I’ve been a visitor to the Keys many times, first in my cruise ship days, docking only for a few hours until the pandemic, when we rented 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! As long as you have air conditioning, you will be fine, just be prepared for hot and humid weather.  Bring a hat, sunblock, and an umbrella too!  😉

“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 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 1900s.  In 1935, a devastating hurricane destroyed the Keys’ railroad & bridges, making way for a highway, known as U.S. Highway 1, the overseas highway that runs from Key Largo south to Key West today.  

Check out the Top 5 Scenic Routes for a Summer Road Trip for more details and the other 4 epic road trips!

Conchs of Key West 

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. 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 a 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 for seven years, you become a freshwater conch.”

Transportation in Key West- Best way to get around!

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.

The best way to see Key West is on foot, by bicycle, or in a golf cart. Park your vehicle and use one of these methods to get around this very small island.  Yes, you can rent a scooter, but I don’t recommend it as they are dangerous & are noise makers.  I think the locals feel the same, just being honest.  Biking or walking is really the best way to get around, plus it’s safer! 

Accommodations in Key West

Personally, I’ve stayed mainly in short-term rentals while in Key West, but there are plenty of hotel accommodations to choose from, believe it or not. If you’re planning a stay in Key West and want top-tier accommodations with distinct atmospheres, these three resorts offer exceptional experiences. Hyatt Centric Key West Resort & Spa, located near Mallory Square, offers a peaceful yet central location just steps from Old Town’s dining, shopping, and nightlife. This waterfront resort blends coastal luxury with casual comfort, featuring a full-service spa, private balconies, and direct access to water activities like jet skiing and snorkeling. For those craving a more vibrant, boutique vibe, Ocean Key Resort & Spa sits right on Duval Street at the edge of the Gulf of America. It boasts one of the best sunset views in Key West, alongside an award-winning spa, the lively Hot Tin Roof restaurant, and elegant suites with private balconies overlooking the water. In addition, the historic Casa Marina Key West, Curio Collection by Hilton, offers a refined and spacious oceanfront retreat on the quieter side of the island. Dating back to 1920, this iconic property features a private beach, two oceanfront pools, and a timeless blend of Old Florida charm with modern luxury—ideal for travelers seeking serenity and upscale amenities. Each of these resorts delivers its own unique version of the Key West experience, whether you’re after relaxation, nightlife, or historic elegance. 

Activities for all ages- well, not quite…

Dry Tortugas National Park is still on my bucket list!  Yes, it’s booked for months out, so plan ahead… far ahead!  Transportation is only by seaplane or ferry. 

Fort Zachary Taylor State Park spans 54 acres and sits on the tip of Key West. Great spot for both its military history and its recreational activities. It is also the location of one of Key West’s favorite beaches, a stretch of sand with turquoise water sometimes called “rocky beach.”

Hemingway House is a MUST-see on your trip to KW.  Beautiful scenery & approximately 60 of the 6-toed cats are a sight to see.  If you like to eat and drink, the Hemingway Food and  Walking tour is a perfect way to incorporate both entertainment and a history lesson. Cheers to Hemingway!  A personal favorite for me!

Harry Truman Little White House is another pop-in visit, especially if you really love history.  If you want to skip the museum tour, you can browse the gift shop, which has a room full of history. 

A Key West Sunset Sail is definitely the way to get out on the water and enjoy a magnificent sunset.  In my opinion, one of the best in the world!  There are too many to choose from, so take your pick.  I love the small tiki hut boats as it’s a small, intimate setting for your sunset sail.  

Mallory Square is one of those touristy-type activities (to be honest) that you can check off your list.  It’s fun, festive, and great for people watching!  😉 Even if you just pop in for a quick view, however, I suggest being on the water for the sunset.  

Key West Butterfly & Nature Conservatory is a perfect spot if you enjoy nature, butterflies & if you want to get out of the sun/rain. 

 Add the Southernmost Point Buoy as the perfect postcard photo stop.  The 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.  Hot tip!  Go at sunrise when it’s quiet; otherwise, expect to wait in lines for a photo.  Here’s the webcam!

When in the Keys, a water tour is highly recommended!  We did the most comprehensive tour that included jet skis, an ocean water park, snorkeling, a banana boat (hold on) & parasailing.  My favorite was the parasail! 

