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Ultimate Guide to Duval Street

Running north to south from the Gulf of Mexico to the Atlantic Ocean, Duval Street is the epicenter of Key West’s famous party atmosphere. The thoroughfare was named in honor of William Pope Duval, the first territorial governor of Florida. This mile-long stretch of pavement draws millions of visitors from around the world who want to experience the legendary lifestyle of the Conch Republic. Whether you want to find a souvenir to bring home, grab a quick bite to eat during the day or kickback with a cocktail at sunset, “it’s 5 o’clock somewhere” and Duval Street is the place to be.


This popular street is lined with famous retail shops, restaurants and nighttime hotspots like Sloppy Joe’s Bar, opened in 1933 and designated a National Historic Landmark. Even famed writer and Key West local Ernest Hemingway spent more than a few boisterous nights up and down Duval Street. A National Park Service survey conducted in 1967 identified 18 buildings, including Sloppy Joe’s, as historically significant. Four years later, the National Register of Historic Places designated a six-block area as a historic district. With so much to see and do, you could spend your entire vacation here and not be able to take it all in.


Whether it’s shopping, dining or the party atmosphere that lasts from sunset until dawn, you’ll find it along Duval Street.

Shop ‘Til You Drop
Here on the main drag, you can find a wide assortment of one-of-a-kind galleries, shops and boutiques. There are stores dedicated to hammocks, swimsuits and flip-flops as well as everything Cuban and Jimmy Buffet. You can find designer clothes, handmade jewelry and unique Key West memorabilia. Even more quirky, the local Walgreen’s drugstore is housed in the historic Strand Theater. The former old-time movie palace once accommodated over 800 people. Walgreen’s restored the building’s exterior, including the decorative figurines. Take in the whole scene as you stroll along the boulevard window-shopping and watching the colorful people.


Your Taste Buds Will Thank You
In addition to a Hard Rock Café, Duval Street is home to the original Margaretville. Escape the mundane and enjoy an authentic Key West experience. Jimmy Buffet has been known to drop in for an impromptu jam session with the local band. The upscale Nine One Five Bistro is housed in a restored Victorian-era home. You can have dinner outside on the beautiful porch. Entrees made from fresh seafood and other locally sourced ingredients await diners at the Grand Café, which features a stylish courtyard and a wraparound porch overlooking the main thoroughfare. Enjoy al fresco dining on the veranda at the waterfront Hot Tin Roof located at 0 Duval Street as well as the casual fun atmosphere and American cuisine at Fogarty’s.

Cheers to Paradise
Sloppy Joe’s Bar is just the beginning. Duval Street plays host to numerous legendary bars and entertainment venues. Occupying the same spot as the original Sloppy Joe’s, Captain Tony’s Saloon is one of the oldest bars in the city. The establishment is built around a tree that served as the town’s gallows. Once a dive bar popular with submariners stationed at the former Key West naval base, the iconic Green Parrot Bar has been voted one of the best local watering holes in the country. And for those looking to dance the night away, Rick’s Bar/ Durty Harry is a combination of eight nightspots in one, including a piano bar and dance club. You can also enjoy the live entertainment at the La Te Da and Cowboy Bill’s Honky Tonk Saloon.

Mark Your Calendar
Duval Street hosts the Key West Food & Wine Festival and is the center of the action for the Conch Republic Independence Festival when the Florida Keys’ celebrate their self-proclaimed independence with a weeklong festival that includes food, music and fun activities. The Key West Poker Run brings in motorcycle lovers from around the country for a weekend of fun with fellow riders. A free concert, arts and crafts along with plenty of crustaceans are just a part of the four-day Lobsterfest, which marks the start of the fishing season. Duval Street is also the backdrop for a number of popular festivals and street fairs throughout the year. Key West’s annual 10-day, adults-only Halloween event is a one-of-a-kind spectacle featuring flamboyant costumes, themed parties and a parade.

Oldest House Museum and Garden
The Oldest House Museum and Garden is a conch cottage built in 1829 by Captain Francis Watlington. The museum has three historic buildings along with a landscaped garden. In addition to period furnishings, you can see maritime artifacts and family heirlooms.


Butterfly and Nature Conservatory
Wander through an enclosed tropical paradise and observe more than 50 different species of these multicolored creatures at the Butterfly and Nature Conservatory. The climate-controlled indoor habitat is also home to a variety of colorful birds and flowering plants set against a background of lush vegetation and sparkling waterfalls.

San Carlos Institute
The San Carlos Institute occupies a restored historic building featuring an imposing Spanish-style façade. The Institute was founded in Key West in the 1870s by Cuban émigrés and serves as the Cuban cultural center. It has been housed at its current location for over 100 years.

St. Paul’s Episcopal Church
St. Paul’s Episcopal Church is a historic house of worship that traces its roots back to the early 1830s. Several previous sanctuaries were met with disaster from fire and hurricanes. The current edifice, noted for its stained glass windows, dates from 1919 and is the oldest congregation in Key West. The church sponsors regular organ concerts.


When to Visit
Duval Street can become very crowded when a cruise ship docks for the day at the pier near Mallory Square. Crowds also gather for special events like Hemingway Days, the Duval Street Pub Crawl and October’s 10-day Halloween event. Some of the well-known local watering holes and entertainment establishments are family-friendly until approximately 9 p.m. After that time, they switch to adults-only. Check with each establishment for their particular policy.

Getting There
The best way to see all of Duval Street, and do a little people watching, is aboard the Old Town Trolley. Sit back and relax as the conductor entertains you with a fun and informative narration about many of the popular sights and attractions in Key West. There are multiple stops along Duval Street that allow you to hop off the trolley, explore the area, and hop back on the trolley to continue the tour.



Mallory Square
Mallory Square is a waterfront plaza located in Key West’s historic Old Town. It is situated on the Gulf of Mexico just west of the northern end of Duval Street. The plaza features shops, restaurants and an assortment of street performers. Mallory Square hosts the nightly Sunset Celebration, a street fair where visitors and locals gather to watch the sun dip below the horizon. The square is also the setting for the Memorial Sculpture Garden that contains bronze busts of individuals who have made a lasting contribution to the city.

Ernest Hemingway House and Museum
The Ernest Hemingway House and Museum was the home of the famed author for almost a decade. The museum includes the office where Hemingway penned several of his famous works, including The Snows of Kilimanjaro. You will also see the author’s gardens and descendants of his beloved six-toed cat, Snowball.

Key West Lighthouse
The Key West Lighthouse and Keeper’s Quarters Museum chronicles the lives of the men and women who operated this navigation beacon for over 100 years. Climb the stairs to the top for a wonderful view of the surrounding area.

Key West Lighthouse

Southernmost Point
The Southernmost Point Buoy is a colorful concrete buoy that marks the southernmost publicly accessible place in the continental United States. Located at the intersection of Whitehead and South streets, the buoy is 90 miles north of Cuba. It is also one of the most photographed attractions in Key West.