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Top 10 Key West Plus One More

Top 10 Key West – Plus One More

I absolutely love the Florida Keys and Key West! It’s like a little taste of the Caribbean right in the US.  It’s a doable drive from Orlando and worthy of the drive it takes to get there.  You can easily add it onto your Disney World & Universal Studios vacation or make it a vacation all it’s own.

Key West Sunset from Mallory Square

I was easily able to compile a top 10 must do’s in Key West.  The harder part was keeping it to just 10 must do’s.  I couldn’t and wound up capping it at 11.  There’s so much more to do but let’s get this Key West party started with these 11.

1. Old Town Trolley Tour or Conch Train in Key West

Old Town Trolley Tour Key West

I absolutely love the Old Town Trolley Tour in any city I visit.  It’s the perfect way to get a feel for the city and a broad overview of all there is to do. 

Key West is no different.  Start your vacation in Key West with the tour so that you have a full picture of all there is to see and can get a lay of the land.  Key West is a small island so you can do the tour in a day.  We picked the Old Town Trolley Tour because it had more stops and covered the whole island whereas the Conch Train Tour only converted a portion of the island.  Choose what’s best for your family and hop onboard. 

Another thing I love about the Old Town Trolley Tours is the history and fun facts about the area you’re visiting.  Sure you can walk or drive by any of the sites on your own but you won’t necessarily know what you’re seeing or why it’s there. 

Old Town Trolley Tours are hop on hop off and therefore a great means for transportation in the area you’re visiting.

2. Rent a Bike 

Renting and riding bikes in Key West

Seems silly but bikes are a way of life in Key West!

All of the streets are bike-friendly including the busiest of streets like Duval.  There’s bike parking everywhere and truthfully it’s much easier to park a bike than a car! 

But the thing I loved most about riding a bike was taking the back roads with the breeze in our hair and seeing all of the Key West old historic homes. 

My husband was not thrilled we were doing this but I’d say afterward everyone was appreciative we took the time to see the town by bike.  It was more than we could cover on foot but definitely a different view than you’d see by car.

To rent bikes I suggest using Island Safari Rentals which is located just south of Duval and within walking distance of the cruise port and Mallory Square.

3. The Key West Butterfly & Nature Conservatory

flamingo at the Key West Butterfly and Nature Conservatory

Trust me on this one.  Personally, it was not high on my must-do list but my mom was with me and really wanted to go.  I’m all for experiencing things I wouldn’t normally pick on my own and getting a feel for new ideas and exploration.  So I dove right in! And it was well worth it! 

The greenhouse atmosphere was tranquil and exciting full of tropical plants, which I love and more butterflies than you would think possible. 

Plus the two flamingos, Rhett and Scarlet, added to the ambiance and fun.  Definitely stop in at the Key West Butterfly & Nature Conservatory for an hour, that’s about all it takes.  The kids will enjoy it too!  What kid doesn’t love butterflies and flamingos?  Keep your eyes peeled for a few other animal friends as well like baby birds, turtles, and fish!

4. Duval Street

Duval is the main street through “Old Town”, the “drag” if you will. 

It starts near Mallory Square at the Gulf of Mexico and ends 1.25 miles south at the Atlantic Ocean.  The street is filled with historic buildings turned museums and stores with some great Key West fare. 

Along the street, you can see the original Jimmy Buffet store, old theater, and oldest house.  Not to mention Key Lime everything from pie to drinks along the way.  Walk or bike the whole length, and enjoy the coastal laid back vibe.

5. Mallory Square

Mallory Square Sunsets in Key West Florida

This historic square is home to some of the best sunsets!  Really, they’re glorious here!

The square is named after Stephen Russel Mallory, a US Senator and born and raised resident of Key West. Locals and visitors arrive two hours before sunset to enjoy music street performers and Key West vendors prior to being mesmerized by the Southernmost Sunset.

It’s possible you’re thinking a sunset is a sunset, or I can skip this one.  I was kinda on the fence about going to a specific location to see the sunset too.  But I have never been more mesmerized by the beauty of the ocean and the ever-changing colors in the sky.  Make sure it’s on your bucket list!

6. Key Lime Pie AND Chocolate Covered Key Lime Pie on a Stick

Gluten Free Key Lime Pie at Kermits in Key West

Let’s talk, Key Lime Pie in the Keys is the BEST you’ll ever have! 

Add it to a stick covered in chocolate and where could you possibly go wrong?  My first encounter with Key Lime Pie on a stick was this trip.  I shouldn’t really eat this seeing as how I have a gluten and dairy allergy.  But, I did.  And it was worth it!  (Please note, I don’t have celiac’s, only an allergy).

