Two operators run Key West Christmas lights tours in 2026, and both call the tour “Holiday Sights and Festive Nights”. The Old Town Trolley version runs Dec. 7 to 27, 2026 from Mallory Square. The Conch Tour Train version runs Dec. 8-9, 11-14 and 16-27 from Key West High School, with departures every half hour from 6 to 8:30 PM. Each lasts about an hour and goes to decorated houses and neighbourhoods. Below is a side-by-side from the operators’ own pages, checked Oct. 21, 2026. Christmas in Key West is an independent planner published by LPE Realty LLC. We are not the City of Key West, Schooner Wharf, the Historic Seaport, the Lodging Association or any venue, and we sell no tickets.
- Old Town Trolley: "Old Town Trolley's Holiday Sights and Festive Nights Tour". "WHERE Mallory Square", "WHEN December 7-27, 2026.", "DURATION 60 minutes". "Limited capacity: 35 seats per trolley." "VIP passes cannot be accepted or used for Holiday Tours." Old Town Trolley Tours: Key West Holiday Tours
- Conch Tour Train: "Holiday Sights and Festive Nights Tour", "an hour tour that takes you to all of the island's most elaborately decorated houses, buildings and neighborhoods and caroling." "2026 Dates: December 8-9, 11-14, and 16-27." "6:00 pm, 6:30 pm, 7:00 pm, 7:30 pm, 8:00 pm, and 8:30 pm." "Departs from: Key West High School, 2100 Flagler Avenue." "Limited capacity: 48 seats per train." "Tour includes special holiday lights glasses!" Conch Tour Train: Holiday Sights and Festive Nights Tour
Trolley or train, side by side
| Old Town Trolley | Conch Tour Train | |
|---|---|---|
| 2026 nights | Dec. 7 to 27 | Dec. 8-9, 11-14, 16-27 (none Dec. 10 or 15) |
| Departs from | Mallory Square | Key West High School, 2100 Flagler Avenue |
| Departure times | Not listed on the operator page | 6:00, 6:30, 7:00, 7:30, 8:00, 8:30 PM |
| Length | 60 minutes | About an hour |
| Seats | 35 per trolley | 48 per train |
| Adult | From $33.95, plus 5% city fee | From $32.25 |
| Child | $22.95 (ages 3-12), plus 5% city fee | $21.80 (ages 4-12) |
| Free | Ages 2 and under, on a parent’s lap | Ages 3 and under, on an adult’s lap |
| Extras listed | VIP passes not accepted | Caroling; holiday lights glasses |
- Old Town Trolley: "Adults: From $33.95*", "Children (3-12): $22.95*", "Ages 2 and under ride free. Must ride on parent's lap.", "*5% city fee added to all tickets". Departure times are not listed on the page. Old Town Trolley Tours: Key West Holiday Tours
- Conch Tour Train: "Prices starting at $32.25 for adults, $21.80 for kids (4-12)", "Ages 3 and under ride free (must ride on the parent/adult lap)." "Reservations required. Reservation-based tickets are non-refundable. You may reschedule up to 24 hours in advance of tour time." Phone "(305) 707-5775". Conch Tour Train: Holiday Sights and Festive Nights Tour
Prices are the operators’ “from” or “starting at” figures, not quotes for a given night. The cost calculator further down this page adds up a group for either tour.
The Conch Tour Train tour
The Conch Tour Train describes an hour tour of decorated houses, buildings and neighborhoods, with caroling, and says the tour includes special holiday lights glasses. It leaves from Key West High School, 2100 Flagler Avenue. Reservations are required. Reservation-based tickets are non-refundable, and you may reschedule up to 24 hours before your tour time. The operator’s phone is (305) 707-5775.
Nights with no train
There are no Conch Train holiday tours on Thursday, Dec. 10 or Tuesday, Dec. 15, 2026. The train does run on Saturday, Dec. 12, the night of the Lighted Boat Parade, and on both inn tour Fridays.
The Old Town Trolley tour
The Old Town Trolley holiday tour leaves from Mallory Square, lasts 60 minutes and seats 35 per trolley. Adults are from $33.95 and children 3 to 12 are $22.95, with a 5% city fee added to all tickets; ages 2 and under ride free on a parent’s lap. VIP passes cannot be used for the holiday tours. The page did not list departure times when we checked, so we do not give any. Book through the operator to see the times on offer for your night.
The two calendars disagree on dates
The Holiday Fest calendar run by Key West Inns lists the Conch Train tours as Dec. 8 and Dec. 11 to 23, and the Trolley tours as Dec. 8 to 23. The operators’ own pages say Dec. 8-9, 11-14 and 16-27 for the train and Dec. 7 to 27, 2026 for the trolley. We use the operators, since they sell the seats.
