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Conch Tour Train Holiday Lights Tours — 6:30 and 8:30 p.m. Dec. 16-17, 20-23 and Dec. 26, departs from Key West High School, 2100 Flagler Ave. Caroling passengers ride through streets and neighborhoods to revel in the magically illuminated city of Key West. 305-294-5161

Old Town Trolley’s Holiday Lights and Sights Tours — Dec. 16-17, 20-23 and Dec. 26, leaves from Mallory Square. Twice nightly tours convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West. 305-296- 6688

Sugar Rum Cherry: A Burlesque Nutcracker — Dec. 16-17, Key West Theater, 512 Eaton St., Key West. Put on your stockings and pull out your sugarplums for this naughty but nice holiday two-act reverie. Social-distancing measures currently in place. All performances subject to change. Call before you attend. 305-985-0433;

Holiday Historic Inn Tours – 6-8 p.m. Friday, Dec. 17. Explore some of the most romantically decorated inns on the island. Tickets: 305-296-4959;;

A Positive Step 5K Rudolph Red Nose Run – the PJ Edition — Saturday, Dec. 18, starting and ending at the Southernmost Beach Café, 1405 Duval Street, Key West. Runners and walkers of all ages and abilities are welcome to participate – in their holiday jammies.

Key West Artisan Market: Holiday Shop Local — 10 a.m.-2 p.m. Sunday, Dec. 19, Indigenous Park, 1801 White St., Key West. Keys-made items perfect for gift giving. Bring your own bag.

Children’s Concert at Key West Botanical Garden — 1 p.m. Sunday, Dec. 19, Key West Tropical Forest & Botanical Garden, 5210 College Road on Stock Island, Key West. A family friendly children’s concert featuring local classical guitarist Mateo Jampol performing songs especially for children in the courtyard. A craft project follows. Treats for sale. $5 per child or $10 per family. 305-296-1504 or visit

Holiday Jazz in the Gardens — 5-7 p.m. Dec. 24-26, at the Gardens Hotel, 526 Angela St., Key West. A festive outdoor jazz performance in the famous garden, with a full cash bar on site.

SV Argo Narvis Christmas Brunch — 11 a.m.-1 p.m. Saturday, Dec. 25. Have Christmas morning brunch on board the luxury catamaran sailing yacht with bottomless mimosas, premium wine and craft beers, eggnog, juices, coffee.

Key West Artisan Market: “Present Yourself” Edition — 10 a.m. – 2 p.m. Sunday, Dec. 26, at Indigenous Park, Higgs Beach. Spend your holiday money. Full bar and a variety of food choice, live music. Bring your own bag.

Key West New Year’s Eve Celebrations — Tuesday, Dec. 31.; 305-296-4959.

¦ The Conch Shell Drop at Sloppy Joe’s Bar on Duval Street

¦ The world-famous Red High Heel Drop at the Bourbon St. Pub.

n the lowering of the “pirate wench” from the mast of a schooner in the Historic Seaport.


Key West 62nd Home Tours 2021-2022 — Dec. 28-29, Jan. 14-15, Feb. 18-19 and March 18-19. Hosted by Old Island Restoration Foundation and the Oldest House Museum & Gardens, 322 Duval St., Key West. Homes may be seen in any order and viewings may be split over two days. Since parking is challenging in Key West, it is best to bicycle or to combine walking with the free Duval Loop Bus. Tickets for the tour are $55.

Pole Vault In Paradise Competition — Jan. 6-8. Vaulters from age 9 to 75 to compete alongside some of the best pole-vaulting elites from around the country. Sponsored by the nonprofit Key West Track & Field Club.

The Key West Literary Seminar: “A Seminar Named Desire” — Jan. 6-9, the Coffee Butler Amphitheater, 21 Quay Road, Key West. Each year the seminar explores a particular theme. Writers attending include Jami Attenberg, Amy Bloom, Judy Blume, Jericho Brown, Michael Carroll, Billy Collins, Garth Greenwell, Lauren Groff (keynote speaker), Karina Longworth and a dozen more. Registration fee is $675. Scholarships available. Waitlist.

