Visiting Key West - Tips & Tricks For Your Trip!
- Christine
- May 12, 2025
- 9 min read
Key West! It's one of those places where you can do a lot, or do a little. This was my first visit to the island that is the most southern location in the continental U.S., and I can tell you it definitely won't be my last. You can experience everything there from beautiful sunsets and views, to loud bars, to amazing food. There's even a place where you can experience more butterflies than you have probably ever seen.
With so many things to see and do, as well as so many restaurants and bars to choose from, planning a trip there can be overwhelming. When we visited recently, we spent four nights and three full days in Key West. In this post I'll share some of the best spots we found - many of which are a bit off the beaten path - that will help you develop your own itinerary for your visit.
Are you ready for some island life? Keep reading!
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About Key West
Key West is an island in the Straits of Florida. The island is about 4 miles long and 1 mile wide. It's the southern most city in the continental U.S. and the western most island in the Florida Keys.
Duval Street is the main street on the island where you'll find a lot of the activity. The street is 14 blocks long (1.1 miles) and stretches from the Gulf of Mexico to the Straits of Florida and the Atlantic Ocean.
Key West is where U.S. Route 1 - the longest north-south road in the U.S. - ends. It's divided into Old Town - which is on the western portion of the island and where you'll find all of the major tourist attractions - and New Town - which was actually manmade.
The weather in Key West is a tropical savanna climate. Daytime temperatures stay warm all year, and can get quite hot and humid in the summer. The lowest temperature ever recorded in Key West was 41 degrees Fahrenheit. We visited at the end of April and the weather was absolutely perfect - warm sunny days with lower humidity and a nice breeze, and a little bit of cooling overnight.
Arriving in Key West
Getting to Key West can be a little challenging. The good news is that once you're there, it's very easy to get around without a car.
By Plane: Key West does have its own airport - the Key West International Airport. Note that the airport is quite small, so it might be a bit of a challenge to find a flight. If you are having trouble with flights into Key West, you can also check the Florida Keys Marathon International Airport. That airport is about 50 miles north of Key West. For even more flight options, you can also fly into Miami International Airport, which is about 160 miles north of Key West.
By Car: Most people arrive in Key West by car - whether they rented a car and drove from one of the further away airports, or whether they drove from home. We live about 660 miles north of Key West, so we chose to drive. It's a long drive, but we just split it up over a couple of days and it was very manageable. The drive through the Florida Keys is a beautiful drive, so if you're able to do it, take advantage!
Tip #1: If you drive your own car or rent a car, be aware of what the parking situation is where you are staying. Parking in the old part of Key West can be challenging, so if your hotel doesn't have free parking on-site available, you'll need to come up with somewhere to keep your car. We parked our car at our hotel when we checked in and never got in it again until we left. All of the Old Town area is very walkable.
Tip #2: If you are driving down, note that once you start to get close to Miami, traffic can be challenging. There is only one road in and out of the Keys, and if there is any sort of construction or other traffic issue, it can be slow going. Pack your patience!
Where To Stay
There are lots of options for staying in Key West. When deciding where to stay, you should ask yourself what your priorities are when you are there. If your priority is to spend most of your time by the pool or on the beach, I'd suggest looking for a hotel or rental with beach access. Note that staying in that location might make it a bit more challenging to get to the "heart" of downtown and some of the tourist attractions, so plan accordingly. If your priority is to spend your time at the various tourist attractions, restaurants and bars in the historic area, I'd suggest looking for accommodations on or around Duval Street.
For us, the priority was being in the center of everything, so we stayed at Wicker Guesthouse, which is located right in the middle of Duval Street. It's a small boutique hotel, but the rooms were very nice and it was surprisingly quiet for being right in the middle of everything. They did have two pools, although they were quite small. The southernmost beach on the island was about a 15 minute walk or so from the hotel.
Tip #3: As mentioned above, if you have a car in the historic area, parking can be a challenge. One of the reasons I picked Wicker Guesthouse was because they offered free parking. However, we did have to leave our car keys at the front desk and they parked the car for us. We kind of joked about whether our car would still be wherever they parked it once we checked out. Good news is that it was, but it was just parked on the street around the corner (and not parked very well with one of the tires on top of the curb). Free parking, but definitely required a little faith on our part!
What To See
While a lot of people visit Key West to just relax and hang out at the beach or at the bars, there is a lot of history there as well as some really cool things to see. My advice on your first day is to do the hop on/hop off trolley to get a good overview of the island. The first stop on the route is at Mallory Square, which is where you can purchase your ticket as well. The trolley stops at a number of places around the island and the driver provides commentary and information as you go. A ticket allows you to ride all day, so you have the ability to get off the trolley at any stop. You just jump on the next trolley when you're ready. You can get more information here.
