I’ve been a visitor to the Keys many times, first in my cruise ship days docking only for a few hours until the summer of 2021 and renting a house for a month with my family.  One suggestion, if you don’t like the HEAT, I don’t recommend going in the summertime… EVER!

“Key” is derived from the Spanish word cayo, meaning small island. The island is only 8 square miles, four miles long and about 2 miles wide at its widest. 

Ponce de Leon discovered Key West in 1521 during his expedition to Florida in search of the Fountain of Youth. He named the island Cayo Hueso, which means Bone Island in Spanish, for the bleached limestone rock formation of the island. For many years, Key West was the largest town in Florida as it was well located for trade with Cuba and the Bahamas and the on the main trade route from New Orleans. The Keys were only accessible by water until visionary & developer to the Atlantic coast, Henry Flagler developed the overseas railway in the early 1900’s.  In 1935 a devasting hurricane destroyed the Keys railroad & bridges, making way for U.S. Highway 1 known as the overseas highway that runs from Key Largo south to Key West today.  

Key West Conch

Have you heard of a Key West Conch?  Technically it’s a large sea snail that lives in the Gulf of Mexico surrounding the Florida Keys, but if you are visiting the Keys, most often it refers to a Key West native. 

A bit of history:  After the war, the unpopular Tories (British conservative political party) fled to the southern states to the next British colony, the Bahamas. Unfortunately, the British Parliament started taxing the Bahamians on their food. The Bahamians said they would rather eat conch than pay taxes, so they came up with 27 different ways to eat conch! To this day if you are born in Key West, you are a conch.  When a baby is born, a conch shell is placed on a stick outside.  If it is point end up, it is a boy and if it is open end up, it is a girl.

“To this day if you are born in Key West you are a conch. If you are born elsewhere but live here seven years you become a fresh water conch.”

The most scenic way to Key West is by driving the 113-mile Overseas Highway, U.S. Route 1 through the Florida Keys to Key West.  If you don’t have time to drive the scenic highway, there is an international airport.

Modes of transportation in Key West

The best way to see Key West is by foot, bicycle or a golf cart. Park your vehicle and use one of these methods.  Yes, you can rent a scooter, but I don’t recommend as they are dangerous & are noise makers.  I think the locals feel the same, just saying.  Here are the recommendations for bike and golf carts:

• https://hydrothunderofkeywest.com/
• https://thebikeshopkeywest.com/

Accommodations in Key West

Personally, I’ve only stayed in short-term rentals while in Key West, but there are plenty of hotel accommodations. Here are a few suggestions or I can help book a hotel.  Just reach out, I’m happy to help!

• Hyatt Centric Key West Resort & Spa – http://hyatt.com/
• Ocean Key Resort – https://www.oceankey.com/
• Casa Marina- https://www.hilton.com/en/hotels/eywcmqq-casa-marina-key-west/

