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What is on this date?

Choose your nights, then the route

Plan a Key West Christmas trip, 2026

The short answer

To plan a Key West Christmas trip in 2026, choose your nights first. The Harbor Walk of Lights is on every evening from Nov. 25 through New Year's Eve, the street parade is Saturday, Dec. 5 and the boat parade is Saturday, Dec. 12. Sunset Celebration runs nightly at Mallory Square. On Christmas Day, City facilities close and Key West Rides does not run.

Last checked October 25, 2026

Late-afternoon view from a wooden boardwalk to the Mallory Square dock crowded with people waiting for sunset, with gulls overhead, turquoise water, lamp posts, and a yellow resort building with palms behind.
Photo: Hugodesouza1984, CC BY-SA 4.0 (cropped)

A Key West Christmas trip in 2026 starts with one choice: which evenings. The Harbor Walk of Lights is lit every night from Nov. 25 through New Year’s Eve, so any date gives you the lights. Two Saturdays add a parade, Dec. 5 on Duval Street and Dec. 12 on the water. On Christmas Day itself, City facilities are closed and Key West Rides does not run. This page sets out each kind of evening and then lets you build one stop by stop. 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 or any other organiser, and when their published details differ from this page, theirs are the ones to follow.

Two kinds of evening

A Harbor Walk evening, any night of the season

keywestchristmas.org says the 21st Harbor Walk of Lights is on every night from Thanksgiving Eve through New Year’s Eve. It runs along the seawall past Greene, William and Margaret Streets to the Key West Ferry Terminal, with a nautical theme honoring the maritime history of the waterfront. The organiser says its 2026 display sends “Lots of Love from the heart of Key West to Jimmy Buffett”. On a night with no parade there is no fixed start time and no street closure: walk the seawall at your own pace, eat at the Seaport and stay as long as you like. More on the Harbor Walk of Lights.

A parade night

The Hometown Holiday Parade on Saturday, Dec. 5 starts on Truman Ave. at White St. and runs down Duval St. to Eaton St., as keywestchristmas.org gives the route. That site says it starts at 6:30; the City lists 7 PM. The Lighted Boat Parade on Saturday, Dec. 12 is free to watch from the Harbor Walk, with the reviewing stand at Schooner Wharf. The organisers suggest coming early for music, dinner and a look at the decorated boats still in dock. Read the holiday parade and the boat parade pages before you go.

Doing both in one trip

A parade night gives you a set time, a set place and a closure to plan around. A plain Harbor Walk evening gives you the lights without a timetable. The Harbor Walk is lit on parade nights too, so a trip covering Dec. 5 or Dec. 12 can include both. If you want an overlap-free evening, check the December calendar for which nights already hold two events.

Build your evening

The planner below places sourced stops around the Historic Seaport and Old Town in walking order. Choose your date and the kind of evening you want; each stop shows where its facts come from and when we checked them. Distances are straight lines from the Seaport, not walking routes.

Decision tool · evening planner

Plan your Key West evening

Choose how long you have and what you enjoy. The planner picks sourced stops in Old Town, puts them in walking order from the Historic Seaport, and points you to a City lot if you are driving.

Or start from a ready-made plan:

Harbor Walk lights and dinner

Start on the lit Harbor Walk after dark, eat at the Seaport, finish at a bar on Greene Street.

  1. Key West Historic Seaport (201 William Street): The Harbor Walk along Key West Bight. keywestchristmas.org says the Harbor Walk of Lights is lit every evening from its Nov. 25, 2026 lighting through New Year's Eve, and the Lighted Boat Parade passes here on Saturday, Dec. 12.
  2. Schooner Wharf Bar (202 William Street): On the Harbor Walk at the foot of William Street since 1984. It runs the Lighted Boat Parade and lists the judges' stand here.
  3. Half Shell Raw Bar (231 Margaret Street): On Margaret Street at the Seaport, open every day 11 AM to 10 PM by its own listing.
  4. Captain Tony's Saloon (428 Greene Street): On Greene Street in a building its owners say was built in 1851 as an ice house.

