ONGOING
Randy Roberts Live!
Key West: Spotlighted on television’s hit series “America’s Got Talent,” Randy Roberts shines in this live, multi-media tribute to some of the world’s most beloved performers. His uncanny impersonations of Cher, Better Midler, and Mae West are spot-on. He’ll have you rolling in the aisles when he performs a titillating striptease as the bawdy Gypsy Rose Lee. Catch this fantastic show at La Te Da’s Crystal Room Cabaret, 1125 Duval St, Key West. Tickets and info: 305-296-6706; lateda.com.
ONGOING
Christopher Peterson’s Eyecons
Key West: Christopher Peterson is, without a doubt, one of North America’s foremost female impressionists — both visually and vocally. Often compared to the legendary Jim Bailey, master of impersonations, his hit show, EYECONS, is one of the hottest tickets in town. You’ll be amazed by how he transforms himself into more than a dozen famous women right before your eyes with the help of his “magic closet.” See him in the Crystal Room Cabaret at La Te Da, 1125 Duval St, Key West. Tickets and info: 305-296-6706; lateda.com.
Daily
Mini Golf
Ramrod Key: Come play the southernmost and only mini-golf course in the Florida Keys. This kid-friendly 18-hole course is a perfect family adventure. It boasts a fun caveman theme with two giant waterfalls and four fountains. And get this: If you’re 21+, you and your friends can have a cocktail or glass of wine while you putter around. Happens daily from 10 am — 10 pm at Boondocks Grille & Draft House at 27205 Overseas Hwy (MM 27.5) on Ramrod Key. Be sure to check out their special party packages and tournaments. Info: 305-872-4094; boondocksus.com.
Daily
Green Pineapple Key West Yoga
Key West: Whether you’re a beginner or seasoned practitioner, this Hatha-based yoga studio offers daily classes designed for every skill level. Based on the foundations of traditional yoga practices, categories include Vinyasa, Yin, Restorative, Gentle, Breath and Mindful Movement, Pilates, and Meditation. The Green Pineapple Yoga Shala also offers workshops to feed your body, mind, and soul. Private or Group Classes are also available. Come early or stay after class for a fresh juice, a cup of tea, or a super healthy Zen-Bite in the plant-based Wellness Cafe. Find it nestled inside The Green Pineapple Wellness Center, 1130 Duval Street, Key West. Info: 305-509-7378; greenpineapplewellness.com.
Daily
Mario Sanchez Original Works & Lecture
Key West: Learn about the real “Old Key West” from Mario Sanchez, Florida’s most important folk artist. Nance Frank has curated multiple exhibits of famed Cuban artist Mario Sanchez with catalogs for his exhibition presented by The American Folk-Art Museum, The Museum of the City of New York, and Cuba’s National Museum. Her daily presentation about Sanchez’s life and work is absolutely fascinating. Takes place daily at 2 pm at Gallery on Greene, 606 Greene St. Info: 305-304-2323; galleryongreene.com.
Daily
Historic Marker Tours
Key West: Discover a little piece of paradise during this self-guided tour which explores Key West’s 120 Historic Markers in the Largest Historic District of Frame Buildings in the United States. See photos and listen to the history and stories these buildings tell. Info: 305-295-6616; kwahs.org.
Nightly
Key West Sunset Celebration
Key West: Each evening, about two hours before sunset, flocks of people gather at Key West’s Mallory Square and on the pier behind the Opal Resort & Marina on Front Street to watch the sun slowly sink into the Gulf of Mexico and to revel in the colorful street performers, local artists, psychics and food vendors who have made Key West’s Sunset Celebration a world-famous, multicultural happening.
Nightly
Aquaplex
Key West: With five venues all under one roof, Key West’s state-of-the-art entertainment complex is where it’s all happening. SideBar, a world-class dance club with high-tech lighting and an industrial vibe, connects each venue, including a lovely outdoor garden bar called the Back Bar. Poké in the Rear is a fun backyard Hawaiian eatery open until 11pm. The 22&CO bar is known for its tutu-wearing clientele, neon flamingo décor, and unique glittering cocktails. There’s also the original Aqua Nightclub, renowned for its outrageous drag shows. What more could you ask for? Find it all at 711 Duval St. Info: 305-294-0555; aquakeywest.com.
