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X-ORIGINAL-URL:https://www.historichideaways.com
X-WR-CALDESC:Events for Historic Hideaways
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DTSTART;VALUE=DATE:20260805
DTEND;VALUE=DATE:20260810
DTSTAMP:20260403T172020Z
CREATED:20230105T212024Z
LAST-MODIFIED:20260403T172020Z
UID:706-1785888000-1786319999@www.historichideaways.com
SUMMARY:Key West Lobsterfest
DESCRIPTION:Get Ready to Crack! Key West Lobsterfest 2026 Dates are Set!\n\nThe wait is officially over! Get your butter warmers ready because we are thrilled to announce the dates for the biggest and tastiest summer celebration on the island: Key West Lobsterfest 2026 is happening from Wednesday\, August 5th through Sunday\, August 9th! \nJoin us for five unforgettable days as we celebrate the opening of the Florida Spiny Lobster season with an island-wide party. From the savory kickoff Lobster Boil to the massive Duval Street Fair with live music and endless crustaceans prepared every way imaginable\, this is the ultimate crustacean celebration. \n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n \nHistory of Key West Lobsterfest\n\n\n\nBorn from a Brawl (Over Lobster\, No Less!)\n\n Believe it or not\, Key West Lobsterfest started with a friendly (or maybe not-so-friendly) dispute. Two friends couldn’t agree on who made the best Lobster Chilau\, a Key West staple. What else to do but settle it with a cook-off? The inaugural throwdown went down in the courtyard of Rick’s & Durty Harry’s Entertainment Complex\, with secret family recipes and judges galore. The event was such a hit (though we’ll keep the winner a secret)\, they knew they had to take it bigger. The next year\, Lobsterfest moved to the bustling Duval Street\, welcoming more participants\, spectators\, and sponsors than ever before. Fast forward to today\, and this epic food fight has transformed into a 4-day extravaganza that takes over the entire island! \n\nKEY WEST LOBSTERFEST 2026 28th Annual\nAll information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)\nWEDNESDAY\, AUGUST 5 \n6:00 PM – 9:00 PM Key West Lobsterfest Kick-Off Party Rick’s & Durty Harry’s Entertainment Complex 202 Duval Street\, Historic Old Town \nHome of the inaugural Lobsterfest — this is where it all began with a contest for the best lobster dish on the island. Join us to kick off the 28th Annual Key West Lobsterfest. We need to empty the freezers to make room for freshly caught lobster! \nEnjoy amazing lobster pizza and drink specials featuring our Official Sponsors Sun Cruiser Iced Tea and Cuervo 1800 Tequila. \n\nTHURSDAY\, AUGUST 6 \n6:00 PM – 9:00 PM Lobster Boil at The Porter Mansion Courtyard – 429 Caroline Street\, Historic Old Town \nJoin us for our annual seafood lobster boil in a beautiful Key West setting with a full bar\, music\, and delicious food. \n\nFresh lobsters\nJumbo Key West shrimp\nRed skin potatoes\nFresh corn on the cob\nFresh baked jalapeño corn bread & melted butter\n\nEach ticket is good for one guest’s admission and meal. \n\nFRIDAY\, AUGUST 7 \n3:00 PM – 6:00 PM Pool Party at The Marker Resort – Key West Harbor Resort – 200 William Street \nFree Admission – Relax and soak up the fun. \n8:00 PM – Midnight Lobsterfest Duval Pub Crawl Check-in: The Marker Resort Pool Bar\, 200 William Street \nJoin us for the 28th Annual Lobsterfest Pub Crawl! The fun starts immediately after sunset and goes until midnight. \nWhat’s included: \n\nOfficial Lobsterfest T-shirt\nSouvenir lanyard\nAmazing drink specials on Sun Cruiser Iced Tea and Cuervo 1800 Tequila at participating bars\n\nTickets: $25 in advance / $30 at the door. A portion of proceeds benefit the Key West High School Scholarship Fund. Pick up your T-shirt\, lanyard\, and crawl instructions at the Marker Resort Pool Bar on August 7th from 3:00 PM – 7:30 PM. All items must be picked up in person. \n\nSATURDAY\, AUGUST 8 \nNoon – 11:00 PM – Street Fair & Concert 100–500 Blocks of Duval Street – Free Admission \nArts & crafts\, merchandise\, and more lining Duval Street all day. \nLocal bars and restaurants will be serving fresh Florida Lobster — everything from appetizers to full meals. No entrance fee; food and drinks sold individually. \nLocal bars will also be set up on Duval Street featuring ice-cold Corona\, Blue Chair Bay Rum cocktails\, and more. \nLive Music Lineup: \n1:00 PM Just George – Duval St. & Greene St. \n3:00 PM Fried Newt – Main Stage \n5:30 PM Jordan Oaks – Main Stage \n8:00 PM The Durtbags – Main Stage — then continuing late night at Durty Harry’s
URL:https://www.historichideaways.com/event/key-west-lobsterfest/
LOCATION:FL
CATEGORIES:Festivals,Outdoor Activities
