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A 5 Day Romantic Getaway in Key West

A Key West Itinerary

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View from Fort Jefferson

Key West is the last key in the Florida Keys, located just 90 miles north of Cuba. It is a unique location that gives the feel of a Caribbean vacation, but is accessible via vehicle from the continental US. Key West offers great beaches, great food, great nightlife, and plenty of water activities. Our trip to Key West began with some setbacks at the airport, but turned out to be a great experience!

Amongst many airport delays we ended up renting a car and driving the 190 miles from Fort Lauderdale to Key West, Florida (and I am glad we did). Hearing that the island was very small our original plan was to get around by foot or public transportation. I cannot say how glad I am that we ended up with the rental, it definitely came in handy! The best part, however, was the drive on the Overseas Highway. The views were stunning and stopping in each Florida Key was a great and unique experience! If traveling to Key West, I would definitely recommend driving the Overseas Highway. We arrived at our destination at approximately 11pm and luckily just in time to check into the hotel before closing.


We stayed at Simonton Court, located just one block away from Devaul Street and three blocks away from Mallory Square (I will get in to these later on.)  Right on arrival we were greeted by pleasant staff and beautiful scenery. Despite being located in the middle of town, it truly felt like a secluded getaway. The property is covered with trees and fences with private courtyard areas that make you feel like you are away from it all. The property has 4 swimming pools. We stayed in the second floor townhouse which featured a jacuzzi. It was very clean and home like. The property even had a friendly cat that hung around during our stay and joined us for dinner meals on the balcony. The only somewhat negative thing I could say about the property is that the parking lot is located around the corner and is a short walk away, but compared to the benefits this is a very minor inconvenience.


We started the first day out with some water sports, including our attempt at steering a sail boat, kayaking, kayaking, and parasailing, followed by some relaxing time on the beach. Kayaking was a great experience and everything went well. The sail boating though-I can’t say the same. We were provided lessons on sail boating, but as soon as the guide left, we found ourselves sailing off to sea with little we could do (or knew how to do). The guide had to run out through the water to catch the boat before we were too far out  (he received a large tip). Parasailing was also a great experience. The thought of it was very scary at first, but I was determined to do it. Once up in the air I quickly discovered that it was not scary at all. The views were great the breeze was a nice break from the hot summer air (did I mention this trip was in August? ).

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Day two we spent with Sunset Watersports on a Safari Snorkel Tour. This was quite an eventful trip.  We spent the day snorkeling and exploring unpopulated back country beaches. The views were stunning and it was great to get away from the crowds and enjoy a relaxing walk along the beach. All went well until we were headed back to shore. My boyfriend at the time was driving the mini speed boat, his first time doing so. Driving back he was not paying attention to the warning signs and ended up steering the boat into low water and entangling us in seaweed. The rescue crew had to be sent out to tow the boat back into deeper water. Embarrassing, yes, but it has turned into one of my clearest memories from the trip.

The third day was spent on a day trip to Dry Tortugas National Park. We took the approx. 2 hr. and 15 min. boat ride to the Fort Jefferson, where we spent the day exploring the historic fort and snorkeling the shoreline. If you are a history buff, this is a must on your trip to Key West! Even for those who are not big on history, exploring the tunnels of the fort and climbing to the upper levels will provide you with an unforgettable experience and stunning views.

Day four was spent exploring Mallory Square and Devaul Street. Both locations offer great shops and restaurants. We ate at the Hard Rock Café, but Duvaul Street offers many great options for seafood, Mexican food, and Italian food, as well as some fast food options. And of course don’t forget Key Lime Pie! Devaul Street is lined with many brand name shops as well as many local, smaller souvenir shops. We also spent some time exploring the Key West Aquarium, which I have to say as far as aquariums go was not that impressive, but was a nice break from the summer heat.

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The morning of day five was spent relaxing at the hotel and enjoying the pools. After checking out we spend some more time walking Devaul Street and finished our trip with some relaxing beach time before heading to the airport to head home.

Key West is a great location for a romantic getaway and has no shortage of great activities and experiences. When traveling to Key West a couple tips for making the most of it include:

  1. Drive! While you can get to Key West via plane or boat, the Overseas Highway is a great option. It provides stunning views and takes you through the many Florida Keys.
  2. Don’t forget the sunscreen! Key West is an island, and with that comes many outdoor/water activities. If you forget your sunscreen your skin will likely pay the price (Trust me-I learned the hard way!).
  3. Avoid going in the summer if you can! Our trip was in August and it was hot! If you can go during the cooler months the weather will be more pleasant (although prices may be higher). You have to find the happy medium.

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