My First Time in Key West

Several months ago, I received an invitation from the team at the Pier House Resort & Spa in Key West to journey down to Florida last month for a long weekend away. I have to admit, I was initially skeptical, as I didn’t think the Florida Keys were my type of vacation, per se. But, I was open to being pleasantly surprised, and after some research on the property, I made the decision to head down with my boyfriend the first weekend in September.

The Pier House sits at the top of Duval Street, which anyone who has ever visited Key West knows is the primary vein of the island. You’re walking distance to loads of restaurants and nightlife options. One of the other great features of the property is a rare private beach. Key West isn’t necessarily known for its beaches (something I didn’t know until I got there), but thankfully, you can dip your toes in the sand without leaving the property.

The Deluxe Ocean View Suites are the best option at a property like this. You get stunning views, a huge bath tub (win!), and thoughtfully decorated rooms with homey touches. For someone like me, who doesn’t have the luxury of fully unplugging while traveling, these suites offer the perfect balance of a place to escape and get some work done as well. And answering emails is always better done with a view, amiright?!

A quick walk from the property, you’ll find Eaton Street. Here you’ll cast your gaze on some of the most picturesque homes on the entire island. The architecture reminds me a bit of New Orleans, but it still has a dose of tropical charm.

One of our favorite parts of the trip was getting out onto the water. We found a small private charter, called Sunset Sail Key West, and boy am I glad we did. It was a sweet, and salty, escape. And, we counted our lucky stars as the massive sunset charters sailed around us with people packed bow to stern, with music blasting. That is definitely not my idea of a relaxing night on the water. The crew with Sunset Sail Key West was super nice, and even snapped the below picture without us even knowing and sent it to us after. So thankful!

After the evening on the water, we stopped into Half Shell Raw Bar for a casual dinner featuring oysters, shrimp, and a tasty finish of a token slice of key lime pie. If you’re looking to just pull up a picnic bench and crush some raw bar, this the place to do it. Make sure to check out all of the license plates on the wall — I found a few from my home state that made me smile.

Oh, and the plethora of tasty eats continues with our favorite meal of the trip — brunch at Pepe’s, the oldest restaurant on the island. And, they’ve stuck around for good reason! We crushed their specials of the day, and devoured our favorite slice of key lime pie on the trip. The spot is first come, first serve, but totally worth the wait.

The walk back to Pier House is full of little gems like the ones below.

After a tasty breakfast at Pepe’s, we headed to La Concha, Pier House’s sister resort, to experience a massage at Top Spa. This is the highest building on the entire island, and boasts some pretty impressive views. They have a few cabanas outside to lounge in while you wait for your service, or after you’ve been pampered, and the spa suites are spacious, with couches, and plenty of room for a couple’s massage, which my boyfriend and I love to try to fit in on our trips.

After, we headed to the other side of the island to check out lunch at a new spot: Matt’s Stock Island Kitchen & Bar. Everything on the menu is delicious, but make sure you get the crab beignets; you won’t regret it!

On our final day on the island, we skipped over to a house that is equally photogenic as it is interesting, the Ernest Hemingway Home. It costs $14 a person to get in (a little steep in my opinion, but still worth it). You go for the history and architecture, but you stay for the kitties. The place notoriously has cats everywhere, and they are so relaxed and adorable. If I was having a bad day, I would go here with a handful of kitty treats and just live my best life. We didn’t get to stay here quite as long as I would have wanted to because we had to rush off to the airport, but I would definitely add this stop to your itinerary on your future trip.

The day ended with us rushing to the airport, only to be met by a delayed flight notification. My boyfriend notoriously jokes that I have the worst luck with flights. Considering the ratio to delayed and cancelled flights with how many I take a year, he’s not wrong… However, I used my wherewithal to get us rebooked on another airline (for free) out of the island, so we could make a connection back home. Winning!

While we were waiting for our other flight, I had some time to reflect. While Key West is notorious for being a party town, there is definitely a few good opportunities to have a refined vacation on the island. If you’re looking for something a little more low key, don’t rule Key West out.