fort zachary park in Key West Florida
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Perfect Weekend in Key West: Your New Favorite Getaway

ByKasia Kalemba Hours
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I always imagined Key West as a destination for older couples who have seen a lot in their lives and now just spend their winters in this “wild-dad” destination. Naturally, I had to go and check out what the hype is all about. I rented a convertible BMW with my best friend and we drove down to Key West from Miami to check out this little paradise.

Was Key West all that I imagined it would be? Yes. There were many older couples having the time of their lives there. However, there was also everyone else having an amazing time too. I honestly cannot wait to go back and spend more time in Key West. It feels like a tropical destination without leaving the country.

In this itinerary, you will find some travel logistics, and cool things to see, and be able to download a weekend in Key West itinerary for your travels. If you’re going to South Florida, don’t forget to check out my Miami Guide and a Miami Girls Weekend getaway!

travel sign in Key West Florida
Table of Contents show

Logistics of Visiting Key West

Where and how long to stay in Key West

Key West can be expensive for accommodation, so it may be more cost-effective to stay in a location closer to the action on Duval Street. If you are traveling with a group, you could consider renting an Airbnb or VRBO, but these options may not offer significant cost savings. There is a hostel in Key West, but at $90 per bed in a dorm room, it may be more economical to stay in a hotel.

I personally stayed at the Douglas House, an awesome pick in town. There was parking onsite, the staff was super helpful and friendly giving us recommendations outside of the typical tourist trail and the rooms were huge! A cute little pool along with a stunning garden were also great additions to the property.

As far as length, you can see everything in a day or two but chances are you’re not going to Key West looking for cultural adventures. It’s a place to relax, have a drink, and lay on the beach. So spend a weekend there and you should be ok, especially with the high prices in town. Although pricey, it’s not ideal to see Key West in one day.

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How to get to Key West

Key West is the Southernmost point of the US which makes it a unique destination. Its tropical vibes will make you feel like you’ve traveled further than you actually have. You can either fly to the small airport located right in town but these can get crazy expensive. Another option is to drive from Miami which will take you about 3.5-4 hours without any stops. However, I will go into which Keys are worth stopping at as this is one of those bucket list drives that people romanticize.

There are buses that have daily departures for a simple Key West day trip from Miami which are an awesome option if you just want to get there without driving or stopping. For as low as a $50 roundtrip on a Greyhound, you can snooze until the very last Key. Lastly, if you’re taking a cruise in the future, a lot of ships stop there too.

When you get to town, don’t use a car unless you’re venturing to a beach a little further away. Most of Key West is walkable but you can also utilize the free shuttle that takes you around town. Another awesome option is renting a bike in town which not only allows you to get some exercise but also covers more ground in a shorter amount of time.

  • Siesta Key to Key West: 370 miles
  • West Palm Beach to Key West: 230 miles
  • Miami to Key West: 160 miles
  • Key Largo to Key West: 97 miles
  • Marathon Key to Key West: 50 miles
renting a car to drive to Key West Florida
I rented this gem on Turo for my Miami to Key West drive! Totally worth the splurge.

People & Safety in Key West

I met a couple of locals working in restaurants and bars. People living in tourist destinations are usually friendly and that’s exactly what I experienced there. All others are tourists so prepare to come across a lot of characters.

Key West is super safe. It can get rowdy at night with all the drunks on Duval Street. When you’re in crowded places like where you watch the sunset, for example, use common sense not to get pickpocketed.

Food in Key West

There is a lot of good food stops in the area but Key West is pricey so plan well. Since the island is little, you will often find the same recommendations on a lot of websites. My favorite picks for the area are Grand Vin, a wine bar serving delicious cheese plates, Santiago’s Bodega, an amazing tapas place, or my absolute favorite Key West Cuban Coffee, the best spot for food and some strong coffee!

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Perfect Things To Do On Your Weekend in Key West

Drive through the Keys

When I was planning my trip, I insisted on driving to Key West from Miami while stopping at some landmarks along the way. It was one of those romanticized ideas in my head that I always wanted to do. A convertible car, palm trees, and crossing long bridges all the way down. Well … it was that but wasn’t actually as cool as I imagined.

When I was doing my research on multiple travel blogs, many “Ultimate Lists” for the Key West drive from Miami make it seem like there is an overabundance of jaw-dropping activities on the way there. There are a couple of spots that you can enjoy for a little and unless you have a lot of time and can break up the drive into two days just pick a couple not to waste time. Here are the most popular highlights for your drive:

