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Event calendar courtesy of — The Tourism & Development council of the Florida Keys

Calendar of Events for January, 2019


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Key West / January 01 to August 31
Key West Fishing Tournament
Anglers of all ages and abilities can target more than 40 species of fish in the Key West Fishing Tournament, a free-entry multidivision challenge that takes place Jan. 1 to Aug. 31, 2019. The tournament features divisions for men, women, junior anglers ages 10 to 15 and Pee Wees under 10 years old — making it ideal for extended families and multigenerational groups who want to share the angling experience.
Contact: Doris Harris 305-923-5934

Key Largo / January 03
Orange Bowl Swimming Classic
Some of the best college swimmers - and perhaps future Olympians - in the country compete at Jacobs Aquatic Center, mile marker (MM) 99.6 oceanside, in a competition that is part of the celebration surrounding the annual Orange Bowl college football game in Miami. Spectators are invited to attend this free event, meet the swimmers and coaches. Racing is set to begin at 10 a.m.
Contact: 305- 453-7946

Key West / January 03 to January 31
Studios of Key West presents Four New Exhibitions
Four new exhibitions open in January: O’Miami Poetry Retrospective, West African Portraiture, Portraits by Annie Dillard and Painted Photographs by Larry Blackburn. The public is invited to the opening reception Jan. 3, at The Studios of Key West, 533 Eaton Street for the First Thursday event from 6-8 p.m. Exhibitions by O, Miami, Rhonda Bristol, Annie Dillard, and Larry Blackburn fill all three floors of The Studios’ landmark building in Old Town. The shows remains on view through January 31. Gallery hours are 10am-4pm, Tuesday through Saturday.

Key West / January 05 to January 06
Studios of Key West presents: Darius by Jean-Benoît Patricot
An unexpected encounter between an extraordinary mother and a great perfumer prompts a surprising journey into olfactory memory. Directed by Murphy Davis, Featuring Rosi Ware and Stephen Kitsakos Dinner menu designed and executed by Martha Hubbard. General seating $55, for a 7:45 p.m. arrival. Show starts 8 p.m., 533 Eaton St.

Key West / January 05
Pole Vault in Paradise presents: Pole Vaulting Champions
Pole Vault in Paradise is a one-day competitive event open to pole vaulters of all ages and abilities. Spectators can watch as top athletes from around the United States join high school, college, and Masters pole vaulters. Admission is free, begins at 9 a.m. and continues throughout the day, at Truman Waterfront Park.

Islamorada / January 05
Matecumbe Historical Trust's “29 Points of Interest” Historical Trolley Tours
Enjoy an enlightening trolley ride through time. Guided trolley tours depart at 10 a.m. from the Islamorada Moose Lodge at 81573 Old Highway in Islamorada.The one-hour, colorful and much acclaimed historical tours feature 29 points of interest on the islands of Islamorada. A monitor is located at the front of the trolley showing photos of the past as you see them as they are today. Tickets may be purchased on site or call in advance. Adults are $15, children six and under are free.
Contact: Barbara Edgar 305-393-0940

Key Largo / January 10 to January 20
Uncorked ... the Key Largo and Islamorada Food & Wine Festival
The 10-day food, wine and spirits showcase features 30-plus savory events to please virtually every palate and budget, spread among numerous Upper Keys venues with fresh, locally sourced seafood and international-style dishes. The festival's outdoor 'A Grand Tasting,' is set for Jan. 19. What better reason to 'Uncork' and unwind in the Florida Keys. For a complete events schedule, visit website.
Contact: 305-522-1300

Key West / January 10 to January 13
37th Annual Key West Literary Seminar
The 2019 topic is "Under the Influence." Literary aficionados from around the world are to gather for readings, discussions and lectures led by some of contemporary literature's most acclaimed writers. KWLS has assembled some of today's most dazzling writers for a journey through literary archetypes—from Shakespeare and Homer to African folktales and early 20th-century novels and comic-book heroes—as we seek to understand the nature of literary influence.
Contact: 888-293-9291