Sunset to the Seaport

Sunset at Mallory Square, a walk up Duval, then the Harbor Walk lights.

  1. Mallory Square (400 Wall Street): The waterfront square at the end of Wall Street where the nightly Sunset Celebration is held. Its operator and mallorysquare.com give different start times, so arrive early.
  2. Duval Street (Duval Street): The main street from the Gulf side near Mallory Square to the Atlantic. The Hometown Holiday Parade on Dec. 5, 2026 ends on Duval.
  3. Key West Historic Seaport (201 William Street): The Harbor Walk along Key West Bight. keywestchristmas.org says the Harbor Walk of Lights is lit every evening from its Nov. 25, 2026 lighting through New Year's Eve, and the Lighted Boat Parade passes here on Saturday, Dec. 12.
  4. Conch Republic Seafood Company (631 Greene Street): On Greene Street at the Seaport; its site says open daily from 11:30 AM.

A museum day, lights at night

Three museums in daylight, the fort and its beach, then back to the Seaport after dark.

  1. Ernest Hemingway Home and Museum (907 Whitehead Street): The museum says it is open daily, 365 days a year, 9 AM to 5 PM, with guided tours starting every 15 minutes. Tickets at the main gate only.
  2. Key West Lighthouse & Keeper's Quarters (938 Whitehead Street): Opened in 1848, says the Key West Art & Historical Society, with 88 steps to the top. Check last admission before you go.
  3. Fort Zachary Taylor Historic State Park (601 Howard England Way): A state park open 8 AM until sundown, 365 days a year (Florida State Parks), with a fort tour at 11 AM and a beach.
  4. Key West Historic Seaport (201 William Street): The Harbor Walk along Key West Bight. keywestchristmas.org says the Harbor Walk of Lights is lit every evening from its Nov. 25, 2026 lighting through New Year's Eve, and the Lighted Boat Parade passes here on Saturday, Dec. 12.

Stops come from our sourced list of Key West places (checked 2026-10-21). Distances are straight lines between OpenStreetMap coordinates, not walking routes, and time per stop is your chosen time split evenly. Holiday hours are published for only some places, so check each one before you go.

Back on the island every December? See what living in Key West involves.

Living in Key West

Sunset Celebration at Mallory Square

Sunset Celebration describes itself as a nightly arts festival at Mallory Square. Its history page says the Key West Cultural Preservation Society was formed in 1984 and manages Sunset under a lease with the City. The start time depends on whom you ask: the operator says people gather around one hour before sunset, while mallorysquare.com says the celebration begins two hours before. With sunset at 5:40 pm on Dec. 12 (U.S. Naval Observatory), that means arriving somewhere between about 3:40 and 4:40 pm. After dark the Harbor Walk lights are on, so the two fit into one evening along the Old Town waterfront.

Is anything open in Key West on Christmas Day?

  • Hemingway Home and Museum: "Museum is open daily, 365 days a year", "9:00am-5:00pm for walk-in visits", "Tours start every 15 minutes with the first tour starting at 9:15am". Adult "General Admission – $19"; "Children 5 and younger are FREE". Ernest Hemingway Home and Museum: Rates & Info
  • Florida State Parks: Fort Zachary Taylor Historic State Park, "Hours 8 a.m. until sundown 365 days a year", "$6 per vehicle". "the park is the southernmost state park in the continental United States" and "boasts Key West's favorite beach, located at the southern end of the park, providing opportunities for picnicking, swimming, snorkeling, paddling and fishing." Florida State Parks: Fort Zachary Taylor Historic State Park
  • The City of Key West calendar lists City office closures for Thanksgiving Day (Nov. 26, 2026), the day after (Nov. 27), "Christmas Extension" (Thursday, Dec. 24, 2026), Christmas Day (Friday, Dec. 25, 2026) and New Year's Day (Friday, Jan. 1, 2027), "All city facilities". City of Key West: Calendar event notice
  • 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

Some places say so in writing. The Hemingway Home and Museum says it is “open daily, 365 days a year”, with walk-in visits from 9 am to 5 pm and adult general admission at $19. Florida State Parks lists Fort Zachary Taylor as open 8 a.m. until sundown, 365 days a year, at $6 per vehicle. Sunset Celebration’s operator calls it nightly.

