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Weekend Getaway in Key West, Florida

Weekend Getaway in Key West, Florida

First, let me start out by saying if you have an option definitely spend longer in Key West than 36 hours.  John and I originally planned this trip to spend a Thursday-Sunday. At the last minute, another business opportunity came up so we ended up arriving Friday night around 7 pm and left Sunday morning at 11 am.  A SUPER quick trip but we had a wonderful time and I wanted to share the highlights and what to do with 36 hours in Key West with you!

How to Get to Key West


John and live in Georgia, but still found the most efficient way to get to Key West is by air.  We took a direct flight out of Atlanta on Delta.  American Jet Blue, and Silver Airlines also fly into the Key West.  One of my best tips is to use Google Flights to find the best option in your area!

Trains… (just kidding) BOATS

Key West is a very popular stop for cruise ships, so if you only want to spend a little time in the Conch Republic this is another way to get to the Island.


Key West, Florida is the southernmost tip of the continental United States.  This being said US-1 is the only road on and off of the Island. If you are down for a bit of a road trip, Key West is about three and a half hours from Miami by car.

Where to Stay

Casa Marina a Waldorf Astoria Resort

We used Hilton points to stay at Casa Marina, a Waldorf Astoria property. My very honest opinion is that you should not waste your points or money to stay here. It is one of the only properties on the island that has private beach access, but this alone is not enough of a draw to overcome the dated rooms and lack of service.  John and I spend over 100+ nights a year in hotels and I would say this was one of the worst experiences I have ever had a Hilton property much less Waldorf Astoria which is supposed to be the premier brand for Hilton.

H2O Suites

Lena, the photographer we worked with during our stay recommended H2O suites. I would definitely look into staying here the next time we visit because they are adults only and have a really pretty rooftop pool or the option for a private plunge pool on your balcony.


I found several great options through Air BnB.  Whether you are looking for a private room or an entire house, I would be sure to check them out first!

Where to Eat

Moon Dog Cafe & Bakery

We ate at Moon Dog Cafe & Bakery for brunch the morning that we were leaving, we really loved the laid back atmosphere and the really cool mural they had on the wall. They had several gluten and dairy free options for me! Overall I would say this is a great place to stop for brunch or swing by for a coffee and pastry.

Cuban Coffee


If you want great coffee, look no further than the Cuban Coffee Queen. I mean, it says it right in the name.  They have a couple of locations in Key West, but both locations have the same menu. We stopped by both and enjoyed great coffee at each. To my very pleasant surprise, they also had almond milk so I could enjoy my favorite cafe con leche!

El Siboney

Y'all El Siboney is some of the best Cuban food I have ever eaten and I've been to Cuba… twice. I really enjoyed their Vaca Frita which is the shredded beef with onions on the right-hand side of the picture. John's dish is the Siboney Steak which is a skirt steak. Both were delicious and it was very reasonably priced. A MUST visit while in Key West.

The Sugar Apple Natural Foods 

Vegans and dietary restricted people, this one is for you! I had a delicious organic smoothie here and I saw several vegan meals at the cafe and they all looked super yummy.  The cafe is attached to the market where you can pick up organic items for your stay.

Cafe Marquesa 

John and I ate here for dinner and were blown away with how good the food is.  You need to make a reservation because the dining room is very intimate. The service is excellent and it is truly a great experience.  I had the grouper over a crab and zucchini succotash and John had tuna topped with fried oysters.

What to Do

Like I said earlier, John and I were only in Key West for a brief 36 hours so we did not have a lot of time to explore. This list is by no means comprehensive but can serve as a starting point for you!

Meet up with a Local Photographer

We met up with Lena from Lena Perkins Photography and spent about an hour walking around taking pictures. You guys know I love meeting up to shoot a few photos with local photographers when I travel because the photos are my souvenirs, I make a new friend, and they ALWAYS have great local tips that are not touristy and off the beaten path. Lena is the one who recommended Marquesa and Moondog Cafe.  I typically find the photographers I meet up with off of Instagram by searching the hashtag of where they are from /photography. For instance #KeyWestPhotographer

Key West Butterfly & Nature Conservatory 

If you want to be surrounded by a ton of beautiful butterflies this is the place for you. Alternatively, if you do not want to be surrounded by a ton of children this is NOT the place for you. It was a great way to get out of the heat and see some beautiful butterflies, but I wouldn't plan an entire afternoon around it unless you have kids.

Bahama Village Market

Bahama Village Market is home to a group of people who immigrated from the Bahamas in the early 1800's.  It's kind of touristy, but definitely fun to walk around to hear the Caribbean music, see the local shops, and grab a snack at one the restaurants.


I'm a big fan of just seeing where the day takes us on vacation.  Neither John nor I are huge planners and really prefer to be spontaneous.  Let me know in the comments below what you have found in your Key West Explorations and where we should visit next time. For more ideas for weekend getaways check out my travel guides for Sedona and Banff National Park.

Here is the video from our weekend in Key West from our YouTube Channel! Make sure you pop over there and subscribe so you don't miss any of our behind the scenes videos of our travels. 

John and I recently took a quick trip to Key West and I wanted to share the Moderately High Maintenance guide for a weekend getaway in Key West, Florida! John and I recently took a quick trip to Key West and I wanted to share the Moderately High Maintenance guide for a weekend getaway in Key West, Florida!