Nightly
The Aquanettes
Key West: Key West’s own talented female impressionist troupe transforms themselves into a bevy of beauties using elaborate costuming, makeup, and lip-sync. Renowned for their outrageous and comic numbers, this adult-oriented, interactive show is one of the hottest tickets in town. Takes place Monday -Wednesday at 9 pm and on Thursday through Sunday at 7 pm and 9 pm. See it at the Aquaplex, 711 Duval St. Info: 305-294-0555; aquakeywest.com.
Nightly
Cabaret @ D’Vine Wine Gallery
Key West: This is an excellent hang if you want to kick back with a fine glass of wine and settle in for an intimate cabaret performance by some of Key West’s favorite performers, like classical guitarist Matteo Jampol and pianist Bobby Green. Takes place from 5 – 7 pm at The Gardens Hotel and Cottages, 526 Angela St. Info: 305-294-2661; gardenshotel.com.
Nightly
Jazz at Tavern N’ Town
Key West: Some of Key West’s top talent, including “Island Chanteuse” Carmen Rodriquez, and Michael Thomas, perform nightly from 5 – 7pm during Key West’s best Happy Hour. Takes place at Marriott Beachside Resort, 3841 N. Roosevelt Blvd. Info: 305-296-8100; tavernntown.com.
Tuesday – Saturday
Movies at the Museum
Islamorada: This ongoing series of fascinating Shorts runs throughout the day and includes films about Henry Flagler’s Overseas Railroad, the Keys 1935 Hurricane, and an overview of Islamorada area State Parks. Films begin at 10:30 and continue throughout the day, with the last showing at 4 pm. Takes place at the Florida Keys History & Discovery Center, 82100 Overseas Hwy (on the grounds of the Islander Resort) in Islamorada. Info: 305-922-2237; keysdiscovery.com.
Wednesday – Saturday
Cabaret in The Gardens
Key West: Key West’s Gardens Hotel is one of the most beautiful boutique hotels on the island. Every Wednesday through Saturday from 5 – 7 pm, you can enjoy outstanding, live piano music in the Hotel’s intimate Cabaret. Full bar and stellar wines are the coup de gras. Find the Gardens Hotel at 526 Angela St. Info: 305-294-2661; gardenshotel.com.
Every Thursday
Key West Waterfront Market
Key West: Every week, you’ll find traditional farmer’s market fare, including produce, seasonal fruits, cheese, pickles, nuts, honey, seafood, fresh bread, hot sauces, and more. There are food stands and food trucks. Artists, crafters, flea market goods, jewelry, clothing/t-shirts, local organizations, cigars, and CBD. An eclectic group of small businesses who collectively offer one-stop shopping at our weekly pop-up island bazaar. Takes place from 2 pm – 7 pm at the Truman Waterfront (end of Southard St). Bring your own bags. Info: 305-731-3385; keysartisanmarket.com.
Every Thursday
Glow Hours on Hugh’s View
Key West: This weekly rooftop Happy Hour comes with the best views in town. Hugh’s View sits on the roof of The Studios of Key West. It boasts panoramic vistas across the rooftops of Old Town, from the Gulf of Mexico to the Atlantic. Takes place weekly from 6 – 8 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; TSKW.org.
Every First Friday
First Fridays on Fleming
Key West: “The Fabulous 500 Block of Fleming Street” showcases boutiques, galleries, and eateries with all kinds of cool events, including jewelry trunk shows, art openings, book signings, tastings, and libations. It takes place from 6 – 9 pm. Info: 305-304-9001; shoplocalkeywest.com.
Every Saturday
Open-Air Market
Ramrod Key: Forget about driving miles to find local Florida Keys art, handmade jewelry, one-of-a-kind creations, fresh organic produce, greens, and flowers! You’ll find all that and more right at Boondocks. Takes place from 9 am – 2 pm in the parking lot of Boondocks Plaza at MM 27.5 on Ramrod Key. Info: 305-872-4094; boondocksus.com.
