8 Great Key West Tips For Your Next Florida Keys Vacation

Our quirky, fun, and secret Key West tips include where to find amazing Cuban food, to walk around Key West, and see quirky Conch Republic celebrations and sites.

Key West vacations are magical and every Key West visit is memorable. In the Conch Republic, people are friendly, life is peaceful, and the weather is always gorgeous. Where else in the world can you watch a US Gulf Coast sunset and sunrise over the water on the same day?

Below are 8 Great Key West tips, some pictures and descriptions, and suggestions for things to do in Key West.

1. Getting to Key West Florida

No matter how you travel to Key West FL, it will be a fun experience. Most visitors enjoy the scenic drive from Miami to Key West; Overseas Highway is one of the world’s great scenic drives.

On one Florida Keys trip, I flew into Key West airport for the first time and it is wonderful to see the beautiful islands from the air. Here are the non-stop flights to Key West airport.

If you visit Key West by private boat, well, you are just special.

Also, many cruise ships include Key West as a port of call.

McCool Travel tip: it was less expensive for me to fly to Key West and rent a car than to fly into Miami.

artsy view under the Seven Mile Bridge in Florida Keys
stop at Seven Mile Bridge on the drive between Miami and Key West

Where is Key West?

Key West is 159 miles southwest of Miami International Airport and 105 miles off the Florida peninsula. You will drive over dozens of bridges and islands (keys) to reach the end of the line, Key West. There you will only be 90 miles from Cuba.

Here is a map of Key West FL

Wondering where is the Conch Republic? What is the Conch Republic?

The Conch Republic is as much a state of mind as it is an actual place.

Conch Republic was formed on April 23, 1982 after a boat skirmish in Key West Harbor. In the Great Battle of the Conch Republic, soon-to-be-Conch Republicans (the good guys!) on a schooner tossed conch fritters, stale bread, and water balloons at a US Coast Guard vessel. Rum was most likely also present.

This heated and decisive moment came about after a Border Patrol blockade at the Last Chance Saloon in Key West. This blockade caused a 17 mile back up as authorities checked IDs and for contraband (so the story goes).

Today’s Conch Republic Military is all over the world. The Conch Republic Independence Celebration is one of our top April events on Gulf Coast.

2. Where to Stay in Key West

Like most amazing tourist destinations, Key West has a variety of lodging options.

Instead of a typical hotel, stay in a condo, B&B, inn, guest house, or on a boat. On my last Key West vacation, I found a great place called the Pilot House Inn, on a quiet street just one block from Duval Street. Since I walked in at 6:20pm as the office was closing, I was offered the one available room for less than half the listed price—which was less than the price for the cheapest Key West lodging suggested by a member at the nearby visitor center.

This was a much better room and location—for less money. Note that the Pilot House pool area is clothing optional—”When you stand up, cover up.

US Gulf Coast Travel Update: The Pilot Inn is now Marquesa 4-1-4, across the street from and part of The Marquesa Hotel. I do not know the status of the pool or anything else about the new place. Let me know!

porch of the Marquesa 4-1-4 in Key West
Pilot House (now Marquesa 4-1-4) is a fun place to stay in Key West FL

Key West is one of our Favorite US Gulf Coast Spring Break Destinations

3. Cuban Food in Key West

Since you are as close to Cuba you you can get without being there, you might as well have some great Cuban food. El Meson de Pepe has an incredible location, adjacent to Mallory Square. They serve the strongest mojito I have had (but I have not had one everywhere!) and fantastic Cuban food. Only sit inside if the weather is intolerable—but when will that EVER happen in Key West?

Whereas El Meson is a classic bar and outside eats, El Siboney has great casual Cuban food. Many say it is better; it is definitely less expensive and popular with more local residents (excellent Key West tip). It is a perfect place to order a Materva (rather than a mojito) with your lunch or dinner.

For more places to eat along the US Gulf Coast see: Fun Gulf Coast Restaurants

McCool Travel tip: visit the deli section of Fausto’s Food Palace on Fleming Street, right around the corner from the Pilot House. Every day is a different theme. Thursdays is Cuban food and I got a small container of plaintains for $2.40; it had seven versus the two and a half that restaurants serve.

For more fun Florida road trips, see: Fun Scenic Drives in Florida.