The City lists all City facilities closed on Thursday, Dec. 24 and Friday, Dec. 25, 2026, and says Key West Rides has no service on Christmas Day. Everything else has not published Christmas Day hours on the pages we read, so call ahead. The closures for each holiday are listed on the dates page.

With kids

  • keywestchristmas.org: "Thursday, December 3", "6:00pm" to "8:00pm", "21st Annual Pet Pictures with Santa", "At the 16' Nautical Christmas Tree on the Harbor Walk of Lights at William St." and "Pictures with Santa are $25 (Cash and Cash App accepted) to benefit our local Boys & Girls Club." Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights)
  • Truman Foundation: "The Second Annual Great Gingerbread Build" on "Saturday, December 19, 2026"; "The event will take place between 11:00am and 2:00pm." "This event is free and open to the public." Key West Harry S. Truman Foundation: Events 2026
  • 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
  • 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

Several events list children’s prices or free entry. The Truman Foundation’s Great Gingerbread Build on Saturday, Dec. 19 is free, 11 AM to 2 PM. Pet Pictures with Santa on Dec. 3 is $25 a photo. The Conch Tour Train’s holiday tour starts at $32.25 for adults and $21.80 for kids 4 to 12, with ages 3 and under free on a lap. Old Town Trolley lists adults from $33.95 and children 3 to 12 at $22.95, plus a 5% city fee, with ages 2 and under free on a lap. The tour cost calculator is on the lights tours page.

December weather in brief

NOAA’s 1991-2020 normals for Key West International Airport give December an average high of 77.7 F, an average low of 68.3 F and 2.16 inches of rain. The parades, the lights and the lights tours all happen after dark, so pack for the low end of that range as well as the afternoon. Water temperature, sunset times and the end of hurricane season are on the weather page.

Getting around once you are here

  • City of Key West Bus Fares: "Effective July 7, 2025", City "One Way" $2 full fare, "One Day Pass" $4, "7-Day Pass" $8; Keys (Lower Keys) one way $4. "One Day Super Pass Valid on City and Lower Keys Routes $ 12". Payment by "cash and credit card via Token Transit" (Key West Rides page). City of Key West: Bus Fares
  • 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

City buses cost $2 one way, $4 for a One Day Pass and $8 for a 7-Day Pass. The City’s Key West Rides service picks up and drops off between bus stops from 6 AM to 8 PM. The City’s fares page still lists a $1 Duval Loop, 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, so we do not treat it as running. See getting here and parking.

Places to see and eat

These lists come from the City, the operators and OpenStreetMap. Each entry shows its hours and fees as that operator publishes them, and the date we read them.

  • Key West Historic Seaport

    historic waterfront district and Harbor Walk (boat-parade waterfront)

    201 William Street, Key West, FL 33040 (Key West Bight; Harbor Walk)

    City: the Key West Bight is "a twenty-acre facility" in the Historic District; "The Harbor Walk is lined with restaurants, shops, attractions and other businesses." The Seaport's own site: it "is located along the harborwalk waterfront at the ends of Front Street, Greene Street, Elizabeth Street, William Street, Margaret Street & Grinnell Street." Distances in this file are straight lines from this point.

    Source: City of Key West: Key West Historic Seaport and Marina; Key West Historic Seaport (official site), checked 2026-10-21

  • Mallory Square

    waterfront square (nightly Sunset Celebration)

    400 Wall Street, Key West, FL 33040

    City: Mallory Square "is located on the waterfront in Key West's historic Old Town, adjacent to the cruise ship port" and "runs the entire length of Wall Street." Its Sunset Celebration "includes arts and crafts exhibitors, street performers and food carts."

    City: the Sunset Celebration "begins two hours before sunset, every day of the year."