Key Lime Pie in Key West is one of the best flavors I’ve ever tasted.  You can find these at Kermit’s Key West Lime Shoppe, which has several convenient locations in Key West.

You should know that when you add chocolate to the Key Lime Pie it takes away a bit of the tangy flavor from the Key Lime.  Both versions are so good!  And for my gluten-free friends, don’t despair Kermit’s had a gluten-free Key Lime Pie too! 

7. Ernest Hemingway House

Ernest Hemmingway House in Key West

I was only mildly interested in the Ernest Hemmingway House.  I can’t say I have some great love for Hemmingway or his writings but I do love houses, architecture, and history so that helped to peak my interest. 

The house and grounds tour did not disappoint!  The grounds are well kept and the stories that you’re told on the house tour helped to bring the history alive and understand a bit about Hemmingway and his somewhat tragic life. 

The 6 toed cats that are lazily sleeping EVERYWHERE we’re especially fun.  They’re all descendants of Hemingway’s original 6 toed cat Snowball and are loved and taken care of by the staff.  Visiting the Hemmingway House is a must on your Key West vacation.  It takes a few hours and is well worth the time.

six toed cat at the Ernest Hemmingway House in Key West

8. Chocolate Martini at Martins

Chocolate Martini at Martins in Key West Florida Duval Street

Move over Key Lime Pie Martini, yes you were fabulous but the Chocolate Martini at Martin’s on Duval takes the cake. 

This rich yet sophisticated chocolate flavor is made with custom Belgian chocolate liquor right there in the kitchen. It’s rich enough to share but I’d be lying if I said I couldn’t finish it on my own!

9. Eat at the Conch Republic Key West

Peel and eat shrimp at Conch Republic Key West

Conch Republic is a Key West staple and one we eat at each and every time we visit! 

The food is amazing, how can fresh seafood not be good?  And the atmosphere is even better!  The restaurant is a large open-air space right on the marina and water. 

A live band is often playing and the outside is bustling with boat activity.  The marina is home to boats of all sizes including deep sea fishing charter boats and private yachts.  My personal favorite is the Key West Pink Peel & Eat Shrimp.  I swear they’re the biggest shrimp you’ve ever seen!  I also love the Blackened Shrimp dish with Cuban Rice.  Yum!

10. Southern Most Point & Mile Zero

Southern Most Point icon Key West Florida

It’s a must-do for anyone visiting Key West.  Yes, it’s a bit of a tourist attraction but that’s ok!  Be the tourist and take it all in!  Check it off the bucket list and snap your picture next to both the buoy and the Mile 0 street sign. 

Note that these lines can be long and it is sunny and hot.  Pack your patience and go early in the morning or later in the evening shortly before dark.  The heat of the day can be tough.  Bring your umbrella not only for rain but more so for shade while you wait outside.  You can thank me later!

And my bonus MUST do in Key West…

11. Get on a Boat in Key West

boating in Key West Florida

The type of boat you choose is up to you but it’s a must when you’re in the Keys! 

Pick from a large group Sunset Cruise or a Private Charter Boat for deep-sea fishing.  Or if you’re comfortable you can rent a boat on your own to explore.  Don’t worry, they’ll give you directions on landmarks to follow so you can return safely to the island.  Jet Ski Tours are also available and another fun way to see the mangroves and sandbars in the area.

Here are a few suggestions on how to get on a boat!

I hope you enjoy your Key West adventure!  If you’re looking for the perfect hotel or home rental in the area please email me for options!   I look forward to hearing from you!


*Links in this post may be affiliate links and provide me with a commission when you book through them.  Thank you for your support of my small business.

Jamie Rumph
Jamie Rumph
Hi, I'm Jamie, traveling mama, entrepreneur, and travel advisor. I'm addicted to Disney, traveling and exploring the world with my family, and have a passion for helping families experience the magic of travel. My home is filled with love and chaos, 2 crazy girls, 2 large dogs, and the most spectacular architect and Disney Cast Member I call my husband. We live in Florida and spend our weekends playing at Orlando's many theme parks and visiting the beach. In 2015, after helping numerous families plan their vacations to various Disney Destinations, I started a blog to answer all of the many travel questions I received daily. In 2016, the blog grew into a travel agency, and Love of the Magic Vacations was born. With a team of nearly 20, we spend our days creating family vacations around the world. What started as a blog is now a full service, worldwide vacation destination planning service. I create custom itineraries for each of my clients that not only meets but exceeds expectations. There is no greater gift than making memories while sharing the world and its cultures with your kids.


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