BEGIN:VCALENDAR
VERSION:2.0
PRODID:-//Key West Historic Seaport - ECPv6.17.3//NONSGML v1.0//EN
CALSCALE:GREGORIAN
METHOD:PUBLISH
X-WR-CALNAME:Key West Historic Seaport
X-ORIGINAL-URL:https://keywesthistoricseaport.com
X-WR-CALDESC:Events for Key West Historic Seaport
REFRESH-INTERVAL;VALUE=DURATION:PT1H
X-Robots-Tag:noindex
X-PUBLISHED-TTL:PT1H
BEGIN:VTIMEZONE
TZID:America/New_York
BEGIN:DAYLIGHT
TZOFFSETFROM:-0500
TZOFFSETTO:-0400
TZNAME:EDT
DTSTART:20250309T070000
END:DAYLIGHT
BEGIN:STANDARD
TZOFFSETFROM:-0400
TZOFFSETTO:-0500
TZNAME:EST
DTSTART:20251102T060000
END:STANDARD
BEGIN:DAYLIGHT
TZOFFSETFROM:-0500
TZOFFSETTO:-0400
TZNAME:EDT
DTSTART:20260308T070000
END:DAYLIGHT
BEGIN:STANDARD
TZOFFSETFROM:-0400
TZOFFSETTO:-0500
TZNAME:EST
DTSTART:20261101T060000
END:STANDARD
BEGIN:DAYLIGHT
TZOFFSETFROM:-0500
TZOFFSETTO:-0400
TZNAME:EDT
DTSTART:20270314T070000
END:DAYLIGHT
BEGIN:STANDARD
TZOFFSETFROM:-0400
TZOFFSETTO:-0500
TZNAME:EST
DTSTART:20271107T060000
END:STANDARD
END:VTIMEZONE
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260603
DTEND;VALUE=DATE:20260608
DTSTAMP:20260909T194327Z
CREATED:20260323T151335Z
LAST-MODIFIED:20260909T194327Z
UID:10000335-1780444800-1780876799@keywesthistoricseaport.com
SUMMARY:Key West Pride 2026
DESCRIPTION:  \nKey West Pride 2026\nEvery June\, Key West Pride turns the island into a vibrant\, inclusive festival full of color\, community\, and celebration. This weeklong event welcomes LGBTQ+ visitors\, allies\, and locals alike\, offering a packed schedule of pool parties\, drag shows\, comedy nights\, street fairs\, and sunset sail cruises—along with educational programs and cultural tributes that honor the history and resilience of the LGBTQ+ movement. The festival culminates in the spectacular Pride Parade\, where revelers dance along Duval Street carrying a 100-foot segment of Key West’s signature Sea-to-Sea flag in a dazzling display of unity and pride. \nOrganized by the Key West Business Guild and Gay Key West\, this year’s theme\, “Still Rising\,” reflects a spirit of perseverance and joy throughout the LGBTQ+ community. Anchored in Key West’s longstanding motto of “One Human Family\,” Pride seamlessly blends festive energy with meaningful moments—like the “Generations of Strength” Street Fair\, trolley tours honoring queer history\, and a floating Tea Dance at sunset. With its tropical setting\, eclectic events\, and inclusive vibe\, Key West Pride stands out as one of the most beloved and dynamic celebrations of identity and belonging in the Florida Keys. \n  \n \n  \n\nDaily Activities\n\n\nMuseums: 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 Museum\, Hellings Curry Museum/ Home of the Key West Woman’s Club\, Ernest Hemingway Home & Museum \nLand Activities: Key West Food Tours\,  iWitness True Crime Tours\, Fort Zachary State Park\, West Martello Tower\, KW 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\, Key West Fine Wine\, Key West Wildlife Center\, Tart Tales. \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\, Hindu Charters\, Land Boat Charters\, Namaste All Day Key West \, Schooner America\, Sunset Sail Key West\, Sunset Watersports\, SV Argo Navis\, Yankee Freedom III \nFor all the details\, visit https://gaykeywestfl.com/pride/ 
URL:https://keywesthistoricseaport.com/event/key-west-pride-2026/
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2017/06/Pride-Flag-2012-TDC-2.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260701
DTEND;VALUE=DATE:20260706
DTSTAMP:20260626T143251Z
CREATED:20260623T151648Z
LAST-MODIFIED:20260626T143251Z
UID:10000340-1782864000-1783295999@keywesthistoricseaport.com
SUMMARY:The Annual Key Lime Festival 2026
