Key West City Guide
Duval Street: The Cultural Spine of Key West
Duval Street is Key West's legendary 1.25-mile main avenue, slicing straight across the island from the Gulf of Mexico at Mallory Square to the Atlantic Ocean at South Beach. Named after William Pope Duval, Florida's first territorial governor, the street presents two radically different personalities: 'Lower Duval' (the northern half near Front Street) is the high-energy epicenter of live music, historic saloons like Sloppy Joe's, and bustling street patios; 'Upper Duval' (the southern half toward the Butterfly Conservatory) is a leafy, tranquil enclave of fine art galleries, Victorian guesthouses, and intimate Caribbean bistros. The wider island directory and travel planner starts on the Key West City Guide homepage.
Quick answer Upper vs Lower Duval dividing line, transit, and historic bars
Read on 10 September 2026: Duval Street is completely free and pedestrian-friendly. Truman Avenue acts as the sharp cultural boundary: north of Truman is Lower Duval (lively bars, souvenir shops, evening nightlife); south of Truman is Upper Duval (art galleries, Victorian boutique inns, quiet dining). Ride the free Duval Loop bus to hop on and off along parallel streets without paying for parking.
Key takeaways
- Take the free Duval Loop bus: the pink-and-blue city bus runs every 15 minutes along Whitehead and Simonton streets parallel to Duval.
- Visit historic saloons during daylight hours: Sloppy Joe's and Captain Tony's Saloon offer live folk and rock music with minimal lines before 5:00 PM.
- Stroll Upper Duval in the morning: explore boutique clothing shops, local jeweler studios, and French bakeries in tranquil shade.
- Open alcohol containers in public streets are legally prohibited; finish your drinks before exiting licensed bar patios.
Key facts
Opening hours
| Daily | Public thoroughfare open 24 hours; shops typically open 10:00 AM - 9:00 PM; bars close at 4:00 AM |
|---|
Planning it
- Time needed
- 2 to 3 hours for a complete stroll
- Book ahead
- Recommended — a few days
- Address
- Duval Street, Key West, FL 33040
Duval Street is a public avenue with no admission fee, but guided walking tours and historic pub crawls offer rich local lore:
Stroll the sidewalk independently, or book a guided tasting and historical pub tour:
| Experience | Type | Highlights | Best For | Rate | Book |
|---|---|---|---|---|---|
| Self-Guided WalkIndependent travelers strolling the 1.25-mile coast-to-coast avenue | Public access | 14 blocks from Gulf to Atlantic, historic architecture, window shopping | Walkers & shoppers | Free ($0.00) | Official site |
| Historic Food Tasting TourFood lovers wanting to sample authentic conch fritters and Key lime pie along the route | Food walking tour | 5 tastings at historic eateries across Old Town and Duval | Culinary travelers | $89.00 | Check Availability |
| Ghosts & Gravestones TourEvening sightseers fascinated by haunted saloons and Victorian ghost legends | Trolley & walking | Narrates Duval Street fires, cemetery lore, and Captain Tony's hanging tree | Night owls | $41.95 | Check Availability |
| Old Town Trolley TourSightseers traveling between Duval Street and outer island attractions | Hop-on hop-off | Stops at both ends of Duval Street (Truval Village and Mallory Square) | All-day transit | $48.50 | Check Availability |
Join guided culinary tastings, ghost excursions, and sightseeing trolleys along the Duval corridor.
from $120.00
Key West: Full-Day Eco-Tour of Key West National Wildlife Refuge
Danger Charters' legendary backcountry sail. Rated among the highest quality excursions in the Keys for its small-group ethos, pristine shallow-water sandbar access, and premium wine selection.
Check Availability
from $64.00
Key West: Glass Bottom Boat Coral Reef Eco-Tour
The premier option for non-swimmers, families with toddlers, or visitors wanting to see the barrier reef without donning a mask and snorkel. Marine biologists explain brain corals, sea fans, and fish species.
Check Availability
from $48.50
Key West: Old Town Trolley 13-Stop Hop-On Hop-Off Tour
Full-day transport covering 13 stops across the entire island from Mallory Square to New Town. Ideal for travelers visiting Key West without a rental car or avoiding costly Old Town parking.
Check Availability
from $42.95
Key West: Conch Tour Train 75-Minute Sightseeing Tour
The quintessential 75-minute loop through Old Town operating since 1958. Best for orientation and first-timers who prefer continuous live storytelling over walking in midday Florida heat.
Check AvailabilityPrices, ratings and details are the platform's own, checked in Q3 2026; dollar figures are the listed prices — the platform bills in your account's currency.
Upper Duval vs. Lower Duval: understanding the divide
First-time visitors often assume all of Duval Street is a loud party strip. In reality, the 14-block thoroughfare changes character completely at Truman Avenue.