If you want some fun nightly entertainment, there is a great drag show on Duval to spice up your night with a group of your rowdy friends.  Our group of 4 gals had a blast!  I suggest purchasing tickets ahead of time.  Adults ONLY.

Attention Shoppers!

Key West is known for its quirky charm and abundance of souvenir shops, but if you’re looking for something more curated and stylish, there are a few standout boutiques that are my favorites. At Kino Sandals, a local tradition since 1966,  where you can pick up handcrafted, affordable leather sandals made right in the shop.  It’s a fun spot for a group of gals or family.  My personal favorite is The Green Pineapple, where you can browse a beautifully curated selection of wellness-inspired fashion and gifts, take a yoga class, and then unwind with a glass of wine or a healthy bite in their organic café. Tucker’s Provisions is a vintage-inspired general store with a coastal flair, offering everything from classic apparel to beach gear with a touch of nostalgia. And ladies, don’t miss Key West Local Luxe—a treasure trove of high-end, handcrafted jewelry. Trust me, you’ll want to set aside some time (and money) for this one. Be sure to introduce yourself to Barb, the charismatic owner—she’s a hoot and quite the saleswoman! These shops are perfect for discovering one-of-a-kind finds that go way beyond the typical tourist fare.

Restaurants Galore in Key West!

Are you a foodie—and a seafood lover at that? Then Key West is going to be your paradise. Despite being a small island, the culinary scene is overflowing with flavor, creativity, and ultra-fresh seafood. These are ALL spots I’ve personally tried, some more than once, don’t judge 😉

Start with the Café at the Mansion for their famous lobster pizza and mojitos! It’s casual, oceanfront, and absolutely delicious. The Thirsty Mermaid serves up fresh-caught seafood in a cozy setting that always hits the spot. For breakfast or a great Happy Hour, Moondog Café is a must; their Elvis French Toast is decadent and unforgettable. Always stop at Moondog when in KW!  Craving a lighter start? Frenchie’s is a relaxed breakfast spot, while La Grignote offers divine pastries and quiche that rival those in Paris. Blue Heaven is a local icon, known for its laid-back atmosphere and hearty breakfasts, and bonus the roosters greet you when you arrive. For a lobster fix, head straight to The Lobster Shack.  Don’t miss Seven Fish for their famous Key Lime martinis, and if you’re in the mood for something bold, 915 Duval has a dish called “the Devils” that you have to try. And finally, for a truly special dining experience, make reservations at Latitudes, which is set on the private island of Sunset Key. It’s a short boat ride away and perfect for a romantic sunset meal. Each of these restaurants showcases the fresh, flavorful essence of Key West.  Bon Appétit!

Libations & FUN!

If you’re in the mood for libations and a little (or a lot of) fun, Key West has you more than covered. Start your crawl at the laid-back Rum Bar, located in the historic Speakeasy Inn, where you’ll find an impressive selection of rums and friendly bartenders who know their stuff. Then head to Sunset Pier for tropical cocktails and unbeatable sunset views over the Gulf—this is the place for happy hour with a view. If you don’t have a chance to book a sunset sail, then Sunset Pier is the next best option.  No trip is complete without a stop at the legendary Green Parrot, a no-frills, all-fun dive bar with live music and a local vibe that keeps people coming back. For a multi-level experience, check out The Bull, but be warned: if you take the stairs all the way up, you’ll find yourself at the Garden of Eden. Yes, believe it or not, it’s a clothing-optional rooftop bar that’s very Key West. If you really want to turn up the heat, plan your trip around Fantasy Fest.  Started in 1979 by a small group of locals to bring visitors to the island during the off-season. Guess what, it worked!  Fantasy Fest is an over-the-top, adults-only, 10-day celebration in October featuring outrageous costumes, themed parties, parades, and a whole lot of uninhibited fun. Cheers to letting loose, island style!

Of course, these are just a few of my personal favorites in Key West. If Key West is not your vibe, then go north, as there’s way more to see in the Florida Keys. 

If you need more travel planning advice, I’m here to help.  Send me an email or direct message on any of my social media channels @travelcharlee

If you are interested in more Florida gems, take a peek at Florida’s Best Kept Luxury Secrets!