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Florida, United States

Old Town & Duval Street

Two nights in Old Town for sunset at Mallory Square, Cuban food and three midnight drops along Duval. We have mapped 1 sight, 4 activities and 3 places to eat here, each with a reason to go.

Plan Old Town & Duval Street with friendsBrowse 9 places
Old Town & Duval Street, Florida, United States
Places
9

1 See · 4 Do · 3 Eat · 1 Stay

Curated routes
1

Key West New Year's Eve

Best season
Dec 30 – Jan 1

from our route notes

Warmest month
August

30°C / 86°F avg high

Coolest month
January

23°C / 73°F avg high

Wettest month
September

about 177 mm rain

Climate: NASA POWER 2001–2025 averages for Key West, the nearest city we track.

Things to do in Old Town & Duval Street

9 places from our curated routes, grouped by what you will do there. Each one has its own page with the address and full notes.

See

1 sight worth building a day around in Old Town.

  • Mallory Square in Old Town & Duval StreetPhoto: C Watts · CC BY 2.0
    See

    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.

    • Old Town
    • Free
    • 1.5 hr
    • Sunset

Do

4 activities for when the group wants to do more than look across Old Town, Upper Duval and Historic Seaport.

  • Sloppy Joe's conch shell drop in Old Town & Duval StreetPhoto: Bubba73 · CC BY-SA 3.0
    Do

    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.

    • Old Town
    • $$
    • 2 hr
    • 11 p.m. to 12:30 a.m.
  • Do

    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.

    • Upper Duval
    • $$
    • 1.5 hr
    • 11:30 p.m. to 12:30 a.m.
  • Schooner Wharf Bar pirate drop in Old Town & Duval StreetPhoto: Stuart Locke · CC BY-SA 3.0
    Do

    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.

    • Historic Seaport
    • $$
    • 2 hr
    • 10 p.m. to 12:30 a.m.
  • Fort Zachary Taylor Historic State Park in Old Town & Duval StreetPhoto: Julian Lupyan · CC0
    Do

    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.

    • Truman Annex
    • $
    • 2.5 hr
    • Jan 1 morning

Eat

Where we would book a table in Old Town & Duval Street across Casa Marina and Bahama Village.

  • Eat

    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.

    • Casa Marina
    • $$$$
    • 2 hr
    • Early dinner
  • El Siboney in Old Town & Duval StreetPhoto: Todd Van Hoosear · CC BY-SA 2.0
    Eat

    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.

    • Bahama Village
    • $
    • 60 min
    • Late lunch
  • Blue Heaven in Old Town & Duval StreetPhoto: Steven Miller · CC BY 2.0
    Eat

    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.

    • Bahama Village
    • $$
    • 75 min
    • Jan 1 breakfast

Stay

1 place to stay we would book in Old Town.

  • La Concha Key West in Old Town & Duval StreetPhoto: Acroterion · CC BY-SA 4.0
    Stay

    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.

    • Old Town
    • $$$
    • Dec 30 to Jan 2

How to fit Old Town & Duval Street into a trip

Old Town & Duval Street is stop 1 of 2 on our Key West New Year's Eve route. Follow it as-is or lift Old Town & Duval Street into your own plan.

Getting here and onward

Distances are straight-line estimates between destination centers, not road distances.

Weather by month, based on Key West

Our climate figures for Old Town & Duval Street come from Key West, about 3 km (2 mi) away. Average daily highs run from 23°C / 73°F in January to 30°C / 86°F in August. September is the wettest month, with about 177 mm of rain. Outlined months fall in the best season on our routes.

Average daily highs, NASA POWER 2001–2025 averages for Key West. Key West weather (covers Old Town & Duval Street) →

Near Old Town & Duval Street

8 other destinations from our guides within about 400 km (249 mi), measured in a straight line.

Old Town & Duval Street questions, answered

How many days do you need in Old Town & Duval Street?

Our route notes suggest 2 nights in Old Town & Duval Street. On our Key West New Year's Eve route it is stop 1 of 2 in a 3-day trip. The listed visit times for our 9 places add up to roughly 14 hours, before travel between them, so you will need to choose.

What is Old Town & Duval Street best known for?

Two nights in Old Town for sunset at Mallory Square, Cuban food and three midnight drops along Duval. Standouts on our list: Mallory Square (The nightly sunset celebration on the Gulf side, with street performers, food carts and boats crossing the horizon); 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); 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).

When is the best time to visit Old Town & Duval Street?

Our Key West New Year's Eve route is best Dec 30 – Jan 1. NASA POWER 2001–2025 averages for nearby Key West put the warmest highs in August (30°C / 86°F), the coolest in January (23°C / 73°F) and the most rain in September (about 177 mm).

What are the best things to do in Old Town & Duval Street?

Start with Sloppy Joe's conch shell drop, Bourbon Street Pub red shoe drop, Schooner Wharf Bar pirate drop, Mallory Square and Fort Zachary Taylor Historic State Park. Our guide lists 9 places in all, from 1 sight, 4 activities, 3 places to eat and 1 place to stay.

Where should a group eat in Old Town & Duval Street?

Our picks: Louie's Backyard (Casa Marina); El Siboney (Bahama Village); Blue Heaven (Bahama Village). Reservations are recommended year-round; book New Year's Eve dinner weeks out (Louie's Backyard).

What is near Old Town & Duval Street?

The closest destinations in our guides are Key West (about 3 km / 2 mi), Bahia Honda & the Lower Keys (about 56 km / 35 mi) and Everglades (about 122 km / 76 mi). Distances are straight-line estimates, not road distances.

Plan Old Town & Duval Street with your crew

Open the Key West New Year's Eve route in TripsCircle, invite friends with a link, settle which of these 9 places make the cut with a quick poll, then split costs and share one packing list.

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