As you may have gathered from all of my recent fashion posts (here, here, and here), I recently had the chance to visit Key West, Florida. My friend and photographer Maritere and I ventured down to the southernmost point in the the continental US for a fun adventure. While we were only there for a weekend, we managed to see and experience quite a bit – particularly in the way of food apparently! Keep reading for all of our Key West recommendations, plus a photo diary of sorts from our trip. Many thanks to Maritere for capturing the essence of Key West through photos so well!

Key West Recommendations

As I mentioned, we were only there for a weekend, and it was the first time for both of us. We are both big believers in exploring by foot – or on bike, as is often the case in Key West. Whether in Key West or Europe or Asia, exploring a place by foot allows you to experience the location in such an authentic, natural way.

So, we opted not to do any boating excursions or any tours this time. Instead, we just wandered around the island. If you are at all familiar with Key West, you’ve probably heard of Duval Street. This famous street runs about a mile long, the width of the island. Many fun restaurants and shops are situated on this street. However, I must say that our favorite finds were off the beaten path. There are so many charming homes, beautiful trees and flowers, and lovely people to encounter away from the main hubs.

Hotel Recommendation: The Gates Hotel

The impetus for our trip was an invitation from The Gates Hotel to stay at their property. Given that I had always wanted to visit Key West and given the great reviews I had heard from friends who had visited (like Ashley and Christie), I knew we had to visit.

The Gates is a new hotel, having opened in the last year or so. The new hotel is clearly a renovation of an older, existing property. But the renovations that were made to the hotel are spot on. The decor is all light and airy, evoking that classic Key West beach vibe. The hotel gives off retro vibes in its format. The rooms have doors that open to the outside toward the pool in the middle of the property. With an onsite craft cocktail bar called Rum Row and a great food truck called The Blind Pig, you’ll be set for a day of lounging by the pool.

A word to the wise: The Gates is located on the northern end of the island, meaning that it’s a few miles from the heart of the action. Since we had a rental car, that didn’t present a problem for us. If you are in shape and time permits, you can also bike into town on one of the bicycles provided by the hotel.

We very much enjoyed our stay here. If you’re looking for a laid back, casual, authentic experience, you’ll love the Gates.

Coffee Recommendation : Cuban Coffee Queen

The Cuban Coffee Queen is a quaint little coffee stand that serves the most delicious coffee. It was so good that Mari and I had to return each morning we were there. When we stopped by on the last day, I met the proprietor of the coffee shop. I asked him about what Cuban coffee means and why he started the shop. He told me about traveling to Cuba and meeting a lady who made the best coffee. He knew he had to bring that same coffee back to the Keys. “I will never forget the Cuban Coffee Queen,” he said.

The coffee stand also happens to be the home of the iconic “Greetings from Key West” mural pictured above. Be sure to visit, order some coffee, and snap a pic!

Breakfast Recommendation: Glazed Donuts

Glazed Donuts is located on Eaton Street, right next to the theater, which is painted in the loveliest turquoise hue. When we were there, it happened to be National Donut Day, so we were obliged to participate in the holiday. Everything here is made from scratch. We sampled the maple bourbon donut with candied bacon and the cherry pie donut. They also serve a key lime pie donut, which regrettably we did not try.

Also, their organic coffee is not to be missed. So, start your day off right with a cup of coffee, some donuts, and a newspaper. You’ll enjoy this local gem in the heart of old Key West.

Brunch Recommendation: Blue Heaven

Our favorite meal of the trip was brunch at Blue Heaven. Perhaps our love for Blue Heaven was exaggerated by the fact that we were drained of energy by the heat and humidity and starved for food. But truly the food here is wonderful! And the entire vibe is very quintessential Key West. We sat on the patio, where even the tables had artistic personality! Did you catch the photo above where we dressed our table lady up with sunglasses, earrings, and lipstick? Ha!

As for the food, we loved it! I had the lobster omelet, while Mari had the Blue Heaven eggs benedict. And of course, we couldn’t leave without trying the key lime pie!

Lunch Recommendation:  Louie’s Backyard

On our last day in Key West, we had lunch at Louie’s Backyard. While I had heard this restaurant is wonderful for watching the sunset while you have dinner, we just weren’t able to make that work with our schedule. But we did want to try the restaurant, as so many people had recommended it to us.

It did not disappoint! By Key West standards, Louie’s Backyard definitely falls in the fine dining category. The atmosphere is elevated above the usual casual options in Key West. The restaurant has two options for dining: inside in a formal dining room, or outside on the deck. We chose outside, even though storms were threatening that day. Even with the cloud cover, it was nice to sit there and enjoy the breeze and the view.

We shared a salad, calamari, and conch fritters that day. And of course, we once again sampled the key lime pie!

Snack Recommendation: Tutti Frutti Juice Bar

When you are strolling along Duval Street in the heat of the day and need a refreshing break, Tutti Frutti is your place! Tutti Frutti serves delicious whole pineapple drinks. Whether you prefer alcoholic or non-alcoholic, they’ve got you covered. Take your pineapple to go and enjoy while you walk along Duval Street, or take a seat at the little space provided behind the bar. Either way, you’re in for a treat!

Dinner Recommendation: Santiago’s Bodega

We didn’t capture any images of this establishment, as it was after dark when we got there. But nevertheless, Santiago’s Bodega merits a mention. When we arrived (without reservations), the only seating available was at the bar. While this didn’t seem ideal at first, it turned out to be wonderful! The bartender led us down the right path with sangria and tapas. His recommendations were wonderful all evening!

Bar / Live Music Recommendation: Sloppy Joe’s

To get to Key West, we flew from Houston to Miami, rented a car, and drove to Key West. While the drive is very scenic, I’m not going to lie – it’s pretty long. The distance between Miami and Key West is not that great, but it turns out the roads are pretty narrow with slower speed limits. It took us over three hours to get there.

Once we arrived, we were both hungry and thirsty. So, we kicked off our time in Key West by heading directly to Sloppy Joe’s on Duval Street. This legendary, historic establishment is of course known for its namesake: sloppy joes. We opted for the sloppy joe nachos, plus indulged in the frozen “pain in the ass” cocktail – a rum runner and pina colada combination.

What we didn’t anticipate was how much fun the place would be! Even early in the evening when we were there, the live music was going strong. A word of caution: I certainly wouldn’t deem this place family friendly. The music was all in good humor, but a little raunchy. It’s definitely intended for a more mature audience that’s not easily offended.

Sunset Recommendation: Sunset Pier

Located at the Ocean Key Resort and Spa, Sunset Pier restaurant and bar is not to be missed! Sunset Pier is often named the best waterfront bar in Key West. And who can resist the colorful tables and bar stools? Order a drink, pull up a stool, and enjoy the sunset at this picturesque location.

Have you been to Key West? I’d love to hear your recommendations. I’d definitely like to visit again when we have more time for other activities and sightseeing. But we certainly got a great initial taste for this charming island!

For more Key West recommendations, check out this article by Travel + Leisure. For more details on what I wore in Key West be sure to check out these three articles.

Thanks as always for stopping by Wear + Where + Well! Have a great day.

All photos by Maritere Rice in Key West, Florida