Sloppy Joe's Bar is a historic drinking spot in Key West, Florida, whose colorful past stretches way back to 1933. The bar's owner, Joe Russell, ran a speakeasy during the Prohibition era. When it was over, he opened a small drink stand originally known as "The Blind Pig".

The joint quickly gained popularity among locals for its lively atmosphere and cheap drinks and, over the years, played host to a number of notable patrons and events. It was a favorite haunt of writer Ernest Hemingway, who lived in Key West for many years and was a regular here. In fact, it was Hemingway who suggested that the bar changed its name to Sloppy Joe’s through association with his favorite watering hole in Havana, Cuba, which bore the same moniker (for being owned by one Jose Garcia), that he felt would suit this place just as well – and it did.

In 1937, following a quarrel with the landlord, Russell moved the establishment to its current location at the corner of Duval and Greene streets, where it has remained ever since. Today, Sloppy Joe's is still going strong, as it was in the days of Hemingway, and remains one of the most popular gathering spots in Key West.

It's an old but fun space, full of tourists and live music, so be encouraged to grab a few drinks here, as they're stronger and cheaper than most others in the area (you will even find that they serve Kenny Chesney's line of rums – Blue Chair Bay). The Caribbean-American comfort food is really good, too, so have at least one meal here during your trip. While at it, take some time to look around and you will notice all the historic photos, including lots with Ernest Hemingway, their most famous patron.

Although not exactly the same place frequented by Hemingway, Sloppy Joe's continues to celebrate the life of the great author with the Annual Hemingway Look-Alike Contest every July. As for the original Hemingway location nearby, it is currently occupied by Captain Tony's Saloon.

Note:
They always ask to see your photo ID along with your credit card, when paying the bill, as a precautionary fraud measure.

Duval Street is the main street in Key West, stretching across the island and acting as the city’s central strip for food, nightlife, shopping, and people-watching. It’s the place most visitors end up on at some point, because so many bars, restaurants, cafés, galleries, and small local shops are clustered here. The atmosphere is lively and casual, and it shifts depending on the time of day-quieter in the morning, busy by afternoon, and fully active once the evening starts.

As you walk along Duval, take a moment to look up as well as straight ahead. Many of the street’s best details are above eye level: wraparound balconies, old wooden trim, hanging plants, and faded signs that hint at how long some businesses have been around. Pay attention to the architecture too-some buildings look polished and updated, while others still have that weathered character that fits Key West. As you walk, also glance down the side streets, where the noise drops quickly and you can spot shady lanes, smaller historic homes, and tucked-away patios.

In the middle section of Duval Street, it’s worth slowing down and noticing how the blocks change. One area may feel like a restaurant row, while the next is all bars and music. Listen for live performances coming from open doors, watch the mix of locals and visitors, and notice how quickly crowds form around certain corners. If the sidewalks feel crowded, stepping into an open-air courtyard for a minute can make a big difference-many places have garden-style seating hidden behind the street-front entrance. This is also where you’ll see the widest range of “Key West energy,” from laid-back afternoon drinks to busier late-night scenes.

Duval Street isn’t a single attraction so much as a snapshot of the city’s personality. It’s social, loud in places, relaxed in others, and full of small moments that make the walk interesting-street performers, music spilling out, and the constant movement of people. Even without a plan, it’s easy to spend longer here than expected.

The Southernmost Point is one of the most photographed landmarks in Key West. Marked by a large painted concrete buoy, it’s known for the bold message claiming it as the “Southernmost Point Continental U.S.A.” and for the simple feeling of being at the edge of the island with open ocean nearby. It’s a quick stop, but it’s a classic Key West moment that almost everyone wants to see at least once.

As of September 2025, the original site at the corner of South Street and Whitehead Street is closed due to a major reconstruction project involving the seawall, roadway, and plaza (with completion expected in late 2026). In the meantime, visitors can still get the iconic photo at a full-scale replica buoy installed at Duval Street Pocket Park, 1400 Duval St, which serves as the temporary Southernmost Point photo spot.

Even though it’s called the “southernmost point,” it’s worth knowing that it’s more of a symbolic landmark than a precise geographic measurement, and it’s mainly famous because it’s easy to recognize and fun to visit. Many people also notice how close Cuba is listed on the buoy, which adds to the sense of how far south Key West really is.

Because it’s such a popular photo stop, it helps to expect crowds and a bit of waiting time, even at the temporary location. Early morning tends to be quieter, and later in the day the light can be better for pictures. After the photo, it’s easy to keep walking through the nearby streets, where you’ll find small homes, palm trees, and that relaxed end-of-the-island atmosphere.

The Ernest Hemingway Home & Museum is one of Key West’s most popular historic attractions, located in Old Town just a short walk from Duval Street. Ernest Hemingway, the American novelist and journalist, lived here in the 1930s, and the house still feels personal and lived-in rather than staged. Visitors come for the literary connection, but the property itself-its rooms, gardens, and famous cats-makes it memorable even for people who haven’t read his books.