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20260810
DTEND;VALUE=DATE:20260817
DTSTAMP:20260527T155803Z
CREATED:20260527T155803Z
LAST-MODIFIED:20260527T155803Z
UID:3180-1786320000-1786924799@www.historichideaways.com
SUMMARY:Key West Rum Fest
DESCRIPTION:Key West Rum Fest 2026 — August 10–16 \nThe Florida Keys’ Key West Rum Fest returns August 10–16\, 2026\, with a week of global rum tastings\, live music\, culinary events\, and island excursions. Proceeds benefit MARC Inc.\, a Keys-based nonprofit serving adults with developmental disabilities. Set against the backdrop of Key West’s tropical island culture\, the festival pairs premium rum tastings from around the world with live performances\, food-driven experiences\, and themed excursions. Every ticket supports MARC Inc.’s mission to provide programs and services for adults with developmental disabilities in the local community. \n\n\n\n\n\n\n\nKey West Rum Fest 2026 — Schedule of Events\n\nSubject to change and errors and omissions – confirm on the official website for the event! \n\n\n\n\n\n\n\n\n\n\n\n\n\nMonday\, August 10\n\nDay Trip to Bahamas — Roundtrip from Key West airport. Arrive by 7 AM\, return by 6 PM. Passport required. (Waitlist only — text Neil at 910-599-6430)\n\nTuesday\, August 11\n\nDay Trip to Cuba — Roundtrip from Key West airport. Arrive by 7 AM\, return by 6 PM. Visit the Hemingway home\, the original Pilar boat\, and Hemingway’s favorite bars. Passport required. (Waitlist only)\n\nWednesday\, August 12\n\nDay Trip to Cuba — Same itinerary as Tuesday; lunch and “other goodies” included\nSunset Trip\, 6:30–8:30 PM — Leaves Garrison Bight. Daiquiri bar with Neil and Jess (Coasting Cocktails)\, visit to the site of Hemingway’s bar at Cottrell Key\, rum & ice cream\, custom hat for each attendee\, dolphin viewing. Tank-top dress code. Available only via Water Package.\n\nThursday\, August 13\n\nDay Trip to Cuba (waitlist only)\n5-Course Luncheon & RUMposium — At Casa Marina Hotel\, with rum ambassadors Ian Burrell\, Jeff “Beachbum” Berry\, and Ed Hamilton\nReggae Pool Party\, 2–4 PM — More details to come. No tickets necessary.\nMeet the Owners\, 4:30–5:30 PM — SALT Gallery\, 209 Simonton St (next to Pilar Distillery). Neil’s new artwork on display and for sale. No tickets.\nSunset Sail Kickoff — Check-in 5:30 PM\, boarding 6:00 PM. Meet at First Legal Distillery for a tour and complimentary piña colada\, then walk to board the Fury (corner of Greene & Elizabeth\, by Conch Republic Seafood Co.). Sunset sail with First Legal Rum Distillery and the Cory Heydon Band.\nAfter Party at Tiki House\, 9 PM — Featuring Worthy Park Rum. 21+. No tickets needed.\n\nFriday\, August 14\n\nDay Trip to Cuba (waitlist only)\nSandbar Trip\, 9:30 AM–1:30 PM — Leaves Garrison Bight. All cocktails included; live music by Dawson Wright with Key West Cocktail Cruises. Sponsored by Bombarda Rum. More info coming soon.\nRum Fest Book Signing — Time TBA. With rum authors Ian Burrell\, Jeff “Beachbum” Berry\, and Shawn Martin. Rum tasting with Down Island. Free admission.\n“Landsharks at Lagerheads” — Cliff Cody\, 2–2:30 PM — Live at Lagerheads Beach Bar\nMojito Pool Party\, 3–6 PM — Marker Resort Pool Bar\, custom mojito sponsored by Nauti Beach. Free admission; donations accepted for MARC House.\nMeet & Greet Jesse Rice Concert\, 3:30–5 PM — Key West Theater\, max 60 people\nPapa’s Pilar Rum Dinner — Time TBA. Tropical flavors and rum culture\, tickets via Hyatt Centric.\nCliff Cody and Sharese (Local Artists) — Doors 7 PM\, ends ~10 PM. Opener: Dawson Wright. Includes the 2026 Rum Cake Competition (call/text Neil to enter).\nAfter Party at Sloppy Joe’s\, 10 PM — 21+\, no tickets needed\n\nSaturday\, August 15 (National Rum Day)\n\nSandbar Trip\, 9:30 AM–1:30 PM — Leaves Garrison Bight. All cocktails included; live Dawson Wright music with Key West Cocktail Cruises. Sponsored by Marsh House Rum. More info coming soon.\nRum Lunch\, 11 AM–1 PM — Hot Tin Roof. Agricole class with Ed Hamilton. $100 includes gratuity.\nGrand Tasting\, 2:30–5:30 PM — Key West Theater (3:30 entry for general admission). 40+ vendors. 100% of proceeds benefit MARC House.\nJesse Rice in Concert with Full Band — Berkley Lindley 7–7:15 PM\, Dawson Wright 7:15–8:05 PM\, Jesse Rice 8:05 PM onward\nSaturday Night VIP After Party\, 10:30 PM–close — Live music by Jesse Rice\n“After-After Party” — Time and location not published. Word of mouth only; reach out to Neil.\n\nSunday\, August 16\n\nRum Brunch with Bahama Bob\, 11:45 AM–2 PM — Hot Tin Roof. Rum cocktails sponsored by Rhum Clement.\nGoing Away Party\, 1–4 PM — Southernmost Beach Resort @ Pineapple Pool. No tickets necessary.