    Source: City of Key West: Sightseeing Attractions directory (Mallory Square), checked 2026-10-21

  • Duval Street

    main street (bars, shops, restaurants)

    Duval Street, Key West, FL 33040

    Runs from the Gulf side near Mallory Square to the Atlantic at South Beach. City: South Beach "is located at the southern end of Duval Street." The City lists Duval Street as a facility with no further detail.

    Source: City of Key West: Duval Street (facility listing), checked 2026-10-21

  • Southernmost Point Buoy

    landmark

    1499 Duval Street, Key West, FL 33040 (temporary location); original site at South and Whitehead Streets

    City: "The buoy was erected in 1983 by the City of Key West" at "the corner of South and Whitehead Streets". "On September 4, 2025, a temporary buoy was established at the southern end of Duval Street while seawall and roadway repairs are underway. The new temporary location is at 1499 Duval Street." No reopening date for the original site is published on the City page.

    Source: City of Key West: Southernmost Buoy, checked 2026-10-21

  • Ernest Hemingway Home and Museum

    historic house museum

    907 Whitehead Street, Key West, FL 33040

    Tours include "a 20-30 minute guided tour"; "Tours start every 15 minutes with the first tour starting at 9:15am." "Tickets are only available at our main gate. No Reservations are required."

    "Museum is open daily, 365 days a year 9 a.m. to 5 p.m."

    Source: Ernest Hemingway Home and Museum: Rates/Info, checked 2026-10-21

  • Harry S. Truman Little White House

    presidential museum

    111 Front Street, Key West, FL 33040 (Truman Annex)

    City: "the winter White House for President Harry S. Truman for 175 days during 11 visits", "located in the Truman Annex neighborhood of Old Town." Museum: "Please check in with booth agent for next available house tour." Ticket prices are sold online and were not in the page text read.

    "MUSEUM OPEN DAILY 9:30AM-5PM"; "Open 365 days a year"

    Source: Truman Little White House: Museum Tickets; City of Key West Historical Buildings directory, checked 2026-10-21

  • Key West Lighthouse & Keeper's Quarters

    lighthouse museum

    938 Whitehead Street, Key West, FL 33040

    KWAHS: the lighthouse opened in 1848 "with a woman as its keeper" and visitors may "walk up the 88 steps to the top of the light." The U.S. Coast Guard decommissioned it in 1969.

    "Open Monday to Sunday 10:00 a.m. – 5:00 p.m. (last admission 4:30 p.m.)"

    Source: Key West Art & Historical Society: Key West Lighthouse & Keeper's Quarters, checked 2026-10-21

  • Key West Museum of Art & History at the Custom House

    art and history museum

    281 Front Street, Key West, FL 33040

    KWAHS: opened "in 1891 as the island's Custom House, Post Office, Federal Courthouse and 7th District Lighthouse Offices." City: added to the National Register of Historic Places on September 20, 1973. HOURS CONFLICT: the City listing says "Daily 9:30 am to 4:30 pm"; KWAHS (operator) says 10:00 a.m. to 5:00 p.m. Use the operator's hours.

    "Open Monday to Sunday 10:00 a.m. – 5:00 p.m. (last admission 4:30 p.m.)" (KWAHS)

    Source: Key West Art & Historical Society: Key West Museum of Art & History; City of Key West Historical Buildings directory, checked 2026-10-21

  • Audubon House & Tropical Gardens

    historic house museum and gardens

    205 Whitehead Street, Key West, FL 33040

    City: built by Captain John Huling Geiger in the 1840s; saved in 1958 by the Mitchell Wolfson Family Foundation, a restoration that "sparked Key West's restoration movement." Operator: "on certain days, we may close early due to events being held in our gardens. To ensure entrance, please plan to arrive prior to 3pm or call ahead." Ticket prices are on the online store form and were not in the page text read.

    "Monday – Sunday: 9:30am – 4:15pm"; "Gallery & Gift Shop: 9:30am – 5:00pm"

    Source: Audubon House & Tropical Gardens, checked 2026-10-21

  • Key West Cemetery

    historic city cemetery

    701 Passover Lane, Key West, FL 33040 (main entrance at Angela and Margaret Streets)

    City: established in 1847 after the hurricane of October 11, 1846; 19 fenced acres; "an active cemetery with about 100 interments a year." "A free comprehensive self-guided tour map is available at the cemetery's front entrance." Guided tours by contacting the Sexton's office (305-809-3986), open "8:30 to 3:30, Monday through Friday."

