Fritzie Estimond has been appointed Executive Director of the Key West Business Guild. A longtime member of the Guild team and a dedicated community leader, Estimond will build on the organization’s nearly 50-year legacy of promoting Key West as a welcoming destination for visitors from around the world. (Photo Credit: Peter Arnow) August 4, 2026 – (KEY WEST, FL). The Key West Business Guild, the nation's first LGBTQ+ destination marketing organization, is proud to announce the appointment of Fritzie Estimond as its new Executive Director, marking an exciting new chapter in the organization’s nearly five-decade history.
Since its founding in 1978, the Key West Business Guild has been dedicated to promoting Key West as one of the world’s most welcoming LGBTQ+ destinations while supporting the success of the island’s diverse business community. Today, the Guild represents more than 475 member businesses, welcomes approximately 250,000 LGBTQ+ visitors each year, operates the Gay Key West Visitor Center, and produces nationally recognized signature events including Key West Pride, Tropical Heat, Womenfest, and the Headdress Ball. Together, these efforts generate meaningful economic impact while celebrating the inclusive spirit that makes Key West a destination for everyone. As the Guild looks toward the future, Estimond brings the ideal combination of experience, vision, and passion to lead the organization forward. Having spent the past nine years helping shape the Guild’s growth, she understands its mission and impact while embracing new opportunities to strengthen the organization for its members, visitors, and the community. “Fritzie is the right leader at the right time for the Key West Business Guild,” said Dr. Cori Convertito, President of the Guild’s Board of Directors. “She has earned the trust of our members, built strong relationships throughout our community, and has consistently demonstrated her ability to think creatively and build partnerships. Just as importantly, she shares the Board’s vision for the future – one that builds on our proud history while embracing new ideas that will ensure the Guild remains a vibrant and innovative organization for years to come.” A passionate advocate for Key West and the Florida Keys, Estimond is deeply invested in the community she serves. Her dedication to collaboration, volunteerism, and civic engagement has made her a respected leader both within and beyond the Guild. As Executive Director, she will ensure the organization continues to evolve while remaining true to its mission of promoting Key West as a premier LGBTQ+ destination that welcomes all. “I am incredibly honored to serve as the next Executive Director of the Key West Business Guild,” said Estimond. “This organization has meant so much to me throughout my career, and I believe wholeheartedly in its mission and the role it plays in our community. Together with our Board, members, volunteers, and partners, I look forward to building on the Guild’s extraordinary legacy while creating new opportunities for our members and welcoming visitors from around the world.” Under Estimond’s leadership, the Key West Business Guild will continue building on its nearly five decades of success while embracing new opportunities to support its members, strengthen its programs, and promote Key West as one of the world’s most welcoming destinations. About the Key West Business Guild The Key West Business Guild is a 501(c)(6) nonprofit organization dedicated to promoting Key West to LGBTQ+ travelers while supporting the island’s business community. Founded in 1978, the Guild is the nation's first LGBTQ+ destination marketing organization and today represents more than 475 businesses across the island. Through year-round destination marketing, visitor services, and internationally recognized events including Key West Pride, Tropical Heat, Womenfest, and the Headdress Ball, the Guild helps welcome approximately 250,000 LGBTQ+ visitors to Key West each year, reinforcing the island’s reputation as one of the world's premier LGBTQ+ destinations.
