We believe everyone should experience the Florida Keys at least once. Don’t miss Duval Street, which runs to the Atlantic Ocean from the Gulf of Mexico. It’s the epicenter of the party atmosphere in Key West.
Ultimately, the thoroughfare was named after William Pope Duval, the first territorial governor of Florida. You’ll enjoy a mile-long stretch of road that draws millions of people from around the world.
Called Cigar City USA because of the Cuban cigar stores that used to be prevalent, this area will help you experience the Conch Republic lifestyle. Whether you hope to find souvenirs to take home, enjoy a cocktail at sunset, or grab a bite to eat, Duval Street is the top place to be and one of our favorite vacation spots.
Parties Everywhere
Duval Street has famous restaurants, retail shops, and nighttime hangouts, such as Sloppy Joe’s Bar, which opened in 1933 and is now a National Historic Landmark. Famed writer Ernest Hemingway was a Key West local and spent many boisterous nights on this street.
In 1967, a National Park Service survey was conducted and identified 18 Historic American Buildings. Four years after that, the National Register of Historic Places claimed that a six-block area was also historically important.
Then, the City of Key West created and approved Historic Architecture Guidelines in 2000, setting stringent standards for new construction projects along Duval Street.
Things to Do Near the Atlantic Ocean on Duval Street Key West
Overall, Duval Street is one of our favorite places because it has a party atmosphere, but there are plenty of dining and shopping options available. Here are just a few things you can do:
Shopping Options
On the main drag, you’ll find various unique art galleries, boutiques, and shops. Some stores are dedicated to swimsuits, hammocks, and flip-flops. Whether you like handmade jewelry, interesting Key West memorabilia, or designer clothes, it’s all here.
Plus, there’s the local Walgreens drugstore, which is found in the historic Strand Theater. In its glory days, the old-time movie palace accommodated 800 people. Now, the building’s exterior has been restored to include decorative figurines.
Entice Your Taste Buds
Along with the Hard Rock Cafe, Duval Street houses the original Margaritaville. You can enjoy an authentic Key West Experience here. Jimmy Buffet often drops in for some jam sessions with whatever local band is playing.
If you’re more into upscale dining, the Nine One Five Bistro is found in an old Victorian-era home. Eat dinner out on the porch.
Another great choice is the Grand Cafe, which serves locally sourced ingredients and fresh seafood. There’s a beautiful wraparound porch and a stylish courtyard that overlooks the main thoroughfare.
Stop in for some key lime pie at the Hot Tin Roof, which is found at 0 Duval Street. Enjoy dining outside on the veranda here. Alternatively, you can head to Fogarty’s for a casual atmosphere and tasty American cuisine.
Tasty Beverages
Duval Street plays host to various legendary entertainment venues and bars, so Sloppy Joe’s Bar is just the beginning. Captain Tony’s Saloon is the oldest option in the city; it’s built around a tree and is considered the town’s gallows.
You’ll also find the Green Parrot Bar. At one time, it was a dive bar that was popular with submariners from the Key West naval base. Now, it’s considered the best watering hole in the country.
After visiting Green Parrot Bar, you can dance the night away at Durty Harry/Rick’s Bar. It’s not just a bar. In fact, there are eight nightspots in one location.
Don’t forget about the live music at Cowboy Bill’s and La Te Da. They’re both exciting and interesting.
Various Festivals
Ultimately, Duval Street hosts many events, such as the Key West Food and Wine Festival. It’s also where the Conch Republic Independence Festival takes place. This is where the Florida Keys celebrates its self-proclaimed liberation with live music, treats, and activities.
There’s also the Key West Poker Run, which attracts motorcyclists from around the country. They can all enjoy fun and rides with fellow motorcycle lovers.
We recommend going during the four-day Lobsterfest. Generally, it marks the start of the area’s fishing season and includes free concerts, crafts, arts, and plenty of tasty crustaceans.
Overall, Duval Street is the backdrop for many popular street fairs and festivals throughout the year. For example, Key West hosts an annual 10-day Halloween event for adults only. It’s a fun spectacle that features a parade, themed parties, and flamboyant costumes.
The Oldest House Museum/Garden
Captain Francis Watlington built the Oldest House Museum/Garden in 1829. This conch cottage has a landscaped garden and three historic buildings. There are various family heirlooms, maritime artifacts, and period furnishings inside.
San Carlos Institute
The San Carlos Institute is actually in a restored historic building and has a beautiful Spanish-style facade. It was founded in the 1870s in Key West by Cuban emigres and is the Cuban cultural center.
Currently, it’s on the National Register of Historic Places.
The Butterfly and Nature Conservatory
Wander around the enclosed tropical gardens, and see 50 species of creatures at the Butterfly and Nature Conservatory. Enjoy the climate-controlled habitat that’s home to various birds, plants, and waterfalls.
St. Paul’s Episcopal Church
If you enjoy places of worship, St. Paul’s Episcopal Church is a historic place with roots that go back to the 1830s. While it’s been updated and remodeled after hurricanes and fires, the current edifice has stained glass windows and was built in 1919. It’s the oldest congregation found in Key West.
Visitor Information
When planning your Key West vacation, it’s important to know how to get there, when to go, and where to stay. Here are some tidbits of information to help:
When to Visit
Duval Street often gets crowded when cruise ships dock near Mallory Square. Likewise, people will gather for the 10-day Halloween event, the Duval Street Pub Crawl, and Hemingway Days.
Typically, the local entertainment establishments and watering holes are family-friendly until 9 PM. Then, they switch to an adults-only theme.
Getting There
We want you to see everything Duval Street has to offer, and do some people-watching while there. Therefore, it’s best to get on the Old Town Trolley. The conductor will entertain you with informative and fun narrations about the attractions and sights in Key West.
You’ll find many stops on the Old Town Trolley, which will allow you to explore certain areas and get back on. One of them is the Key West Aquarium, and we truly enjoyed this attraction. Pet a shark if you dare!
Where to Stay
There are many places to spend the night, and we recommend staying for a couple of days. Options include the:
- Southernmost House Hotel
- Southernmost Beach Resort
- Crowne Plaza Key West La Concha Hotel
- New Orleans Guesthouse
- Pier House Resort
- Orchid Key Inn
Nearby Attractions
Here are the top attractions to experience:
Southernmost Point
Enjoy the Southernmost Point Buoy, which is a colorful concrete buoy marking the southernmost publicly accessible place within the Continental United States. It’s found at South Street and Whitehead Street and is one of the most photographed areas of Key West.
Key West Lighthouse
The Key West Lighthouse also features a Keeper Quarter’s Museum, which showcases the lives of the people who operated this beacon for the last 100 years. You can climb the stairs to see a beautiful view of the area.
Ernest Hemingway House/Museum
Stop by the Ernest Hemingway House/Museum. This was where the famed author lived for about a decade and showcases his office and the gardens.
Mallory Square
Mallory Square is in the historic Old Town of Key West. The waterfront plaza is found on the Gulf of Mexico at the northern tip of Duval Street. It features restaurants, street performers, and shops.
Plus, Mallory Square hosts the Sunset Celebration each night. We enjoyed the street fair, and countless locals and visitors came to watch the sun drop below the horizon.
About Peter C.
Peter is a digital nomad who largely writes from Asia, Europe, and South America. Always following the "vibe," he sets up shop in hostels and AirBNB's and continues to entertain us with wild stories from life abroad. Ask him anything in our community forum.
