Let’s Plan this trip together! – Key West

Hey everyone! I’m Sam Kieft, wife of Zach Kieft. Over the years, I’ve become the main planner for our trips – mainly due to my type A personality lol. I get major anxiety about safety, having housing, spending money, or forgetting to plan something crucial like a train ticket. So for me, it was always best to own the planning so I could ensure everything was accounted for. 

The main thing I hear from most of my colleagues is “I can’t wait to start traveling” but then it never happens. My gut tells me it comes from either anxiety of planning it and going somewhere you don’t know, or from not having the money to do it. Both of these are valid concerns, and are two topics that I excel in. 

For those struggling with the anxiety roadblock, that’s what this blog is for. All of my “Let’s Plan This Together” posts will be me helping you step-by-step plan and book your trip 🙂 


So let’s get to it – let’s plan this trip to Key West together!

The best thing to remember is all you really need at the end of the day is how to get there, how are you getting home, where are you sleeping, and how do you want to get from place to place? So once you have your flights, hotel, and rental car you’re pretty much 80% done! 

Choose your dates  

If you don’t have to be at your destination for specific dates, I’d recommend beginning your search on Google because they will show you how much flights are by day. 

Pro Tip: Open a private browser prior to searching for flights. It stops airlines from seeing what your recent searches are which can result in them upping the price the next time you search for the same trip. 

If you google “flights from BLANK to Key West” google will show you flight results that look like this: 

Once you hit SHOW FLIGHTS, it’ll load your screen to a calendar like below which shows you the price per day. 

This is how we usually pick our dates. It’s showing you the cheapest option you’ll have for the round trip. Someimes that lowest price is for a lower company like Spirit or Frontier so prices will go up from there, but it can also show you cheaper date trends. 

Google is also awesome because they’ll always have a price graph that tells you if the dates prices are normal or not for that time of year.

From all of this, you should be able to choose the dates that you want.

Plane tickets (if you aren’t driving) 

Plane tickets are straight forward once you choose what brand you want. What I’ll share from our experience is we used to fly with cheaper airlines like Spirit or Frontier but over the years, we’ve had our share of delayed flights with these companies; which has lead us to book with more expensive airlines. 

So now we usually fly with Southwest or Delta. Since switching to these companies in 2018, we haven’t had a single delayed or cancelled flight. 

Another thing to consider for this trip is where do you want to fly into? 

Your options are either Key West, or Miami. I’d recommend looking into how much each flight is. For us, we flew into Miami because it saved us $800 round trip. It meant we had to get our rental car in Miami and drive 3-4 hours but for us that was worth it. If you have any questions about what that drive was like, comment below and I’ll make sure to answer them! 


If you’re staying in Key West, get ready for pricy hotels. We have began to stay in more luxurious hotels the past couple of years and luckily they’ve all been worth it but, you can also look into cheaper options than the one we stayed at. 

$ Hotel: Seashell Motel and International Hostel

Cheapest stay in Key West. Has 2 stars and 6.8 rating on Booking.com

It’s located in a quieter area of Key West, right next to Casa Marina Beach. 

It’ll be about a .7 mile walk to get to the heartbeat of Duval Street. 

$$ Hotel: Southern Inn Adult Exclusive

Has 3 stars, and 7.9 rating on Booking.com

It’s located pretty close to the beginning of Duval street next to lots of great breakfast spots like Banana Café and La Grignote 

$$$ Hotel:  Kimpton Winslow’s Bungalows

This is where we stayed. It has 3 stars and 8.5 rating on Booking.com

It’s located just a 3 block walk to the middle of Duval street. 

It was absolutely beautiful! On some nights, it’s only $100/night more than the Southernmost Inn which is why we picked it. 

So it comes down to what you want from a hotel. My favorite parts of where we stayed was definitely the greenery/landscape as well as lounge areas to sit outside and have a drink/lunch. 