    City: "Summer Hours 7:00 AM to 7:00 PM"; "Winter Hours 7:00 AM to 6:00 PM"

    Source: City of Key West: Key West Historic Cemetery, checked 2026-10-21

  • Fort East Martello Museum

    Civil War-era fort museum (far, by the airport)

    3501 S. Roosevelt Blvd., Key West, FL 33040

    KWAHS: abandoned unfinished by the Army after the Civil War; KWAHS opened it as its first museum in 1950. Current exhibits include Robert the Doll. About 3 miles east of the Seaport by straight line; not walkable for most visitors.

    "Open Monday to Sunday from 10:00 a.m. – 5:00 p.m. (last admission 4:30 p.m.)"

    Source: Key West Art & Historical Society: Fort East Martello Museum, checked 2026-10-21

  • Fort Zachary Taylor Historic State Park

    state park and Civil War-era fort

    601 Howard England Way, Key West, FL 33040 (end of Southard Street through Truman Annex)

    Florida State Parks: "Come see the largest collection of seacoast guns and take the daily tour at 11 a.m." City: designated a National Historic Landmark in 1973. The beach is listed separately under beach.

    "The park is open from 8 a.m. until sundown, 365 days a year. The fort closes at 5 p.m."

    Source: Florida State Parks: Fort Zachary Taylor Historic State Park, Hours & Fees, checked 2026-10-21

  • Bahama Village

    historic neighborhood

    Bahama Village, Key West, FL 33040 (west side of Old Town, around Petronia and Whitehead Streets)

    City of Key West: the Bahama Village Redevelopment Area is one of two redevelopment subareas managed by the City's Community Redevelopment Agency; the Bahama Village Redevelopment Plan was adopted in 1995 and updated in 1998. Blue Heaven (729 Thomas Street, corner of Petronia) and the Hemingway Home border it.

    Source: City of Key West: Community Redevelopment Agency (CRA), checked 2026-10-21

  • Key West Aquarium

    aquarium

    1 Whitehead Street, Key West, FL 33040 (Mallory Square)

    Operator: guided presentations and feedings "are all included in your general admission ticket"; "Occasionally the aquarium will close early due to special engagements." HOURS CONFLICT: the City facility listing shows 10:00 AM to 4:30 PM daily; the operator says 9 a.m. to 6 p.m. Use the operator's hours. Ticket prices were not in the page text read.

    "Hours of Operation – 9 a.m. to 6 p.m."; "Last entrance is at 5:30 p.m."; "Open Daily"

    Source: Key West Aquarium: Visitor Information, checked 2026-10-21

  • Key West Shipwreck Treasure Museum

    history museum with lookout tower

    1 Whitehead Street, Mallory Square, Key West, FL 33040 (booth location given by the museum)

    Operator: exhibits "emulate the feel of a 19th-century wrecker's warehouse" and "combine artifacts, actors and films." "Reservations are NOT needed or accepted." Ticket prices were not in the page text read.

    "Open everyday 9am to 5:30pm, final entry 5pm."

    Source: Key West Shipwreck Treasure Museum, checked 2026-10-21

  • Key West Butterfly & Nature Conservatory

    butterfly conservatory

    1316 Duval Street, Key West, FL 33040

    City: houses "from 50 to 60 different species of live butterflies" in "a climate-controlled, glass-enclosed habitat." Operator: "Large pay to park lot conveniently located next door." Ticket prices were not in the page text read.

    "Conservatory – 9am-5:00 pm"; "Last Admission – 4:30pm"; "Gift Shop – 9am-5:30pm"

    Source: Key West Butterfly & Nature Conservatory, checked 2026-10-21

  • Mile Marker 0

    landmark sign

    490 Whitehead Street, Key West, FL 33040 (corner of Whitehead and Fleming Streets)

    City: "Located at the corner of Whitehead and Fleming Streets, a green and white sign marks the beginning and/or end of U.S. Route 1."