Florida Keys Celtic Festival — Jan. 8-9, Marathon Community Park, MM49, U.S. 1 Oceanside, Marathon. Get lost in the legend and lore of Celtic culture this family-friendly event featuring the Drake Irish Dancers and, Albannach, The Screaming Orphans, West of Galway and The Byrne Brothers. There’s also sheepdog herding, children’s glen, Celtic Village, and Highland athletics. The Police Pipe & Drum Corp, the all-female Blue Skye Pipes & Drums. Food, beer. 305-743-6412;

RokIsland Festival — Jan. 14-17, Truman Waterfront Park Amphitheater, 21 E. Quay Road at Southard St., Key West. A four-day rock festival featuring Bret Michaels, Night Ranger, Winger, Firehouse, Steelheart, Loverboy, Skid Row, Warrant, Dee Snider, Dokken/Lynch Reunion, Slaughter, Jackyl, Lita Ford and more. Single day passes begin at $99. 844- 765-7338;

Florida Keys Seafood Festival —11 a.m. to 8 p.m. Saturday and 11 a.m. to 5 p.m. Sunday Jan. 15-16, at Key West’s Bayview Park, Truman Avenue and Jose Marti Drive. A family-friendly gathering with grilled Florida spiny lobster, fried fish baskets or platters, stone crab claws, smoked fish dip, peel-and-eat Key West pink shrimp caught, prepared and served by Keys commercial fishermen and their families. $10 adults, good for both days, and includes entry in a raffle for $250 worth of seafood. Free for younger than age 12.

The annual Key West Half Marathon & 5K Run — 7 a.m. start Sunday, Jan. 16, beginning at the corner of Caroline St. and Grinnell St., Key West. More than half of the course runs along the Overseas Heritage Trail directly on the Atlantic. It’s a bucket list run for many.


Mile 0 Fest — Jan. 25-29, Coffee Butler Amphitheater, 35 E. Quay Road, Key West. The best of red dirt and Americana music from Stoney Larue, the Randy Rogers Band, Reckless Kelly, Ryan Bingham, Shane Smith and the Saints, Wade Bowen, The Great Divide, Park McCollum. $569 and $139 per day at Info: 305-985-0433;

The 36th Key West Craft Show — Jan. 29-30 at its original location on Whitehead Street between Greene and Eaton Streets and along Caroline Street in Truman Annex community. The event is a fundraiser for the Key West Art Center & Gallery. 305-294-1241;

Headdress Ball 2021 — 8 p.m. Feb. 26, Coffee Butler Amphitheater — 35 E. Quay Road, Key West. This is the premier LGBTQ+ event of the Fantasy Fest celebration. Tom Luna returns as the outrageous emcee with Rude Girl from WEOW 92.7 radio rocking out our sound. The Aquanettes will open the show and are joined by some of the best local talent including Christopher Peterson and the cast of the Waterfront Playhouse’s Rocky Horror Picture Show. An introduction of new King and Queen of Fantasy Fest. More than 15 contestants will parade their Headdress creations on the amphitheater stage to vie for the $3,000 first prize. Premium table and grass seating. 800-535-7797. 808 Duval St., Key West;


Key West Farmers Market — 3-8 p.m. Thursdays, Truman Waterfront, at the end of Southard Street. Tents are set up along the quay near the USCG Ingham. Fresh produce, orchids and native plants, artisan meats and cheeses, pickles, honey, crafts, gifts. Take the free Duval Loop, which stops near the market. htm; 305-731-3385.

Market on the Green — 10 a.m.-2 p.m. Jan. 1 and the first Saturday of the month, Sunset Green Event Lawn, 3820 N. Roosevelt Blvd., Key West. A local artisan market. Also Feb. 5.