DESCRIPTION:Key Lime Festival 2026 — Love & Limes in Key West\nDates: July 1 – July 5\, 2026Location: Key West\, Florida\nThe Key Lime Festival 2026 returns to the Florida Keys this Independence Week\, delivering five days of citrus-inspired fun\, culinary delights\, and island culture. Known as America’s Favorite Citrus Celebration\, this event highlights what makes Key West unforgettable: its eccentric characters\, lively parties\, and\, of course\, the iconic Key Lime Pie. \nDaily Key Lime Highlights\nThroughout July 1–5\, festivalgoers can experience a vibrant mix of food\, drink\, and entertainment: \n\nMini Pie Baking Classes at Key West Key Lime Pie Co.\nSpecialty Menus featuring Key Lime Tiramisu at Better Than Sex\, citrus-infused dishes at Café Sole\, and tropical flavors at Kaya Island Eats.\nRum Tastings at Key West First Legal Rum Distillery with award-winning Key Lime spirits.\nHappy Hours & Live Music at venues like The Alamo.\nVendor Village at Southernmost Beach Resort with lime-themed art\, jewelry\, and gifts.\n\nSignature Events Not to Miss\n\nKey Lime Kick-Off Party at The Avalon – Music and entertainment to start the celebration.\nKey Lime Pie Hop – Walk through town sampling pies while collecting a festival t-shirt.\nKey Lime Sip & Stroll – Taste and vote on the best lime cocktails across the island.\nWorld Famous Pie Eating Championship – Contestants attempt to devour a 9-inch pie the fastest.\nPie Drop at the Lighthouse – Homemade contraptions tested in a zany pie drop challenge.\nBattle of the Bartenders – Six mixologists compete with Key Lime Liqueur creations.\nFamily Fun Zone – Crafts\, conch-blowing\, games\, and mermaid meetups for children.\n\nIndependence Week Celebrations\nThis festival also coincides with 4th of July traditions\, giving visitors a patriotic and tropical holiday blend: \n\n4th of July 5K Run/Walk – Start the day with energy and philanthropy.\nStars & Stripes Pool Party at Dante’s – Celebrate with DJs\, sunshine\, and cocktails.\nFireworks at Indigenous Park – A dazzling display under the island night sky.\n\nWhy Experience the Key Lime Festival 2026?\n\nAuthentic Key West Flavor – Hosted in the birthplace of Key Lime Pie.\nUnmatched Culinary Variety – From pies to cocktails\, every bite bursts with citrus.\nIsland Culture & Entertainment – Music\, comedy\, cabaret\, and family-friendly fun.\nHoliday Festivities – Celebrate July 4th in paradise with fireworks and local flair.\n\nPlan Ahead: Select events sell out quickly. Tickets are available now\, along with volunteer opportunities.
URL:https://keywesthistoricseaport.com/event/the-annual-key-lime-festival-2026/
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2023/06/KeyLimeFestivalLogo1.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260725
DTEND;VALUE=DATE:20260727
DTSTAMP:20260623T151259Z
CREATED:20260623T151259Z
LAST-MODIFIED:20260623T151259Z
UID:10000339-1784937600-1785110399@keywesthistoricseaport.com
SUMMARY:37th Anniversary Hemingway 5K Sunset Run & Key West Beach N' Beer Mile
DESCRIPTION:  \nRunners and walkers can test their skills and celebrate Ernest Hemingway’s sporting lifestyle Saturday\, July 25th and the Beer Mile on July 26th during the Hemingway 5k Sunset Run and Beer Mile. The athletic challenges are part of Hemingway Days!  \n  \n\n\n\n\nHEMINGWAY 5K SUNSET RUN\nRACE SCHEDULE\nJuly 22-26\, 2026 – Hemingway Days – Click here for more information\nSaturday\, July 25\, 2026 – RACE DAY!\n3:00 pm – 7 pm: Race Registration Booth \n\nLocation:  Outside Southernmost Beach Cafe\, 1405 Duval Street\n\n7:30 pm: Start of 5K Run/Walk \n\nLocation: Southernmost Point\n\n\n\n\n\n8:00 pm – 10 pm The Awards/Beach Party featuring Tastings of Papa’s Pilar Rum\, Islamorada Beer and Snacks\, raffles and live entertainment! \n\nLocation:  Outside Southernmost Beach Cafe\, 1405 Duval Street\nInside will be extended happy hour and select menu specials till closing for all participants.\n\n\n\n\n\n\n\n\n\n\n\n\n\nSunday\, July 26\, 2026\n12:00 pm Key West Beach N’ Beer Mile! 4 Loops\, 4 Beers from Islamorada Beer Co.\, Custom Shirt.  Price: $55. Race is NOT TIMED! \nThe Beach N’ Beer Mile bib has 4 beer tickets on your bib. This casual and fun beer mile takes place on the beach at the Southernmost Beach Cafe\, 1405 Duval Street\, event starts at 12 pm. Look for the Key West Half Marathon sail flags and cones! Costumes are encouraged and we will be giving various prizes out for the best costumes. \n\nLocation:  Outside Southernmost Beach Cafe\, 1405 Duval Street\nPrizes awarded for:\n\n1. Best Team Spirit\n2. Best Dressed\n3. Least Dressed \n4:00pm – 6:00 pm Pool Party at The Backyard – Pool and Social Club | Blue Flamingo Resort – 3280 N Roosevelt Blvd\, Key West\, FL 33040
