Key West Holiday Events and Historic Inn Tours
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Artistic rendering – Event may differ

Key West Holiday Events and Historic Inn Tours

Key West transforms into a festive wonderland during the holiday season, offering a warm escape from the cold. Visitors can enjoy a variety of events from late November through December, including illuminated light displays along the Historic Seaport, unique artisan markets perfect for holiday shopping, and lively parades. Experience cultural performances like 'Fiesta de Navidad Tropical' and a special Keys-themed 'Nutcracker Key West' ballet. Family fun abounds with activities like ice skating, festive bike rides, and opportunities to meet Santa. Don't miss the historic inn tours showcasing beautiful holiday decorations.

What to Expect

Warm holiday celebrations in a tropical island setting.

Know Before You Go

  • Tickets: $$ – Get tickets
  • Accessibility: The website offers various accessibility features including font resizing, keyboard navigation, readable font, link underlining and highlighting, cookie clearing, and animation removal.
  • Pets: Pet-friendly for some events (e.g., Pet Pictures with Santa), otherwise not specified.

Other Christmas Events Near Key West

Local Insight & Ratings

Family Friendly

πŸŽ„ πŸŽ„ πŸŽ„ πŸŽ„ πŸŽ„ (5/5)

Best For

Families, couples, holiday shoppers

Vibe

Festive, tropical, relaxed, charming

Energy Level

Moderate

Budget

$$

Photo Friendly

πŸ“· πŸ“· πŸ“· πŸ“· πŸ“· (4/5)

Weather Sensitivity

Low

Special Events & Promotions

  • Lighting of the Harbor Walk of Lights
  • Black Friday Shopping Extravaganza
  • Pet Pictures with Santa
  • Holiday Historic Inn Tours
  • Waterfront Winter Wonderland ice skating and rides
  • Lighting of the Menorah ceremony

Tags

holiday marketfamily friendlySanta visitsfestive foodholiday shoppingcommunity celebrationlight displaysseasonal activitiesholiday traditionballet

Location

Various Locations
Key West, FL

Event Details

Duration

Varies by event

Ages

All ages

Neighborhood

Various Key West neighborhoods

Timed Entry

No

Featured Performers

  • Bahama Village Music Program’s Joyful Voices Choir
  • House of Pan Steel Pan Drums ensemble

Organizer

Rent Key West Vacations

Food & Drink

Food trucks and beverage vendors available at many events, including festive food and libations.

Quick Actions

Tips & Advice

  • Book accommodations and tickets for popular events well in advance, as Key West is a sought-after holiday destination.
  • Pack light clothing suitable for warm weather, but also bring a light jacket or sweater for cooler evenings or air-conditioned venues.
  • Utilize bicycles, golf carts, or scooters for easy navigation around Key West, as parking can be challenging.
  • Check the specific event details for exact times and locations, as many events occur on different dates and at various venues across the island.
  • Be prepared for potential tropical weather; while it's a warm holiday season, brief rain showers can occur.

Frequently Asked Questions

What kind of weather can I expect in Key West during the holidays?

Key West offers a warm holiday season, typically with pleasant temperatures. While it's a tropical climate, occasional brief rain showers can occur.

Is transportation easy around Key West during the holiday events?

Yes, many visitors find that bicycles, golf carts, and scooters are practical and fun ways to get around. Walking is also a great option for exploring Old Town.

Are there specific events for families with young children?

Absolutely! Events like the Holiday Village, Waterfront Winter Wonderland with its ice rink and rides, and the Hometown Holiday Parade are very family-friendly.

What kind of shopping is available during the holiday season?

Key West hosts several artisan markets and shopping events, such as the Black Friday Shopping Extravaganza and the Artisan Market, offering unique gifts and handmade items from local creators.

Are there any specific events for Hanukkah?

Yes, the City of Key West holds its annual Lighting of the Menorah ceremony at Bayview Park, providing a traditional observance of Hanukkah.

Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.

Contributors & Updates

Last Updated: Nov 2, 2025
Original Submitter: Sep 17, 2025 The Christmas Events Near Me editorial team

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