Staying at a Historic Inn in Key West

In August we spent a couple of nights at Ridley House, a 100 year old Historic Inn in downtown Key West. This place was cozy, full of history and within walking distance of countless restaurants, bars and activities. 

Below is our 24 hr Key West itinerary when we visited via the Key West Express ferry. To see the full experience following this itinerary watch our Key West Youtube episode linked above. 

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Morning Drinks with a View

If you are like Skylar and like to start your vacation morning with a Bloody Mary, you might want to start your day (after complimentary breakfast at Ridley House) at Sunset Tiki Bar. We made it there during Happy Hour which meant Bloody Mary's were 2-for-1. We really enjoyed the view of the water and being able to see the variety of boats go by, including the Key West Express ferry.

Now if you are like Jamie and like to start your days on vacation with a latte, you might want to start off at Koffie House. While there were no views of the water here, there were plenty of bright murals to enjoy. We loved that they made several of their syrups and offered seasonal flavors.

The Secret Garden

Nancy Forrester's Secret Garden is one of those destinations you could easily walk past if you didn't know it was there. The entrance is on the side of the house that leads into a backyard that feels like your are in the jungle – surrounded by birds. This place is a home for rescued parrots. The entrance fee is $10 for adults and $5 for kids, which helps support caring for the animals. Each enclosure has information about the birds inside, including their names, what phrases they say as well as their likes and dislikes. At times Nancy herself or a volunteer may be present to share more information about the birds and bring out the ones who are interested in socializing more. Other times the experience is more of a self guided tour.

Lunch at a Diner

For lunch we'd recommend heading over to Harpoon Harry's, but be sure to stop by the ATM first as they are cash only. This place feels like an old diner with a Key West twist. We found the prices to be reasonable and the portions to be large. 

Drinks at the Southernmost Brewery

After lunch we walked over to First Flight, the Southernmost Brewery. It does seem a little crazy that it took us 4 visits to Key West before Skylar got to try a beer here! We enjoyed learning about the building as it was the original location of Pan American World Airways. 

Live Music in Key West

After the brewery we were on a mission to experience some of the live music scene Key West is famous for. We started out at Hog's Breath Saloon, which is exactly what you'd expect in Key West, an open air joint, with brick floors and roosters roaming around. 

Next we made our way to the water to experience a true Florida dive bar, Schooner Wharf. This open air bar has been in business since 1984, and it looks like it has been collecting items since way before then!

Our third music stop was Surly Siren, which is located across the street from Mallory Square, on the 2nd floor above a $5 shop. While you might not see it right away, you can definitely hear the live music blocks away.

Not your Typical Burger Joint

After bouncing around to the different live music spots, it was finally time for us to grab some dinner, which took us down Duval Street to Frita's Cuban Burgers. Their burger patties are a mixture of beef, pork, chorizo and Spanish spices. We tried their yucca fries and the Frita Confundita, which translates to confused Frita. Skylar thought they were the best yucca fries we've ever had, and Jamie loved the unique flavor of the burgers as well as the non traditional toppings.

Unplanned Late Night Stop

On the way home from Frita's we walked passed Sloppy Joe's and we couldn't resist stopping in. An energetic cover band was playing that had the dance floor packed. If you are looking for a great spot to dance to live music, Sloppy Joe's should be on your list.

Morning Coffee

The next morning we walked down to Front Street to grab a coffee and do some shopping. We stopped in at Caribbean Coffee. This place was light and bright and offered a couple homemade syrups. If you do stop in, keep in mind that they do not have a public restroom so you will have to walk over to the Shops at Mallory Square.

Early Happy Hour

After shopping we stopped in at Pepe's Cafe, which is known as being the oldest eatery in the Florida Keys (and the 2nd oldest in the state of Florida). Pepe's has and open air patio and a small interior space. We chose to eat inside to take a break from the heat and had to try their peel and eat shrimp and fish dip. We really enjoyed both items, as well as their variety of hot sauces and the cheap beer!

Dessert on Duval Street

After happy hour we had to head to one of the best rated dessert spots in all of Key West, Mattheessen's. While they offer giant cookies and Key Lime Pie, we were visiting to try their homemade ice cream, which did not disappoint. We found it to be creamy, thick and full of flavor.

One Last Drink

Before heading back to the ferry terminal to board and go back to Fort Myers Beach, we had to stop and Dante's Pool Bar. This place is right next to the ferry terminal. Here you can enjoy a drink in the pool or just soak up the energetic vibes. We happened to visit during Happy Hour and were able to enjoy 2-for-1 beers.

The end of our Key West Getaway

Our ferry ended up leaving a bit early (it was scheduled for 6 pm) and we made it back to Fort Myers Beach before 10 pm. But we still had to drive home from there. We were exhausted from everything we packed into our quick Key West getaway. After a few days of editing and recovering we got back out to start filming another Florida episode. If you don't want to miss our future Florida adventures and travel itineraries, be sure you are subscribed to our YouTube channel and follow us here on Plannin!

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