Coffee Butler Amphitheater — 35 E. Quay Road, Key West. 305-985-0433;

¦ Rok Island Fest — Jan. 14-17. Featuring on Jan. 14: Bret Michaels, Night Ranger, Firehouse, Winger and Steelheart. On Jan. 15: Loverboy, Skid row, Warrant, Bulletboys and Enuff Z’Nuff. On Jan. 16: Dee Snider, Dokken/Lynch Reunion, slaughter, Last in Line and Faster Pussycat. On Jan. 17: Jackyl, Lita Ford, Jack Russell’s Great White, Vixen and Bang.

¦ Mile O Fest — Jan. 25-29.

Comedy Key West — 218 Whitehead St., Unit 5, Key West. 305-985-7370;

¦ Dwayne Perkins — Dec. 16-18.
¦ Paint ‘N Chug — 7 p.m. Dec. 20 and 27,
Jan. 3, 10, 17, 24 and 31.
¦ Bob Dibuono — 8:30 p.m. Dec. 21-22.
¦ Christmas Comedy Special — 8:30
p.m. Dec. 23-24.
¦ The MadHouse — 8:30 p.m. Dec. 28
and Jan. 4, 11, 18 and 25.
¦ Local Showcase — 8:30 p.m. Dec. 29.

¦ Patrick Garrity — 8:30 p.m. Dec. 30-31.
¦ Gwen Filosa — 8:30 p.m. Jan. 16.

Key West Theater — 512 Eaton St., Key West. Social-distancing measures currently in place. All performances subject to change. Call before you attend. 305-985-0433;

¦ Tommy Prine — Dec. 18.
¦ Jethro Tull’s Martin Barre Band —
Jan. 7.
¦ Marc Broussard — Jan. 8-9.
¦ Cash Unchained — The Ultimate
Johnny Cash Experience — Jan. 11.
¦ Judy Collins — Jan. 12.
¦ Ketch Secor of Old Crow Medicine
Show & Molly Tuttle — Jan. 16.
¦ Gaelic Storm — Jan. 23.
¦ The 5 O’Clock Somewhere Show —
Jan. 29.
¦ An Evening with Vice Admiral Walter “Ted” Carter — Jan. 30.
¦ Tab Benoit — Feb. 2.
¦ Tom Papa — Feb. 11.
¦ The Life and Music of George
Michael — Feb. 12.
¦ Rat Pack Together Again — Feb. 20.
¦ Livingston Taylor — Feb. 21.
¦ Kevin Martin of Candlebox Acoustic Show — Feb. 22.
¦ David Bromberg Quintet with Rob
Ickes & Trey Hensley — Feb. 25.
¦ 10,000 Maniacs — Feb. 27.
¦ Jason Adamo — March 5.
¦ Kevin Nealon— March 13.
¦ Get The Led Out — March 15-16.
¦ Sinbad — April 17.

Red Barn Theatre — 319 Duval St., Key West. 305-296-9911 or

¦ “Cats Talk Back,” by Bess Wohl — Dec. 28-Jan. 29.

¦ “Quarantine for Two,” by Hy Conrad — Feb. 15-March 12.

¦ “Hurricane Diane,” by Madeleine George — March 22-April 16.

¦ “How to Eat Like a Child” — April 29-May 1.

Tennessee Williams Theatre — The College of the Florida Keys, 5901 College Road, Key West. 305-295-7676;

¦ Paradise Big Band: Legacy Concert I — Jan. 16.

¦ South Florida Symphony: Tchaikovsky ‘Pathetique’ and Gottsch World Premiere — 7:30 p.m. Jan. 22. $25.

¦ The Choir of Men — Jan. 27
¦ An American in Paris — Feb. 5.
¦ Drew Peterson — Feb. 8.
¦ Peking Acrobats — March 1.

¦ South Florida Symphony: Mozart and Mendelssohn — 7:30 p.m. March 26. $25.

The Waterfront Playhouse — 407 Wall St., Key West. 305-394-7445;

¦ “All Is Calm: The Christmas Truce of 1914” — Through Dec. 25.