URL:https://keywesthistoricseaport.com/event/37th-anniversary-hemingway-5k-sunset-run-key-west-beach-n-beer-mile/
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260805
DTEND;VALUE=DATE:20260810
DTSTAMP:20260827T132206Z
CREATED:20260728T191139Z
LAST-MODIFIED:20260827T132206Z
UID:10000342-1785888000-1786319999@keywesthistoricseaport.com
SUMMARY:Key West Lobsterfest 2026
DESCRIPTION:Lobsterfest is a signature Key West tradition. Whether you’re here for the buttery tails or the island vibes\, this is one summer celebration you won’t want to miss! \nWednesday – Kick Off Party. keywestlobsterfest.com/#35c908d7-4e8f-497c-86d0-3fc07800a7ac \nThursday – Lobster Boil keywestlobsterfest.com/#7bfcf2f9-de7c-4e31-8b0f-7b6242560829 \nFriday – Pool Party & Pub Crawl. keywestlobsterfest.com/#9bdc06e8-f84e-4ae7-8c0a-cc3a4ccd1470 \nSaturday – Street Fair & Free Concert. keywestlobsterfest.com/#19c0f77f-d56c-45cb-af9d-70e35b7915e3 \nSunday – Brunch & Farewell Pool Party
URL:https://keywesthistoricseaport.com/event/key-west-lobsterfest-2026/
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260903
DTEND;VALUE=DATE:20260908
DTSTAMP:20260827T132806Z
CREATED:20260827T132432Z
LAST-MODIFIED:20260827T132806Z
UID:10000343-1788393600-1788825599@keywesthistoricseaport.com
SUMMARY:Just A Few Friends Festival
DESCRIPTION:Just A Few Friends Festival 2026\n \nKey West will host the third annual Just a Few Friends festival from September 3 through September 7\, 2026. The five-day event honors the late singer-songwriter Jimmy Buffett on the island where he created his tropical rock musical style and wrote several of his signature songs. \nThe schedule features musical performances\, beach parties\, margarita tasting tours\, and interactive contests across various local venues. Featured artists include members of Buffett’s Coral Reefer Band\, such as Mac McAnally and Nadirah Shakoor\, alongside musicians Will Kimbrough\, Gary and the Landsharks\, The Wheeland Brothers\, and Howard Livingston and the Mile Marker 24 Band. \nActivities begin on September 3 with a beach cooking competition\, a concert\, storytelling at the Chart Room Bar\, and an after-party at the Margaritaville Café. On September 4\, the city will hold a proclamation ceremony outside Buffett’s Shrimp Boat Sound recording studio\, followed by a look at Michael Kirk’s upcoming documentary about the facility\, a look-alike contest\, and a tribute concert. \nOn September 5\, attendees can participate in margarita bar strolls along Duval Street and the Historic Seaport district\, as well as sunset sailing cruises. The main event takes place on September 6 with the Second Line Memorial Walking Parade down Duval Street\, leading into a free public party at Truman Waterfront Park with live music\, artisan booths\, and food vendors. \n\n\n\n\nEVENT SCHEDULE: https://www.justafewfriendskeywest.com/schedule-at-a-glance\n\n\n\n\nThe festival concludes on Labor Day\, September 7\, with additional musical performances\, sailing trips\, a waterfront sunset concert by Cayman and the Mango Men\, and a pencil-thin mustache contest. Souvenir badge contributions from the festival benefit local charities\, including Reef Relief\, the Bahama Village Music Program\, and student scholarships through the Community Foundation of the Florida Keys. \nFollow them on social media:\nFacebook • Instagram • Tiktok • Newsbreak
URL:https://keywesthistoricseaport.com/event/just-a-few-friends-festival/
ATTACH;FMTTYPE=image/avif:https://keywesthistoricseaport.com/wp-content/uploads/2026/08/3rd-annual-Just-a-Few-Friends-header.avif
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20261016
DTEND;VALUE=DATE:20261026
DTSTAMP:20260827T140638Z
CREATED:20260827T133827Z
LAST-MODIFIED:20260827T140638Z
UID:10000344-1792108800-1792972799@keywesthistoricseaport.com
