Two Days in Key West, Florida

Last week, I took a trip to Key West for two days. Here’s what I did, where I ate, and how I got there.

Travel. We drove to KW from Miami, which took about three and a half hours. The drive there is so beautiful! It includes over 30 bridges, one of them being seven miles long. You pass through Key Largo, Islamorada, Marathon, and a whole bunch of other islands, or “keys”. While there’s plenty of food and shops you can stop at on the drive, we only stopped once for a stretch break and to take a picture at the end of the seven mile bridge. There’s a parking area on the right just as you exit the bridge, and a pedestrian bridge you can walk where people like to come fish.

Seven mile bridge, which has a parking area and a pedestrian bridge where people come to fish! Shorts: Zara | Top: Nordstrom Rack (J Crew) | Shoes: Sam Edelman

Once we got to Key West, we stopped at Five Guys for a late lunch. The first thing I noticed was that there are wild chickens everywhere! We then checked into our hotel, the Herron House, which is located a block away from the famous Duval Street. We actually avoided Duval Street during our stay, but it’s a prime place for souvenirs, food, and lots of entertainment. Herron House was located conveniently in the middle of everything we wanted to see, and we were able to walk everywhere during the trip.

The hotel room had a nice mirror wall and I was able to take all my selfies there.
Dress: Amazon | Hat: Amazon.

Happy Hour. After checking in and taking a much needed nap, we walked over to the White Tarpon, which had outdoor waterfront dining and happy hour. This restaurant has a nice view of the marina, and is located next to some other great food spots. I had a Waterfront Brewery Crazy Lady to drink (this brewery being a short walk away, which we would actually go to the next day), and gator bites to eat! Gator didn’t really taste any different than chicken, just a little chewier. All drinks and small bites were half off during happy hour.

Half off small bites and nice view of the marina, at White Tarpon’s happy hour.

Sunset views. After happy hour, we walked over to Mallory Square to wait for the sunset. Mallory Square was quite busy, and the walkway was lined with all kinds of vendors selling foods and souvenirs, and live music. I got a pineapple drink and a shell engraved with my name on it. The sunset was beautiful, and this is by far the best spot in Key West to go view it.

Catamaran ride and water sports. The next morning, we woke up early and headed out on a catamaran ride. We booked this trip with Sebago Watersports, which included a six hour trip including snorkeling, parasailing, kayaks, jet skis, drinks, and lunch. We left around 10AM, and returned around 4PM.

Siri, play “Listen to the music” by the Doobie Brothers

Cuban Coffee Queen. This little joint has a few locations in Key west, and some great coffee + food! I got a cafe con leche with sugar.

Half Shell Raw Bar. We went here for dinner after our day out at sea with the water sports. Our Sebago trip dropped us off right in front of this restaurant. Half Shell has indoor and outdoor seating, with a great view of the docked boats in the marina. I had calamari as an appetizer, and ordered a sampler, which had shrimp, clams, and mussels. This is the best restaurant to grab dinner if you’re in the mood for some seafood!

Waterfront Brewery. Just a short walk away from Half Shell is Key West’s very own brewery. This place has some great brews + food and a great atmosphere. In the back they have a whole arcade, and you can tour the brewery portion as well! I got a flight of beers, and ended up loving the Key Lime Gose and ordering a pint of it.

Flight of four beers from Waterfront Brewery.

Southernmost point. On the southern (duh) end of Key West is a marker that reads “Southernmost point in the continental U.S. 90 miles to Cuba”. This marker is a great photo spot, and one of the main attractions of Key West. Many gift shops have magnets, key chains, etc. that show this marker! I recommend going early, because a long line forms during the day.

Brunch. We had brunch the next day before heading home, at Two Friends Patio Restaurant. I ordered the crab cake benedict, which was delicious! They also had other seafood on the menu incorporated into typical brunch foods and a key lime pie stuffed french toast, so if you’re looking for brunch with a key west twist, I highly recommend it.

Bucket list for next time. Having only two days in Key West, I’d say I had a pretty good itinerary. Next time, I’d like to see the Ernest Hemingway home, explore the nightlife a little more (sunset cruise anyone?), and spend some time on the beach! I also hear there’s a drag queen show…

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