Events

key west christmas parade

Key West Hometown Holiday Parade

Dec 6 2025 - 7:00pm
Kick off the Christmas season with the Key West Hometown Holiday Parade—a beloved local tradition that brings together marching bands, floats, and festive characters. Families line the streets of Old Town to watch the colorful procession and enjoy the warm island spirit that makes this...Read more
Holidays
celebrate the holidays in key west lighted boat parade

Schooner Wharf Annual Lighted Boat Parade

Dec 13 2025 - 6:00pm
Watch the waters of Key West light up during the annual Schooner Wharf Lighted Boat Parade! Dozens of creatively decorated boats, from fishing vessels to luxury yachts, cruise through the harbor, each one decked out in twinkling lights and holiday décor. The waterfront becomes a...Read more
Holidays
nutcracker ballet

Nutcracker Key West

Dec 1 2025 - 9:45am to Dec 30 2025 - 9:45am
Experience a tropical twist on a timeless classic with Nutcracker Key West! This enchanting performance brings the holiday ballet to life with island-inspired flair, vibrant costumes, and local talent. Perfect for families and visitors alike, it’s a magical evening of music and dance unlike any...Read more
Holidays
key west holidays

Key West Holiday Fest

Nov 27 2025 - 11:15am to Dec 31 2025 - 11:15am
Celebrate the holidays in Key West at Key West Holiday Fest!Read more
Holidays
christmas lights in key west

Key West Harbor Walk of Lights

Nov 27 2025 - 5:00pm to Dec 31 2025 - 10:00pm
Kick off the holidays island-style at the Key West Harbor Walk of Lights! From late November through New Year’s Eve 2025, the Key West Historic Seaport glows with dazzling light displays, festive music, and nautical cheer. Wander along the waterfront as boats, palm trees, and...Read more
Holidays
key west food and wine fest

Key West Food & Wine Festival

Jan 28 2026 - 11:00am to Feb 1 2026 - 10:00pm
When: January 28-February 1, 2026 Where: Restaurants, resorts, and venues across Key West Tickets/Admission Cost: Ticketed tastings, dinners, and events (prices vary) See More Key West Events Frequently Asked Questions: Key West Food & Wine Festival Are all events ticketed? Yes, most tastings, dinners, and...Read more
Festivals
conch republic days

Conch Republic Days

Apr 17 2026 - 2:00pm to Apr 26 2026 - 2:00pm
Only in Key West will you find a festival celebrating the island’s tongue-in-cheek “secession” from the U.S. Conch Republic Days bring parades, lively parties, quirky competitions, and plenty of island pride. t’s a uniquely Key West experience you won’t find anywhere else. Conch Republic Days...Read more
Festivals
key west songwriters festival

Key West Songwriters Festival

Apr 29 2026 - 2:00pm to May 3 2026 - 2:00pm
Each May, Key West turns into a giant music stage as the Songwriters Festival takes over bars, beaches, and theaters. From intimate sets to lively street performances, you’ll hear top songwriters share the stories and sounds behind their biggest hits. When: April 29-May 3, 2026...Read more
Festivals
hemingway lookalike contest

Hemingway Days

Jul 22 2026 - 10:00am to Jul 26 2026 - 10:00pm
Brief Event Description: Hemingway Days celebrates the life and legend of Key West’s most famous resident. From the iconic Hemingway Look-Alike Contest to deep-sea marlin fishing tournaments and literary readings, this July event blends history, sport, and fun. When: July (annually around Hemingway’s birthday) Where:...Read more
Festivals
ghost tour

Key West Ghost & Mysteries Tour

Oct 25 2025 - 9:15pm to Oct 25 2026 - 9:15pm
Explore Key West’s spooky side on the Ghost & Mysteries Tour, a guided evening walk through the haunted streets of Old Town. Hear true stories of spirits, strange happenings, and the island’s dark past as you visit some of its most legendary sites. Equal parts...Read more
Holidays

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