Every Saturday & Sunday
Big Pine Flea Market
Big Pine Key: Discover all kinds of great finds at unbeatable prices at this long-time Lower Keys Flea Market that showcases an eclectic mix of both used and new merchandise, as well as locally made soaps, tools and tarps, fishing supplies, watches and jewelry, fresh seafood and produce, homemade ice cream, weekend Fish Fry, and inflatable park. Open from 8 am – 2 pm every Sat and Sun. Free admission and parking. Find it at 30250 Overseas Hwy, oceanside, on Big Pine Key. Info: 305-872-4103; bigpinefleamarket.com.
Every Sunday
Jazz in The Gardens
Key West: Enjoy some hot jazz amidst lush flora and fauna during this free hang that draws Key West’s top jazz cognoscenti. Full bar, champagne, and fabulous wines. Takes place from 5:30 – 8 pm at the Gardens Hotel, 526 Angel St, Key West. Info: 305-294-2661; gardenshotel.com.
Weekly (Check Website for Dates)
Glow Hours: Rooftop Happy Hour on Hugh’s View
Key West: For a headier Happy Hour, head on up to Hugh’s View, where the bar is open, admission is free, and everyone looks great in the golden twilight. Hugh’s View sits on the roof of The Studios of Key West. It offers panoramic vistas across the rooftops of Old Town, from the Gulf of Mexico on one side to the Atlantic on the other. Takes place from 6 – 8 pm at The Studios of Key West, 533 Eaton St. Info: tskw.com.
MONTHLY: Third Wednesday
Immerse Yourself!
Islamorada/Virtual: This free monthly presentation takes place both on-site and virtually. Come by the museum or tune in from wherever you are as experts share fascinating information related to maritime history, archeology, diving, and marine science. To find out about each month’s topic, which may include presentations like “Searching for Treasures,” “Great Whites of Guadalupe,” and “Sponge Research,” call 305-664-9737 or visit divingmuseum.org. Virtual registration: programs@divingmuseum.org.
MONTHLY: First Thursday
Art & Shopping Walk
Key West: Grab a pair of comfortable shoes and stroll this collection of great galleries, unique boutiques, and design studios, spanning from The Studios of Key West at Eaton and Simonton to Guild Hall Gallery on Duval; as well as all the galleries and boutiques in the neighboring 500 Block of Fleming. Takes place from 6 – 9 pm. Info: tskw.org.
MONTHLY: Third Thursday
Walk On White Gallery Walk
Key West: One of Key West’s original art walks includes exhibitions and receptions at galleries and shops along White St, from Southward to United. Takes place from 5 – 9 pm. Info: walkonwhitekeywest.com.
MONTHLY: Third Thursday
Morada Way Arts & Cultural District Art Walk
Islamorada: Fine arts, live music, and “culinary art” are the hallmark of this festive local happening in the Morada Way Arts & Cultural District. Takes place from 6 – 9 pm on Old Hwy, MM 81.5, Oceanside. Info: 305-664-2471; moradawayarts.org.
MONTHLY: First Fridays
Upper Duval Street Stroll
Key West: Galleries, boutiques, and cafes open late for exhibitions and receptions on Duval St from Truman to United. Starts at 6pm.
MONTHLY: First Friday
First Fridays on Fleming
Key West: “The Fabulous 500 Block of Fleming Street” showcases boutiques, galleries, and eateries with all kinds of cool events, including jewelry trunk shows, art openings, book signings, tastings, and libations. It takes place from 6 – 9 pm. Info: 305-304-9001; shoplocalkeywest.com.
MONTHLY: First Saturday
Market on the Green
Key West: Shop some amazing local arts at this fun artisan market. Takes place from 10 am — 2 pm at the Sunset Green Event Lawn located between the Gates Key West Hotel and 24 North Hotel, 3852 N Roosevelt Blvd. Info: 305-400-4117; thekeyscollection.com.