    Source: City of Key West: Sightseeing Attractions directory (Mile Marker 0), checked 2026-10-21

  • Truman Waterfront Park

    waterfront city park

    End of Southard Street, Key West, FL 33040

    City features: ADA Accessible, Bike Trail, Parking, Picnic Areas, Playground, Restrooms, Trails, Water; Splash Pad subfacility. The Coast Guard Cutter Ingham Maritime Museum is reached through the park (City). Parking lots and rates are in parking.json.

    City listing: 7:00 AM to 11:00 PM, Monday to Sunday

    Source: City of Key West: Truman Waterfront Park, checked 2026-10-21

  • Florida Keys Eco-Discovery Center

    nature center (free)

    35 East Quay Road, Key West, FL 33040 (Truman Waterfront)

    City: "Admission and parking for the Florida Keys Eco-Discovery Center is free." Exhibits on the plants and animals of the Florida Keys National Marine Sanctuary.

    City listing: Tuesday to Saturday 9:00 AM to 4:00 PM; closed Sunday and Monday

    Source: City of Key West: Florida Keys Eco-Discovery Center, checked 2026-10-21

  • Schooner Wharf Bar

    open-air bar and restaurant (Harbor Walk)

    202 William Street, Key West, FL 33040

    "An island institution since 1984" on the site of the old Singleton Shrimp factory, "At the foot of William Street on the Historic Harbor Walk." The Seaport lists it as pet friendly. Its own events list includes a tree trimming party and the Lighted Boat Parade (see research/events.json for dates).

    Breakfast: "Breakfast served Mon. thru Thurs. 8:30 am – 11:00 am"; "Fri. & Sat. 8:00 am – 11:00 am & Sun 8 am till Noon." Bar hours not published on the home page.

    Source: Schooner Wharf Bar (official site), checked 2026-10-21

  • Half Shell Raw Bar

    seafood restaurant and raw bar (Historic Seaport)

    231 Margaret Street, Key West, FL 33040

    On the Seaport's dining list. The City runs a 19-space "Half Shell Raw Bar Parking Lot" at the same address (parking.json).

    "Open Everyday" "11:00 am – 10:00 pm"; happy hour "7 Days a week 4:30 PM to 6:30 PM"

    Source: Half Shell Raw Bar (official site), checked 2026-10-21

  • The Waterfront Brewery

    brewery and restaurant (Key West Bight)

    201 William Street, Key West, FL 33040

    Own site: "A Craft Brewery located at the Historic Key West Bight with a great beer selection, a full food menu." Hours not in the home page text; check before going.

    Source: The Waterfront Brewery (official site), checked 2026-10-21

  • Conch Republic Seafood Company

    seafood restaurant (Historic Seaport)

    631 Greene Street, Key West, FL 33040

    On the Seaport's dining list.

    "Open Daily at 11:30am"; listed Monday to Sunday "11:30am – 9:30pm"; "Closing times vary, so please call!"; "Daily Happy Hour from 4-7pm"

    Source: Conch Republic Seafood Company (official site), checked 2026-10-21

  • B.O.'s Fish Wagon

    casual seafood shack

    801 Caroline Street, Key West, FL 33040

    On the Seaport's dining list. Hours not in the official site's page text; check before going.

    Source: B.O.'s Fish Wagon (official site), checked 2026-10-21

  • Fisherman's Cafe

    cafe (Historic Seaport)

    205 Elizabeth Street, Key West, FL 33040

    On the Seaport's dining list at 205 Elizabeth Street. Not the same as 'The Old Fisherman's Cafe' that OSM maps on Front Street.

    "Open 7 days a week 7am – 5pm"

    Source: Fisherman's Cafe (official site); Key West Historic Seaport: Food, checked 2026-10-21

  • Sloppy Joe's Bar

    historic bar and restaurant

    201 Duval Street, Key West, FL 33040

    "Est. 1933 | Corner of Duval & Greene Since 1937!" "Live music every day 10 a.m.- 2:00 a.m."

