Journey Through the Florida Keys- Key West


Now Entering- KEY WEST

Mile Markers: 6 to zero…including Stock Island.

duval_street_key_west-floridaWelcome to Key West…the end of the road. It’s been a fun and exciting journey through the Florida Keys and now you have reached the southernmost city in the continental United States. If Key West was your destination from the start, we hope that you were able to learn about and explore the places you travelled through along the way. If you drove straight through, we suggest you come back (soon and often) and stay a few nights in Key Largo, Islamorada, Marathon and the Lower Florida Keys. After all, Key West is home to only a fraction of the natural beauty and exciting attractions waiting to be discovered in the Florida Keys. So remember, each of the islands you passed through along your journey is a destination in itself.

As you begin your decent into Key West you will first travel through Stock Island (MM 6-4), home to many local fishermen, shrimpers, lobstermen and crabbers. While Stock Island is often overlooked by travelers in a rush to reach Key West, we recommend taking a few moments to check out a few of the joints that we like to hang out at. For fresh seafood, try the Shrimp Shack at Fishbusterz (Front Street- oceanside). Enjoy freshly prepared catches of fish, Key West pink shrimp, and other tasty seafood creations while overlooking one of the Keys’ largest shrimpin’ fleets. Just down the road, Hogfish Bar & Grill is another local’s favorite and “old Keys” establishment (also located on Front Street)). Grab a delicious hogfish sandwich (our favorite fish to eat!), or just enjoy a cold beer by the water.

Stock Island is also home to the Lower Keys Medical Center (MM 5-B) and the Key West Golf Course (MM 5-B) – the only regulation length golf course in the Florida Keys that is open to the public. Call the pro shop, or check their website for special rates. Greens fees can be a bit pricey during the peak tourist season (November-March) so our favorite time to play is in the summer when they offer discounts. The layout of the course is quite challenging- especially when the winds kick up, and it’s pretty cool to play golf on an island.

florida_keys_palm_tree-key-westAs you drive into Key West you’ll come to a traffic light (MM 3.9), signaling the end of the single-road navigation that guided you in. If you take a right at the traffic light you will merge onto North Roosevelt Blvd. – to the left is South Roosevelt (aka A1A). This is where the majority of hotels outside of “Old Town” Key West are located. While there are many excellent accommodations in this area, we suggest looking for a room or vacation rental closer to Old Town if you haven’t yet booked your accommodations. The hotels in this part of the island are 3 to 4 miles away from the popular tourist attractions and the restaurants that you’ll want to visit, and you’ll either have to drive, take a cab, or find a hotel shuttle to take you back and forth. If you want to avoid the crowds, or want to be closer to one of the Key West beaches, this may be where you’ll want to stay. Also note that if you “bid” on a hotel room using auction sites such as or, this is likely where you’ll end up. Read below about the hotels we recommend staying at closer to Old Town Key West.

If you take a right at the light, North Roosevelt will lead you through the commercialized part of town- where you’ll find retail stores, chain restaurants and fast food joints.  While this isn’t the part of Key West you came to explore, the area does offer many conveniences if you’re looking for a quick bite to eat or you forgot to pack an item for your trip. As you continue on North Roosevelt you will see Garrison Bight Marina, home to some of the best Key West charter fishing boats. Take a right at charter boat row (Palm Avenue) and head over the causeway. At the end of Palm Avenue take a left onto Eaton Street. This will take you towards the end of Duval Street where you’ll find popular bars such as Sloppy Joes, Captain Tony’s Saloon, Irish Kevin’s- and Mallory Square, where you’ll want to head for the “sunset celebration.”

Take a right on Margaret or Grinnell Street (just before you get to Duval) and you’ll be led to the Historic Seaport, where you’ll find the ever-popular Schooner Wharf Bar (good happy hour), and many of our favorite waterfront dining options including Conch Republic Seafood, Raw Bar, and Turtle Kraals. This is also where you’ll find the City Marina, where even more professional charter captains and flats fishing guides ready to take you out for a memorable day on the water. The ferry to Fort Myers, and the boats that take you over to the Dry Tortugas National Park also depart here.

If you stayed straight on N. Roosevelt (instead of turning at the marina), the road will become Truman Avenue and take you towards the other end of Duval Street. This is the location of a variety of art galleries, great shopping, and some of Key West’s more eclectic restaurants. Head past Duval and take the first right on Whitehead Street. Just a hundred yards down the road you will come to the Ernest Hemingway Key West Home and Museum- where “Papa” lived and wrote for over ten years. We recommend taking the guided tour that teaches you many interesting facts about our favorite writer.