SUMMARY:Fantasy Fest 2026
DESCRIPTION:Fantasy Fest 2026\nThis year’s Fantasy Fest takes place from October 16-25 in Key West\, Florida! \nAbout Fantasy Fest:\nFantasy Fest is Key West’s legendary 10-day party in paradise — a vibrant celebration of creativity\, community\, and pure island magic. What began in 1979 as a local idea to liven up the island’s quiet season has transformed into an internationally recognized festival that takes over the streets of Old Town every October. \n \n\nEach year\, artists\, adventurers\, and free spirits from around the world flock to Key West to transform the island with spectacular costumes\, lively parades\, and unforgettable parties. Imagination runs wild\, costumes turn heads\, and the island pulses with unstoppable energy. \nNow more than four decades strong\, Fantasy Fest isn’t just an event — it’s a Key West tradition\, a state of mind\, and a one-of-a-kind experience you’ll never forget. \nCheck out a video for this year’s festival: https://vimeo.com/1215637081?fl=pl&fe=sh
URL:https://keywesthistoricseaport.com/event/fantasy-fest-2026/
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2026/08/slide-4-scaled.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20261104
DTEND;VALUE=DATE:20261109
DTSTAMP:20261022T174626Z
CREATED:20261022T174626Z
LAST-MODIFIED:20261022T174626Z
UID:10000355-1793750400-1794182399@keywesthistoricseaport.com
SUMMARY:World Champion Powerboat Races
DESCRIPTION:TWO GREAT WAYS TO WATCH THE RACES\n\n\n\n\nCome feel the thrill and experience the energy! You can be a part of all the action onboard Fury during the 2026 Key West World Championship Power Boat Races hosted by Race World Offshore. There is no better way to watch this event than on an official viewing boat\, featuring multiple levels and everything you need for an unforgettable day. Fury will put you so close to the action you’ll feel like you’re in the driver’s seat. Don’t miss out! \n\n\n\n\nCATCH ALL THE ACTION ON ONE OF OUR OFFICIAL VIEWING BOATS LOCATED JUST OUTSIDE THE RACE COURSE AT TURN 2 & TURN 3! \n\n\n\n\n\n\nAll trips will include a delicious Continental Breakfast\, Mimosas\, a Buffet Lunch\, Beer\, Wine\, and Soda. All you need to bring is yourself and a camera! \n*A full liquor bar upgrade is available with drink tickets! (Drink tickets available for purchase on board or at check-in.) \n\n\n\n\nTRIPS SELL OUT FAST\, BOOK TODAY!\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\nVIEW EVENT DETAILS\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\nOR CALL TO BOOK \n\n\n\n\n(855) 517-8482
URL:https://keywesthistoricseaport.com/event/world-champion-powerboat-races/
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2026/10/unnamed.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261104T113000
DTEND;TZID=America/New_York:20261107T230000
DTSTAMP:20260923T184108Z
CREATED:20260923T181808Z
LAST-MODIFIED:20260923T184108Z
UID:10000341-1793791800-1794092400@keywesthistoricseaport.com
SUMMARY:Powerboat Village in the Key West Historic Seaport
DESCRIPTION:Powerboat Village in the Key West Historic Seaport\nNovember 4 at 11:30 AM – November 7 at 11:00 PM\nRight outside Conch Republic Seafood Co. on the Harborwalk! \n \nCome peruse the many Powerboats\, Vendors\, Trucks\, Beautiful Boats\, Expensive Yachts\, awesome Happy Hour\, Music and much much more courtesy of the Florida Powerboat Club!\nThe Florida Powerboat Club was founded in 1993 as a membership-driven organization\, to promote safe\, responsible powerboating in a group setting and assist performance boating enthusiasts in many ways to achieve the maximum enjoyment from their Florida powerboating lifestyles.\n\nThe club founder is committed to the objective of improving the sport for its participants\, while fostering a positive image with the general public.\n\n\n\n\n\n\nFlorida Powerboat Club welcomes both beginners to the sport\, as well as seasoned veterans\, to cultivate an atmosphere where individuals from different socio-economic backgrounds and cultures may interact and share in the pursuit of this exciting recreational sport.
