Mallory Square & Margaritaville Resort 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 Margaritaville Resort 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. If you’re really lucky, you may even witness the rare “Green Flash.” Experience it nightly at the end of upper Duval Street. Info: 305-294-2787.
Nightly
Jazz At Tavern N’ Town
Key West: Some of Key West’s top talent including “Island Diva” Carmen Rodriquez and Michael Thomas, perform here nightly from 5 – 7 pm during Key West’s best Happy Hour. Takes place at Marriott Beachside, 3841 N. Roosevelt Blvd. Info: 305-296-8100
Tuesdays
Mario Sanchez Original Works & Lecture
Key West: Owner of Key West’s renowned Gallery on Greene, Nance Frank has curated multiple exhibits of famed Cuban artist, Mario Sanchez with catalogs for his exhibit presented by The American Folk Art Museum, The Museum of the City Of New York as well as Cuba’s National Museum. Her weekly presentation about Sanchez’s life and work is absolutely fascinating. Takes place at 2 pm every Tuesday at Gallery On Greene, 606 Greene St, Key West. 305-304-2323; galleryongreene.com.
Monthly
Snook’s Luau & Pig Roast
Key Largo: Swivel your hips and feast like a king during this monthly tropical extravaganza that boasts fire dancers, hula dancers, great live music and continuous live entertainment that will keep you jumpin’ all night long. The party kicks off at 6:30 pm on Sat. Nov 24, Sat, Dec 29, Sat, Feb 23, Sat March 23 and Sat, April 20. Sells out fast so be sure to make reservations. Takes place on the waterfront at Snook’s Bayside & Grand Tiki, MM 99.9, Bayside, Key Largo. Info: 305-453-5004; snooks.com.
Monthly
Third Thursday Morada Way Art Walk
Islamorada: Fine arts, live music and “culinary art” are the hallmarks of this festive monthly event which showcases both national and local artisans in galleries along the Morada Way Arts & Cultural District. Takes place from 6 – 9 pm on Old Hwy, MM 81.5, Oceanside, Islamorada. Info: 305-393-6012.
Wednesday – Saturday
Cabaret in The Gardens
Key West: Key West’s Gardens Hotel is one of the most beautiful boutique hotels on the island and every Weds. through Sat. from 5 – 7 pm, you can enjoy wonderful, live piano music in the Hotel’s intimate Cabaret. Full bar and stellar wines are the coup de gras. Find at 525 Angela St, Key West. Info: 305-294-2661; gardenshotel.com.
First Friday
MM 104 Block Party
Key Largo: Stroll among artists, do some gift shopping, enjoy street bites from local eateries and more during this fun monthly Block Party. Takes place on the First Friday of every month from 6 – 10 pm, rain or shine along the Overseas Hwy at mile marker 104 in Key Largo. FYI: You can park at any of the MM104 businesses and walk along the bayside bike pathway. Info: keylargofirstfriday.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 and special Pop-Up stores. Open from 8 am – 2 pm every Sat and Sun through July. Free admission and parking. Find it at 30250 Over-seas Hwy, Oceanside on Big Pine Key. Info: 305-872-4103.
Every Sunday
Jazz in The Gardens
Key West: Enjoy some terrific 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
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Monthly
Fort Taylor Living History Weekend
Key West: On the third weekend of each month, Fort Taylor Zachary Taylor Historic State Park is transformed into a Union-occupied encampment where local and regional re-enactors portray life as it was in 1861 during the American Civil War. Firing and cooking demonstrations are all part of the excitement as you embark on a trip through time to see, hear and smell what life was like in a Federal Fort during the War. Takes place from 10 am – 2 pm at Fort Zachary Taylor Historic State Park, 601 Howard England Way Key West. Info: floridastateparks.org.
November 3 – 11
Florida Bay Music Festival
Islamorada: Southern rock legends 38 Special and country star Chris Janson highlight this special fundraiser for Casting for Cats, Big Dog Rescue Ranch, and Mangrove Mike’s Everglades Education. Gates open at 3 pm; Music at 5 pm. Takes place at Founders Park, MM 87 in Islamorada. Tickets and info: 305-664-2012; castingforcats.org.
November 4 – 11
37th Annual Key West Championship Races
Key West: High-speed offshore powerboats race in Key West Harbor and surrounding waters in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor where racers can achieve speeds above 140 mph and provide fans with breathtaking displays of skill and power. Info: 305-296-6166.