After visiting Hemingway’s house turn around and head south on Whitehead Street. At the end of the road you’ll see a structure that looks like a large stone “JuJubee” candy. Actually, this is the monument that marks the Southernmost Point in the continental United States. The real southernmost point is in the nearby Truman Annex, but since that land is owned by the Navy and off-limits to civilians, we recommend getting your picture taken here so you don’t wind up in the brig.

southern_most_point_key_west-floridaIf you take South Roosevelt at the US-1 split (way back at the traffic light) you will drive past the Key West International Airport, and the Key West beaches. The first beach you will see on your left is Smather’s beach, which is two-miles long and Key West’s largest beach. REMEMBER- Key West is not known for its beaches. You won’t find endless stretches of white sand and crashing waves here like you will on Florida’s east and west coasts-the barrier coral reef keeps this from occuring. Still, Smather’s Beach, as well as South Beach, and the beach at Fort Zachary Taylor State Park, offer great opportunities to swim, sunbath, windsurf and snorkel in the tropical sun and warm water. Just past Smather’s Beach, South Roosevelt will veer to the right. Take the first left on Atlantic Blvd, a right onto Whitehead Street, and then a left onto South Street and you again will reach Duval and will be able to access the “southernmost Jujubee”.

If you have any trouble with directions just pick up one of the coupon guides you’ll see along the way. It’s best not to seek advice from the more “colorful” Key West residents (you’ll recognize them by their long beards, bicycles, and cardboard signs) as we’re not quite sure they even know where they are. If you get lost just remember that Duval Street runs north and south from the Atlantic Ocean to the Gulf of Mexico, and Roosevelt and Truman, run east and west.

Now that you’re here, you’ll want to know about Key West’s rich and fascinating history. The island of Key West was originally named “Cayo Hueso” or “Bone Island” by Spanish explorers who came ashore and found the island littered with skeletal remains- either from an ancient burial ground, or from a bloody battle fought between indigenous tribes who had been pushed south by “Old World” settlers of Florida.

Key West was colonized in the early 1820s and around the same time was claimed as an official US territory by the United States Navy. About that same time, Cayo Hueso was renamed “Key West” by English speaking inhabitants who either incorrectly translated “hueso” to mean, “West,” or because of the island’s westward geographical location. As the deepest port between New Orleans and Norfolk, Virginia, and because of its close proximity to the heavily travelled shipping route of the Florida Straits, Key West’s population rapidly grew.

key_west_lighthouse-florida-keysInto the decades that followed Key West’s economy would flourish as a result of the wrecking and salvage industries. Many citizens became wealthy thanks to the valuable cargo that was “claimed” by Key West wreckers after trade ships crashed into the nearby reef. People from all over the world came to the island to purchase the salvaged goods of Spanish Galleons; and for a time- Key West was the richest city in all of Florida. The fishing industry, cigar trade, and most notably- the sponge industry, prospered around this time as well. This is also the era when immigrants from the Bahamas, referred to as “Conchs” (say conk), began arriving. We still use the word “conch” today to refer to lifelong Keys residents.

Key West’s population and economy was in decline until Henry Flagler connected the isolated island to the Florida mainland in 1912. This marked the start of Key West as a tourism epicenter and began the creation of the town you now see today. During the prohibition era Key West became a popular destination for bootleggers who took on the task of running booze into the U.S. from Cuba and the Bahamas. The endless miles of coastline, multitude of hiding spots, and difficult geography for the Coast Guard to patrol, made the islands a popular drug smuggling “port” all the way through the 1980s.

One of Key West’s more colorful moments happened in 1982 when the island declared itself the Conch Republic and “mockingly” succeeded from the Union. This took place in protest of a U.S. Border Patrol roadblock in Florida City, where cars traveling into the Keys were stopped and checked for drugs and illegal immigrants. Seeing this as a major obstruction for Key West tourism-then Mayor Dennis Wardlow, standing in Mallory Square, declared war against the United States, quickly surrendered, and then demanded a billion dollars in foreign aid for Key West’s war relief effort. Shortly thereafter the blockade was lifted, and the lure of the “Conch Republic” was born. If you’re in Key West in late April, be sure to check out the Conch Republic’s annual week-long Independence celebration.

Over the years many famous celebrities have made their home in Key West. The list includes President Harry Truman, Ernest Hemingway, Tennessee Williams, Mel Fisher, Jimmy Buffett, Shel Silverstein, John Audubon, and Calvin Kline.

Today, Key West has changed a great deal since the days of wreckers and rum runners, but still possesses a charm unlike anywhere in the world. Palm lined-streets, exhausted cemeteries and run-down conch homes tell of a time long since passed- while modern sidewalk cafes, art galleries, gourmet restaurants, lively nightlife, and risqué entertainment (like Fantasy Fest), continue to lure visitors to the island.