URL:https://keywesthistoricseaport.com/event/powerboat-village-in-the-key-west-historic-seaport/
LOCATION:Conch Republic Seafood Company\, 631 Greene St.\, Key West\, FL\, 33040\, United States
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2026/09/conchrepublicpowerboatvillage.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20261114
DTEND;VALUE=DATE:20261115
DTSTAMP:20260923T191621Z
CREATED:20260827T134710Z
LAST-MODIFIED:20260923T191621Z
UID:10000345-1794614400-1794700799@keywesthistoricseaport.com
SUMMARY:Key West Oyster Fest
DESCRIPTION:Key West Oyster Fest 2026\nA New Celebration Hits the Key West Historic Seaport!\n\nOn Saturday\, November 14\, 2026\, the Key West Historic Seaport will become the center of Florida’s oyster-loving community as the inaugural Key West Oyster Fest makes its debut in front of Half Shell Raw Bar. \nThe event is a collaboration between Half Shell Raw Bar\, Everglades Oyster Company\, and Oyster Reefers\, the team behind Miami’s popular Oyster Fest\, which has become a favorite annual celebration for oyster enthusiasts from across South Florida. \nFor Everglades Oyster Company\, the event represents an exciting opportunity to celebrate Florida oysters\, connect coastal communities\, and bring people together around great food and waterfront culture. The partnership with Half Shell Raw Bar feels like a natural fit. Both share a deep appreciation for fresh seafood\, local waters\, and the traditions that make Florida’s coastal communities unique. \nVisitors can expect a lively day filled with oysters\, seafood\, waterfront views\, and the easygoing spirit that makes Key West such a special destination. \nVisit Half Shell Raw Bar online for more information and festival details!
URL:https://keywesthistoricseaport.com/event/key-west-oyster-fest/
ATTACH;FMTTYPE=image/png:https://keywesthistoricseaport.com/wp-content/uploads/2026/08/Screenshot-1223.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261125T170000
DTEND;TZID=America/New_York:20261125T230000
DTSTAMP:20261021T154508Z
CREATED:20261021T152745Z
LAST-MODIFIED:20261021T154508Z
UID:10000346-1795626000-1795647600@keywesthistoricseaport.com
SUMMARY:The Lighting of the 21st Annual “Harbor Walk of Lights”
DESCRIPTION:Wednesday\, Nov. 25 – Free\nThe Lighting of the 21st annual “Harbor Walk of Lights”\nat the Key West Historic Seaport\nMain Harbor Walk Lighting at the 2026 “Fishing Buoy Christmas Tree”\nLights come on at 6:00pm – holiday music starts at 5:00pm – Greene and Elizabeth St. plaza.\nSanta and Mrs Clause will be making a NICE list and passing out treats! \nSECOND lighting of the 2026 “Lobster Trap Christmas Tree”\nLights come on at 7:00pm\, holiday music starts at 6:00pm – Margaret St. plaza (Old Lands End Village).\nThere will be holiday cookies and candy canes for the children! \nEnjoy creative holiday displays and thousands of lights honoring the “Maritime History of Key West”. \nWith 3 blocks of sparkling holiday lights and displays around the Key West Bight Marina and Historic Seaport\, the 2026 Key West “Harbor Walk of Lights” is destined to bring miles of holiday smiles to our One Human Family of visitors and locals alike. \nHarbor Walk of Lights is on every night from Thanksgiving eve through New Year’s eve! \nPlease join us at the “Lighting of the Harbor Walk” to kickoff the “Cheryl Cates Toy Drive”.\nBring a toy\, or toys will be available at the “Imagination Station” table to purchase and donate.\nALSO\, be there for a special announcement from the Cheryl Cates Toy Drive.