    Bar: Mon. – Sat. 9:00 am – 4:00 am; Sunday 10:00 am – 4:00 am. Kitchen: Mon. – Sat. 10:00 am – 10:00 pm; Sunday 11:00 am – 10:00 pm.

    Source: Sloppy Joe's Bar (official site), checked 2026-10-21

  • Captain Tony's Saloon

    historic bar

    428 Greene Street, Key West, FL 33040

    Own site: the building at 428 Greene Street was built in 1851 as an ice house.

    "Mon-Fri: 10:00am – 2:00am"; "Saturday: 10:00am – 2:00am"; "Sunday: 10:30am – 1:00am"

    Source: Captain Tony's Saloon (official site), checked 2026-10-21

  • Hog's Breath Saloon

    bar and restaurant

    400 Front Street, Key West, FL 33040

    Live music sets listed daily on its calendar.

    Bar Hours: "10am – 1am | 7 Days a Week" (kitchen and shop hours on the same page are garbled and are not quoted)

    Source: Hog's Breath Saloon (official site), checked 2026-10-21

  • Blue Heaven

    restaurant (Bahama Village)

    729 Thomas Street, Key West, FL 33040

    Own site: "on the corner of Petronia and Thomas, just two blocks from Duval." "Please call for dinner reservations. Walk ins welcome!" CHRISTMAS DAY: closed (own site).

    "8am – 2:30pm: Breakfast & Lunch"; "3:30pm – 5pm: Happy Hour"; "5pm – 10pm: Dinner"; "Open daily except on Thanksgiving & Christmas Day"

    Source: Blue Heaven (official site), checked 2026-10-21

  • Green Parrot Bar

    historic bar (live music)

    601 Whitehead Street, Key West, FL 33040

    Own site: "Since 1890." Gift shop beside the Southard Street doors.

    "Sunday – Thursday 10am – 2am"; "Friday & Saturday 10am – 4am"

    Source: Green Parrot Bar (official site), checked 2026-10-21

  • El Siboney Restaurant (Downtown)

    Cuban restaurant

    900 Catherine Street, Key West, FL 33040

    Own site: "Authentic Cuban Cuisine"; asks guests to call "at least one hour in advance" to reserve the Paella Valenciana. Three locations (Downtown, Stock Island, Marathon); this is Downtown. Hours are not in the page text; check before going.

    Source: El Siboney Restaurant (Downtown) (official site), checked 2026-10-21

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

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.

Source: Old Town Trolley Tours: Key West Holiday Tours

What is the BeLighted Bike Ride?

A lighted bike parade after the Holiday Village at the Coffee Butler Amphitheater on Friday, Dec. 4, 2026. The City notice gives the route: Amphitheater, Southard, Whitehead, Front, Duval, United, Whitehead and back. The Holiday Fest calendar says the ride departs at 8:00pm.

Source: City of Key West: Calendar event notice

Is there ice skating in Key West at Christmas?

The Coffee Butler Amphitheater describes a Waterfront Winter Wonderland with an ice skating rink, but its page gives no 2026 dates. keywestchristmas.org says it is closed Christmas Eve and Christmas Day.

Source: Coffee Butler Amphitheater: Waterfront Winter Wonderland

What holiday events are at the Truman Little White House?

The Truman Foundation lists a free Great Gingerbread Build on Saturday, Dec. 19, 2026, 11:00am to 2:00pm, and evening holiday house tours on Dec. 22 and 23 ($20 members, $35 non-members on Dec. 22).

Source: Key West Harry S. Truman Foundation: Events 2026

Dates, rules and hours can change. The organisers have the final word: City of Key West: Visitors

After the holidays

December in Key West every year? Ask what owning here would involve.

This planner is owned by LPE Realty LLC, a licensed Florida real estate brokerage. If you keep coming back for the boat parade and the Harbor Walk lights, we can walk you through buying or selling a home in Key West: process, timing and costs, with no pressure.

Visit LPE Realty LLC Call LPE Realty LLC (561) 652-6917

What is it like to live in Key West? · Thinking of selling a home in Key West?