URL:https://www.historichideaways.com/event/key-west-rum-fest/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20260812
DTEND;VALUE=DATE:20260817
DTSTAMP:20260706T194804Z
CREATED:20230105T211816Z
LAST-MODIFIED:20260706T194804Z
UID:703-1786492800-1786924799@www.historichideaways.com
SUMMARY:Key West Tropical Heat
DESCRIPTION:Tropical Heat is the HOTTEST annual 5-day party for gay men ages 21 and up in Key West and the Florida Keys! The all-male themed parties\, pool parties\, clothing optional events\, and adult-oriented entertainment promise to be HOT! August on our tropical island is always HOT\, but during Tropical Heat it promises to be even more so! What better way to experience our tropical paradise than joining us for 5 days with hot guys!? In addition to all our scheduled events\, you can also enjoy our many other activities on land and sea!\n\n\n\nTropical Heat 2026 Schedule of Events\n\n\n\n\n\n\n\n\n\n\n\n\n\n\nWednesday\, August 12th\n\n\n\n5 PM– Cowboy Ken’s PINK Pool Party  AND Kick-off @ Island House  – 1129 Fleming St.\nThink pink at the southernmost mojo-dojo-casa-house! Pink cowboy hats\, pink hankies\, pink speedos\, OR LESS! Just make it PINK! Free appetizers and ½ price cocktails. VIP band holders can also pick up their bands at this events. Bands can also be picked up at the Gay Key West Visitor Center at 808 Duval St. through Tropical Heat between the hours of 9 am and 5 pm. For more info call (305) 294-4603. \n\n\n\n\n\n\n\n\nThursday\, August 13th\n\n\n\n10:30 AM – All Male Day Trip 🏳️‍🌈Ages 18+ • 4 Hours • BYOB *Snorkel\, Sandbar or Kayak on Blu Q \nTrip includes: \n\nAll Male + Clothing Optional\nSnacks & Water Included\, BYOB\nSnorkel & Kayak Gear Included\nCaptains-Choice: activities tailored to the day’s weather conditions. We all want to have an amazing Key West day on the water!\nFree Cancellation up to 6 days (144 hours) prior to scheduled departure time.\nBring a towel\, and feel free to bring your own drinks! Our amazing crew will make sure your drinks stay cold in our coolers. They’re great at keeping track of who brought what and will keep you refreshed all day.\n**Sandbar and Snorkel is our typical day on the water\, but on certain weather and tide days\, it can be tough to go to a sandbar\, so we offer the option to kayak instead.\n\nTickets are available HERE \n\n9:30 PM – Nightly Karaoke at Bobby’s Monkey Bar – 900 Simonton St \nUnpretentious dive bar at 900 Simonton St in Key West (a block off Duval)\, known island-wide as one of the best karaoke spots in town. Karaoke runs nightly from 9:30 until late\, with the place typically just getting going around 10pm and rocking by 11. \n\n10:00 PM – Dancers on The Bar at Bourbon St Pub – 724 Duval St \nThe Bourbon St. Pub has been known all around the world for its Hot Men. And you can catch them each and every night on top of the bar for your viewing pleasure\, starting at 10 PM. \n\n\n\n\n\n\n\n\nFriday\, August 14th\n\n\n\n10:30 AM – Tropical Heat Snorkel Trip @ Blu Q Key West – 120 Margaret St. \nIf you haven’t set sail on Blu Q yet\, you’re missing out on the best gay experience in Key West! Blu Q guests keep coming back for more and it’s no surprise why. Their four-hour Tropical Heat trip is the perfect way to experience the turquoise waters of Key West while basking in the Florida sun. You can snorkel\, kayak\, swim\, or just relax on the boat – it’s totally up to you! Our crew is always ready to make your trip unforgettable\, with their warm smiles\, expert guidance\, and a hard work ethic. So what are you waiting for? Hop on board the Blu Q and let’s make some memories! This one sells out quickly. Tickets available HERE \n\n1 PM – 5 PM  Splash Pool Party @ Bourbon St. Pub – 724 Duval St. \nJoin World Famous