Calendar of Events

To honor and thank those serving in the military, on Armed Forces Day the History of Diving Museum will hold complimentary guided tours included with your admission ticket. These will take place at 11 AM and 2 PM on Saturday, May 17. This date also marks the beginning of the 2025 Blue Star Museums Program, which offers free admission to active-duty military and up to five members of their family. Blue Star Museums begins on Armed Forces Day, Saturday, May 17 and ends on Labor Day, Monday, September 1.

To honor and thank those serving in the military, the History of Diving Museum takes part in the annual Blue Star Museums Program, which offers free admission to active duty military and up to five members of their family. Blue Star Museums begins on Armed Forces Day, Saturday, May 17 and ends on Labor Day, Monday, September 1.

The History of Diving Museum’s new limited-time featured exhibit is open to the public! Starting May 21^st, dive into the Museum’s 20^th Anniversary Special Exhibit to learn about what it took to create the world’s largest collection of diving equipment on public display, how the Museum has evolved and grown over the past two decades, and what visitors have to look forward to in the future. Info: (305) 664-9737; www.divingmuseum.org

The History of Diving Museum’s new limited-time featured exhibit is open to the public! Dive into the Museum’s 20^th Anniversary Special Exhibit to learn about what it took to create the world’s largest collection of diving equipment on public display, how the Museum has evolved and grown over the past two decades, and what visitors have to look forward to in the future. Info: (305) 664-9737; www.divingmuseum.org

Turn up the volume and tease out your hair! Fringe Theatre is bringing back the beat with its summer production of Beehive: The 60s Musical. This high-octane tribute to the trailblazing women who redefined popular music runs July 29 through August 2, at 7 PM, in the historic Armory at 600 White Street.

Beehive: The 60s Musical was created by Larry Gallagher, a working agent looking for a way to get his performers on stage and in front of audiences. He had already earned early acclaim for his hit musical revue Ain’t No Mountain High Enough in the early 1980s. Just a few years later, Beehive was a smash hit Off-Broadway—and it has remained in worldwide production ever since.

Learn More: www.FringeTheater.org or

Join us for free family fun before school starts! Hot dogs, school supply giveaways, crafts, games, a touch tank, animal encounters, bounce house and more! Join us for a FREE fun family day!

Sponsored by the Presbyterian Women’s Association

Let’s eat lobster in the air conditioning this year! Restaurants will put out their best lobster, dishes, and appetizers as well as the Key west Cooking School will teach you how to cook lobster as you sit back and enjoy drinks and appetizers and on Sunday the Artisan market will have everything lobster including food trucks. Come join us for some fun times and let’s enjoy the opening of lobster season!

Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.

Studios of Key West invites all to visit during First Thursday Open House, where art, conversation and community come alive after hours. Wander through the galleries showcasing the newest exhibitions, sip drinks under the stars at the Hugh’s Rooftop terrace, and explore the creativity in the third-floor artist studios. Take in the vibrant energy, connect with fellow art lovers, and discover hidden gems at Books & Books. Mingle, marvel, or make memories!

Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.

Key West is famous for tropical heat, mouth watering seafood and some of the best rum you can get your hands on, among many other things. Rum Fest Key West showcases the best rum from around the world. Experiences include sunset sails, sandbar trips, rum strolls, food and cigar events featuring rum, two Jesse Rice concerts and a third concert with Cliff Cody and Sharese during the annual rum cake competition at Key West Theater, a rum grand tasting and more.

Rum Fest Key West: A Celebration of Rum

The Matecumbe Historical Trust next free presentation will be held on Tuesday, August 12^th at 6:00 pm in the Islamorada Public Library located at mm 81.5.  The presentation “Keys Worst Hurricanes” is from the Irving R Eyster collection and will show several of our local Hurricanes starting with the 1733 Spanish Treasure Fleet, leading up to the 1935 Hurricane, Hurricane Donna in 1960 and Hurricane Irma in 2017.  These were some of the most destructive hurricanes in Florida Keys history with the 1935 Hurricane being the strongest storm of the century.

The Presentation is free and open to the public.  For more information call 305-393-0940.

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.

This year’s lineup includes:

• All-male pool parties at iconic LGBTQ+ resorts
• Exclusive nightlife events and themed dance parties
• Clothing-optional excursions and male-only boat cruises
• Happy hours, brunches, and mingling throughout historic Old Town

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.

Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.

Key West favorites Cliff Cody and Sharese perform from 8 to 10 p.m. as part of Rum Fest Key West. In between the music enjoy the festival’s Rum Cake Competition! Doors open 7 p.m., show at 8 p.m. 512 Eaton St.

The Key West Art & Historical Society is pleased to announce the next installment of its engaging lecture series, “Happy Hour with the Historian,” set for Thursday, August 14, from 5:00 p.m. to 6:00 p.m. at Comedy Key West, 218 Whitehead Street.

Next month’s featured lecture, entitled “An Architectural Crown Jewel: A History of the Custom House,” will be presented by Key West Art & Historical Society curator and resident historian Cori Convertito, Ph.D.

Whether arriving by land, sea, or air, visitors to Key West are inevitably drawn to the grand, red brick Custom House, a towering icon of the island’s architectural and cultural history.  In her lecture, Dr. Convertito will explore the compelling story behind the building—from its original 1891 role as a federal hub housing the Collector of Customs, the Postal Service, and the Federal Courthouse, to its modern-day function as a world-class museum.

Learn More: What’s On | Key West Art & Historical Society

Join the History of Diving Museum at 11 AM and 2 PM for a special guided tour of the exhibits! The tour is included in your admission price. August’s tours will coincide with the 91^st anniversary of William Beebe and Otis Barton’s historic dive in the Bathysphere, which took the two men to 3,028 feet in 1934. These tours will feature highlights of the Bathysphere and its incredible feats.

