16 Mistakes To Avoid In Key West Florida

Are you traveling to Key West Florida and wondering what mistakes not to make so that your trip is as smooth as possible? From understanding travel details to helpful reminders, it’s good to know what to do and what not to do when traveling somewhere new.

If you’re traveling to Key West, we have the Ultimate Guide To Key West that you can use to plan your whole trip. It has great tips on when to go, a list of 100 things to do in Key West and what to bring. If you just would like to know the top 30+ things to do in Key West, you can also check out that guide.

Also, for those who are traveling the whole of the Florida Keys, our Ultimate Florida Keys Guide helps you plan the whole road trip. Whichever plan you have for your trip, here are some mistakes not to make once you finally make it to Key West, Florida.

Mistake #1 – Booking Last Minute

Key West is one of the most popular destinations in Florida making it a place where you don’t want to wait until last minute to book something. While you can still find places to stay and things to do, it might not be your first choice. Booking last minute may mean not only higher prices but fewer hotel options, especially for those that are closer to Old Town.

During peak season, availability can also disappear fast for the popular excursions so to make sure you have the most epic trip to Key West, be sure to book things weeks if not a few months ahead of time.

Mistake #2 – Not Booking Water Activities

There are all types of travelers, but Key West is all about the water activities. For the more adventurous, there are snorkeling reef tours and dolphin encounters, as well as kayaking, paddleboarding, jet skiing, and parasailing.

For those who want a more laid back vacation, getting out on the water is also a wonderful way to spend time in Key West. There is a beautiful sunset cruise where you can enjoy drinks or even a dinner while sailing as the sky turns stunning bright colors. Another option is a sail after dark where you get a narration of the night sky.

Water activities are a major highlight of Key West offering unmatched views, a look at the marine life, and unforgettable memories.

Mistake #3 – Forgetting Your Sunscreen

One of the most painful mistakes you can make in Key West is to forget your sunscreen. The Florida sun is intense year-round and with so much time being spent outdoors, the sun exposure can be harsh.

Even on the cloudy days, UV rays are strong enough to cause burns. If you get a bad sunburn in the beginning of your trip, it can derail your entire trip and make it miserable. And you definitely don’t want to be traveling while having a bad burn, that’s just very uncomfortable.

It’s important to bring reef safe sunscreen with you to protect both your skin and the delicate ecosystems and marine life. Make sure to reapply often and wear hats and sunglasses for optimal sun protection.

Mistake #4 – Not Having A Transportation Plan

It’s better to plan ahead for how you’re going to get around the island. Old Town Key West is a popular place to stay because a lot of things are walking distance. However, Old Town can be more expensive for this reason so if you choose to stay in another part of the island, make sure to have a plan for transportation.

Some hotels have a free shuttle to Old Town included with your stay. Other options can be to take Uber, rent bikes, or rent a golf cart.

We only recommend renting a car in Key West is if you want to explore the other Keys. Otherwise, parking is very limited in a lot of places so you don’t want to be stuck with a car especially in Old Town with nowhere to park it.

Mistake #5 – Planning Too Much For One Day

If you’re in Key West for a short time, it’s natural to want to try to fit in a lot of activities. But the island’s charm has a laid-back style and rushing from one activity to the next can be quickly exhausting.

Take your time to slow down and enjoy the activities you want to do most. Choose two must-do experiences per day and then let the rest unfold naturally. Give yourself time to truly soak in the island’s charm and make the trip memorable.

Mistake #6 – Not Using Passes And Resources

Did you know you can purchase a pool day pass or a drink pass in Key West? Not using these passes can cost you money and convenience.

Many resorts and hotels offer day passes that give you access to different amenities such as pool access (and sometimes private beach access), lounge chairs and towels. In some places you can rent a whole cabana for the whole day for a little bit extra.

For the Key West’s party pass, you get a pass that you can use everyday that is valid for the whole year. You can get discounts like buy one drink and get one free or even 15% off your tab at select establishments.

Mistake #7 – Assuming There Are Beaches Similar To The Mainland

You won’t find beaches here like in Panama City, or Siesta Key, or Miami. Assuming Key West has beaches like the mainland is a common mistake for first-time visitors. If you are traveling here for the beaches, maybe it’s better to plan a vacation to somewhere else in Florida.

That being said, there are still plenty of lovely beaches in Key West that are smaller and some of them rockier. Fort Zachary Taylor State Park has one of our favorite beaches in Key West while Smathers Beach is another popular and free one.

Key West’s appeal lies in its boating, snorkeling, sunset sails, historic charm, and a lively atmosphere. If a beach is still a priority, consider driving up to Bahia Honda where the beaches are some of the best in the Florida Keys.