URL:https://keywesthistoricseaport.com/event/the-lighting-of-the-21st-annual-harbor-walk-of-lights/
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2024/11/F-f8IhFa4AAEUbm.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261203T180000
DTEND;TZID=America/New_York:20261203T200000
DTSTAMP:20261021T155829Z
CREATED:20261021T154725Z
LAST-MODIFIED:20261021T155829Z
UID:10000347-1796320800-1796328000@keywesthistoricseaport.com
SUMMARY:21st Annual Pet Pictures with Santa™ – Hosted by The All Animal Clinic
DESCRIPTION:Thursday\, December 3 – FREE to Attend\n6:00pm – 8:00pm\n21st Annual Pet Pictures with Santa™ – Hosted by The All Animal Clinic\nProfessional photos by Rob O’Neal\nLOCATION: At the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William St. \nSanta pics with pets and kids big and small\, treats for all! Pictures with Santa are $25 (Cash and Cash App accepted) to benefit our local Boys & Girls Club. \nGet professional furry family photos for that special holiday card this year\, and also support the Kids in the lower Keys! \nPhoto: Rob O’Neal
URL:https://keywesthistoricseaport.com/event/21st-annual-pet-pictures-with-santa-hosted-by-the-all-animal-clinic/
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2023/11/santa-pets-rob-oneal-2021-dsc09441-web.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261205T183000
DTEND;TZID=America/New_York:20261205T230000
DTSTAMP:20261022T170236Z
CREATED:20261021T170035Z
LAST-MODIFIED:20261022T170236Z
UID:10000348-1796495400-1796511600@keywesthistoricseaport.com
SUMMARY:2026 Key West City Hometown Holiday Parade
DESCRIPTION:Saturday\, December 5 – FREE\n2026 Key West City Hometown Holiday Parade\nStarts at 6:30pm \nLOCATION: Parade starts on Truman Ave. (at White St.) then proceeds to Duval St.\, then down Duval St. ending at Eaton St. The most charming hometown parade you’ll ever see with holiday floats\, and tons of kids (of all ages). Of course Santa will make a guest appearance!
URL:https://keywesthistoricseaport.com/event/12292/
ATTACH;FMTTYPE=image/png:https://keywesthistoricseaport.com/wp-content/uploads/2019/09/Screen-Shot-2019-09-16-at-3.06.16-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261206T180000
DTEND;TZID=America/New_York:20261206T220000
DTSTAMP:20261022T172043Z
CREATED:20261021T170223Z
LAST-MODIFIED:20261022T172043Z
UID:10000349-1796580000-1796594400@keywesthistoricseaport.com
SUMMARY:Schooner Wharf Bar 2026 Tree Trimming Party and Toy Drive
DESCRIPTION:jSchooner Wharf Bar 2026 Tree Trimming Party and Toy Drive\nSunday\, December 6 – FREE to Attend\nSchooner Wharf Bar 2026 Tree Trimming Party and Toy Drive\nStarting at 6:00PM\nLOCATION: Schooner Wharf Bar and Galley On the Harbor Walk of Lights at William St. \nMaritime merry makers will deck the halls and make dreams come true at the popular waterfront winter wonderland. Great PRIZES for the Best Handmade Ornaments that are: \n\nMost Original\nMost Nautical\nMost Popular with the holiday crowd\n\nAll tree trimmers will be treated to a free holiday cocktail — egg nog\, hot apple jack or Swedish Glogg. \nThen step into Santa’s southernmost workshop at Schooner Wharf. Share the holiday spirit\, as local artists and authors sign and sell ORIGINAL WORKS for HOLIDAY GIFT GIVING. \nBring a donation for the “Cheryl Cates Memorial Toy Drive” by Angles Just 4 Kids! \nEach of Santa’s helpers who donates an unwrapped gift will also receive a free holiday drink from Schooner Wharf Bar. \nSome of our favorite local musicians will be playing Holiday Tunes\, Reggae\, and Calypso with the island sound of Steel Drums to round out the festivities.