Puddin’ Tane for some fabulous pool games and get a chance to meet the Adult Stars of Saturday Night’s Big ‘O’ Party while you beat the heat with ice cold drink specials from Key West Pride’s award-winning bartenders! Entrance and free clothes check included with your weekend pass bracelets! $20 or FREE \n\n9PM – 4AM Heat Stroke: Leather Gear and Underwear Party @ Saloon One – 504 Petronia St  \nWhether you’re rocking your favorite leather\, stripped down to your best underwear\, or somewhere in between\, this is your space to let loose\, connect\, and own the night. Expect pulsing beats\, a bold crowd\, and an unapologetically sexy atmosphere. Dress to impress\, or undress to express. \n\n\n\n\n\n\n\n\nSaturday\, August 15th\n\n\n\n10:30 AM–Enjoy a 4-hour Male All Day Trip with Blu Q Key West. \nIf you haven’t set sail on Blu Q yet\, you’re missing out on the best gay experience in Key West! Blu Q guests keep coming back for more and it’s no surprise why. Their four-hour Tropical Heat trip is the perfect way to experience the turquoise waters of Key West while basking in the Florida sun. You can snorkel\, kayak\, swim\, or just relax on the boat – it’s totally up to you! Our crew is always ready to make your trip unforgettable\, with their warm smiles\, expert guidance\, and a hard work ethic. So what are you waiting for? Hop on board the Blu Q and let’s make some memories! This one sells out quickly. Tickets are available HERE \n\n12 PM –Five-Alarm Pool Party@ Island House – 1129 Fleming St \nAll fireman report to the pool deck for this high-energy firefighter themed pool party! Slide down the pole and get ready to get blasted by our pool boy CO2 cannon! Expect hot men & cold cocktails to make the perfect sizzling summer memory with friends! \n\n10 PM – The Big “O” Exhibition @ Bourbon St. Pub – 724 Duval St. \nA Voyeurs Dream Come True! The biggest blow out of the weekend! Foam party. Play areas. Pool & Jacuzzi. Hot Exotic Dancers and Adult Industry Performers. \nLive Exhibition Shows. Free entry with your VIP bands\, or $20 for non pass holders at the door. Free clothes check! \n\n\n\n\n\n\n\n\nSunday\, August 16th\n\n\n\n\n12 PM –Hot Naked Pool Party@ Island House – 1129 Fleming St \nAfter church\, and before T-Dance\, comes Island House! For over two decades\, this party brings visitors and locals together in true Gay Key West spirit! Hot-Naked-FUN! \n\n\n\n\n\n\n\n\nDaily Activities\n\n\n\nMuseums: Ernest Hemingway\, Key West Butterfly Conservatory\, Little White House\, Key West Aquarium\, Mel Fisher Maritime Museum\, Key West Firehouse Museum\, Key West Light House\, Key West Ship Wreck Museum\, Audubon House\, Oldest House and Garden Museum\, USCGC Ingham Museum\, Tennessee Williams Exhibit. \nLand Activities: Key West Food Tours\, Up the Keys Eco Tour\, Fort Zachary State Park\, West Martello Tower\, A & M Scooter Rental\, Key West Tropical Forest and Botanical Garden\, Key West Cemetery\, Key West Adventures\, Papa’s Pilar Rum Distillery\, Ghost Hunt\, Old Town Trolley Tours\, Conch Tour Train\, Haunted Key West\, Ghosts and Mysteries\, Ghosts and Gravestones\, D’vine Wine Gallery\, Perky’s Key West Excursions. \nWater Activities: Argo Navis\, Blu Q\, Classic Harbor Lines\, Cruisin’ Tikis\, Danger Charters\, Fish N Chicks\, Fury\, Island Vibe Charters\, Island Vibe Charters\, Java Cat\, Jolly Rover II\, Key West Eco Tours\, Key West Sailing Center\, Key West Snorkeling. Land Boat Charters\, Off the Charts\, Schooner America\, Sunset Sail Key West\, Sunset Watersports\, SV Argo Navis\, Yankee Freedom.
URL:https://www.historichideaways.com/event/key-west-tropical-heat/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Festivals,Outdoor Activities
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