Key West New Year's Eve

Destination 01

Old Town & Duval Street

9 places

Two nights in Old Town for sunset at Mallory Square, Cuban food and three midnight drops along Duval.

• Photo: Bubba73 · CC BY-SA 3.0

  Sloppy Joe's conch shell drop

  A giant lit conch shell lowered from the roof of Sloppy Joe's at midnight, watched by a crowd that fills Duval Street.

  Tip Stand on Duval at Greene Street by 11 p.m.; the bar itself is at capacity hours earlier.

  DoOld Town$$2 hr11 p.m. to 12:30 a.m.

• Bourbon Street Pub red shoe drop

  A drag performer rides a giant red high heel down from the balcony at 724 Duval, the gay end of the street's New Year.

  Tip Come by 11:30 p.m. and watch from the sidewalk across Duval for the clearest look at the balcony.

  DoUpper Duval$$1.5 hr11:30 p.m. to 12:30 a.m.
• Photo: Stuart Locke · CC BY-SA 3.0

  Schooner Wharf Bar pirate drop

  A pirate wench is lowered from the mast of a schooner at the Historic Seaport at midnight, with cannon fire over the harbor.

  Tip The open-air bar is first come; arrive by 10 p.m. for a spot facing the boats.

  DoHistoric Seaport$$2 hr10 p.m. to 12:30 a.m.
• Photo: C Watts · CC BY 2.0

  Mallory Square

  The nightly sunset celebration on the Gulf side, with street performers, food carts and boats crossing the horizon.

  Tip Arrive 45 minutes before sunset on Dec 31; it sets around 5:50 p.m.

  SeeOld TownFree1.5 hrSunset

• Louie's Backyard

  A long-running restaurant on the Atlantic side of the island, with dinner on tiered decks over the water.

  Tip Reservations are recommended year-round; book New Year's Eve dinner weeks out.

  EatCasa Marina$$$$2 hrEarly dinner
• Photo: Todd Van Hoosear · CC BY-SA 2.0

  El Siboney

  A family-run Cuban restaurant on a residential corner, known for roast pork, plantains and Cuban bread.

  Tip Go for a late lunch on Dec 31, before the dinner crowds.

  EatBahama Village$60 minLate lunch
• Photo: Steven Miller · CC BY 2.0

  Blue Heaven

  An outdoor restaurant in a Bahama Village courtyard where chickens wander between tables and the key lime pie is piled with meringue.

  Tip Go for breakfast on Jan 1; expect a wait after 9 a.m.

  EatBahama Village$$75 minJan 1 breakfast
• Photo: Acroterion · CC BY-SA 4.0

  La Concha Key West

  A 1926 hotel on Duval Street, the tallest building in Old Town, with a rooftop bar above the street.

  Tip Ask for a high floor facing Duval; you can walk to all three midnight drops.

  StayOld Town$$$Dec 30 to Jan 2
• Photo: Julian Lupyan · CC0

  Fort Zachary Taylor Historic State Park

  A Civil War-era fort with the best swimming beach in Key West, shaded by pines at the island's southwest tip.

  Tip Go on Jan 1 morning with snorkel gear; there is a state park entry fee.

  DoTruman Annex$2.5 hrJan 1 morning

Destination 02

Bahia Honda & the Lower Keys

6 places

A slow Jan 1 drive up the Overseas Highway to a beach, old railroad bridges and Key deer.

• Photo: KimonBerlin · CC BY-SA 2.0

  Bahia Honda State Park

  A wide sandy beach on clear, shallow water, about 40 miles up the Overseas Highway from Key West.

  Tip Arrive before 10 a.m. on Jan 1; the park closes its gate when parking fills.

  DoBahia Honda Key$3 hrJan 1 morning
• Photo: Sergiy Galyonkin · CC BY-SA 2.0

  Old Bahia Honda Bridge

  A section of Flagler's 1912 railroad bridge inside the park, with a walkway on top that looks over the channel.

  Tip Walk up from the park's west end; the light is best late in the afternoon.

  SeeBahia Honda KeyFree30 minLate afternoon
• Photo: EdoDodo · CC BY-SA 3.0

  Blue Hole

  A freshwater pond in an old quarry in the National Key Deer Refuge, where small Key deer and alligators are often seen.

  Tip Drive slowly on Big Pine; the deer cross roads, and feeding them is illegal.

  SeeBig Pine KeyFree45 minMorning

• No Name Pub

  A pizza and beer stop on a back road of Big Pine Key, its walls covered in signed dollar bills.

  Tip Bring cash for tips and follow the signs; the road ends at the old No Name Bridge.

  EatBig Pine Key$60 minLunch

• Looe Key Reef

  A shallow coral reef in the Florida Keys National Marine Sanctuary, reached by snorkel boats from Big Pine and Ramrod Key.

  Tip Book a morning boat; afternoon trips are often canceled when the wind picks up.

  DoLower Keys$$4 hrMorning
• Photo: Raychristofer · CC BY-SA 4.0

  Old Seven Mile Bridge

  A 2.2-mile walk or bike ride on the restored old bridge from Marathon out to Pigeon Key.

  Tip Start at the Knights Key end in Marathon and bring water; there is no shade.

  DoMarathonFree1.5 hrLate afternoon