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Key West, FL — April 30, 2026 — Gay Key West, Inc. is proud to announce the Key West Pride 2026 Street Fair and Community Celebration, taking place on Saturday, June 6th, from 4:00 PM to 9:00 PM. This vibrant event will bring the island together in a colorful showcase of creativity, diversity, and community spirit. Embracing this year’s theme, “Color the Island: A Celebration of Identity through Creativity and Color,” the Street Fair will feature more than 50 vendors offering some of the very best products, services, art, and experiences that Key West has to offer. From local artisans to community organizations, attendees can expect an engaging and dynamic atmosphere that reflects the heart of the island. Adding to the excitement, this year’s celebration will feature two stages of entertainment. The main stage, once again hosted by the incredible Miss Bouvee, will present an array of talented performers sure to captivate audiences throughout the evening. Keeping the energy high and the crowd moving is returning favorite DJ “Mr. Enjoy” (Angel), known for delivering unforgettable sets that keep the celebration alive. New for 2026, Pride will introduce a second stage within the “Family Zone,” designed to engage and entertain kids of all ages while providing a welcoming space for families to enjoy the festivities together. This expansion reflects Key West Pride’s continued commitment to inclusivity and community connection across generations. Vendors are encouraged to take part in this exciting event. Those interested in becoming a vendor can find more information at gaykeywestfl.com, email [email protected], or contact the Key West Business Guild office at 305-294-4603. The Key West Pride Street Fair and Community Celebration continues to be a cornerstone event, bringing together LGBTQ+ individuals, allies, residents, and visitors in a shared celebration of identity, expression, and unity. For more information about Key West Pride 2026, visit gaykeywestfl.com. Key West, FL: The Key West Business Guild (KWBG), the nation’s oldest LGBTQ+ business organization, is proud to announce its acceptance as an official member of the National LGBT Chamber of Commerce (NGLCC), the nation's largest advocacy organization dedicated to expanding merit-based economic opportunities and advancements for LGBTQ+ and other allied and interested businesses. As an Affiliate Chamber of the NGLCC, the Key West Business Guild joins a nationwide network of LGBTQ+ chambers and business organizations working together to support and promote inclusive economic growth. Membership provides KWBG and its members with access to expanded resources, business certification opportunities, and a stronger voice in national advocacy for LGBTQ+ businesses and entrepreneurs. “This is a milestone moment for the Guild,” said Rob Dougherty, Executive Director of the Key West Business Guild. “Our acceptance into the NGLCC reflects the strength and vibrancy of our members and our community. It also opens new doors for business development, partnerships, and advocacy on behalf of LGBTQ+ and allied businesses here in Key West.” The Key West Business Guild, founded in 1978, has been a driving force in promoting Key West as the nation’s premier LGBTQ+ destination while supporting local business growth, tourism, and community engagement. Becoming part of the NGLCC network strengthens the Guild’s ability to amplify the voices of its members and further its mission to foster economic resilience and inclusivity. For more information about the Key West Business Guild and its programs, visit gaykeywestfl.com Key West, FL – August 26, 2025: The Key West Business Guild invites the public to a special community meeting on Thursday, August 28, 2025, to discuss the future of the city’s iconic rainbow crosswalks. The meeting will take place from 6:00 to 8:00 PM at the Frederick Douglass Community Center (111 Olivia St.), with doors opening at 5:30 PM. The meeting, moderated by Key West Business Guild Board President, Dr. Cori Convertito, will bring together city leaders, advocates, and community voices to provide updates on the legal status of the crosswalks, reflect on their history and significance, and explore contingency plans should removal move forward. Panelists include: ·Brian Barroso, City Manager – Legal and procedural updates on the removal request. ·Joe Saunders, Equality Florida – Advocacy insights and statewide context for LGBTQ+ visibility. ·Additional Community Historians/Advocates – Reflections on the original installation of the crosswalks and their meaning for Key West. The evening will feature a panel discussion followed by an open community dialogue, where residents will be invited to share their perspectives and ideas. A key focus of the discussion will be exploring alternatives to preserve LGBTQ+ visibility and safety in the event the crosswalks are removed. These crosswalks are not just symbols of LGBTQ+ pride; they are a reflection the spirit of Key West, a community that values diversity, freedom, and self-expression. Their removal, driven by outside political overreach and pressure, sends a troubling message: that decisions made by and for this community can be overridden without