URL:https://keywesthistoricseaport.com/event/schooner-wharf-bar-2026-tree-trimming-party-and-toy-drive/
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2019/09/Schooners-Tree-Trim-Ad-2.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261212T180000
DTEND;TZID=America/New_York:20261212T230000
DTSTAMP:20261022T171800Z
CREATED:20261021T170330Z
LAST-MODIFIED:20261022T171800Z
UID:10000350-1797098400-1797116400@keywesthistoricseaport.com
SUMMARY:Schooner Wharf Bar & Galley and Absolute Vodka 35th Annual Key West Lighted Boat Parade 2026
DESCRIPTION:Schooner Wharf Bar & Galley and Absolute Vodka\n35th Annual Key West Lighted Boat Parade 2026\nLife in Key West revolves around the water—so does Christmas! The days are getting shorter and the breeze in the air means only one thing—-it’s almost time for the Annual Schooner Wharf Bar & Galley Lighted Boat Parade. \nThe famous nautical parade is December 12th but the clock is ticking for entrants to conjure their best holiday ideas and start stringing lights on the rigging. December 14th will be the Awards Ceremony. \nJoin the fun and enter your boat in this community marine event. Parade your vessel bedecked in beautiful lights and your festive holiday spirit. Vessels of all sizes – kayaks\, dinghies\, fishing vessels\, sailing ships\, private yachts and charter boats – are welcome. \nThe procession starts from the Key West Bight at the Historic Seaport and by Schooner Wharf Bar where the judges’ stand with local dignitaries will be located. The route then continues along the harbor. \nCaptains: Great prizes up for grabs this year for the 12 winning places with a Free Raffle which includes Great Prizes from the Mel Fisher Family\, Water Sport Adventures\, Dining Gift Certificates\, Schooner Wharf Bar Tabs\, Opal Key Resort & Marina and much MORE! \nEnter by December 4th and your entry fee is waived! A Captains’ Meeting will take place December 10th at 8pm at Schooner Wharf Bar’s in the Sail Loft with complimentary beverages and hors d’eourves.
URL:https://keywesthistoricseaport.com/event/schooner-wharf-bar-galley-and-absolute-vodka-35th-annual-key-west-lighted-boat-parade-2026/
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2016/08/2015-Lighted-Parde-Schooner-Wharf-Bar.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261212T193000
DTEND;TZID=America/New_York:20261212T213000
DTSTAMP:20261022T173321Z
CREATED:20261021T170515Z
LAST-MODIFIED:20261022T173321Z
UID:10000351-1797103800-1797111000@keywesthistoricseaport.com
SUMMARY:Schooner Appledore Lighted Boat Parade Party
DESCRIPTION:Saturday\, December 12\nSchooner Appledore Lighted Boat Parade Party\n7:30pm – 9:30pm \nBe a participant in the 2026 The Lighted Parade aboard the Schooner Appledore II Parade Boat!\nTrip Includes: Premium beer\, boutique wines\, wines and soft drinks. Very Limited Seating!
URL:https://keywesthistoricseaport.com/event/schooner-appledore-lighted-boat-parade-party-2/
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2023/11/boat-parade-c-tedesco-5q0a7079-web.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20261219
DTEND;VALUE=DATE:20261225
DTSTAMP:20261022T173607Z
CREATED:20261021T171047Z
LAST-MODIFIED:20261022T173607Z
UID:10000353-1797638400-1798156799@keywesthistoricseaport.com
SUMMARY:Cocoa and Carols: Live Holiday Music Cruise Aboard Schooner America 2.0
DESCRIPTION:Saturday\, Dec. 19 – Thursday\, Dec. 24\nCocoa and Carols: Live Holiday Music Cruise Aboard Schooner America 2.0\n7:00 – 8:30pm and 1:30-3:00pm on select dates\nJoin us for a festive Christmas cruise featuring live holiday music and cheer! \nPlease join us for this special Key West holiday cruise tailored for friends\, family\, and all your loved ones during the Christmas season. Step aboard our beautiful 105-foot Schooner America 2.0 in full holiday decor for a 1.5-hour cruise in Key West harbor while we listen to some of our favorite Christmas hits played live from our decks! Delicious hot cocoa\, cookies\, and treats for all our guests are included!