Mallory Square: This is the main "touristy" area of Key West. There are a lot of shops, bars, restaurants and tourist attractions. Additionally, each night they do a sunset celebration that features performers, live music, vendors, and - of course - the sunset. You can find more information on Mallory Square here.
Tip #4: If you want to enjoy the sunset without the big crowd in Mallory Square, check out the Sunset Tiki Bar. Go a couple of hours before to grab a prime spot and enjoy a few drinks and some live music.
The Key West Butterfly and Nature Conservatory: One of the coolest things we did during our trip was visit this place. It's absolutely magical! Not only does it feature more butterflies than you have ever seen, but it also has beautiful plants and birds, along with some turtles. It doesn't take long to walk through and is definitely worth a stop. Get more information here.
Tip #5: When you visit the Key West Butterfly and Nature Conservatory, I would suggest taking a quick walk a little further south and stopping at the southernmost point (it's the picture everyone has to get when visiting Key West). And, if you love nature and want to see more, take a 15 minute or so walk even further and visit the Key West Garden Club at Fort West Martello. Admission is free!
The Ernest Hemingway Home & Museum: If you are a fan of Hemingway's books, this is a must stop. Even if you aren't, it's worth a visit and the quick 30 minute tour that's full of great information about Hemingway and the area. You can get more information here.
Tip #6: Speaking of books, if you are a fan of author Judy Blume, be sure to stop in Books & Books @ The Studios of Key West. Blume is a co-founder of the shop, and if you're lucky, you'll find her stocking the shelves in the shop like I did! Even if Blume isn't there when you visit, it's a fantastic independent book store. Be sure to check out the Judy Blume section and grab one of her classics that she's autographed.
Where To Eat (And Drink)
There are so many choices of restaurants and bars in Key West. We barely scratched the surface during our visit. Here are a few places that I'd definitely recommend you check out.
Breakfast
Blue Heaven is a favorite spot for a lot of people. We did Sunday brunch there and it was good, but nothing fantastic. The service was great and it's a very cool spot, so we'd definitely give it another shot. It was quite busy, so be prepared to wait for a table.
We really enjoyed the breakfast club, too. The food was amazing and the portions were large. Our server was absolutely fantastic! I'd put this at the top of my list for a sit down breakfast.
Our favorite breakfast, by far, was at the Cuban Coffee Queen. The Key Wester breakfast sandwich was possibly the best breakfast sandwich either of us have ever had. It was so good, that we stopped a second time to grab another sandwich on the day we were leaving. And the coffee is very good too!
Lunch/Dinner
Definitely plan to have lunch or dinner at Conch Republic Seafood Company. It's a busy place, but we were able to snag a couple of seats at the bar, so we didn't have to wait for a table. The food was fantastic!
If you are looking for a casual meal, BO's Fish Wagon is the place to go! Great prices and amazing food. Don't expect anything fancy and it's cash only. Also, they don't serve alcohol, but you can go across the street to Pepe's and order a drink to go and bring it back.
Bars
Best Dive Bar: Bobby's Monkey Bar - This is definitely a neighborhood dive bar. On the night we were there, they were doing karaoke and show tunes seemed to be quite popular. Drinks are cheap. People and bartenders are friendly. Cash only.
Best Tiki Bar: Sunset Tiki Bar - See my sunset tip, above.
Best Drag Show Bar: 801 Bourbon Bar - Good drinks. Great bartenders (they even gave us free donuts). And, of course, the drag queen show is super fun!
Best Happy Hour: Viva Argentinian Steakhouse - Our hotel was right next door to this place, so we checked it out for happy hour. Happy hour at the outside tiki bar is from 3 to 5, but it keeps going until 10 p.m. at the inside bar. Be sure to check out their happy hour food menu too!
Tip #7: Drinking in Key West is not cheap, so happy hour will be your friend. In addition to all the usual happy hours, Old Town Tavern & Beer Garden does a second happy hour from 11 p.m. to 1 a.m. if you are looking for a late night drink. Their kitchen also stays open late, so you can order off the full menu until 1 a.m.
Key West In General
We really enjoyed our visit to Key West and plan to make it a regular trip. In addition to beautiful weather, it offers something for everyone - beach, bars, restaurants, history, nature. The people are friendly and it has a very laid back feel to it.
We also found some great little spots to stop for lunch on our trip driving down and back up. Be sure to check out my Instagram or FB page for pictures and more details on those spots!
Have you been to Key West? If so, share some of your tips! Comment below or e-mail me at tips2livebywriter@gmail.com.
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