Islamorada / January 10 to January 20
Uncorked ... the Key Largo and Islamorada Food & Wine Festival
The 10-day food, wine and spirits showcase features 30-plus savory events to please virtually every palate and budget, spread among numerous Upper Keys venues with fresh, locally sourced seafood and international-style dishes. The festival's outdoor 'A Grand Tasting,' is set for Jan. 19. What better reason to 'Uncork' and unwind in the Florida Keys. For a complete events schedule, visit website.
Contact: 305-522-1300

Marathon / January 10 to February 02
Marathon Community Theater presents: Drinking Habits
Drinking Habits takes place during the early 1960s in the impoverished Oregon convent of the Sisters of Perpetual Sewing. Two nuns at the ‘Sisters of Perpetual Sewing’ have been secretly making wine in order to keep their poverty stricken convent afloat - behind the back of their alcohol-detesting Mother Superior. Unbeknownst to them, a local wine (theirs) has won a $500,000 award, and Paul and Sally, two newspaper reporters, who are ex-fiancés, are trying to discover the winning winery and break the story. The reporters go undercover as a nun and a priest, but their presence, combined with the arrival of a new nun, spurs paranoia throughout the convent that spies have been sent from Rome to shut them down. Wine and secrets are inevitably spilled as everyone tries to preserve the convent and reconnect with lost loves. Show times 8 p.m.

Key West / January 10
Key West Theater presents: The Wailers
The legendary Wailers band is carrying its revolutionary sound and message to faithful fans around the world. Steered by famed bassist and founder Aston “Familyman” Barrett, and joined in solidarity with original Wailers Junior Marvin and Donald Kinsey, The Wailers are making musical history! The Wailers promise to not only deliver music and talent perfected over more than 40 years, but thankfully introduces fans to new-generation talent who have ties to the Bob Marley & The Wailers family and legacy. Doors open 7 p.m., show starts 8 p.m., Key West Theater, 512 Eaton St.

Key West / January 11
Key West Theater presents: Gary Puckett
Gary Puckett and the Union Gap was one of the most successful musical groups of the sixties. Gary's unmistakable signature voice garnered six consecutive gold records and top ten Billboard hits, he has performed on more than thirty network television shows and prime time specials during his career, even adding a command performance for the President and Prince Charles at the White House. Doors open 7 p.m., show starts 8 p.m., Key West Theater, 512 Eaton St.

Marathon / January 11
Wounded Warrior Project's Soldier Ride
Servicemen and women — many wounded in Iraq and Afghanistan -- are to cycle across the Seven Mile Bridge in the Florida Keys. The event is staged to provide inspiration and raise funds for their injured comrades recovering in American military hospitals. The ride across the Seven Mile Bridge is part of two days of cycling events in the Keys for the soldiers. The Keys cycling events are organized by the Wounded Warrior Project, a nonprofit, apolitical group whose mission is to raise public awareness and support for the needs of severely injured members of the military. The organization’s cross-country and local bicycle trips provide rehabilitative opportunities for injured soldiers. Come watch and support these amazing veterans. Group is expected to leave Marathon Fire Station around noon, cycle through Marathon, then cross the Seven Mile Bridge.

Key West / January 11 to March 30
Key West Burlesque presents: Backroom Burlesque
 Key West Burlesque is back and better then ever! It has found its home at the Back Space inside of SideBar, 504 Angela Street. Join the excitement two nights  a week (Fri & Sat) for this amazing show. Ticket Prices are $35 VIP seating next to the stage; $25 High cocktail table and bar stool; $20 Standing room.  
Contact: 305.294.0555

Marathon / January 11 to January 13
Island Boat Show & Festival
Come enjoy a great show with loads of the top boat brands , auction items, food, vendors featuring a variety of merchandise, great fishing seminars presented by local captains... all at a very reasonable $10 admission. Hours are 10 a.m. to 6 p.m. Sat & Sun., 10 a.m. to 2 p.m. Monday. A silent auction and fishing seminars hosted by Captain Rich Tudor, co-host of Saltwater Experience, and other Keys captains, round out the weekend. Venue at Hawks Cay Resort.
Contact: Bob Phelps 239-691-3290

Key West / January 12
Wounded Warrior Project Soldier Ride
From 10:30 a.m. to noon completes the warrior ride in South Florida, riding from Boca Chica Field at Naval Air Station, 12 miles to Bayview Park at 1320 Truman Ave., Key West. A community ride between 12:45 p.m. and 2 p.m., from Bayview Park to Truman Little White House, 111 Front St., guides warriors through Key West’s historical landmarks. This Solder Ride event kicks off the Wounded Warrior Project® (WWP) 2019 Soldier Ride season that will take warriors across the nation, visiting dozens of American cities, including New York City; Chicago; San Diego; Portland; Pittsburgh; and Washington, DC.