A destination race in paradise!! The City Bikes Key Largo Triathlon is set at world famous John Pennekamp Coral Reef State Park in Key Largo (just a short drive from Miami) and will take place on August 17, 2025. This event will feature an Olympic and Sprint distance Triathlon and Duathlon, as well as an Olympic distance Aquabike race. Come for the weekend or make it an escape. The flat calm, crystal clear water is calling your name! The picturesque swim takes place at the main beach at John Pennekamp Coral Reef State Park (MM 102.5). The beautiful clear salt water with no current, will be warm and relatively shallow. Your bike will be out and back on Overseas Highway/Card Sound Road. The 10K/5K run takes you through a lovely, laid back Florida Keys neighborhood where you will take in the sights of the colorful conch houses in a relaxed atmosphere. Finish back at John Pennekamp Coral Reef State Park and bask in the glory as you receive your corral reef finisher medal. There will be hand-crafted, “reef” awards 3 deep for age-groups to 80+! Space is limited. Sign up today! The first undersea park in the U.S., John Pennekamp Coral Reef State Park encompasses approximately 70 nautical square miles. While the mangrove swamps and tropical hammocks in the park’s upland areas offer visitors a unique experience, it is the coral reefs and their associated marine life that bring most visitors to the park. Many enjoy the view of the reef from a glass-bottom boat tour, but visitors can get a closer look by scuba diving or snorkeling. Canoeing and kayaking through the park’s waters are popular activities; fishing is permitted in designated areas. Visitors can enjoy walking on short trails, picnicking, or swimming at the beach. The Visitor Center has a 30,000-gallon saltwater aquarium and nature videos are shown in its theater.

Islamorada: Join the History of Diving Museum as it hosts Make Ward of DiveLab, who will take us through DiveLab’s mission, the testing and research development it takes part in, and its contributions to commercial, military, scientific, and recreational diving. Presentation will be in-person and take place at 7 PM on August 20^th at the History of Diving Museum, 82990 Overseas Hwy (MM 83 Bayside). Be sure to come early for the Museum’s extended hours and see Celebrating 20 Years! Featured Exhibit. Donations welcome. Info: (305) 664-9737; www.divingmuseum.org

Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.

Join award-winning writer Alicia DeFonzo for Write Where You Are: Key West Edition, a free pop-up writing workshop happening on August 22, 2025, from 10:00 to 11:00 AM EST at Key West Gardens.

This one-hour session is designed to help you sharpen your voice, start your story, and find your people in a welcoming creative space. Attendance is free, but space is limited—registrants will be notified by email by August 13, 2025, to confirm their spot and receive full event details.

Register at Write Where You Are: Key West edition

The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82 at 151 Morada Way.

Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets.

Founded in 2011, The Morada Way Arts & Cultural District (MWACD) is a 501(c)3 not for profit organization registered with the State of Florida.

The MWACD is the driving entity behind the creation of The Upper Keys’s Arts & Cultural District, which is defined within a 6-block corridor marked by the cornerstones of the iconic Green Turtle Inn and the Hurricane Monument; the primary thoroughfare is Morada Way.

The MWACD fosters the ONLY downtown area, “Main Street” and neighborhood between Key West and Miami. It is a place where the public can gather to safely enjoy a lively, beautiful, and bustling corridor with galleries, restaurants, and studio spaces. This grassroots accomplishment has channeled arts and culture integration into surrounding parks, bike paths and business establishments adjacent to the Art & Cultural District.

Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.

Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.

Key West Brewfest is an annual celebration of beer and local flavors. Join us for tastings, events, and live entertainment in beautiful Key West, Florida!  Brought to you by the Key West Sunrise Rotary and the Southernmost Beach Resort

Join us in Key West for Labor Day weekend to celebrate the 2nd Annual Just a Few Friends memorial, honoring our favorite son, the late Jimmy Buffett. Festivities kick off with an official pre-party meetup on Thursday, August 28. On Friday morning the City of Key West will proclaim “State of Florida Jimmy Buffett Day,” followed by activities on and off the water, foodie events, and great times. Saturday features a run/walk, the Margarita Bar Crawl, along with tours, lectures, rum tastings, and music events across town. Sunday’s highlight is the epic Second Line Parade starting at 5 pm culminating in a free music festival at Truman Waterfront Park with local and national entertainment, food trucks and vendors. Come Monday continue the celebration with a variety of activities and entertainment options to suit every interest

Come Run/Walk on Saturday, August 30th at 8:00AM and be part of the 2nd Annual Labor Day weekend celebration – Just a Few Friends Key West – honoring Key West’s favorite son, We will start and finish at Irish Kevin’s for this awesome 5K & Flip Flop Mile event and rockin’ post-race party because Somewhere it’s 5 o’clock! NOT READY FOR A 5K? NO PROBLEM! Register for the Flip-Flop Mile (only 3/4 mile) which begins after the 5K takes off. Get all the Swag without the Sweat! Grab your drink, wagon coolers and flip-flops and fast track your way past the Shrimp Boat Sound Recording Studio and then to the post-race party! Proud to have Reef Relief as our charity partner.

Join Shots and Giggles & The Key West Chamber of Commerce for the 6th Annual BBQ Rib Battle! BBQ grill masters will participate in an all out cookoff to show off their skills for cash prizes. Come on down to Ann Street on Sunday, August 31 to cheer on your favorite cook, watch the contest and enjoy homemade BBQ ribs and delicious sides, music, and drinks! See you there!