Travel Series:  Key West, Starting your Stay

Travel Series: Key West, Starting your Stay

Click Here for an Update to the Key West Travel Series after Hurricane Irma.


Starting your Stay

Life in Key West is lived outdoors and on two wheels.  Two wheels come in all varieties, the loud motorcycles and their softer cousins, the mopeds.  Throughout the day you can hear the distinctive whine of the mopeds as they slowly move through the streets Key West. Mopeds are frequently carrying groceries or small dogs, who delight in this means of transportation.

Bicycles come in all different shapes or sizes, a few are motorized, many are three wheels.  There are all kinds of homemade inventions…some with three wheels in the front to carry children and dogs.  Most two wheeled bicycles are cruisers called Key West cruisers although they weren’t invented here. Their simple construction offers 1-3 gears and allows you to ride erect at your chosen speed.  Key Westers frequently decorate and modify their bicycles, with streamers, tall handle bars, artificial flowers and lights. I use my bicycle for everything groceries, chores…but my favorite is riding down South Roosevelt along Smathers Beach.  Florida doesn’t require helmets for adults, I know that I should wear one, but I love the feel of the wind going through my hair. 

There are many bicycle shops where you can rent bikes.  I recommend that you make arrangements before you get there.  Sometimes in high season the shops run out of bikes. 

So, get on your bike and let’s go.


Learning about the geography and neighborhoods of the Island

Key West is surrounded by the Gulf of Mexico to the west and the Atlantic Ocean to the east.  On the White Street Pier you can see the sun rise on the Atlantic and set on the Gulf. Key West has neighborhoods, the most well-known being Duval Street and Old Town, Bahama Village, New Town, Casa Marina, the Meadows and Truman Annex.

Duval and Old Town are what most tourists experience.  Duval Street connects the Atlantic Ocean to the Gulf of Mexico.  There are typical tourist stores, t-shirts, memorabilia, souvenirs, art galleries, hotels and jewelry, but you will find some hidden gems as well, handcrafted, one-of-a-kind clothing, jewelry, rugs and art.  Duval is most famous for its bars and restaurants.  The Duval Pub Crawl is a rite of passage for serious partiers; they must get a drink from each of the historic bars and pubs on Duval Street. At night Duval feels like a carnival with talented bands whose music flows into the streets.  Pedicabs, trollies, bikes, mopeds, cars, and the Conch Train all contribute to the celebration of life.  Expect to see Conchs with decorated bikes.  The dress is always casual, shorts, shirt and flip flops, even in the most elegant restaurant, the only rule is that you must wear clothing.  During Fantasy Fest this is sometimes difficult to enforce.

At the northern end of Duval is Mallory Square.  Mallory Square is a gathering place to view the sunset, with the carnival atmosphere of performers and tourists alike who clog the boardwalk to experience the sunset.  If you want to see a more sedate sunset, you can go to White Street Pier, which is at the end of White Street in the Casa Marina district.

Old Town is the residential area of Key West that visitors associate with Key West. It is on the Northeast side of Duval Street.  Take your time to see the charming Conch houses, eyebrow houses and a few graceful Queen Anne homes.  Old Town is a vibrant neighborhood bursting with fantastic restaurants, bodegas, and tiny plots with small homes where life is lived outdoors. 

On the opposite side of Duval is Bahama Village.  The original Bahamian settlers and decedents of former slaves and free-men created Bahama Village.  It has the charming Conch houses as well as affordable housing. Except for the sign, it is indistinguishable from Old Town. Once a marginalized area, it is undergoing gentrification and now hosts many of the island's most popular restaurants.

The Truman Annex, adjacent to Bahama Village, got its start in 1845 as part of Fort Zachary Taylor, a U.S. Army installation. The base was eventually taken over in 1947 by the U.S. Navy and renamed the "Fort Zachary Taylor Annex."  New docks were added in the 1930s to include submarines, but modern submarines are too large, so they went elsewhere. Truman Annex got its name because Harry S. Truman was one of its frequent visitors and called his residence, the Little White House.  He loved the friendliness and easy ways of Key West and enjoyed walking down the street without being recognized.  Simpler times.  Eventually most of the annex was sold to developers who made it a gated residential community.

