Illustration of a generic other scene (Old Town Trolley Holiday Sights and Festive Nights Tour)
Other Christmas Activities

Old Town Trolley Holiday Sights and Festive Nights Tour

Experience the magic of the holiday season in Key West with Old Town Trolley's Holiday Sights and Festive Nights Tour. This unique trolley ride showcases the island's historic homes, beautifully decorated with a dazzling array of lights and festive touches. Enjoy engaging narration that shares fun facts and local history, making it a perfect way to celebrate the holidays island-style.

What to Expect

Island-style holiday trolley tour with festive light displays.

Event Details

Duration

60 minutes

Ages

Children (3-12): $22.95*, Ages 2 and under ride free. Must ride on parent’s lap.

Timed Entry

Yes

Organizer

Old Town Trolley Tours

Food & Drink

Food and drinks are welcome on board, but alcoholic beverages are prohibited.

Get Tickets

Local Insight & Ratings

Family Friendly

πŸŽ„ πŸŽ„ πŸŽ„ πŸŽ„ πŸŽ„ (5/5)

Best For

Families, couples, holiday enthusiasts

Vibe

Festive, cheerful, historical

Energy Level

Low

Budget

$$

Photo Friendly

πŸ“· πŸ“· πŸ“· πŸ“· πŸ“· (4/5)

Weather Sensitivity

Low

Location

Mallory Square
Key West, FL

Know Before You Go

  • Tickets: $$ – Get tickets
  • Parking: Recommended parking at the City Parking Garage on Grinnell Street or paid lots near Mallory Square.
  • Accessibility: Wheelchair-accessible trolleys are available with hydraulic lifts. Advance phone notification is requested.
  • Pets: Service animals are welcome. Pets and emotional support animals are not permitted.

Tips & Advice

  • Book tickets online in advance for the best rates and to secure your spot, as capacity is limited to 35 seats per trolley.
  • Arrive at the departure point at Mallory Square at least 15 minutes prior to your scheduled tour time to check in.
  • While strollers are allowed, they must be collapsed and stored at the front of the trolley to ensure safety and space.
  • Consider the warm Key West climate even in December; dress in light layers and comfortable footwear for the trolley ride.
  • Check the tour updates link for any potential route or stop changes on the day of your tour.

Special Events & Promotions

  • Annual Key West Holiday Lights Contest with a $500 First Place prize.
  • Limited capacity tours with 35 seats per trolley.
  • Option to reschedule up to 24 hours in advance.

Quick Actions

Frequently Asked Questions

What is the duration of the Holiday Sights and Festive Nights Tour?

The tour is approximately 60 minutes long.

Are reservations required for the Holiday Sights and Festive Nights Tour?

Yes, reservation-based tickets are required for this holiday tour, and capacity is limited.

Can I bring my pet on the trolley?

Only ADA-defined service animals are permitted on the trolley. Pets and emotional support animals are not allowed.

What is the starting point for the tour?

Tours depart from Mallory Square.

What is the policy on rescheduling tickets?

You may reschedule your tour up to 24 hours in advance of your scheduled time, provided seats are available.

Tags

holiday light displaysfamily friendlyseasonal activitiesholiday traditionfestive decorationscommunity celebrationguided tours

More Christmas Events Near Key West

More Christmas Events near Key West

Open the map around Key West β†’

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: Sep 14, 2026
Original Submitter: Sep 17, 2025 The Christmas Events Near Me editorial team