- The Holiday Fest calendar lists the Conch Train tours as "Dec. 8 and Dec. 11-23" and the Trolley tours as Dec. 8 to 23, departing "from Key West High School" (Conch) and Mallory Square (Trolley). The operators' own pages say Conch Train Dec. 8-9, 11-14 and 16-27, and Trolley Dec. 7-27, 2026. Use the operator pages. Conch Tour Train; Old Town Trolley; Key West Inns (Lodging Association of the Florida Keys and Key West): Holiday Fest Calendar
The Holiday Lights Contest
Old Town Trolley says the Annual Key West Holiday Lights Contest among area homeowners is “for bragging rights and a $500 First Place prize”. No list of entered homes or addresses was published when we checked, so there is no self-guided contest route to give.
- Old Town Trolley: "the Annual Key West Holiday Lights Contest" is "for bragging rights and a $500 First Place prize" among "area homeowners". Old Town Trolley Tours: Key West Holiday Tours
Truman Little White House holiday evenings
The Key West Harry S. Truman Foundation lists holiday house tours with a presidential holiday card presentation on Tuesday, Dec. 22 and Wednesday, Dec. 23, 2026. The Dec. 22 page gives 6 to 8 PM, with tours at 6:00, 6:45 and 7:30 PM, and tickets at $20 for members and $35 for non-members. We did not capture the Dec. 23 times. Booking is through the Truman Foundation.
- Truman Foundation lists "Happy Holidays at the Harry S. Truman Little White House – House Tours and Presidential Holiday Card Presentation" on Tuesday, Dec. 22 and Wednesday, Dec. 23, 2026. The Dec. 22 page: "6-8pm", "tours will start at 6:00, 6:45, & 7:30 PM", "Tickets are $20 for members and $35 for non-members". Key West Harry S. Truman Foundation: Events 2026
Lights you can see without a ticket
- Harbor Walk of Lights: nightly from Nov. 25 through New Year’s Eve along the Seaport seawall. Free.
- Custom House light show: keywestchristmas.org says a holiday light show by Key West High School’s Conch 5 Studios is projected on the Custom House at the free Holiday Concert and Bazaar, Friday, Dec. 11.
- Lighted Boat Parade: Saturday, Dec. 12, free to watch from the Harbor Walk.
- BeLighted Bike Ride: Friday, Dec. 4, a rolling lighted bike parade through Old Town (on the City notice; not confirmed by its host). See our holiday parade page.
- keywestchristmas.org describes the Annual Holiday Concert & Bazaar at the Custom House, 281 Front Street, as "This festive free party" with "a holiday light show designed by Key West High School's Conch 5 Studios, which will be projected on the face of the Custom House." KWAHS's page mentions "Animated Holiday Projections" and its "Festival of Trees". Key West Art & Historical Society: Holiday Concert & Bazaar; keywestchristmas.org
Getting to the departure point
The trolley leaves from Mallory Square; the train leaves from Key West High School, 2100 Flagler Avenue. The City’s Key West Rides on-demand buses run 6 AM to 8 PM, so a late tour may leave you without that option for the trip back. A note on the Duval Loop: the City’s bus fares page still lists a Duval Loop fare, but the Key West Citizen reported on Dec. 31, 2025 that the route would be suspended from Jan. 2 and replaced by Key West Rides. Do not plan around it. It is a City bus route, not a lights tour, in any case. Parking options are on our parking page and transport into town on getting here.
- City of Key West: "Key West Rides On-Demand is an innovative form of transportation that will replace the North and South Lines". "This is a bus stop-to-bus stop service". Hours "Monday" to "Sunday 6 AM" to "8 PM", "(No service on Thanksgiving Day, Christmas Day, and New Year's Day)." Booking help: "305-809-3910". City of Key West: Key West Rides On-Demand Bus Service
- The City's Bus Fares page still lists "Duval Loop – $1". The Key West Citizen reported on Dec. 31, 2025 that "the Duval Loop bus route will be suspended beginning Jan. 2, with service replaced by the Key West Rides on-demand transit program" and that "Fares were free until July of this year when they were increased to $1 per ride" (secondary source, news). Do not call the Duval Loop free or running. Key West Citizen (news, secondary); City of Key West: Bus Fares
Picking a night
Sunset runs from 5:38 PM on Dec. 1 to 5:50 PM on Dec. 31 (U.S. Naval Observatory), so every listed departure is after dark. December nights average a low of 68.3 F at Key West International Airport (NOAA 1991 to 2020 normals), which matters on an open-sided train or trolley. To avoid a clash with the parades, check the December dates checker and the full events list.