Residents who first fall in love with Key West, are usually besotted with Old Town, but after several years, they often make their way to the Casa Marina or the Meadows districts.  Primarily residential districts, the Meadows and Casa Marina differ in the housing and plot size.  The Meadows is filled with the charming homes of Old Town, but has few restaurants or shops.  Casa Marina has larger land plots but hosts more modern homes that follow the Miami-style architecture.  Casa Marina residents live near the beach.  I count myself as a Casa Marina resident who loves the three block walk to the ocean.  Both the Meadows and Casa Marina are separated by White Street.  The Meadows is bordered by White Street and North Roosevelt.  Casa Marina is bordered by Truman Street and the west side of White Street.  White Street used to be the primary residence of the Cubans and the Cuban cigar factories. Those factories have been replaced by galleries, restaurants and yoga studios.  But it is best known as having the best Cuban coffee on the Island. Follow White Street down to Higgs Beach and the White Street Pier.  The White Street Pier is a place where you can see the sunrise on the Atlantic and the sunset on the Gulf.

New Town and Mid-Town houses the Conchs, self-defined residents who have stayed for boom and bust cycles.  New Town was created by the U.S. Navy, when it filled in this part of the island to expand it.  Unfortunately, they didn’t put in enough fill, so it floods during hurricanes.  It is also the unfortunate recipient of the 50s style bungalows with low ceilings, square rooms and little to recommend them besides the larger lots.  Although it is larger than Old Town and only about two miles away, tourists rarely see it.

Fun things to do on your bike

Before you begin there are a couple of rules that you should follow. 

  1. You cannot go the wrong way on a one way street (and sometimes even the relaxed Key West cops will ticket offenders). 
  2. Children must wear helmets. 
  3. Bikes must have lights (so make sure that your rental provides them).  Be prepared to see all of the colorful lights and decorations that residents put on their bikes…ride around at night, it is fun to watch.
Ride the Loop

You can circle ¾ of the island and not be out of sight of water.  For most of the “loop” the sidewalks are broad and designed for cyclists.  I usually start on North Roosevelt, which borders the Gulf of Mexico and continuing biking until the bend where it becomes South Roosevelt Street.  South Roosevelt Street offers Atlantic Ocean views.  You can stop at Smathers or Higgs Beach to rest.  You will find food trucks along Smathers Beach and  Saluté on Higgs Beach.  Saluté is a delightful, very casual restaurant directly on the beach, with much better fare than one would expect from an outdoor beach restaurant.  Take a right on White Street which also has a bike lane for most of the street and that will bring you back to North Roosevelt.  White Street also has restaurants including a diner and great places for authentic Cuban food and coffee.  (About 10 miles.)

Ride around Fort Zachary

Fort Zachary is in Old Town.  There is a park service fee, but it allows you to tour Fort Zachary, eat and relax at one of the best beaches on the Island.

Ride to Stock Island

The adventurous can cross the bridge at South Roosevelt to go to Stock Island.  Stock Island hosts the golf course, the Botanical Gardens and numerous restaurants (Chico’s Cantina , Hogfish Grill and Roostica are among many of the great restaurants on Stock Island).  Although Stock Island is a part of Key West, its real estate is less pricy that Key West and you will ride by many artist studios disguised as junkyards…after all this is Key West. (Depending on where you start about 10-15 miles.)

Ride up the Keys

The truly, truly adventurous can cross the Stock Island Bridge and continue North (east) up the Keys as far as you want to go.  It is stunningly beautiful and most of the way there are bicycle paths.  You can cycle all the way to Miami (160 miles);  or stop and turn back whenever you wish.  There are restaurants and, of course, Cuban coffee shops along the way.  For experienced cyclists, you may wish to go to the Seven Mile Bridge (approximately 40 miles).  The ride is delightful, the weather is great and the views are spectacular.

Seven Mile Bridge--old and new.  Scary!

Seven Mile Bridge--old and new.  Scary!

Learn more about Key West in these posts from Angela:

Welcome to Key West
A Short Version of the History of Key West
Starting your Stay (this post)
Dawn and Dusk
Coming up!
The Tastes
The People of Key West
My Favorite Inhabitants
My Second Favorite Inhabitants -- Flora
Shrimp Boats
The Houses
Key West Quirkiness
Key West's Spirituality

Good Books!

Good Books!

Good Books!

Good Books!