Marathon / January 12 to January 13
The Florida Keys Celtic Festival
Some of America's most celebrated Celtic musical masters are to be featured at the Marathon Community Park, MM 49. The festival will also feature Irish and Scottish dancing, Highland athletics, Celtic merchandise, food and beverage booths and children's activities.

Big Pine & the Lower Keys / January 12 to January 13
15th Annual Nautical Expo
Admission and parking at this event are free, held at the Lower Keys Chamber of Commerce grounds, MM31, from 8AM to 2PM. Find steals and deals on everything imaginable for boating, fishing, diving and more, from dozens of vendors. Crafts, food and beverage, live music and entertainment round out the two-day event.
Contact: 305-872-2411

Key West / January 13
Key West Impromptu Concerts presents: Chaz Bowers
Classical organist and improvisational artist Chaz Bowers has delighted audiences from his native Western Pennsylvania to the shores of Bermuda with masterful performances of pieces from the canon of great organ literature. Drawing on his own experience as church organist and the rich traditions of church music, Mr. Bowers presents programs that are designed to inspire. Show starts 4 p.m., St. Paul's Episcopal Church.

Key West / January 13 to January 27
Key West Artisan Market
Art, food, wine, craft beer, shopping and entertainment. Free admission, from 10AM to 2PM at new location, Higgs Beach. January dates, 13 & 27. Bring your reusable bags.

Key West / January 14
Friends of the Key West Library Lecture Series presents Madeline Miller
Friends of the Key West Library will present New York Times Best-Selling Novelist Madeline Miller as the first speaker in its popular Monday evening lecture series. The talk will be at the Old City Hall, 510 Greene Street. Miller’s appearance is made possible by the generous support of the Key West Literary Seminar. Ms. Miller’ second novel, Circe, was a Number One New York Times bestseller and was at the top of many Best of 2018 lists. Access to the Meeting Room at Old City Hall at 510 Green Street is at the front of the building by foot up a flight of stairs or by elevator located at the rear of the building. The Duval Loop bus has two nearby stops. Admission is free. The talk begins promptly at 6 p.m. Seating starts at 5:30 on a first come, first served basis.

Key West / January 17 to January 20
Key West Kingfish Mayhem
Big fish, big money! Come fish for some of the largest kingfish in Florida Keys waters in this new tournament. Fishing headquartered at Stock Island Marina. First prize could earn $15,000 cash, based on a 50-boat field.
Contact: Jimmy Wickett 954-605-8284

Islamorada / January 18 to January 20
7th Annual Baygrass Bluegrass Festival
Flavorful traditional bluegrass, old-time, “soulgrass” and Americana singing bands are to attract thousands of music lovers The three-day jam features satellite events at local spots and culminates in an all-day main event in a waterfront setting. Friday, a weekend warmup includes a Square Dancing in the Streets party in the Morada Way Arts & Cultural District; Saturday, a Pickin’ Party with performing musicians, barbecue and a craft beer tap takeover is scheduled ; Sunday from 11 a.m. to 8 p.m. at Founders Park, MM 87 bayside on Plantation Key, the weekend’s main event is as much a craft beer festival as a musical one, with over 15 Florida breweries expected to be “on tap.”

