restaurants offering Christmas Day Specials!

Be sure to check back soon as we are adding more restaurants and details all the time!

Azur – 425 Fleming Street. AZUR welcomes you and your loved ones to dine with us Christmas Day! Offering our locals’ favorite menu!

Bistro 245 – 245 Front Street. We will be open on Christmas day! We will be offering our regular menu with the addition of Lobster Bisque, Stone Crab Claws, Paella and Prime Rib starting at 11am.

Cafe Sole – 1029 Southard Street. Old World Christmas dinner served Christmas Eve and Christmas Day from 3pm until 10pm. Slow roasted goose with homemade stuffing, foie gras, plums, gravy and six traditional sides OR Prime rib encrusted with herbs and Hawaiian pink slat with black truffle au jus. Limited regular menu also available. Indoor and outdoor seating available.

Casa Marina – 1500 Reynolds Street. Brunch will be served from 11am until 3pm in the Flagler Ballroom. $65 per adult and $29 per child. Featuring sweet corn and crab chowder, composed salads, chilled seafood display, international meat and cheese table, carving tables featuring pork loin and beef strip loin, seasonal hot brunch offerings, and a selection of holiday inspired desserts. Reservations are required.

Four Marlins – 1435 Simonton Street. 1pm – 8pm. 4 Course Prix Fixe Menu of seasonally inspired dishes, with 4 choices for each course. $75 per person. Kids’ a la carte menu available. Live Music. Reservations recommended through

Hard Rock Cafe – 313 Duval Street. Rock this Christmas with Hard Rock Cafe on Duval Street! Join us for special holiday menus that will make you feel like a Rock Star!

Matt’s Stock Island Kitchen & Bar – 7001 Shrimp Road, Key West FL 33040 – Contact info: Jenny Lorenz at or 305-296-1717.

One Duval at the Pier House – 1 Duval Street. Christmas Eve and Christmas Day dinner specials will be offered in addition to the regular menu. Specials include: Oysters Rockefeller ($14), Beef Tenderloin Carpaccio ($16), Florida Lobster Oscar ($42), and Herb Crusted Rack of Lamb ($38). Call 305-295-3255 for reservations.

Ram’s Head – 804 Whitehead Street. Enjoy Christmas dinner in the open air! PRIME RIB: king cut, truffle mashed potatoes, green beans, rosemary au jus & horseradish pepper cream sauce. KEY WEST LOBSTER: broiled lobster tail with an Oscar style crab meat topping & hollandaise sauce served with coconut mango rice and asparagus. SURF & TURF: 1/2 lobster tail Oscar style or lemon garlic butter sauce, queen cut of prime rib, truffle mashed potatoes & green beans.

Tavern N Town at the Marriott Beachside – 3841 N Roosevelt Blvd. Christmas Eve and Christmas Night Dinner will be available from 4pm until 10pm; enjoy the regular menu along with specials and a hyoid dessert. There will be live music from 5pm until 9pm. For reservations call 305-296-8100.

Christmas Dinner To Go

Fausto’s – $149.99 dinner serves 8-10 people and includes: oven roasted turkey, mashed potatoes, gravy, green beans almandine, sweet potato casserole, cranberry orange relish, bread stuffing. Turkey only: $79.99. Whole spiral ham: $6.99 per pound. Cuban Pork dinner for 6-8 people is $59.99 or for 8-10 people is $99.99 and includes: cuban pork, yellow rice, black beans, plantains, Cuban bread. Orders must be placed at the deli counter by Sunday, December 20, 2020. 522 Fleming Street and 1105 White Street.

Cow Key Cloud Kitchen – Pick Up from 6810 Front Street 5:15 pm – 7:00 pm. If delivery is required, please add your address to the “NOTES” section of the check out page! Thank you!! Cuban Style Christmas Dinner $100.00. Meals are served family style with generous portions to feed 2-4 people and will include: Caribbean Style Conch Salad Appetizer with Plantain Chips -12 ounce Portion, Cuban Bread with Local Honey Butter (On the side), Tossed Salad with Tomato, Cucumber and Island Style Vinaigrette, Mojo Roast Pork with Marinated Onions and Sour Orange, Sweet Plantains, Garlic Infused Yucca, 7 inch Dessert Flan.

Island Genn
Key West Concierge

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