MONTHLY: Second Saturday
I Love Stock Island Art Stroll
Key West/Stock Island: Over 10 local artists at several different locations showcase sculptures, woodworking, mosaics, screen printing, soaps, fabric art, and more. Takes place from 11am – 5 pm at the Stock Island Arts District. Info: 305-731-5780; ILoveStockIsland.org.
MONTHLY: Third Saturday
Native Plant Sale
Key West: Peruse over 2,000 native, rare, and endangered plants from the Keys, Cuba, and the Western Caribbean at this terrific monthly plant sale. Takes place from 9 am – Noon at the Key West Tropical Forest and Botanical Garden, 5210 College Rd. Info: 305-296-1504; keywest.garden.
MONTHLY: Select Sundays
Key West Artisan Market
Key West: Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, a wide variety of food and libations, and local musicians and authors. Takes place from 10 am – 2 pm on Nov 6. & 20; Dec. 14 & 18; Jan 1, 15 & 29 at Sonny McCoy Indigenous Park, 1801 White St. Info: 305-731-3385; facebook.com/KeyWestArtisanMarket.
Now – November 12
Jimmy Buffett’s Escape to Margaritaville
Key West: This hilarious, heartwarming musical features Jimmy Buffett’s most beloved classics, including Margaritaville, It’s 5 O’clock Somewhere, Fins, Cheeseburger in Paradise, and many more. On stage at the Waterfront Playhouse, 407 Wall St in Mallory Square. Info and tickets 305-294-5015; waterfrontplayhouse.org.
Now – November 23
Eco Echos, Marianne Vogel
Key West: Vogel’s fiber art serves as a reflection of and response to her natural world, finding deeper meaning in basic shapes through mindful, slow stitching and beading. Each piece celebrates the beautifully unusual arrangements designed by nature. On exhibit, Tu – Sat from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
Now – November 30
Scarecrows in the Garden
Key West: This lighthearted outdoor exhibit showcases scarecrows crafted from natural and recycled materials by local artists, students, and other community members. The scarecrows are all freestanding and no more than 6′ tall, so they can withstand outdoor weather conditions for the duration of the exhibit. On display daily from 10 am – 4 pm at the Key West Tropical Forest & Botanical Garden at 5210 College Road, Stock Island (Key West). Info: 305-296-1504; keywest.garden.
Now – December
Sponge Hunters
Islamorada: Learn about the fascinating maritime industry of history of sponge hunting with Key West hook boats, Tarpon Springs hard-hat divers, and Bahamian free divers. You’ll also learn about the sponge restoration of contemporary conservationists in the Florida Keys. Takes place daily from 10 am – 5 pm at The History of Diving Museum, 82990 Overseas Hwy, Islamorada. Info: 305-664-9737; divingmuseum.org.
Now – December 11
Key West 200th
Key West: This historic curation commemorates Key West’s 200 years of history and explores Key West’s people, culture, and community. The exhibit begins with settlers and government officials arriving on our remote island in 1822. It traces its historical milestones, including the Civil War, Great Depression, and World War II. Open daily from 9:30 am – 4:30 pm at the Custom House Museum, 281 Front Street. Info: 305-295-6616; kwahs.org.
Now – December 11
Tennessee Williams Exhibit
Key West: In celebration of the island’s ongoing bicentennial celebration, the Tennessee Williams Museum’s educational and historic exhibit now showcases information about Williams’ writing, filming, and premiering of “The Rose Tattoo” in Key West during the 1950s. Discover how Williams’ many cultural and philanthropic contributions made during his thirty-four-year residency helped place Key West on the cultural and literary map. Located at 513 Truman Avenue, the Tennessee Williams Museum is open for self-guided tours from Thursday through Sunday from 9:30 am – 4:30 pm. Info: 305-204-4527; kwahs.org.