Key West / January 18 to January 19
59th Annual Key West Home Tours
Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $45 each, seating is limited. Tickets without transportation are $35 in advance and $40 on tour days. Proceeds benefit the foundation's Oldest House Museum, grant and scholarship programs.
Contact: 305-294-9501

Islamorada / January 19
Salt Water Sportsman National Seminar Series
Hosted by veteran saltwater fishing journalist and broadcaster George Poveromo, the Salt Water Sportsman National Seminar Series is to kick off at 9 a.m. inside the Performing Arts Center of Coral Shores High School, mile marker 89.9 oceanside in Islamorada. Entering its 32nd year, the National Seminar Series is the nation’s longest-running educational course on recreational marine fishing tactics and techniques. Admission is $55 per person and covers five hours of instruction, a course textbook, a year subscription or extension to Salt Water Sportsman magazine, and various boating and fishing product samples. The grand prize at the conclusion of the Islamorada seminar is a Florida Keys fishing trip. Register online.
Contact: 1-800-448-7360

Key West / January 19
South Florida Symphony, Porgy and Bess
An American operatic classic and fine orchestral musicianship are to combine for Florida Keys audiences in the South Florida Symphony’s staging of George and Ira Gershwin’s “Porgy and Bess.” An anticipated highlight of the symphony’s 2019 season, the production is to feature a cast of leading African-American vocalists including Neil Nelson as Porgy and Brandie Sutton as Bess. The masterful offering is to open at 7:30 p.m. Saturday, Jan. 19, at Key West’s Tennessee Williams Theatre, 5901 College Road on the campus of Florida Keys Community College.

Islamorada / January 19
Free Outdoor Pops-in-the-Park: Super Heroes and Space Wars
A free concert held at the ICE Amphitheater in Founders Park, featuring cartoon capers & fright night, broadway & movie favorites, Beatles & classic rock. Performance is outdoors; no chairs provided, bring blankets. Starts at 4 p.m. Admission free.
Contact: 305-853-7294

Islamorada / January 19
36th Annual Art Under The Oaks
Fine art & original crafts, a variety of entertainment, specialty food booths, children's arts & crafts, as well as a raffle of items donated by the artists are part of the annual highlights. San Pedro Church Gardens, 9 a.m. - 4 p.m., Mile Marker 89.5 on Plantation Key in Islamorada. Onsite parking is available for a $5 donation. Free parking is available at Coral Shores High School, with shuttle service to the event.
Contact: 305-360-8556

Key West / January 19 to January 20
14th Annual Florida Keys Seafood Festival
A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. - 8 p.m. on Saturday; 11 a.m. to 5 p.m. on Sunday, at Bayview Park, Truman Avenue and Jose Marti Drive.

Key West / January 20
21st Annual Key West Half Marathon & 5k Run
Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West's balmy January climate. Named as one of the United States' leading winter half marathons, Best Destination Half Marathons and Bucket List Best Half Marathons, is ranked among 13 must-do U.S. half-marathons by
Contact: Barbara Wright 305-240-0727

Key West / January 20
Key West Full Moon
Locals and visitors come together to Experience the culture of the Florida Keys through dance, performances, food, and drink. All are welcome to join us on this beautiful beach, under a full moon, with a friendly atmosphere that helps compliment what is truly a "celebration of us".  Everyone comes for the explosion of Sound and visual performances, but they all stay for the limbo! Donation-based entry fee is a suggested $12 pp.

Key West / January 22 to February 02
Fringe Theater presents: Collected Stories, by Donald Margulies
Fringe Theater presents this gripping drama of two writers who grapple with betrayal. Is ownership of a story in its living or in its telling? Key West Woman's Club, 319 Duval Street. Show starts 7 p.m.
Contact: Rebecca Tomlinson 305-587-8961

Key West / January 22
Conch Revival Picnic at Key West Lighthouse & Keeper’s Quarters
The Key West Art & Historical Society and Isle Cook Key West have teamed up to present a picnic-style Bahamian heritage dinner prepared by acclaimed chefs Martha Hubbard and Dave Furman from 6 to­ 8 p.m. on the grounds of the Key West Lighthouse & Keeper’s Quarters. Tickets $45 for Members and $55 for Non-members.  Kids under 12 admitted free.
Contact: Tickets 305-295-6616

Key West / January 22 to January 29
28th Annual Kelly McGillis Classic International Flag Football Championship
Women and girls from around the world are to meet on the playing field for hard-fought sporting action. Each year, nearly 30 teams from across the United States, Mexico, Central America, Sweden and India participate.
Contact: 305-896-8678

