Key West Travel Diary: Where to Eat, Stay, Go

Jess Ann Kirby relaxes under the palm trees on Smathers Beach in Key West, Florida



A few days in Key West was just what the doctor ordered. Craig and I flew into Fort Lauderdale last week rented a car and headed out on the open road for the Florida Keys. We made a quick overnight stop in Jupiter to visit my grandparents which was really fun. I mentioned on my Snapchat we rented a car through Silvercar which I can’t say enough good things about. The entire process was so easy, affordable and convenient. If it’s available in a city you’re traveling to I suggest trying it out. Use this special referral code QXNJSTFE and get $25 off your first rental.

The drive from Fort Lauderdale to Key West took about 3.5 hours and there’s some gorgeous scenery along the way including a 7 mile bridge. There is an airport in Key West so flying is also an option but since we were stopping along the way we decided to drive. We had tons of good food, swam in the ocean, went for long bike rides and woke up to watch the sunrise. The people in Key West were SO friendly and nice. We also filmed a video while we were down there which you can see here. Hope you enjoy my recap of our visit to Key West.

What To Do

Beaches – There are a few different beaches in Key West all within close distance of each other. Apparently Key West is mostly coral reef, so they bring in sand from the Bahamas every few years to make some of the beaches sandy. We went to both Higgs Beach and Smathers Beach. I think my favorite spot was swimming off of the Higgs Beach Pier. It’s also a great place to catch the sunrise.
Biking – I definitely recommend renting bikes. We got them at our hotel but I noticed several places to rent them around town. Key West is really flat so biking everywhere is easy and fun.
Harbor Cruise – We explored the harbor and walked around the docks to check out all of the boats. There are plenty of options for a boat tour including the Schooner Hindu which our friends Greg & Alana of Antique Yachts work on in the winter months.
Shopping – There’s plenty of shopping in Key West with tons of little boutiques and street vendors along Mallory Square and Duval Street.
Neighborhoods – We rode bikes around the residential neighborhoods throughout Key West and there is no shortage of beautiful architecture and quaint houses throughout. If you have time make stops at the Truman Little White House and Ernest Hemingway Home.


Where To Eat

Blackfin Bistro – A little bit pricier than some of the other dining options but totally worth it. They have tons of fresh fish dishes and an excellent wine list.
Onlywood Pizzeria – After biking and swimming we went to Onlywood for brick oven pizza. We sat in their back patio and sipped on margaritas. So good.
La Grignote Cafe – We had the most amazing breakfast here. It was one of the best almond croissants I’ve ever had and the tropical fruit salad was so good. Craig loved the fresh waffle and he’s a bit of a waffle connoisseur so that’s saying something.
El Meson de Pepe – Delicious Cuban food. Great place to sit outside and enjoy lunch. Order the Cuban sandwich!
Santiago’s Bodega – This is where we had dinner our first night. I recommend making a reservation, it was packed by 5pm when we went. A great place for tapas.
Flamingo Crossing – We stopped here after dinner at Blackfin despite being so full we could barely eat another bite. I’m glad we did because their ice cream and gelato is so good!
Cuban Coffee Queen – Everything from coffee to sandwiches. Great smoothies for something on the go.

Where To Stay

We stayed at the Gates Hotel Key West. The nice thing about Key West is that nothing is that far so you can get to everything fairly easily wherever you stay. The Gates is located right as you drive onto the island. There’s ample parking if you’re driving. We wasted no time getting drinks at the Rum Row Pool Bar and sipping them poolside as the sun went down. On our first morning we grabbed an early breakfast at their onsite food truck, the Blind Pig. They have plenty of bikes if you’re looking to rent one while you’re on Key West which I highly recommend. We had the most fun biking around the island. It’s much easier than driving. The hotel also provides free shuttle service to and from Mallory Square.

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  1. Briana wrote:

    One of my favorite places to eat in Key West is The Cafe at Louie’s Backyard. It’s upstairs in a bright, converted house on the water in the middle of a residential neighborhood. The view and the breeze are wonderful and they have a really good cheese board.


    2.13.17 | Reply
    • Jessica wrote:

      I’m so bummed we didn’t make it to The Cafe at Louie’s it was on our list! Will have to go back. 🙂

      2.13.17 | Reply
  2. Jen wrote:

    You have the best collection of one-piece swimsuits, Jess! Looks like a gorgeous getaway. x

    Jen | affecionada

    2.13.17 | Reply
    • Jessica wrote:

      Thanks Jen!

      2.17.17 | Reply
  3. Natali wrote:

    Such a beautiful photo diary! Thank you for sharing the tips with us! Also, love that laced, yellow dress on you!

    2.13.17 | Reply
  4. Mallory wrote:

    Sorry to read of your troubles trying to get into BVI. Weird things happen, so focus on your great trip to Key West instead.

    2.18.17 | Reply
  5. Driving Directions wrote:

    Great post! I can’t agree more with the tips! It’s useful for travel, thank you so much!

    3.21.17 | Reply

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