Key West {Trip Report}

After returning to D.C. after the holidays, I learned I needed to take a work trip to Miami. Since my work meeting was taking place near the end of the week, Nick decided to join me so that we could take a long weekend and drive down to Key West.

Nick and I have traveled to Miami before and explored much of the South Beach and downtown area, so for this visit we headed to Miami’s Wynwood neighborhood, an area that recently boomed in popularity and one that we hadn’t yet explored. Wynwood is known as Miami’s new art district and is home to dozens of art galleries, museums and small craft businesses.

The area we visited is still very up-and-coming, with cafes and shops sprinkled in between industrial buildings. We started our visit off at Miam Cafe, where we dined outside on some very good quiche and breakfast burritos and the cutest little coffees, while soaking up the warm morning sun.


Nick and I came to this area specifically to visit Wynwood Walls, where incredibly talented grafiti artists showcase their life-sized, colorful drawings on the exterior walls of what used to be decrepit buildings.

Nick and I were blown away by the talent of the artists; I’d definitely recommend a visit if you are in the area.

NickSaraMural Mural1



We explored for a few hours before I had to head off to my meeting. The next morning we hopped into our rental car and started our road trip down to the Keys. The trip is about 150 miles (or 3 hours with no traffic) down U.S. Highway 1, the only major route into and out of the Keys, which can be problematic on busy holiday weekends when heavy traffic clogs the flow.

Some stretches of the highway are scenic, with bright blue water visible on both sides of the road, and some stretches are not. 🙂


One of the most popular parts of the trip is along the scenic Seven Mile Bridge; Nick and I were able to thoroughly enjoy the view from there since we ended up behind a group of bicyclists touring the U.S. and slowly crossing the bridge with a police escort (it took us 45 minutes to cross the seven miles!).

As we’ve often done before, rather than book a hotel, Nick and I rented a small one-bedroom apartment close to the popular downtown area through ( is another of our favorites).

The apartment was small, but very conveniently located, and was equipped with everything we needed.



Our first stop was to the bike rental shop. Roads in downtown Key West are congested and parking is limited; however, the city is very bike friendly and pedaling is probably the best way to get around the small downtown.

Nick and I rented two bikes for 3 days from The Bike Shop, which was about 50 feet away from our rental, and the cost was only about $75.


Our first stop on our bikes was to Fort Zachary Taylor Historic State Park; it’s rocky shore on the west side of the island is a popular and peaceful place to catch the sunset. (There is a small admission fee, I believe it was $4 for Nick and me; cars cost a few dollars more.)



One thing I didn’t realize before visiting Key West, is that the area isn’t known for its beaches, and in fact, only has a few small sandy areas for swimmers (this state park is one of them).

The following day, Nick and I booked a sailing/snorkeling/kayaking adventure with Danger Charters. I’d definitely recommend them – the cost was reasonable, the staff was fantastic and the boat only had room for about 15 guests. Key West is crowded with boat tours, but many of them are packed uncomfortably close and party-boat style (think drunk people and thumping music…something we wanted to avoid).


The guides were very knowledgeable about Key West’s history – the reefs and shallow waters offshore (in some areas the water is measured in inches) caused many ships with valuable cargos to run aground. As a result, wrecking and salvaging soon became the island’s primary business and its shyster citizenry became very wealthy since local law allowed them to take possession of any cargo from ships they rescued.

We kayaked around a small island named Mule Key (named for a local man who often tied lanterns around the necks of mules that wandered around in the shallow waters and lured in unsuspecting boaters who thought they were heading toward a lighthouse and eventually wrecked…the man was hung in Mallory Square for his misdeeds).

We saw all kinds of birds, jellyfish, crabs and stingray on our trip around the islands. Here I am holding a horseshoe crab (Nick and I often see the skeletons of these along the Chesapeake Bay shore, but we’d never seen a live one).


After kayaking, we sailed the boat to a nearby area and donned wetsuits for snorkeling. The water is very clear and we did see some fish and reefs, but after about 20 minutes, the cool water temperature (around 70 degrees) forced us back into the boat.

After the day’s adventures, the charter also provided us with fresh fruit and snacks and beer and wine, which we enjoyed while relaxing and making our way back to port, watching the most glorious sunset over the water.



On our last full day in Key West, we spent the time riding around Key West and hitting all the sightseeing spots we missed earlier in our visit. Duval Street is the center of activity in Key West, running north and south from the Gulf of Mexico to the Atlantic.

The north end of Duval Street (near Mallory Square) is where large cruise ships come into port and the thousands of passengers make their way into the city. This area is very commercialized with many t-shirt and trinket shops selling mostly the same goods and lively, well-known restaurants and bars. 




While Nick and I enjoyed walking through the touristy area, we much preferred the quieter and less crowded south end of Duval Street, which was filled with cafes, art galleries and higher end clothing and home decor shops.

While at the north end, we stopped into Sloppy Joe’s, Key West’s oldest and most well-known bar, and a favorite of author Ernest Hemingway.



Nick and I couldn’t resist getting our picture taken with the Southernmost Point marker. (FYI, there is a picture line that starts at sunrise and ends after dusk, so there’s no avoiding the wait, especially if a cruise ship is at port, but we only stood in line about 10 minutes).


We also stopped at another well-known Key West landmark…mile marker 0 of U.S. Highway 1, which stretches up the entire East Coast from Key West to Maine.


Overall, Nick and I enjoyed our time in Key West and had perfect weather (the forecast was for overcast skies and rain for most of the trip, but we completely lucked out with warm temperatures in the high-70s and not a drop of rain).

Three days felt like the perfect amount of time to spend in Key West; without beaches or a pool to hang out at our rental, we probably would have gotten bored with any more time in the city.

Here are our Key West recommendations (provided by a friend who visits often and another who lives there):


  • Fort Zachery State Park (beach and sunset)
  • Southernmost Point marker
  • Sail/kayak/snorkel (Danger Charters)
  • Rent bikes and tour the city
  • Shop and people watch on Duval Street
  • Tour the butterfly museum


  • Blue Heaven (brunch)
  • Flaming Buoy Filet Company (dinner)
  • Sandy’s cafe (lunch – get the Cuban sandwich)
  • Sloppy Joes (drinks)
  • Louie’s Backyard (dinner/drinks)
  • Conch Republic Seafood Company (lunch or dinner)
  • La Tee Da (brunch/lunch/dinner)

6 thoughts on “Key West {Trip Report}

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