Key West / January 23 to January 27
Key West Food & Wine Festival
Top chefs and restaurateurs display culinary creativity and the Keys' indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively "Old Town Uncorked," neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting.
Contact: 800-474-4319

Islamorada / January 23 to January 24
Islamorada Fishing Club Sailfish Tournament
Presented by the Islamorada Fishing Club, this is the second leg of the Florida Keys Gold Cup Series, with a typical field of up to 30 boat teams of elite sport fishermen. A total cash payout for a full field at the IFC Sailfish Tournament could reach $25,000. Kick off is Jan. 23, one day of fishing Jan. 24, with awards ceremony immediately after.
Contact: Dianne Harbaugh 305-522-4868

Key West / January 23 to February 02
Studios of Key West presents: I’m Gonna Pray For You So Hard
One boozy evening, fiercely competitive actress Ella and her father David deliberate over whether to read the reviews of her Off-Broadway debut... and things unravel from there. This darkly humorous sheds new light on the eternal struggle of parents and children to find common ground. Dates: Jan 23-27, Jan 30-Feb 2 (Wed-Sun) 8p.m. show, 533 Eaton St.

Key Largo / January 23 to May 03
Arts Council Presents the Connections Project 2019 TOUR
The Florida Keys Council of the Arts works to support all the arts, in all the Keys, all the time. The local arts agency is launching its seventh annual Connections Project Keyswide road show with a grand opening reception at the Murray Nelson Government & Cultural Center in Key Largo from 5:30 - 7:30 p.m. featuring a vibrant 24-foot mosaic mural created by local artists and art lovers. The reception with wine and hors d'oeuvres is open to the public. After connecting with the art, patrons can also collect art by making a $50 donation for one canvas or a $125 donation for three at any reception or online. Once the road show has ended, donors receive a randomly selected piece of the mosaic in the mail. Each work includes an artist statement providing insight into the origin of the work and the artist’s thoughts and inspiration. Proceeds from the Connections Project directly benefit Keys artists and arts organizations.

Key West / January 24 to February 09
Waterfront Playhouse presents: A Doll's House, Part 2
A Doll's House, Part 2 is the continuation of Henrik Ibsen's classic A Doll's House. Far from being dry or stuffy, ADH, Pt.2 is hilariously funny, whip-smart and resonant to our gender politics. The story picks up 15 years after Nora famously slams the door on her stifling marriage at the conclusion of A Doll's House. In Mr. Hnath's updated version, Nora is now a successful business woman, who finds her husband, daughter and wise-cracking maid to be as changed as she has become. Fireworks explode as the play explores the rules of society and gender. See website for show dates. Show times 8 p.m.
Contact: Box-Office (305-294-5015)

Islamorada / January 25 to January 27
Cheeca Lodge Presidential Sailfish Tournament
Last in the Gold Cup series. Anglers put 20-pound line and light-tackle skills to the test during the two-day challenge against the high-flying acrobatic fish, known for tail-walking the waves. Only circle hooks can be used. "The Presidential" typically awards sophisticated sculpture trophies to top anglers who release the most sailfish.
Contact: Lisa Thornhill 305-517-4512

Key West / January 25
Rams Head Productions presents: Air Supply at Sunset Green Event Lawn
The trademark sound of Russell Hitchcock's soaring tenor voice and Graham Russell's simple yet majestic songs have created a unique sound that helped Air Supply become a staple of early-'80s radio, producing seven straight Top Five singles. The albums "Lost in Love", "The One That You Love", "Now & Forever", and "The Greatest Hits" sold in excess of 20 million copies during this era. In 2013, the duo was inducted into the Australian Recording Industry Association's Hall of Fame. Air Supply celebrated their 40th anniversary in 2015 and continue to delight audiences all over the world. Doors open 6:30 p.m., show starts 8 p.m. Sunset Green Event Lawn is a multi-purpose event space located at 24 North Hotel .

