The Basics
Who & Why: My very first trip to the Florida Keys was on a spontaneous January trip with 2 car loads of college friends and we drove from Wisconsin and spent time exploring all of the Keys. This trip was a long weekend getaway. Three of my friends and I went on a girls weekend getaway to run the Key West Half Marathon. Two of my friends are working on a 50 states challenge with a half or full marathon in each of the 50 states. Between the four of us, we race a variety of running races and triathlons throughout the year, but we choose one destination race to do with our group of four every year.
What: 3.5 days
When: The race fell over MLK weekend which gave us a long weekend in January.
Where: We wanted to stay close to the ocean and walking distance to the race and all of the fun Key West has to offer. We chose the Pier House for the location, ocean views, beach, pools, spa, and great restaurant.
Learnings
What I’d Do Again
Located at the southernmost tip of the continental United States, Key West is a vibrant island oasis known for history, culture, food, and endless opportunities for fun. Known for its laid-back atmosphere, stunning sunsets, and eclectic charm, this tropical paradise makes a great weekend getaway or even a longer vacation. From the bustling energy of Duval Street and the literary legacy of Ernest Hemingway to the tranquil beaches and crystal-clear waters of the Florida Keys, Key West captivates with its unique blend of relaxation and adventure.
The race was awesome, very well organized and an absolutely gorgeous route along the ocean and through some of the best parts of Key West. As a group of four working moms, our day to day lives are packed. So on this long weekend we opted for the less is more approach. Other than the race, our only planned excursion was a snorkeling trip. We went with a company called Fury Cat. The company has a ton of different types of trips available. This took us 7 miles south of Key West to a reef. Although it was a bit of a choppy day when we went, we still saw some cool fish and even a shark! The staff was amazing and we had a ton of fun enjoying the post snorkel happy hour.
On my last trip, our group enjoyed going to each of the Keys and exploring all of the different beaches and little towns, but for this trip we stayed in Key West. Our group walked everywhere and never felt the need for a car. We loved just being able to stop wherever there was good live music or something we wanted to see. If you had a longer trip, a car might be nice to explore the rest of the Keys. We all absolutely loved laying by the beach and catching up, listening to music, and having time to read.
Every meal was delicious and offered fresh flavors and live music around every corner. Our restaurant selections ranged from casual walk up spots for coffee or snacks to some nicer dinners. We also made sure to try a lot of different slices of Key Lime pie. Our favorite breakfast spot was Blue Heaven and we really loved our dinner at La Te Da.
What I’d Change
We all shared that we wouldn’t change a thing, but rather that we’d come back in a heartbeat. Next time I visit, I’d like to take a trip to Dry Tortugas. It’s accessible by ferry or seaplane, and Dry Tortugas National Park is a must-see for nature and history lovers. The park is home to the impressive Fort Jefferson and offers pristine beaches, crystal-clear waters, and excellent snorkeling and diving opportunities.
Tips for Travelers
Make your restaurant reservations early if you want to eat at some of the fine dining restaurants for dinners, especially if you have a larger group. If you’re looking for nightlife, plan to stay right in the Duval Street area of Key West. If you’d like access to more beaches, you could stay further out from Key West to explore each of the small towns.
Final Words
Key West is a magical, quirky, vibrant little island that feels worlds away, famed for its sunsets, turquoise waters, and cute little houses painted in the pastel pinks and greens of the Caribbean. The vibe is low key, amazing food, sunsets, and more. If you’re looking for a nice long weekend getaway or an escape from winter, this is the place.
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