  • Key Largo: A little over an hour from Miami, you’ll find John Pennekamp Coral Reef State Park. If you like snorkeling, glass-bottom boat tours or just walking around in a nice park make a stop here. There are two cool restaurants in the area, Sundowners known for its sunset views and Mrs. Mac’s Kitchen, a cool bar covered with license plates.
  • Tavernier: The next stop is just 20 minutes away. It’s a famous Key Lime shop called Blond Giraffe. Key lime pie comes from the Florida Keys so it’s a cute and cheesy thing to try in this lime green store.
  • Islamorada: Another popular spot is Rain Barrel Village, which is a little collection of art stores and shops. It’s a small stop for trinket shopping. There are giant sculptures outside of it too. For your half-way point treat make sure to stop for a brew at Florida Keys Brewing Co which has a super groovy beer garden. The one thing I loved in this area was Morada Bay Cafe, a beach restaurant with delicious food a unique dining atmosphere. I actually stopped here on the drive back from Key West for dinner, right before the sunset and I highly highly recommend doing it that way. Oh and the last thing people go nuts for here is feeding some fat tarpon fish at Robbie’s. I liked the bar area better than the creepy fish and I enjoyed some birds at the little port instead.
  • Marathon Key: People recommend staying in if you want to break up the drive and you can find the Turtle Hospital that rescues the hurt little buddies.
  • Then you will cross the Seven Mile Bridge.
  • Bahia Key: Right before reaching Key West, stop at Calusa Beach which is a stunning spot of light blues and turquoise waters with some vibrant green palm trees.
  • Bonus: There is a cool little bar a little off your path called No Name Pub.
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So with all that said, do I recommend driving to Key West from Miami or skipping this part and just heading to there by plane or by bus? It’s a tricky call. If you have the time and reading about the stops above made you smile, then take this US bucket-list drive there. The views along the way are really really nice so just that aspect of it is worth it. However, if know that super touristy restaurants and feeding fish isn’t your thing, spend some extra time in Key West instead.

Southernmost Point of the US

I’m not listing this as the first activity in Key West because it’s the most exciting one but just to get it out of the way. It’s a bouy at the end of some residential street and there is a line of 40+ people waiting to take a picture with it. It’s 93 miles away from Cuba which makes people go wild for some reason. Aside from being a picture spot, there isn’t much to it.

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Notice how I took this photo. You won’t see the line of 40 people next to this thing.

Watching the Sunset

There really is something extremely magical about sunsets in Key West so you should make it a priority to see one. The most known spot for it is the Mallory Square area which floods with people every night for the sunset. They have a little celebration and people gather to admire the amazing colors in the sky. It’s beautiful but crowded.

Another popular option is taking a Sunset Sail with multiple companies offering an open bar and a music option with it. Then there is Sunset Pier at Ocean Key Resort. People also like Truman Waterfront where you can enjoy a sunset without the crowds, sometimes you can find a local market there too. Other good places include the super long White Street Pier or Historic Seaport with boats as your backdrop!

Duval Street

This is a famous party street in town with all the bars and restaurants. During the day it’s fairly “quiet” but still keeps the atmosphere for a party town. It does have some cute shops and pretty buildings on it so you should experience this rather popular side of town.

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I visited in December so Duval decorations were amazing!

At night it gets rowdy with all the music in the bars and balcony drinkers. The more known stops here are Sloppy Joe’s, The Rum Bar, The Smallest Bar, and Green Parrott. If you’re up for an adventure stop at Garden of Eden which is a clothing-optional bar.

I don’t think it’s technically legal to drink in the street but a lot of people do out of plastic cups. If you get too annoying or drunk you will get a ticket though so don’t be that guy.

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Hemingway Home

Do you love cats and old mansions? I love them both and I can’t think of a better combo. When I heard that Hemingway had a mansion in Key West and that there are like 50 cats that all have 6 toes, I was like “Sign me up.” I bought my ticket and explored the beautiful grounds. It was worth it but I’d also recommend getting a guide there to actually learn something.

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Fort Zachary Taylor State Park Beach

I love this spot. It’s a nice beach in a park-like setting which makes it a very unique spot for this area. You can get some food and drinks from a little shop and take great pictures with those travel signs. There is more than just the beach there, you can also bike, fish or paddle. Find the most recent list here.

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Smather’s Beach

Located in a much more quiet area of town, I enjoyed this beach for its tranquility. There aren’t that many people around so it’s a perfect spot to take a stroll and relax for a little. Note, it’s close to the airport. If you’re an enthusiast of watching planes land and take off like I am, this is a great spot for that.

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Historic Port Area

The whole port area of Key West is just amazing. There is something special about ports in any part of the world so whenever I find one, I make sure to spend some time exploring it.

Simply walk around along the water and find some good bars, cute shops, and just soak in the atmosphere of Key West.

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Dry Tortugas

Technically this is not in Key West but the boat will take you to this rather unique destination. It’s a state park with a fort but also some secluded beaches, tons of snorkeling options, and of course turtles. I did not get to go on my trip but one day I shall return.

Here is a map for you too.

FREE downloadable guides for Weekend in Key West

Key West is a great relaxing destination. There isn’t a ton of things to do in town but you’ll be going there to enjoy the “island” lifestyle. You will eat some good food, probably drink a lot and enjoy the beach. There is the possibility that you can only spend one day in Key West but that will only occur if you’re on a cruise ship. If that’s the case, just check out my top things to do there and pick the ones that suit your timeframe.

Whether your weekend in Key West is a two or three-day stay, I prepared a detailed itinerary for both!

Perfect Two Days in Key West

As mentioned, in my opinion, a simple day trip to Key West from Miami is not enough. Two days is a great option for the place although you can easily relax for a week there. However, most of the highlights can be seen in two days.

Keys Two Day ItineraryDownload

Perfect Three Days in Key West

If you’re staying for three days, your first two days will look like the two-day itinerary. On day three, you will have some options for a unique experience in this beautiful town.

Keys Three Day ItineraryDownload
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Kasia is a travel blogger that loves to share her detailed itineraries and travel tips with her community. She's traveled to numerous countries and makes it a priority to explore her home state of New Jersey while still being passionate about her 9-5 career.

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