Key West / January 26 to January 20
Key West Cemetery Stroll
During the stroll, small groups of visitors will be escorted to gravesites where interpreters will tell the stories of the deceased in brief monologues. The groups are scheduled for departures at 9:30, 9:50, and 10:10. Among the gravesites to be visited are those of Frank Booth. Charles DuPont, William Kerr, Thomas Romer, the Los Martires de Cuba, the Figueredo plot; the Benjamin Albury family restoration, and the USS Maine plot. The tour will take approximately 90 minutes. Participants should wear comfortable shoes and plan to walk over a mile on uneven ground. Bottled water will be provided. A cash donation of $20 pp to the Historic Florida Keys Foundation is recommended with all proceeds devoted to cemetery restoration.  Participants should enter the cemetery by either the Windsor Street or Frances Street gate and go to the registration table on 2nd Ave. Reservations are necessary.
Contact: Reservations 305-304-1453

Big Pine & the Lower Keys / January 26
Meet the Fleet Shrimp Boil
Immerse yourself in Keys culture for the annual Key West Food & Wine Festival. Sample the finest fare the Florida Straits have to offer: There’s enough Key West Pink Shrimp — and an array of wines to pair — for everyone to enjoy. Join Matt's Stock Island Kitchen & Bar at The Perry Hotel for a traditional Shrimp boil with the only authentic Key West Shrimp available: Key West Pink Shrimp, Andouille Sausage, Black Bean Fritters, Corn on the Cob, Red Potatoes, Coleslaw, Fresh Bread and Butter, Key Lime Pie.

Marathon / January 26
January Jamboree at Marathon Garden Club
It's expected to be a smorgasbord of tropical plants, "used treasures" as part of a rummage sale, a plant raffle, even baked goods and honey! Attendees can find Keys and South Florida natives, bamboo, palms, heliconias, bromeliads, crotons, orchids and unusual, rare tropicals. Meet plant experts, browse local art vendors. Open from 8:30 a.m. to 3 p.m. at Marathon Garden Club, MM50.
Contact: 305-743-4971

Key West / January 26 to January 27
34th Annual Key West Craft Show
Tens of thousands of attendees browse and buy among juried artisans and crafters who gather to display their talents at this popular outdoor festival on lower Whitehead Street in historic Old Town Key West.
Contact: 305-294-1243

Islamorada / January 26
Matecumbe Historical Trust presents Historical Trolley Tour of Islamorada
Enjoy an enlightening trolley ride through time. Guided trolley tours depart at 10 a.m. from the Islamorada Moose Lodge, MM 81.5. The one-hour, colorful and much acclaimed historical tours feature 29 points of interest on the islands of Islamorada. Tickets may be purchased on site or call in advance. Adults are $15, children six and under are free.
Contact: Barbara Edgar 305-393-0940

Key West / January 27
Wrecker's Race aboard Schooner America 2.0
All hands on deck!  If you enjoy a good sailboat race, it is an absolute must for you to sail on board the Schooner America 2.0 for the Key West Wreckers Race. In old Key West, ships from afar often ran aground on Sand Key Reef. When all the scallywags in Key West heard there was booty to be had, they jumped in their boats and raced to the reef. The first one there could claim the ship’s cargo! Today, celebrate this Key West tradition with monthly races from January to April. It all starts with the firing of the cannon at 1PM.  Enjoy the excitement aboard Schooner America 2.0 and race to defend the title of fastest schooner in Key West. Beer, wine, champagne, and a boxed lunch are complimentary with your ticket purchase.

Key West / January 27
Key West Impromptu Concerts presents: Timothy Chooi
Regarded as one of Canada's most promising and exciting young artists, Timothy Chooi recently was the Bronze Medal Winner of the 2015 Michael Hill International Violin Competition, performed with Pinchas Zukerman and the National Arts Centre Orchestra, recorded his debut album, and was featured at the Ravinia Festival in Chicago. Show starts at 4 p.m., St. Paul’s Episcopal Church.

Key West / January 29 to February 02
Second Annual Mile 0 Fest Key West
Mile 0 Fest Key West is a new music festival considered a "must see" in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off the hopping streets of Duval, or get into a stripped down acoustic set with your favorite band leader at one of the theaters or bars off Duval. Many activities and memorable experiences await.