Mistake #8 – Not Getting Off Of Duval

There is so much more to see in Key West than just Duval Street. While Duval is lively and full of shops and restaurants, it represents only a slice of the island.

Many of Key West’s charming experiences are found just a few blocks away in the quiet historic neighborhoods. There are hidden courtyards, local-favorite cafes and waterfront spots away from the hustle and bustle with a relaxed feel.

Travelers who never venture off of Duval often miss the island’s more authentic side. But exploring further might mean you find the island’s hidden gems, better food, fewer crowds, and a connection with nature.

Mistake #9 – Underestimating The Heat

Unless you are traveling in the winter time, the heat can be intense. The island’s tropical climate and high temperatures along with humidity feels heavier than many travelers might expect. Plan ahead to do something indoors at the hottest time of the day or have a pass to cool off by the pool. Another option is to pop into a restaurant to cool off and get a drink or have another indoor attraction planned.

Another important thing to be mindful of is to keep hydrated. It’s super important in a climate like this so with proper hydration, lightweight clothing, and taking midday breaks it makes a big difference.

Mistake #10 – Not Trying The Different Foods

The Florida Keys are famous for different kinds of foods so while you’re in Key West, be sure to try them. The island’s food scene has a strong emphasis on seafood but it goes beyond that with a unique blend of Cuban, Caribbean, and Floridian flavors.

Don’t miss out on specialties like conch fritters or conch salad, one of the island’s most unique foods. There are also restaurants that serve fresh seafood like Grouper or Mahi-Mahi, and even Stone Crab, especially in season.

Cuban food and coffee is also a must-try when in Key West for its delicious flavors. And of course, don’t miss all of the great places to get Key Lime Pie in Key West.

If you want to try a little bit of everything, you can go on a food tour of Key West.

Mistake #11 – Visiting During Peak Season Or Events

Visiting Key West during peak season or major events is a recipe for big crowds and high prices. Popular times like the winter (until March/April), spring break, Fantasy Fest, or major holidays, bring higher prices, packed hotels, crowded streets, and long waits.

The energy can be fun, especially if you are particularly wanting to visit a certain event, but if you are looking just to visit Key West, then it’s best to avoid these times. If you do go, make your reservations well in advance.

Mistake #12 – Not Being Prepared For Weather Changes

Florida’s weather can be very unpredictable. The island’s tropical climate means weather conditions can change very fast. It can go from a beautiful sunny day without a cloud in the sky to a thunderstorm and winds within an hour.

Plan for afternoon rainstorms, especially in the summer. If you’re out on the water, watch out for far away dark clouds because they can advance fast and the waves get big out in the ocean when a storm comes around.

Mistake #13 – Not Knowing About Local Wildlife Guidelines

The island is surrounded by a delicate ecosystem and protected species from coral reefs to sea turtles. Visitors may not realize that touching coral, feeding wildlife or getting too close to animals can cause harm.

In many cases it can also lead to hefty fines and even jail time. For example, if you’re an avid fisher, make sure to learn what you can, and can’t catch because that’s what happens if you get caught with undersized lobster or other varieties of fish.

Wildlife guidelines exist to protect both animals and people and to ensure the same natural beauty for others to enjoy.

Mistake #14 – Not Visiting Other Islands

Key West is lot’s of fun and it will keep you busy, but the surrounding islands offer some beautiful scenery and experiences. Go up to Bahia Honda to enjoy some of the best beaches or head over to Big Pine Key to see some of the island deer, all located in the Lower Keys.

Also in the Lower Keys is the Blue Hole, a former quarry that attracts deer, birds and alligators. Then stop by the historic No Name Pub that is famous for its walls covered in dollar bills.

Mistake #15 – Not Staying Long Enough

The island may look small but it offers far more than what can be experienced in a quick overnight stay. Between water activities, historic sites, sunsets, day trips, and simply relaxing, time goes by quickly.

We recommend a minimum of two days to experience what Key West has to offer but with five days you will truly get to live the island dream. We have guides for things to do in Key West for two, three, four and five days so that you can pick the itinerary that works best for you.

Mistake #16 – Assuming There Is Nothing To Do In The Evenings

Don’t miss out on some of the best things to do in Key West just because they are happening in the evenings. From watching the sunset on Mallory Square with live music and performers to going on an incredible sunset cruise.

There are other things you can do in Key West in the evenings whether you want to visit a certain restaurant, see a show, or simply have a relaxed walk along the water. Key West’s evenings have a certain fun but relaxed atmosphere.

Bonus Mistake # 17- Not Reading Our Key West Travel Guide

Are you making a trip to Key West? Don’t make the mistake of not reading our Ultimate Key West Travel Guide that will help you plan your whole trip.

We have over 100 things to do in Key West in this guide and the best places to stay and places to eat. This guide will help you plan the most epic trip to Key West, Florida.