¦ “Matilde the Musical” — Jan. 12-29.

¦ Clue (Live on Stage) — Feb. 16-March 5.

¦ “Something Rotten” — March 22-April 16.

The Studios of Key West — 533 Eaton St., Key West. Regular gallery hours are noon-4 p.m. Tuesday-Saturday. Private tours to couples and small

groups.; 305-296-0458.


¦ “Piece By Piece” Winter Members’ Exhibition — Through Dec. 30.

¦ “Pandemic Drawings,” by Nicholas Hill — Jan. 6-27.

¦ “South of Southernmost,” by Mark Hedden — Jan. 6-27.


¦ “When in Doubt, Do Something” Screening and Conversation with Tom Chapin — 4 p.m. Jan. 12. Tom Chapin takes a moment before his concerts to celebrate the life and advocacy of his brother, Harry.

¦ Tom Chapin in concert — 6 p.m. Thursday, Jan. 13, and 8 p.m. Friday, Jan. 14. The New York Times called Chapin “one of the great personalities in contemporary folk music.”

¦ “A Midsummer Night’s Dream” — Jan. 19-22 and 26-29. Conceived and directed by Richard Ericson.

¦ A Fundraiser Concert Honoring Hugh Ware’s 99th Birthday — 6 and 8 p.m. Jan. 30.

First Wednesday Jazz on the Roof — 5:30 p.m. Wednesday, Feb. 2. A series of monthly concerts featuring the critically acclaimed vocalist Libby York and her jazz trio.

¦ Susan Werner in concert — 8 p.m. Feb. 4, 6 p.m. Feb. 6.

¦ Classes and workshops: Both online and in-person classes are offered.


Florida Keys Eco-Discovery Center — 35 Quay Road, Key West.

Flagler Station Historeum — At the historic Key West Seaport, 901 Caroline St., Key West. 305-293-8716;

The Florida Keys History & Discovery Center — 10 a.m.-5 p.m. Wednesdays-Fridays, 82100 Overseas Highway, MM 82, on the property of the Islander Resort. Learn about Keys’ history.

Fort East Martello Museum — 3501 S. Roosevelt Blvd., Key West. 305- 296-3913; fort-east-martello/

Key West Art Center — 301 Front St., Key West. Gallery space also offer classes. 305-294-1241;

The Key West Art & Historical Society Custom House Museum — 281 Front St., Key West. 305-295- 6616;

¦ “Illustrating from Paradise: The Works of Morgan Dennis and Gerald Leake” — Through Jan. 3 in the Bryan Gallery.

¦ “Gouges & Grain: Artists in Wood Exhibit” — Through Jan. 13.

Key West Gallery — 601 Duval St., Key West. 305-923-1696;

Key West Tropical Forest Botanical Garden — 5210 College Road on Stock Island. Open 10 a.m.-4 p.m. daily. 305-296-1504;

¦ Hatha Yoga — 10-11:15 a.m. Tuesday and Thursday on the Lakeside Terrace. 10 classes for $125. Drop-in rate: $15, which includes admission to the garden.

¦ Garden Guardians — Volunteers who help maintain and restore the garden meet from 9 a.m. to noon Wednesday and Saturday. No commitment is needed except for your enthusiasm.

¦ Native Plant Sale — 9 a.m.-noon the third Saturday of the month.

Sunset Pier — Music and more. 0 Duval St., Key West. 305-296-7701.

Tennessee Williams Museum — 513 Truman Ave., Key West. 305-204-

4527; williams

Truman Waterfront Park— 21 E. Quay Road at Southard St., Key West. Tour the USCGC Ingham, a quintessential portrait of Coast Guard history from 1936 to 1988. $10 age 13 and older; $5 age 7-12, free for age 6 and younger. All contributions go toward the restoration and maintenance of this historic ship with over 50 years of service around the world. 305-292-5072. ¦

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