URL:https://keywesthistoricseaport.com/event/cocoa-and-carols-live-holiday-music-cruise-aboard-schooner-america-2-0/
ATTACH;FMTTYPE=image/webp:https://keywesthistoricseaport.com/wp-content/uploads/2026/10/Holiday-Music-1.webp
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261220T110000
DTEND;TZID=America/New_York:20261220T150000
DTSTAMP:20261022T173829Z
CREATED:20261021T170634Z
LAST-MODIFIED:20261022T173829Z
UID:10000352-1797764400-1797778800@keywesthistoricseaport.com
SUMMARY:The Florida Keys Southernmost Car Club 2026 Holiday Classic Car Show & Toy Drive
DESCRIPTION:Sunday\, December 20\nThe Florida Keys Southernmost Car Club presents \n2026 “Holiday Classic Car Show” & Toy Drive\nFREE • 11:00am – 3:00pm\nLOCATION: Conch Republic Seafood Company parking lot – on the Harbor Walk of Lights at Greene St. \nTOY DRIVE: Please bring an unwrapped toy for Monroe County Domestic Abuse Shelter. \nVOTE for the “Peoples Choice” award for: BEST sports car\, pick up\, engine\, interior\, original & custom\, pre & post 1950\, Best in Show. \nSee classic cars from every era decked out for the holidays!\nRun by the Florida Keys Southernmost Car Club\, honoring founder Dick Moody.\nNon-member cars may enter same day FREE with an unwrapped toy!
URL:https://keywesthistoricseaport.com/event/the-florida-keys-southernmost-car-club-2026-holiday-classic-car-show-toy-drive/
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2017/12/CarShow-Lee-copy_preview-1.jpeg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261225T100000
DTEND;TZID=America/New_York:20261225T123000
DTSTAMP:20261022T174146Z
CREATED:20261021T171255Z
LAST-MODIFIED:20261022T174146Z
UID:10000354-1798192800-1798201800@keywesthistoricseaport.com
SUMMARY:Christmas Day Brunch Aboard Schooner America 2.0
DESCRIPTION:Friday\, December 25\nChristmas Day Brunch Aboard Schooner America 2.0\n10:00am – 12:30pm\nEnjoy Christmas morning the Key West way – sailing! \nThis 2.5 hour Christmas Day Brunch Sail features a 3-course brunch\, including spiraled ham\, bagels and pastries\, meats and cheeses\, smoked salmon\, crudités\, and other delicious Christmas day treats! Complimentary mimosas\, holiday cocktails\, wine\, beer\, soft drinks\, and water also included. \n \n\n\nEnjoy your holiday in Key West aboard Key West’s most elegant sailboat\, the 105-foot\, 1851 revival\, Schooner America 2.0. \nTake in the vibrant colors of Key West as you sip champagne\, dine on passed a delicious brunch\, and glide through the crystal clear surrounding waters. \nThis two-hour morning sail features complimentary mimosas\, Bloody Marys\, champagne\, wine\, beer\, soft drinks\, and water. Brunch is provided\, including spiraled ham\, bagels and pastries\, meats and cheeses\, smoked salmon\, crudite\, and other delicious treats! \nSchooner America 2.0 is a state of the art vessel built in 2011. She features teak decks\, mahogany-trimmings\, and 3600 square feet of canvas! Sit back and relax while she plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West brunch experience! \n\n\nWhat’s included\n\nKey Points About This Tour:\n\n2.5-hour brunch and sailing excursion on Schooner America 2.0\nTicket includes brunch featuring spiraled ham\, bagels and pastries\, meats and cheeses\, smoked salmon\, crudite\, and other delicious treats!\nAdult ticket Includes beer\, wine\, champagne\, mimosas\, bloody marys\nEnjoy the iconic Key West waters on a premiere vessel\n\n\n\nHighlights \n\nSome of the sights on this two hour sailing adventure include: \n\nA waterside view of Fort Zachary Taylor\nThe famed Sand Key Lighthouse\, Mallory Square\, and Sunset Pier\nKeep your eyes peeled for wildlife: dolphins\, sea turtles\, and waterfowl\nThe famous Key West “Green Flash” at sunset\n\nBring your family and/or friends and join our courteous and professional crew for this Holiday Brunch sail that completes the Key West experience in comfort and elegance!
URL:https://keywesthistoricseaport.com/event/christmas-day-brunch-aboard-schooner-america-2-0/
ATTACH;FMTTYPE=image/jpeg:https://keywesthistoricseaport.com/wp-content/uploads/2023/11/KeyWestBrunch.jpg
END:VEVENT
END:VCALENDAR