There are a lot of great/beautiful places to stay in Key West. You’ll find cheaper options closer to the airport. I would just consider how do you want to get around during your stay? Duval street is the main attraction of Key West so you’ll need to parallel park and search for parking for awhile during busy days. If that sounds like a drag, it might be better to pay more and stay closer to Duval street so you can come and go by foot.

Pro Tip: Most places in Key West are a resort. So ensure to check for resort fees prior to booking. 

Sometimes it’s not stated in the properties details or important information pages so before you hit “book” double check the total price. Another thing you could do is filter out “resorts” and that should remove any that would have a resort fee. 


Bicycles parked along Duval street

If you are flying into Miami, you’ll definitely want to rent a car. 

My advice, ensure that you read yelp reviews on the company you’re choosing. They have some smaller companies out there that have TERRIBLE reviews. We chose one of them last time.. Luckily we haven’t had any issues yet but there are stories that people get charged months later for damage to the vehicle they rented while out there. So take photos of the car. We also take a video to capture all damage prior and while returning so we have proof down the road if needed. 

Another Miami tip: try to choose a rental car location that isn’t right next to the airport. All of them will be crazy busy due to high tourism but the farther you get from the airport, the quieter it’ll be. Ours was a shuttle bus drive from the airport and we waited an hour to get keys for a reservation we had already booked. 

If you are flying into Key West, most people get around on mopeds/scooters. Bicycle rentals are also available if you want to pick one up to get around Duval street. We stayed about .4 of a mile from Duval Street and walked most of our stay out there. If you are going to want to visit some of their beaches in Key West, I’d recommend booking a moped/scooter/car. 

COVID Protocols

Florida hasn’t had COVID restrictions since fall of 2020, but I would still double check prior to going. You can check the latest news here

When we went in May 2021 we needed to wear a mask in most stores/restaurants prior to seating. That was the only COVID restriction we came across. 

What to Pack 

Florida gets humid and hot during the summer – we visited in May. So double check your weather app for your dates but we mainly wore shorts, tank tops, floral dresses, and sandals/canvas. 

The water there is warm! At our hotel and shallow parts of the ocean, the water was almost room temperature so ensure to pack a bathing suit!They do also have great bathing suit shops out there so in case you don’t have one to pack, I’m sure you’ll find one there! ! I bought one from Bikini Village that’s on Duval street. Most of their bikini shops have the same brand BodyGlove. Their bikinis have fashion tape in them which helps keep them in place.

Bikini I got from Bikini Village

Ensure to bring sun screen! I’d recommend keeping it in your bag/purse that you walk around with. Duval street can keep you entertained for hours so you’ll want to reapply. We got sunburned just on day one. We’re also from Portland so that might have something to do with it lol 

What to expect for the culture 

I was way off for the culture. I thought it was going to be like New Jersey – large accents, huge party night life, loud crowds. Luckily for us, it was none of that.

With it being so close to Cuba, it does have some Spanish culture vibes to it. The workers there are all super nice, and attentive. What caught us off guard was their openness with sexuality. Not the scary, perverted remarks we are used to in America – but more about being proud of who you are. They’d make comments like “flaunt it girl”, “You’d look so good in this!” while shopping in their stores. Overall, we loved the vibes of the locals. It felt super safe, nonjudgemental, and they were nice to you whether you ended up buying something or not. 

Overall the culture is strictly tourism. Lots of people there on vacation and Duval street is there to feed them, give them drinks, and allow them to unwind. We absolutely loved it! Duval street is also filled with live musicians. It seems as soon as you were far enough away to not hear one person singing in a bar, you could already hear the next one coming up. 

What will you eat? 

They have lots of American, Italian, French bakeries, breakfast joints, and loads of Cuban coffee to try! You can read our blog post to learn more about our favorite spots we tried! 

I hope this was a helpful guide to planning your trip! If you wish to know more about a specific topic, please leave a comment and I will share more details with you! 

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