Getting around Key West can be a bit tricky. Watch for pedestrians and people riding bicycles and scooters while you’re driving around. Also look for one-way street signs and make sure not park in one of the many tow-away or permit required zones. Most of the hotels located on Roosevelt offer shuttle services to and from Old Town, and there are plenty of Key West “pink” taxis driving around to also get you where you need to go. If you want to go the “green” route, and soak up some rays in the process, hop aboard a Key West pedi-cab and get peddled you from one end of Duval to the other. If you arrive in Key West on a cruise line, pedi-cabs are a great way to see the town in a short period of time. Also keep in mind that almost anywhere in the Old Town area is within walking distance- once you get down there.

key_west_la_concha-roof-topKey West does offer free parking, but it can be very difficult to find. One of our favorite places to park is off Truman Street before you get to Duval. There are usually spots available on the “outgoing” side of the street as you head away from Old Town. Your best bet is to try the side streets a little further away from Old town and walk to the Duval area. We have also found free parking on and around Eaton Street. Just make sure to not park in residential areas where you need to have a permit. If a space is not marked however, you can usually park there. If you are willing to pay to park (which is often worth it) we recommend parking at the Old Town Garage (951 Caroline) $1.50/hour, or $10.00/day, or the City Hall Parking Garage (525 Angela). Metered parking is also available on most streets but can add up quickly. If you are in Key West during fantasy fest or New Year’s Eve, it may be smart to take public transportation into town from Stock Island or another one of the Lower Keys.

Listed below are the Lower Keys attractions, restaurants and accommodations that “us locals” recommend to OUR FRIENDS. These are our unbiased opinions, and we recommend that you write them down before you spend a night on Duval Street and forget what we told you.

Our Favorite Things to Do in Key West:

  • Fish for Blue Marlin (like Hemingway did) in the Florida Straits.
  • Attend an exciting event- Fantasy Fest, Hemingway Days, Conch Republic Celebration, Offshore Power Boat Races, World Sailfish Tournament- there’s ALWAYS something going on in Key West.
  • Go on a snorkel sunset cruise (Historic Seaport).
  • Watch the sunset and street performers at Mallory Square.
  • Take a tour of Ernest Hemingway’s House (907 Whitehead Street) and question why all the cats have six toes.
  • Head by boat to the Dry Tortugas (Historic Seaport) – a vacation in itself.
  • Walk around, people watch, and admire the city’s beautiful architecture.
  • Swim, relax, and tour the fort at Fort Zachary Taylor State Park (Truman Annex).
  • Party on Duval Street! There’s nowhere else like it.
  • See the treasures of the sea at the Mel Fisher Museum (200 Greene).
  • Head to the top of the Crown Plaza Hotel (430 Duval) for the best view of Key West.

Where we Eat, Drink, and Enjoy:

BARS (Old Town area)

  • Green Parrot (601 Whitehead)
  • The Whistle Bar (224 Duval- drink specials on the second floor)
  • Schooner Wharf (Historic Seaport)
  • Cowboy Bills (618 Duval- for $1 Beers)
  • Finnegan’s Wake (320 Grinnell)
  • Irish Kevin’s (211 Duval) and Sloppy Joe’s (201 Duval) – if you want to do the tourist thing
  • Captain Tony’s Saloon (428 Greene)
  • Rum Barrel (528 Front St.)
  • Two Friends Patio Bar (512 Front St.)


  • Caroline’s (310 Duval)
  • Pepe’s Café (806 Caroline)
  • Salsa Loca (918 Duval)
  • Blue Heaven (729 Thomas)
  • Conch Republic (Historic Seaport)
  • A&B’s Lobster House (700 Front St.)
  • Santiago’s Bodega (207 Petronia)
  • Square One (1075 Duval)
  • Hogfish (Stock Island)
  • Shrimp Shack (Stock Island)
  • Raw Bar (Historic Seaport)

Where we “Sleep Off” the Margaritas and Key Lime Pie:

  • Key Lime Inn (725 Truman)
  • Crown Plaza La Concha (430 Duval)
  • Pier House Resort (1 Duval)
  • La Te Da Hotel (1125 Duval)
  • Almond Tree Inn (512 Truman)
  • Key West B&B (415 William)
  • Alexander Palms Court (715 South St.)
  • Sunset Key Cottages (Sunset Key)


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One comment on “Journey Through the Florida Keys- Key West

  1. Pingback: Journey Through the Florida Keys- Key West | Law just to Me

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