In the Email Travel Guide series, I share messages from my friends who are amazing at researching and writing travel recommendations. This guide comes from David, a Miami native whose friends from up north traveled to the Florida Keys and needed help planning their trip. If you’re looking for a local’s guide to a Key West road trip, this is it. Enjoy!


OK so a lot of this depends on how you want to do division of time available AKA I am giving you too many options. After you read all of this and figure out your planned times for returning to the Miami area we can move on to the next list of activities.

On the drive down…

Option #1 = Knaus Berry Farm – extremely famous locally for their Cinnamon Buns – like you buy 3 dozen at a time famous. They have a separate line for their milkshakes (strawberry is my fav) which are also fantastic. Lines can be long but a) you are going on a weekday plus b) it is getting near the end of their season (they close for summer) = should not be too horrible of a wait. If it looks bad I would go to…

Option #2 = Robert Is Here – not as locally famous but extremely well known specifically for their milkshakes (again still all about that strawberry). They are primarily a fresh fruit stand so tons of other delicious stuff if you so choose to be healthier than I am.

I wouldn’t say no to you doing Robert is Here on the way down and Knaus Berry on the way back and bringing me some buns hahaha (way to hard to pull off probably as you will see below)

Both of these are before you even reach the northernmost Key **make sure to check traffic from here** 90% of the way down it is a 1-lane highway which can cause traffic concerns naturally. At the north part of the keys there is a side route called Card Sound Road which will bypass traffic; but if there is no traffic than it is equal time/not needed. Obviously this is very important to check on the way home too.

I am gonna put a list of things at the end that are items that are of note/options/ideas that exist along the drive. Naturally will not be able to do all of them but why not provide, right ::shrug::

In Key West!!

Key West road trip travel guide - Frayed Passport


I really don’t have a place for you to stay…they are all basically the same so pick on price. Plus, you won’t be in the room much anyway so who cares. Last time me and Sarah went down we stayed at Pegasus International Hotel which was basically a semi-nice hostel lol. But it is very centrally located. If you can get something cheap on Duval St., that is the goal as that is the main avenue of the whole Key.

You NEED to end the physical day at Mallory Square – this is the THE place that everyone goes to watch the sunset. There are street performers and some restaurants (although these get full very early) and basically just sit on the pier to watch the sunset. If you want to avoid the crowd there are sunset cruise type of options. Sarah found this one which was lovely – although 40% of the entertainment were these 4 really drunk gay guys with us. Was like 10-12 people total, very low key. It is not that pricing in the middle of the page – it is the one off to the right for like $75 per person.

The whole Key is relatively small – takes about 30 mins to walk it from end to end. Therefore, while the end point is Mallory Square, I would start on the other side at the Southernmost Point – marquee picture spot and lovely view. Walking up Whitehead street there is two points of interest. The Key West Lighthouse and the Ernest Hemingway Home…happen to be across the street from each other.

The Lighthouse is self directed – naturally would be doing it for the views. The Hemingway House has guided tours with history of Hemingway facts etc.

Off the beaten path, and we didn’t actually do the tour etc. because price seemed like a waste is the Truman Little White House. It was still a nice place to walk to but we were generally over there because it was a block or so away from a microbrewery called First Flight Island.

If you don’t go that route then really just go up to Duval street and walk across the Key and stop wherever. Tons of shops and restaurants; we just picked food at random based on menu looking enticing. Every place is going to be seafood heavy but probably won’t steer you wrong. We did end up one night (across the street from hotel) at a BBQ place called Charlie Mac’s which had absolutely phenomenal sauces and brisket burnt ends!

Key West road trip travel guide - rum! - Frayed Passport

Before sunset but on that side of the island are 2 rum distilleries. We liked Papa’s Pilar better mainly because they gave a lot more free samples hahaha. It is associated with Hemingway via a licensing deal not directly endorsed. The other, which is only a block away so might as well go to both, is Key West First Legal Rum. Very small but cool – missed the tour time so not a lot of info.

If you end up at Mallory Square for sunset vs. boat cruise – there is no booze sold directly on the pier. So either get there early enough to be at a restaurant (we were looking at Sunset Pier)…like Knaus Berry going on a weekday should mean it is easier for you. If not restaurant then double fist mojitos from El Meson De Pepe’s.

Post sunset is obviously made for bars. The most famous one is Sloppy Joe’s – there is some history there where it wasn’t the true “original” one but still a big crowd pleaser. The true “original” location is across the street at Capt. Tony’s Saloon. Outside of those two bars are bars to stumble around and have a good time.

Random Things on the Drive Down

Key West road trip itinerary - Frayed Passport

If you take Card Sound Road…there is a very chill bar called Alabama Jacks – legit the only thing that exists on the entire route. If it is a nice day out it is just pleasant place situated on a river in mangroves…also has some good redneck people watching.

Key Lime Pie!! An absolute stop off at some place. There are millions of opinions on what is the best version yada yada yada. Actually wasn’t something I was super into as a kid so I don’t have a lot of recommendations but the one I know of that is quality is Mrs. Mac’s Kitchen. It is relatively far north so it is one of the first things on the way down or last things on the way out.

Breweries!! Two of them are known, very good, and wide selection. Both are actually pretty close to each other in Islamorada which is in the mid-70s mile marker area I want to say AKA around 1/2 way. Florida Keys Brewing Company and Islamorada Beer Company. I would pick Islamorada over Keys if I could only do one but only because they are my style of beers.

Food!! Same as in Key West there are tons of places that you could go to eat depending on type of cuisine/price point/level of casual you want…

If you will be around for sunset hands down aim for Marker 88 – also in Islamorada – outside seating, bar, small dock, great views, solid food.

Functional food AKA delicious Mexican – also in Islamorada hahaha – Puerto Vallarta…hot sauce is absolutely fire (kinda a theme for me).

Following 3 are all beach bars that serve food…choice is most likely made based on what time you are driving as they are all at differing distances.

Key West road trip travel guide - Florida Keys Brewing Company - Frayed Passport


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About the Author

Sarah Vandenberg

As the managing editor of Frayed Passport, my goal is to help you build your bucket list, plan your travels, and tell your story. I've been to 19 countries and five continents so far, and while I'm based in Miami, I spend one-third of the year traveling to amazing destinations around the world. If you would like to contribute an article to Frayed Passport, feel free to get in touch with me at sarah@frayedpassport.com!