2026 41st Annual Wrecker's Cup Race Series!
2026-03-29 | FL
2026 41st ANNUAL WRECKER’S CUP RACE SERIES!
CALL TO ALL WRECKERS!
Ladies and Gentlemen: Start Your Sails! The third race of the popular and much anticipated Schooner Wharf Bar Wreckers Cup Race Series is set for Sunday, March 29th. This all-in-fun race series recalls the tradition of the wreckers in the Key West of the 1800’s.
The regatta includes 16′ Hobie Cats, sloops of varying sizes, recreational yachts, live aboard vessels and majestic schooners gracing the Key West Harbor! Visiting yachters are invited to join our local “Wrecker’s Fleet.” Come meet fellow
sailors, enjoy a fun day on the water and celebrate the “victor’s spoils” at Schooner Wharf Bar.
Captains’s Meeting is held Saturday, March 28 at 7:00 p.m. in the Schooner Wharf Sail Loft with complimentary Pusser’s Rum Punch and hors d’oeuvres from the Schooner Wharf Galley.
All participating vessels will be eligible for up to 4 BBQ pork dinners for captain & crew at the Awards Ceremony. The race is video taped, see yourself under sail on big screen at the Awards Party! Entry fee for each vessel is $40.00
For more info: www.SchoonerWharf.com/25wreckersrace3.htm or call 305-292-9520.

City of Key West Sport Fishing Championship 2026
2026-04-15 08:00 - 2026-04-19 20:00 (America/New_York) | Conch Republic Seafood Company parking lot – Greene & Elizabeth St., 631 Greene Street, Key West, FL, 33040, United States
Sport Fishing Championship – City Property Event Notice

Wednesday, April 15 – Sunday, April 29, 2026
Event takes place at the Conch Republic Seafood Company paved parking lot at 631 Greene Street and the adjacent dirt parking lot.

Date: April 15-19, 2026

Time: 8:00 AM - 8:00 PM

Address: 631 Greene Street, Key West, FL 33040

Contact: Casey Arnold 305-797-0164

Link:
Click Here for More Information

2026 Conch Republic Independence Celebration
2026-04-17 - 2026-04-26 | FL
Calling Conch Republic Patriots, Pirates and Partiers – Declare Your FUN-dependence! Head to Key West’s 44th Annual Conch Republic Independence Celebration 2026. Conch Republic Days 2026 celebrates Key West’s One Human Family and the diversity of its Conch-stituents dedicated to bringing Humor, Peace and Respect to the world!

Visit https://conchrepublic.com/ for the full schedule of events, details, and sponsors of this year’s Celebration!
Our very own Schooner Wharf Bar is hosting the following events throughout the celebration:
Kick-Off Party & Conch Shell Blowing Contest – April 17
Parade Party & Awards Ceremony – April 23
Victory Party and Surrender Ceremony of the Great Sea Battle – April 24
Pirates’ Ball & Pirate Costume Competition – April 25
Join us for the FUN-dependence!

Kick-Off Party & Conch Shell Blowing Contest
2026-04-17 19:00 - 23:30 | FL
Schooner Wharf Kick Off Party is the start of the Conch Republic Independence Celebration on Friday, April 17 at 7 p.m.
The festivities kick off with the best music this island has to offer! Dance steepin’ hand clappin’ down home fun!
Prizes include Schooner Wharf Bar Gift Certificates, Pilar Rum, Water Adventures courtesy of Sebago Watersports, Spirit of Independence, Schooner America 2.0, Crusin’ Tikis Key West and Sunset Watersports!

Listen to how it all happened! Conch Republic Prime Minister Dennis Wardlow will be on stage recounting the story of the events that led to our secession, as can only be told by the mayor who spearheaded our secession in 1982! We seceded from the United States, surrendered, and demanded foreign aid (we are still waiting on that!)
Long Live the Conch Republic!
Conch Republic Prime Minister Dennis Wardlow will recount our secession in 1982. “We succeeded where others failed!”

Conch Republic Independence Day Celebration Pirates' Ball & Pirate Costume Competition - April 25
2026-04-25 19:00 - 23:30 | FL
Conch Republic Independence Day Celebration Pirates’ Ball & Pirate’s Costume Competition
April 25, 2026

Schooner Wharf Wench Crew

Shiver me timbers…
Schooner Wharf Bar will surrender the booty – for the best pirate costume at its annual Pirates Ball and Pirate’s Costume Competition on Saturday, April 25th at 7 p.m.
The Yo Ho Ho-ing begins with the Pirates’ Costume Contest, with prizes for Best Wench, Best Buccaneer, Best Bustier, and Cutthroat Surprise.

Of course, bottles of rum are up for grabs in addition there is watersport fun and Schooner Wharf booty to be had!
Sea shanties, sword play and swashbuckling will be provided by Key West’s own band of pirates, The Conch Republic Privateers. The troupe in full pirate garb will provide engaging antics and entertainment while you enjoy the Pirates’ Costume competition.
Prizes include Schooner Wharf Bar Gift Certificates, Pilar Rum, Water Adventures courtesy of Sebago Watersports, Spirit of Independence, Schooner America 2.0, Crusin’ Tikis Key West and Sunset Watersports!

Conch Republic Independence Celebration Victory Party and Surrender Ceremony of the Great Sea Battle - April 24
2026-04-26 21:00 - 23:30 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Conch Republic Independence Celebration Victory Party and Surrender Ceremony of the Great Sea Battle
April 24, 2026

Piracy on the high seas must be stopped…
The Conch Republic will be under attack, now is the time for all good men and women to come to the aid of their island!
Join your Conch Republic comrades-in-arms at Schooner Wharf Bar for the annual Conch Republic Naval Parade and Great Battle Surrender Ceremony, Friday, April 24th.
The U.S. Border Patrol will infiltrate the Conch Republic, and all able bodies are commanded to load up on ammunition (wet Cuban bread) and stand their ground against the advancing troops in Key West Harbor.

Let freedom ring with the bread you fling!
Suit up in your battle fatigues (foul weather gear) and prepare for the Coast Guard’s surrender to the Conch Republic.
Then retrieve your wounded comrades and make your war-weary way to Schooner Wharf Bar for the Victory Party and Surrender Ceremony at 9 p.m.
The upbeat vibe of the Andy Westcott Band jammin’ to great R&B, bring your dancin’ shoes! This band definitely gets the dance floor alive!

Key West Pride 2026
2026-06-03 - 2026-06-07 | FL
Key West Pride 2026
Every 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.
Organized 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.

Daily Activities

Museums: 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
Land 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.
Water 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
For all the details, visit https://gaykeywestfl.com/pride/