As you step inside, look at the layout of the home and the everyday details that have been preserved. Notice the dark wood furniture, the shelves, and the way the rooms open into each other, giving the house a solid, comfortable feel. Pay special attention to Hemingway’s writing studio, which sits slightly apart from the main house-this is where he worked, away from distractions, and it’s one of the places people linger the most.

Outside, take your time in the garden areas, because a lot of the charm is there. Watch for the famous polydactyl (or more specifically six-toed) cats, which are descendants of Hemingway’s original cats-there are nearly 60 of them living on the property. You’ll often spot them resting in shady corners, stretched out on porches, or walking along low walls. Many of the cats are quite sociable, but it’s best to let them come to you first and be patient rather than reaching for them right away. The grounds also include a pool, tropical plants, and paths that make it easy to wander without feeling rushed.

The visit combines literature, local history, and the simple feeling of being in a real Key West home from another era. It’s a place where small details matter, and a short tour can easily turn into a longer one once you start noticing everything around you.

The U.S. Coast Guard Cutter Ingham Maritime Museum is a decommissioned ship museum docked in Key West at Truman Waterfront Park. It’s one of the most interesting historic sites on the island because it isn’t a recreated exhibit-you’re stepping onto a real working vessel with tight corridors, steep ladders, and rooms that still look like they did during service. The Ingham served for decades and is best known for its roles in World War II, the Cold War, and later drug interdiction operations.

Walking through the ship gives a clear sense of how demanding life on board was. Visitors can move through key areas like the bridge, crew quarters, and operational spaces, with signs explaining what each section was used for and how the crew lived day to day. The metal surfaces, narrow passageways, and low ceilings make the experience feel very different from a standard museum. It’s hands-on and detailed, with a lot to take in even without reading every panel.

The Ingham is also recognized as a National Historic Landmark, and many displays focus on the ship’s combat history, Coast Guard missions, and the people who served on it. Along the route, you’ll see original equipment, weapons, and ship systems that show how a cutter operated at sea. For anyone interested in military history or ships, it’s the kind of place where you end up stopping often just to look at how everything fits together.

The visit is done mostly at your own pace, and it can take longer than expected because there are so many levels and rooms to explore. Comfortable shoes are a good idea, and visitors should be prepared for steep steps and tight spaces in places. When you step back onto the dock, the harbor feels very different after spending time inside a ship built for hard conditions and serious missions.

The Harry S. Truman Little White House is one of Key West’s most well-known historic sites, located in the Truman Annex area of Old Town. Built in 1890 as officers’ quarters for the U.S. Navy, the home later became a presidential retreat and earned its nickname as the “Winter White House.” Its biggest connection is to President Harry S. Truman, who spent 175 days here across 11 visits between 1946 and 1952, using the house as a place to work and meet with advisors away from Washington.

The building started out as a wooden duplex known as Quarters A and B, meant for naval leadership on the station. In 1911, it was converted into a single-family home for the base commandant, and over time the surrounding shoreline changed as land was filled in. Beyond Truman, the house also hosted other well-known figures, including the renown inventor Thomas Edison during World War I, and later several U.S. presidents who visited Key West for official trips or private stays.

Today, the property operates as a museum, and visits are typically done through guided tours that walk guests through the rooms where Truman stayed and worked. The tour highlights personal items, photographs, and period details, including Truman’s desk area, which helps the space feel less like a formal monument and more like a real working home. The tone of the museum is practical and story-driven, focusing on what Truman did here, why Key West mattered during that time, and how the house functioned during presidential visits.

The grounds include gardens that can be explored at an easy pace, and the house itself is best known for its simple layout and lived-in feel rather than grand architecture. For anyone interested in U.S. history, it’s one of the few places in Florida with a direct connection to the presidency, and it offers a close look at a very specific chapter in Key West’s story.

If you're a dive bar sort of person who enjoys a totally chill, unsophisticated, grungy atmosphere with live music and surprisingly good food, this is the spot.

The Schooner Wharf was originally located on board the Schooner Diamante. It moved ashore in 1984 and was housed in a former shrimp packing warehouse that was renovated to create a rustic and inviting ambiance. For this purpose, the walls have been covered in nautical decor, including old fishing nets, buoys, and flags.

Over the years, the bar has evolved into a very special place, expanded into a neighboring building, and added a second-floor deck with a panoramic view of yacht decks, magical sunsets, and Key West's Historic Seaport. A staple of the local community, this popular waterfront joint is now probably the hottest bar on the shore of Key West and has been featured in articles by The NY Times and Aqua Magazine.

The Schooner Wharf serves a variety of drinks and food, including fresh seafood, burgers, and sandwiches. Its signature drink is the Rumrunner, a tropical cocktail made with rum, fruit juice, and grenadine. Customers can enjoy their food and drinks while sitting at the bar, on the outdoor deck, or the pier overlooking the water.

The bar hosts live music shows almost every night of the week, featuring local musicians playing a variety of genres including rock, country, and blues. The nights when Michael McCloud is there with his band deserve a particular note. There are also special events throughout the year, such as the annual Conch Republic Independence Celebration in April and the Lighted Boat Parade during the holiday season.

A great place to linger after walking all day.