Now – December 23
Robert the Doll
Key West: Author and photographer Mathew Leifheit takes the haunting story of “Robert the Doll” to a whole new level: that of an older man carrying around an effigy of his younger self dressed in a little sailor suit—and reinterprets it as a tongue-in-cheek queer story. Leifheit’s photographs meld history with autobiography and commentary on queer culture. On exhibit, Tuesday – Saturday from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
Now – November 30
Scarecrows in the Garden
Key West: This lighthearted outdoor exhibit showcases scarecrows crafted from natural and recycled materials by local artists, students, and other community members. The scarecrows are all freestanding and no more than 6′ tall, so they can withstand outdoor weather conditions for the duration of the exhibit. On display daily from 10 am – 4 pm at the Key West Tropical Forest & Botanical Garden at 5210 College Road, Stock Island (Key West). Info: 305-296-1504; keywest.garden.
November 3 – 26
Everything I Ever Needed to Now I Had to Learn
Over in My Own Language, Katharine Doughty
Key West: Doughty’s series of alphabet self-portraits began with an “A” in 1999 and finished with a “Z” in 2017. The complete series explores personal mythology, archetypes, and the differences between writing and visual imagery. On exhibit, Tuesday – Saturday from 10 am – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
November 5
11th Annual Stone Crab Eating Contest
Marathon: This annual contest dares contenders to crack and eat 25 crab claws in record time. Open to both individuals and teams. Takes place at Keys Fisheries, 3502 Gulfview Ave, Marathon. Competitors must register by noon. Advance registration at KeysFishMedia@gmail.com. Info: 866-743-4353; keysfisheries.com.
November 6 – 13
Key West World Championship Offshore Races
Key West: High-speed offshore powerboats race in Key West Harbor and surrounding waters during this breathtaking annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs directly through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph. Info: 305-296-6166; raceworldoffshore.com.
November 12
Historic Seaport Sail On Argo Navis
Key West: Brad Bertelli leads a historically illuminating seafaring excursion that explores Captain Benjamin Baker’s foray into pineapple farming during the late 1800s. Enjoy Bloody Marys, mimosas, or non-alcoholic beverages along with a variety of pastries as you also learn about why the construction of Key West’s Civil War-era Fort Zachary Taylor was so important, as well as about the building’s relevance through today. The two-hour tour shoves at 9 am at Argo Navis Sailing Charters, 0 Margaret St in Key West’s Historic Harbor. Presented by the Key West Art & Historical Society. Info: 305-295-6616. Tickets are online at kwahs.org.
November 12
Upper Keys Fall Festival & Open House
Key Largo: This unique festival commemorates the 70th anniversary of the Garden Club of the Upper Keys. Takes place at Francis Tracy Garden Center, 94040 Overseas Hwy. Info: gardenclubupperkeys.org.
November 12
Mote Marine Laboratory’s Ocean Fest: A Community Celebration
Islamorada: Underwater and outdoor enthusiasts, eco-travelers, and families celebrate the marine environment at this fun Upper Keys festival that includes crafts, games, music, food, shopping, and a fabulous silent auction. Takes place from 10 am – 4 pm at Founders Park, 8700 Overseas Hwy (MM 87 Bayside). Info: 941-356-0964; mote.org.
November 16
How to Talk About Your Book at a Cocktail Party with Katrin Schumann
Key West: Bestselling author Katrin Schumann helps writers cut through the noise with tools to succinctly explain their work. More fun than an elevator pitch and certainly more festive, the cocktail party one-liner helps authors grab the attention of would-be readers. Takes place from 1 – 4 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
November 16
6th Annual Smuggler’s Night at the Museum
Islamorada: This signature fundraiser for the Keys History & Discovery Museum is one of the Upper Keys’ most fun annual events. The evening features specialty cocktails, fine wine, an elegant dinner, live music, dancing, and live and online auctions. Takes place from 6 – 10 pm at the Islander Resort, 82100 Overseas Hwy (MM 82 Oceanside). Info and tickets: 305-922-2237; keysdiscovery.com.
November 16
Immerse Yourself: Deep Water Horizon Open Ocean Restoration
Islamorada: NOAA Marine Habitat Resource Specialist, Kristopher Benson, discusses the restoration of mesophotic and deep benthic communities impacted by the Deepwater Horizon oil spill. Takes place at 7 pm at the History of Diving Museum, 82990 Overseas Hwy (MM 83 Bayside). Info: 305-664-9737; divingmuseum.org.