Activities for all ages- well maybe…

• Dry Tortugas National Park– Transportation is only by seaplane or ferry.  Unfortunately, it’s fully booked for months, so plan way ahead.  It’s still on my bucket list! https://www.nps.gov/drto/index.htm
• Fort Zachary Taylor State Park – Great for a history lesson, snorkeling and beach time. https://www.floridastateparks.org/parks-and-trails/fort-zachary-taylor-historic-state-park
• Hemingway Home– Must see on your trip to KW.  Beautiful scenery & the approximately 60 of the 6 toed cats. Admission is cash only! https://www.hemingwayhome.com/
• Harry Truman Little White House– If you want to skip the museum tour, you can browse the gift shop which has a room full of history. https://www.trumanlittlewhitehouse.org/
• Sunset cruise– https://www.coolkeywest.com/tours/sunset-cruises/. Check out the options, there are too many to choose from.  I love the small tiki hut boats as it’s a small intimate setting for your sunset sail.  https://www.cruisintikiskeywest.com/
• Mallory Square/Sunset Pier– https://www.sunsetcelebration.org/. It’s one of those touristy-type activities that you can check off your list.  It’s fun, festive and great for people watching!  😉
• Key West Butterfly & Nature Conservatory is a perfect spot if you enjoy nature, butterflies & getting out of the sun/rain.  https://www.keywestbutterfly.com/
• Fun Photo Stop– the Southernmost Point Buoy is an anchored concrete buoy marking the southernmost point in the continental United States, the lowest latitude land of contiguous North American states. It is 18 feet above sea level.  Go at sunrise when its quiet, otherwise expect lines to wait for a photo.  Here’s the webcam! https://southernmostpointwebcam.com/
• Fury – What an adventurous day on the water!  We did the most comprehensive tour that included jet skis, an ocean water park, snorkeling, banana boat (hold on) & parasailing.  My favorite was the parasail! https://www.furycat.com/key-west/watersports-attractions/
• Adults ONLY– If you want some fun nightly entertainment, this is a great drag show on Duval to spice up your night with a group of friends.  Our group of 4 gals had a blast!  I suggest purchasing tickets ahead of time.   http://lateda.com/cabaret/

Shopping in Key West

Shopping- plenty of souvenir shops, but the ones listed below are NOT. Ha!

• Kino Sandals– homemade leather shoes for all literally made in the shop. https://kinosandals.com/
• Green Pineapple is my favorite as you can shop, take a yoga class & grab a glass of wine or a bite to eat.  https://www.thegreenpineapple.com/
• Tucker’s Provisions– https://www.tuckersprovisions.com/
• Key West Local Luxe– also a favorite and ladies you can spend lots of time and MONEY.  We sure did!  Barb is quite a sales woman!  Introduce yourself to Barb, she’s a hoot! https://keywestlocalluxe.com/pages/meet-barb or https://keywestlocalluxe.com/

Food and Restaurants in Key West

Are you a foodie and a seafood one at that?  Even being such a small island, there are many to choose from, but if you like fresh seafood then you will be in heaven. It’s so fresh and delish!  Below I’ve listed only restaurants that I’ve experienced myself, a few of them more than once and highlights of what I ordered or suggest. Enjoy!

• Café at the Mansion– Lobster pizza & Mojitos!  https://www.seasidecafekw.com/
• The Thirsty Mermaid– Delish fresh seafood!  https://www.thirstymermaidkeywest.com/
• Moondog Café – Happy Hour is great!  For breakfast, the Elvis French Toast  https://moondogcafe.com/
• Frenchie’s- Great breakfast spot  https://www.frenchieskeywest.com/
• La Grignote café – Great pastries & quiche! https://www.facebook.com/La-Grignote
• Blue Heaven- Breakfast spot & atmosphere is so fun! https://blueheavenkw.com/
• The Lobster Shack -What else, lobster! http://www.lobstershackkw.com/-
• Seven Fish- Key Lime Martinis! https://www.7fish.com/
• 915Duval– Try the Devils! Check out the menu for the description.  https://www.915duval.com/
• Latitudes– located on the private island of Sunset Key. Reservations are required as you have to take a boat over to the island.  https://www.sunsetkeycottages.com/key-west-restaurants/latitudes/

Libations & FUN!

• Rum Bar– https://speakeasyinn.com/
• Sunset Pier– great sunset spot with a cocktail! https://www.oceankey.com/key-west-sunset-pier/
• Green Parrot– https://www.greenparrot.com/
• The Bull– Be careful not to take the stairs to the Garden of Eden (wink, wink, it’s clothing optional)  https://bullkeywest.com/

One more idea if you like a little naughty in your life, Fantasy Fest maybe just what you need to lose all your inhibitions!  Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island during the off season.  It’s grown every year since its inception and is now the wildest extravaganza around.  Plan ahead for Fantasy Fest annually in late October filled with costuming, parades, libations, and excitement!