- U.S. Naval Observatory sunset times for Key West (EST): Dec. 1, 2026 5:38 pm; Dec. 12 5:40 pm; Dec. 21 5:44 pm; Dec. 25 5:46 pm; Dec. 31 5:50 pm. Civil twilight ends about 25 minutes later (Dec. 12: 6:05 pm). U.S. Naval Observatory: Sun and Moon Data for One Day (computed for 24.5551 N, 81.7800 W, Eastern Standard Time)
- NOAA 1991-2020 normals for Key West International Airport (USW00012836), December: average high 77.7 F, average low 68.3 F, mean 73.0 F, precipitation 2.16 inches. NOAA NCEI U.S. Climate Normals 1991-2020, station USW00012836 (Key West International Airport)
Questions people ask
Decision tool · what will it cost?
What will the holiday tours cost your group?
Enter how many tickets of each kind you want. We add up the 2026 prices the operators publish for the holiday lights tours, the Truman Little White House holiday evenings and the Old Island Restoration Foundation home tours.
| Ticket | Price | As the operator lists it |
|---|---|---|
| Conch Tour Train holiday tour, adult | $32.25 | Conch Tour Train: "Prices starting at $32.25 for adults" |
| Conch Tour Train holiday tour, child 4 to 12 | $21.80 | Conch Tour Train: "$21.80 for kids (4-12)"; 3 and under ride free on a lap |
| Old Town Trolley holiday tour, adult | $33.95 | Old Town Trolley: "Adults: From $33.95", plus a 5% city fee |
| Old Town Trolley holiday tour, child 3 to 12 | $22.95 | Old Town Trolley: "Children (3-12): $22.95", plus a 5% city fee |
| Truman Little White House holiday evening, non-member | $35.00 | Truman Foundation: "$35 for non-members" (Dec. 22 and 23, 2026) |
| Truman Little White House holiday evening, member | $20.00 | Truman Foundation: "$20 for members" |
| OIRF Key West Home Tour, non-member | $55.00 | OIRF: "$55 per individual for non-museum member" (Dec. 29 and 30, 2026) |
| OIRF Key West Home Tour, museum member | $45.00 | OIRF: "$45 per individual for museum member" |
Old Town Trolley adds a 5% city fee to every ticket, which this total does not include. Train and trolley prices are the operators' "starting at" and "from" prices; the Holiday Historic Inn Tours have not posted a 2026 price.
Prices as each operator lists them, checked 2026-10-21. Sources: Conch Tour Train, Old Town Trolley, the Truman Foundation and OIRF. Conch Tour Train, Old Town Trolley, Truman Foundation and OIRF price pages
Coming back for the lights every December? See what living in Key West involves.
Is the inn tour run by the Old Island Restoration Foundation?
No. The Holiday Historic Inn Tours are listed by Key West Inns and the Lodging Association. The Old Island Restoration Foundation runs separate Key West Home Tours of private homes.
Source: Old Island Restoration Foundation; Key West Holiday Fest (Key West Inns)
When are the Old Island Restoration Foundation home tours in December?
December 29-30, 2026 (Tuesday and Wednesday), 1:00 to 4:00pm each day. Tickets are $55, or $45 for members, and include four private homes plus the Oldest House.
Source: Old Island Restoration Foundation: Key West Home Tours Info & FAQ
Are there Christmas lights tours in Key West?
Yes. The Conch Tour Train and Old Town Trolley both run a Holiday Sights and Festive Nights Tour in December 2026. Both are about an hour and need reservations.
Source: Conch Tour Train: Holiday Sights and Festive Nights Tour
When does the Conch Tour Train holiday lights tour run in 2026?
December 8-9, 11-14 and 16-27, 2026, with departures at 6:00, 6:30, 7:00, 7:30, 8:00 and 8:30 pm from Key West High School, 2100 Flagler Avenue.
Source: Conch Tour Train: Holiday Sights and Festive Nights Tour
How much is the Conch Train holiday tour?
Prices start at $32.25 for adults and $21.80 for kids 4 to 12. Ages 3 and under ride free on a lap. Tickets are non-refundable but can be rescheduled up to 24 hours ahead.
Source: Conch Tour Train: Holiday Sights and Festive Nights Tour
When does the Old Town Trolley holiday tour run in 2026?
December 7-27, 2026, from Mallory Square. The tour lasts 60 minutes, with 35 seats per trolley.
How much is the Old Town Trolley holiday tour?
From $33.95 for adults and $22.95 for children 3 to 12, plus a 5% city fee. Ages 2 and under ride free on a lap.
Dates, rules and hours can change. The organisers have the final word: City of Key West: Visitors