4. Key West Tips: Beaches

Key West is a small island (4 miles long by 2 miles long) and is surrounded by water. It is very difficult to avoid the water—so embrace it. There are countless boating, fishing, swimming, and snorkeling opportunities.

McCool Travel tip: Smathers Beach, along Highway A1A, usually has plenty of free and metered parking. It is a great place to stick your toes in the water when entering the island before continuing into Old Key West.

See our favorite Florida Keys beach: Sombrero Beach

5. Key West Celebrations

Key West always has a celebration. Every day Key West residents and visitors have a sunset celebration in Mallory Square. One local told me the daily sunset is “a gift from God.” Every night on Duval Street is a bacchanalian event. Google “Key West Fantasy Fest” for a real eye opener.

McCool Travel tip: the Westin marina area is less hectic than Mallory Square. This picture was taken there.

photo of an amazing Key West sunset
Key West tips: celebrate sunset every night

The natural sunset is the big draw at Mallory Square but there are also food carts, art displays (and sales), and street performers. My children enjoyed Blue the young Cuban unicycle-riding juggling machine, the Bush Man, and the wacky cat guy in the Westin complex. “Blah blah blah Cho Peen” we finally deciphered to mean “clap clap clap for Chopin”—one of his cats that jumped through a hoop of fire.

McCool Travel tip: Bring some one dollar bills to tip the Key West street performers.

6. Key West Tips: Favorite Attractions

We have visited dozens of Key West stores, shops, attractions, events, restaurants, bars, and more. Here are some of our favorite Key West places to visit.

The Hemingway Home and Museum

Yes, it is true, this property is overrun with cats with six toes. They are fascinating to see up close. But visit The Hemingway Home and Museum for more than the felines. Learn about the life and exploits of Ernest Hemingway, see mementos from his life and family, and explore the property he loved.

Six toed cat at Hemingway House Key West
Six toed cat at Hemingway House Key West

The Key West Butterfly and Nature Conservancy

Leave the mayhem of Duval Street behind and feel your blood pressure drop when you enter the Key West Butterfly & Nature Conservancy. See several dozen butterfly species from around the world, a couple of dozen tropical bird species, and gorgeous tropical flowers and trees supporting them.

Key West Butterfly and Nature Conservancy
Key West Butterfly and Nature Conservancy

Southernmost Point

Taking a photo with the iconic red, black, and yellow Southernmost Point buoy is necessary. But explore the area around the Southernmost Point and learn some fascinating history and trivia.

Key West Southernmost Point
Key West Southernmost Point

Lazy Dog Kayak Tour

Our favorite boat tour in Key West is Lazy Dog Adventures Eco-Tour. They explore mangrove tunnels and regularly encounter sharks, tropical birds, and other marine life. See more at Lazy Dog Adventures.

There are so many other quirky and fun place to visit in key West. Which are your favorites?

7. Walking Around Key West

Once you are in Key West, a car is not needed. You will see lots of scooters, bicycles, and small electric cars. Walking is the easiest and best way to get around.

On one walk along highway A1A, my wife and I saw paddle boarders and kayakers in the mangroves, an Italian guy unsuccessfully trying to spearfish a barracuda, and people from all over the US and the world. Key West is such a fun place to people watch. McCool Travel tip: A great, free self-guided Key West walking tour is around the historic Key West Cemetery.

For more places to visit along the gorgeous Overseas Highway drive, see Spots to Visit in the Florida Keys

8. Quirky Key West

Quirkiness is the rule rather than the exception in Conch Republic. From the official artists to the street performers, wild chickens everywhere, kooky cars and bicycles, you will definitely be entertained. Even the afterlife on Key West is different. Key West cemetery memorial inscriptions include “Devoted fan of Julio Iglesias,” “I’m Just Resting My Eyes,” and this one.

Key West tips: find the humor in the Key West Cemetery
Key West tips: find the humor in the Key West Cemetery

Look for the well-decorated manatee mailbox on your drive between Miami and Key West.

manatee mailbox decorated for Easter in Florida Keys
insider Key West tips: find the manatee mailbox in Florida Keys

Do you have Key West travel tips and tricks to share?

Like this article? Add it to your favorite Pinterest board.

Our quirky, fun, & secret Key West tips include where to walk around Key West, find amazing Cuban food, and see quirky Conch Republic celebrations & sites.

Sharing is caring!