November 3
37th Annual Key Largo Cook-Off
Key Largo: This legendary culinary competition challenges both professional and amateur cooks and chefs, as well as young aspiring chefs, to create their very best soups and chowders, appetizers, main dishes, sides, and salads, as well as desserts. Takes place from 7 – 9 pm at the Holiday Inn, MM100, Oceanside in Key Largo. Tickets on sale at the Key Largo Chamber of Commerce. Info: 305-451-4747; keylargochamber.org.
November 8 – 10
All American Backcountry Fishing Tournament
Islamorada: War heroes and world-class anglers compete for trophies and awards during Cheeca Lodge’s 6th annual catch and release competition.This first-class tournament kicks-off on Thur, Nov 8th with a cocktail reception, rules meeting, patriotic banquet on the beach and auction. Tickets to attend the kickoff dinner and auction are available to the community with advance reservations. Info: 305-712-7166; cheeca.com.
November 9
MaarVelous Pet Rescues “Spay-ghetti & No Balls Holiday Gala”
Key Largo: This fun annual dinner, auction and mega dance party benefits MarrVelous Pet Rescues which is dedicated to uniting pets with loving homes and families. Takes place at 6:30 pm on the waterfront at the beautiful Snook’s Bayside Restaurant & Grand Tiki, MM 99.9 Bayside, Key Largo. Tickets are EXTREMELY limited and not sold at the door. Info and tickets: 305-453-1315; spayghetti.com.
November 10
A Night at The Museum: Bootlegger Bash
Islamorada: This signature fundraiser for the Keys History & Discovery Museum is one of the Upper Keys most fun annual events. For one night only, guests will find a secret Speakeasy behind the Keys History & Discovery Center. The clandestine evening features live jazz, booze, and gaming – a roaring good time! Enjoy a cocktail reception, a delicious surf-and-turf dinner and dessert, as well as an opportunity to bid on enticing trips, jewelry, personal indulgences, and much more in the live and silent auctions. Takes place from 6 – 10 pm at the Keys History & Discovery Center, MM 82 on the property of the Islander Resort in Islamorada. Info and tickets: 305-922-2237; keysdiscovery.com.
November 11
Annual Veterans Day Parade
Key West: Everyone is welcome to cheer on the marching units and pay tribute to service members past and present during this special annual parade. Takes place at 4 pm along Duval St. Info: 305-295-1443.
November 11
Annual Taste of The Islands
Marathon: This award-winning event draws several thousand attendees and features local restaurants, live entertainment, vendors and artists, a tribute to veterans, fashion show, kids’ activities plus live and Chinese auctions. Takes place from 11 am – 5 pm at Marathon Community Park, MM 49, Oceanside, Marathon. Info: 305-923-9976.
November 14 – 18
Key West Film Festival
Key West: This annual event showcases films that exhibit excellence in storytelling and features screenings and special events at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. Info: kwfilmfest.com.
November 15
OIRF 59th Annual Home Tour Kick Off Party
Key West: During the big reveal of this year’s Home Tour Poster Contest Winner, you’ll have an opportunity to meet all of the artists, see some of their other work and get a poster signed by the winning artist. You’ll also hear a little about some of the homes on this year’s tour while you enjoy nibbly food and libations under the stars in the beautiful garden at the Oldest House, 322 Duval St. Info: 305-294-9501; keywesthometours.com.
November 21 – 25
International Sand Art Competition
Key West: Watch leading U.S. and international sand sculptors construct and display large-scale creations over Thanksgiving weekend on the beach at the Casa Marina Resort, 1500 Reynolds St. Info: justsandandwater.com.
November 21 – 31
Key West Holiday Fest
Key West: Key West’s colorful month-long holiday celebration includes all kinds of fun festivities that take place all over the island. From the lighting of the Harbor Walk of Lights at the historic Key West Bight, holiday parades and tours of historic homes and decorated inns to tree lighting parties, art shows, and outrageous New Year’s Eve celebrations, it’s one hoot of a good time. Info: keywestholidayfest.com. 
November 24
Artisan Holiday Market
Key West: Small Business Saturday is the perfect time to support island artists! Enjoy cookies and coffee as you stroll through a friendly, festive indoor market. Each year, over 20 artisans present unique and locally produced gifts: jewelry, textiles, home accessories, and quality crafts. Takes place from 9 am – 4 pm at The Studios Of Key West, 533 Eaton St, Key West. Info: 305-296-0458; tskw.org.
November 24
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. Free admission. Takes place from 8 am – 2 pm at the Lower Keys Chamber of Commerce, MM 31, Oceanside. Info: 305-872-2411; lowerkeyschamber.com.
