Nutcracker Key West

Tennessee Williams Theatre 5901 College Rd, Key West, FL, United States

Performed every other year, Nutcracker Key West is a sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City, returning December 2024. The Key West production comes complete with chickens, roosters, sea fans, anemones, and yes, even a conch shell. Show dates Dec. 5-8 and 13-15. Showtimes vary. Tennessee Williams Theater, 5901 College Rd.

$35 – $110

Key West Farmer’s Market

Truman Waterfront Pier Southard St, Key West, FL, United States

Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.

Key West: Pet Pictures with Santa

Harbor Walk

Bring your festively outfitted pets for professional photos with Santa on Friday evening from 6 to 8 p.m. at the Christmas tree at the foot of William Street at Key West Bight Marina, hosted by All Animal Clinic. Photos are $25 each (cash only) with proceeds benefitting the Boys and Girls Club of the Keys.

$25

Bluewater Key RV Resort: Tiki Time Mixer ft. Mac Calhoun

Bluewater Key RV Resort 2950 Overseas Hwy, Key West, FL, United States

Join us for our Tiki Time Mixer events, when the park comes alive with the sounds of live music, transporting you to a paradise of relaxation and fun! Enjoy lively rhythms featuring local musicians, complimentary refreshments, and good vibes all around. So sit back, soak in the laid-back atmosphere, and let the melodies transport you to the heart and soul of the Conch Republic!

Key West: Holiday Village & BeLighted Bike Ride

Coffee Butler Amphitheater 21 Quay Rd, Key West, FL

The Wesley House Family Services Holiday Village is the family-friendly pre-party for the BeLighted Bike Ride, creating an evening of joy, laughter, and holiday magic for all ages, from 5 to 9 p.m. at Coffee Butler Amphitheater, 21 Quay Rd. The village features over 20 community booths offering games and activities, carnival rides, bounce houses, local food trucks, community performances, snowfalls and Santa! The highlight of the evening is the BeLighted Bike Ride that departs from the event at 8 p.m. The luminous parade of holiday cheer on wheels winds through the streets of Key West. Admission to Holiday Village is $20 per person or four tickets for $70. Children age 3 and under enter free.

$20

Bluewater Key RV Resort: 5 O’clock Somewhere Cart

Bluewater Key RV Resort 2950 Overseas Hwy, Key West, FL, United States

Listen for the music as our 5 O'clock Somewhere Cart makes it way through the resort every Saturday! We'll be serving an array of refreshing beers and hard seltzers, including our Bluewater Breeze – a blend of tropical flavors that'll transport you to paradise with every sip! This unforgettable experience is on the house, courtesy of Liberty Coach. So kick back, relax, and let the good times roll as we bring the party to you, one delicious drink at a time.

Key West Holiday Parade

Duval Street

The Key West Holiday Parade is a festive celebration that brings the island's unique charm to life in the southernmost city of the continental U.S. This annual event features a delightful mix of marching bands, school groups, and both motorized and non-motorized floats, all showcasing the local community's vibrant spirit.

Sheriff’s Animal Farm: Christmas on the Farm

Monroe County Sheriff's Office Animal Farm 5501 College Rd, Key West, FL, United States

Celebrate Christmas at the Monroe County Sheriff's Animal Farm from 1 to 3 p.m. This will be the only open house during the month of December. Visit with the animals and participate in joyful holiday-themed activities. Gifts of fresh produce and other items, as well as cash gifts for the animals, are greatly appreciated!

Gifts of fresh produce

Bluewater Key RV Resort: Sundae Sundays

Bluewater Key RV Resort 2950 Overseas Hwy, Key West, FL, United States

Enjoy a complimentary scoop of delicious ice cream with your favorite toppings every Sunday in the Clubhouse. From colorful sprinkles to decadent chocolate sauce, create your dream sundae while enjoying the company of fellow campers. It's the perfect way to cool off and create lasting memories during your stay with us.

Key West: The Eaton Street Christmas Stroll

Eaton Street becomes a southernmost North Pole Sunday afternoon and evening. Wander the blocks between Whitehead and Simonton, stopping at multiple venues for shopping and special presentations, including United Methodist with a 3:30 p.m. concert, Woman's Club of Key West, Salt Gallery, an open house at The Studios of Key West, classic cartoons at Tropic Cinema at 6 p.m., a 7 p.m. choral concert at St. Paul's Episcopal, and more. The event is free but tickets are recommended.

Bluewater Key: Hot Cocoa Social – Classic & Spiked!

Bluewater Key RV Resort 2950 Overseas Hwy, Key West, FL, United States

Warm up with us at our upcoming Hot Cocoa Social! Join us in the Clubhouse as we enjoy classic and spiked versions of this cozy favorite, perfect for the holiday season. Whether you prefer the traditional marshmallow-topped treat or something a little more spirited, we can't wait to share this delicious treat with you!

Key West Farmer’s Market

Truman Waterfront Pier Southard St, Key West, FL, United States

Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.