November 16 – 26
The Last Five Years
Key West: Two aspiring creatives fall in and out of love in this unconventional and award-winning musical. An emotional tour de force from end to beginning and beginning to end. Produced by Fringe at the Armory, 600 White Street. Showtime: 7pm. Tickets: fringetheater.org.
November 16 – 20
Key West Film Festival
Key West: This annual event showcases films that exhibit excellence in storytelling and features screenings, visiting filmmakers, workshops, and special events at landmark venues throughout Key West. The festival also looks to support the next generation of local student filmmakers with scholarships and other key awards. Info: kwfilmfest.com.
November 18
Sister Season Fashion Show & Auction
Key West: Local designers show off their original creations and auction them off to the highest bidder. The Grand prize is awarded to the designer who receives the highest bid. Tickets include hors d’oeuvres and an open bar. Doors open at 6:30 pm, and the show begins at 8 pm. Takes place at the Key West Theater, 512 Eaton St. Info: 304-304-9828; sisterseason.com
November 19
Preserving Paradise
Key West: George Born, author of “Preserving Paradise,” deciphers the intriguing history of Key West through the island’s unique architecture and building history. Born explains in detail just why Key West is so architecturally unique and why the city’s buildings, streets, and neighborhoods are a repository of history that can be discovered by experts and weekend visitors alike. Takes place at 10 am at The Oldest House Museum, 322 Duval St. Info: 305-294-9501; oirf.org.
November 23
Lighting of the Bight: Key West Harbor Walk of Lights
Key West: The Key West Harbor lights up the waterfront with a 16′ fresh pine Nautical Christmas Tree, a Fishing Buoy Tree, and the original 20′ Key West Lobster Trap Tree. This “Harbor Walk of Lights” honors the maritime history of the Key West waterfront and stays lit nightly through New Year’s Eve. Stretches along the seawall past Greene, William, and Margaret Streets to the Key West Ferry Terminal. The opening night event starts with live music at 5 pm and the lighting at 6 pm. Info: keywestchristmas.org.
November 26
Holiday Maker’s Market
Key West: Enjoy cookies and coffee as you stroll through a friendly, festive indoor market where over 20 artisans showcase unique and locally produced gifts: jewelry, textiles, home accessories, and quality crafts. Takes place from 9 am – 1 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
November 26
Big Pine & The Lower Keys Island Art Festival
Big Pine: This fun annual holiday event always draws a big crowd and includes live music, exhibits, arts and crafts, food vendors, and more. Takes place from 9 am – 3 pm at the Lower Keys Chamber of Commerce, MM 31, oceanside. Info: 305-872-2411; lowerkeyschamber.com.
November 29
ReMARCable Table Top Christmas Tree Auction
Key West: Bid on beautiful Fraser Fir trees, between 3½’ to 4½’ tall, which are
elaborately decorated by local artists, businesses, and private residents. Takes place from 7 pm – 10 pm at the Opal Resort and Marina, with an early preview starting at 6:30 pm. Benefits the Monroe Association for ReMARCable Citizens (MARC). To sponsor a tree and decorate yourself ($100) or to sponsor a tree and have MARC find a decorator for you ($250). Info: 305-294-9526; marchouse.org.
November 29 – 30
Southern Skies Stargazing with Larry Halstead
Key West: Artist and astronomy buff Larry Halstead takes you to the cosmos and back. On night one, you’ll meet in the theater for a presentation on what to expect and how to comprehend where these celestial objects fit in terms of scale, distance, and location in the night sky. The next night, you will use a powerful telescope on the roof for direct observation and stargazing. Takes place at 7 pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
November 30 – December 17
Rock of Ages
Key West: This musical fantasy features songs from Styx, Journey, Bon Jovi, Pat Benatar, Twisted Sister, Steve Perry, Poison, and Europe. On stage at the Waterfront Playhouse, 407 Wall St in Mallory Square. Info and tickets 305-294-5015; waterfrontplayhouse.org.