- Lower Duval (Blocks 100 to 500): From Front Street south to Fleming Street. This is the entertainment core containing legendary bars (Sloppy Joe's, Hog's Breath Saloon, Captain Tony's), live rock music stages, cigar rolling shops, and souvenir storefronts. Expect street musicians, bustling outdoor patios, and vibrant late-night energy.
- Middle Duval (Blocks 600 to 900): From Southard Street to Julia Street. Features casual restaurants, Key lime pie bakeries (including Kermit's), historic churches like St. Paul's Episcopal, and lively open-air bars like the Green Parrot just one block off on Whitehead.
- Upper Duval (Blocks 1000 to 1400): South of Truman Avenue to South Beach. This section is known as 'Truval Village'. It is quiet, refined, and shaded by mature mahogany trees. Here you will find fine art galleries, independent jewelry ateliers, upscale French bakeries like Banana Cafe, Victorian bed-and-breakfasts, and the entrance to the Key West Butterfly Conservatory.
Historic saloon lore: Hemingway and Captain Tony
No exploration of Duval Street is complete without understanding its literary drinking history. At 201 Duval Street sits the world-famous Sloppy Joe's Bar, originally established by Hemingway's close fishing companion Joe Russell on December 5, 1933 (the very day Prohibition was repealed).
However, literary purists should note that Hemingway's original favorite saloon was actually located around the corner at 428 Greene Street, which is now Captain Tony's Saloon. Captain Tony's occupies Key West's oldest saloon building (dating to 1851), built around an ancient hanging tree that still penetrates the ceiling and roof. Hemingway spent hundreds of hours in this exact room between 1931 and 1938, swapping fishing tales with local wreckers and rum-runners.
Practical walking advice and the Duval Loop transit
Walking the entire length of Duval Street from Gulf to Atlantic takes approximately 30 minutes at a brisk pace, but allow at least two hours to browse galleries, pause for fresh conch fritters, and photograph the ornate gingerbread woodwork.
Key West summers are intensely humid. To avoid exhaustion, walk one direction along Duval Street in the morning shade, and return via the free Duval Loop bus. The bus runs along Whitehead Street (one block west) and Simonton Street (one block east) with stops every 2-3 blocks, air conditioning, and free boarding without passes or tickets.
Landmarks accessible directly off Duval Street
Duval Street connects directly to Key West's premier historic districts:
Ernest Hemingway Home and Museum
Hemingway's historic estate situated one block west on Whitehead Street.
2 minutes walk (150 meters from block 900)Key West Butterfly Conservatory
Glass solarium with 50+ living butterfly species, flamingos, and tropical birds.
Directly on street (Block 1300)Mallory Square
Waterfront plaza famous for nightly Sunset Celebrations on the Gulf.
1 minute walk (50 meters from block 100)Frequently asked questions about Duval Street
How long is Duval Street in Key West?
Duval Street is approximately 1.25 miles (2 kilometers) long, spanning 14 city blocks from the Gulf of Mexico at the north end to the Atlantic Ocean at the south end.
Is Duval Street walkable from end to end?
Yes, Duval Street has wide, paved, flat sidewalks on both sides with frequent pedestrian crosswalks. Walking from coast to coast takes about 25 to 35 minutes non-stop.
Can you drink alcohol on the street on Duval Street?
No. Key West municipal code strictly prohibits carrying open containers of alcohol on public sidewalks and roadways. Drinks must be consumed inside licensed premises or on private licensed patios.
What is the difference between Upper and Lower Duval?
Lower Duval (north of Truman Ave) is the energetic entertainment hub with historic bars, live rock bands, and nightlife. Upper Duval (south of Truman Ave) is quiet and upscale with art galleries, boutique inns, and quiet dining.
Where can you park near Duval Street?
Parking directly on Duval Street is nearly impossible and heavily restricted. Use the Old Town Garage at Grinnell Street ($4.00/hour) or the Simonton Street surface lot, then take the free Duval Loop bus.
Key West on video: Duval Street
Verified video walkthroughs and footage of Duval Street, providing visual perspective before your visit.
DUVAL ST Key West - Walking Tour - Southernmost Point USA
Walkthrough of Duval Street by Keys Boating Channel.
Video: keys boating channel[4K] Key West Florida - Duval Street Walking Tour
Walkthrough of Duval Street by Traveling with Andrew.
Video: traveling with andrewKey West Walking Tour | Duval Street to the Southernmost Point - 4K
Walkthrough of Duval Street by JD-Videos.
Video: jd-videosReviewed Q3 2026 (July–September 2026); next review Q4 2026. Prices, hours and terms are set by the venue or operator and confirmed at checkout.
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