our input.," said Rob Dougherty, Executive Director of the Key West Business Guild. “This meeting will give our community a chance to hear the facts, provide input, and work together on how we move forward.” Meeting Details: Date: Thursday, August 28, 2025 Time: 6:00–8:00 PM (doors open at 5:30 PM) Location: Frederick Douglass Community Center – 111 Olivia St. This event is free and open to the public. All are encouraged to attend, listen, and participate in shaping the next chapter of Key West’s commitment to LGBTQ+ visibility and pride. August 13-17, 2025 Key West, FL — The heat is on! The Key West Business Guild is thrilled to announce the return of Tropical Heat, one of the island’s hottest all-male events, happening August 13–17, 2025 in sunny, sizzling Key West. Now in its 23rd year, Tropical Heat is the ultimate summer getaway for men who love men — offering five days of steamy pool parties, clothing-optional adventures, nightlife takeovers, and island-wide indulgence. Set against the vibrant and inclusive backdrop of Key West, the event draws hundreds of visitors from across the country and around the globe for a uniquely tropical experience where “fun in the sun” is just the beginning. “Tropical Heat is more than a party, it’s a celebration of freedom, connection, and everything that makes Key West so unforgettable,” said Rob Dougherty, Executive Director of the Key West Business Guild. “We’re proud to host this event in a city where everyone is welcomed just as they are.” This year’s lineup includes:
Event passes are available now at https://keystix.com/calendar/tropical-heat. For more, visit gaykeywestfl.com to find travel tips, and full event details. Whether you're looking to relax, explore, or let loose, Tropical Heat 2025 promises five unforgettable days of sun, sweat, and celebration in the heart of paradise. Get ready to turn up the heat. Key West is calling. About the Key West Business Guild The Key West Business Guild is one of the nation’s oldest LGBTQ+ business organizations, dedicated to promoting Key West as a premier LGBTQ+ travel destination and supporting a thriving, inclusive local economy. Key West, FL — JT Thompson, the visionary behind the "One Human Family" movement, has been selected to serve as the Grand Marshal for the Key West Pride 2025 parade. Known for his powerful message of unity, love, and inclusion, Thompson's work has had a profound impact on both the local community and the broader LGBTQ+ movement. "One Human Family," which began as a simple but deeply resonant philosophy, has grown into a global symbol of equality, welcoming individuals of all backgrounds, orientations, and identities. The phrase has become synonymous with Key West itself, where it embodies the island’s commitment to diversity and acceptance." Thompson will lead the parade on Sunday, June 29th, 2025, in a vibrant celebration of love, individuality, and acceptance that kicks off at 7:00 PM. The event promises to be a powerful demonstration of the spirit of Pride, marking another milestone in the ongoing fight for LGBTQ+ rights and recognition. Key West Pride organizers have expressed their excitement about Thompson's role in the upcoming festivities. “JT’s impact has been nothing short of transformative—not only here in Key West, but around the world,” said Rob Dougherty, Executive Director of the Key West Business Guild. “JT embraces the spirit of Pride: unity, authenticity, and a joyful celebration of our individuality and community." With the 2025 parade just around the corner, anticipation is building for an unforgettable event, and Thompson’s leadership will surely make it a day to remember. KEY WEST, Florida Keys — Visitors are invited to celebrate the history and diversity of the LGBTQ+ community in Key West and beyond during Key West Pride, scheduled for Wednesday through Sunday, June 22-29, 2025. This year's event is proudly sponsored, in part, by Smirnoff, Hear 4 U Audiology, and DG Interiors, among many other supporters. Presented by the Key West Business Guild, this year’s theme, “STILL RISING,” honors the rich history of the LGBTQ+ community within the welcoming “One Human Family” ethos of this subtropical island, renowned as a premier LGBTQ vacation destination. Attractions will include late-night dance parties, daytime and sunset sailing excursions, film screenings, and drag performances, as well as a STILL RISING bar crawl for costumed participants and Pride’s traditional street fair, which promises a vibrant new twist. The festivities will commence on Wednesday, June 22, with a kick-off party hosted by AquaPlex Key West, located at 711 Duval Street. This two-hour event will set the tone for an exciting week ahead. Highlights for Wednesday, June 25, include a Gay Key West History Trolley Tour, followed by a pool party at the newly remodeled La Concha Hotel. Attendees can anticipate an unforgettable evening featuring “An Evening of Queer Crooning and Comedy,” showcasing former American Idol contestant Beane and the dynamic queer comedian Quin Lamar, and hosted by local favorites, Puddin Tain” and Gwen Filosa. Thursday, June 26, will feature a “Tea on the Sea” sunset sail and a floating tea dance aboard the Fury Catamaran. Later that evening, guests can support their favorite mixologists during the “Key West Local Bartender Competition,” commencing at 9 p.m. at the Bourbon St. Pub, 724 Duval St. Other enticing activities will include a lavish brunch sail on the luxurious Argo Navis, the “We Love Our Allies Pride Party” at 22&Co, 504 Angela St., and a “Slay Under the Sea” dance party hosted by Tike House (203 Duval St). Our LGBTQ+ partners, including Aqua, 801 Bar, Bobby’s Monkey Bar, Island House, and Bourbon St. Pub, will offer a full slate of events throughout the week. Among Saturday's many attractions is the Pride Street Fair and party, scheduled from 4-8 p.m. along the 700 to 900 blocks of Key West's famous Duval Street. This event will feature live entertainment, a diverse array of vendors, and music by DJ Mr. Enjoy. The final day's schedule on Sunday, June 29, will culminate in an inclusive Pride Parade, showcasing a 100-foot segment of Key West’s iconic 1.25-mile-long rainbow flag, originally created in 2003 by the late Gilbert Baker. Slated to begin at 7 p.m., the parade will traverse a route that includes most of Duval Street, allowing participants and spectators alike to conclude their Pride celebrations at La Te Da’s traditional Tea Dance. KEY WEST, Florida — A vibrant vaudeville-style show awaits live entertainment enthusiasts on Saturday, June 21, as "Pride Follies" takes center stage, serving as a prelude to the annual Key West Pride festivities in June. This production will showcase exceptional talents from the island's performing arts community, evoking the charm of a traditional variety show reminiscent of television's classic "Ed Sullivan's Toast of the Town." The performance is scheduled for 7 p.m. at the Key West Theater, located at 512 Eaton St., a historic venue with roots dating back to 1848. Presented by the Key West Business Guild and Gay Key West—now in its 47th year of promoting LGBTQ travel to the area—this event will benefit the mission of the organization. The not-for-profit guild is also responsible for producing annual festivals, including its signature event, Key West Pride, which will take place from June 22 to 29. "Pride Follies" will be directed and hosted by Dominic Paolillo, a Board member of the Key West Business Guild and an active participant in local theatre. Joining him as co-host is Erin McKenna, who is also renowned for her dedication to theatre and the performing arts. Organizers anticipate a diverse lineup of acts, ranging from comedy to vocal performances and dance. Doors will open at 6 p.m. prior to the 7 p.m. performance. The Key West Theater offers full bar service and seating options both downstairs and on an upper mezzanine level. Ticket prices range from $40 to $60 for premium balcony seating, and attendees must be 21 years of age or older. KEY WEST, Florida Keys — Visitors are invited to celebrate seven decades of Pride by honoring the past, embracing the present, and looking towards the future during Key West Pride, scheduled from Sunday, June 22nd through June 29th, 2025. Presented by the Key West Business Guild, this year's event carries the overarching theme of “Still Rising.” The celebration will prominently honor the history of the LGBTQ+ community, highlighting the resilience of the LGBTQ+ movement while promoting the island's inclusive ethos of “One Human Family.” Key West is internationally recognized as a premier LGBTQ vacation destination. This year, in collaboration with the Key West Art & Historical Society and the Stonewall National Museum, Key West Pride will showcase a compelling installation titled "50 Years: The Stonewall Uprising." This exhibit will delve into the individuals, events, and locations of those pivotal June nights in Greenwich Village, NYC, exploring why the Stonewall riots became a catalyst for the movement advocating for equal rights for LGBTQIA+ Americans. Key West Pride will feature a variety of attractions, including late-night dance parties, historical tours of Gay Key West, daytime and sunset sailing excursions, a private beach party, pool parties, film screenings, drag performances, an LGBTQ comedy night, a trolley-ridden bar crawl, and much more. If you are interested in learning how to participate in the largest LGBTQ+ celebration of the year through volunteering, sponsorship, or contributing to the event's organization, please contact Rob at the Key West Business Guild at [email protected] The Key West Business Guild proudly awarded a grant of $5,000 to the GSA at Key West High School. This vital organization serves as an essential resource for youth, fostering a safe environment where students can gather, support one another, discuss matters related to sexual orientation and gender identity, and actively challenge homophobia and transphobia. The grant is presented in collaboration with the Community Foundation of the Florida Keys.
Pictured from left to right are Alan Beaubien, President Emeritus of the Key West Business Guild; Dave Perkins, Assistant Principal, Key West High School; Gabby Davila., GSA Historian; Kaitlin LeBlanc, ESE Access Teacher, and GSA faculty advisor at Key West High School; Rob Dougherty, Executive Director of KWBG; and Fritzie Estimond, Associate Director of KWBG |
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