15 Tips For Planning A Visit To Key West

“Down this street, you will find a blue so deep it will float you. In that alley, there’s a red so loud you can hear it with your toes. Look up and see past the sky. Yellow to wake you and green to sleep you. Feel it all around you, a purple so wide we can all fit in. These are the colors of Key West.” -Fran Decker

Key West. For me, the name conjures visions of spectacular sunsets, crystal blue water, waking up to the sound of crowing roosters, and warm ocean breezes. It is a place we adore and find ourselves returning to over and over again.

As the southernmost inhabited Florida key, Key West, also known as the Conch (pronounced KONK) Republic, is historic, quirky, distinct, rowdy, colorful, laid back, and it has a distinct culture and rhythm all its own. As a result, planning a trip to Key West is always full of anticipation, and over the years, the only firm plans we typically make in advance are limited to how to get there and where to stay.

As you plan your visit, I hope our tips will help you to plan your best vacation ever. 

Greetings from Key West!

Consider driving to Key West

I am sure that you are excited about your trip to Key West and you’re anxious to get there and begin your vacation.  I get it!  And yes, the fastest way to get to Key West is by plane, but let me suggest that this trip should be just as much about the journey as it is about the destination.  In our opinion, the best way to get to Key West is to drive the length of the Overseas Highway or US-1. For us, flying into Miami and driving through the Florida Keys is part of the adventure.  The Overseas Highway is 113 miles long with 42 bridges, including the famous 7-mile bridge, that carries traffic over each Key and over the beautiful, turquoise water.  The trip from Miami to Key West can be between three and a half to four hours, depending on traffic, and longer if you make stops.  And you should stop along the way. 

To enhance your trip down US-1, consider downloading the GyPSy Guide app to your phone and while getting your GPS instruction, learn about the Florida Keys as you drive along and get suggestions for meals and attractions worth visiting along the way.  Read my blog about the GyPSy Guide app at https://letsjustgo247.com/2021/06/14/gypsy-guide-an-awesome-addition-to-your-road-trip/m.  Enjoy the drive!  You won’t be sorry.  It is definitely something you should do at least once in your life.  

ADVICE: Depending on the time of day, traffic along the Overseas Highway can be thick.  Be prepared and plan accordingly.  Also, on our last trip down, we were amazed at the other drivers around us as they pulled into oncoming traffic suddenly and aggressively passed at high speeds into oncoming traffic on the narrowest parts of the highway.  With a volatile mix of frustrated locals and bewildered visitors, extra caution on the roads is highly recommended.  In the Keys, US-1 is one lane in each direction for much of the trip with short sections that allow for passing.  Traffic can be slow or stopped, and the speed limits drop as you travel through some of the individual Keys.  Don’t be in a hurry and watch out for the careless drivers around you. 

The beautiful water of the Florida Keys surrounds you as you drive along the Overseas Highway.

Parking on Key West

While I encourage you to drive to Key West, the irony is that parking is challenging on Key West and can be an added, unwelcome expense if you have to pay to park.  Parking is a premium on the island.  So, as you consider your accommodations, be sure to determine if parking is included.  If so, I would recommend parking your car and leaving it there.   

How to get around Key West

I know, I know!  I’ve recommended that you drive to Key West and then I suggested that you park your car and leave it.  So now you’re asking yourself, “How am I supposed to get around?”  Don’t worry!  Key West is only 2 miles by 4 miles and is a very walkable town and easy to navigate.  However, to see more of the island, there are lots of fun alternative ways to explore. 

All over the island, you will find rental businesses that offer scooters, golf carts, and bicycles.  Some resorts even offer bicycles to their guests so be sure to ask about that if you are interested.  During past visits, we have rented golf carts that have allowed us to explore parts of Key West without having to worry about our car and it was tons of fun.  Remember though, if you rent a scooter or golf cart, you still have to find a place to park it.   There is also a hop-on-hop-off trolley that is a great option for getting around time and seeing all the highlights.

ADVICE: No matter how you plan to get around town, always be aware of your surroundings.  If you drive, besides finding a parking spot, the challenge will be traffic and the pedestrians, bicycles, and other alternative modes of transportation out there.  Sadly, they will not watch out for you. Go slow and be on the lookout for Key West’s chickens too! 

If you are walking or riding a bike, the warning here is to watch out for vehicles that may not see you.  Don’t step off a curb without making sure that it is safe to do so.  If you are riding a bike, scooter, or golf cart, remember that the rules of the road apply to you.  Be careful!  Key West can be a busy place and in some spots, it can often be congested and tight to pass.  You might be on vacation but I’m sure that the Key West Emergency Room is not on your list of sites to see!   

When is the best time to visit Key West?

The state of Florida is a haven for anyone who lives in colder climates during the winter months.  For this reason, the period between December to April is often considered the high season in Key West when the crowds will be at their height.  May is considered a shoulder season when the crowds start to diminish and the temperatures are getting a bit warmer.  Summer months are considered off-season with fewer visitors and “off-season” prices for accommodations but the temperatures can be humid and steamy with the occasional spotty afternoon thunderstorms that quickly pass over.  September through November is another desirable period to visit with cooler temperatures to enjoy. 

Two of our previous visits have been in June and to survive the heat, we planned to get out early in the morning and later in the day, finding something to do inside or take a swim in a pool during the heat of the day. We have also visited in the spring and fall and the weather has been perfect!

Two of my favorite things; ice cream and a Key West sunset!

Hurricane season

Hurricane season stretches between June and November in the Atlantic Ocean and the Gulf of Mexico and if you are not familiar, Key West can often be in the crosshairs of these storms. If a major storm is brewing, Key West could be part of an evacuation order and your vacation could be canceled or shortened.

When planning your trip, it is impossible to know when a storm will form or if it will affect your trip so if you are planning your visit during Hurricane season, be sure to understand cancelation policies around rentals and flights.

Before leaving for Key West or while you are there, watch the weather forecasts and if a storm is approaching, be alert and listen to instructions from local officials. Mandatory evacuations are not up for discussion so stay alert and informed. Hurricanes can be deadly and the lovely people who live in the Keys want to protect you and need to secure their properties.

In addition, if a hurricane affects the Keys prior to your trip, you should stay in touch with rental officials to understand the conditions of the town and your rental property. The storm may be gone but if the damage was severe, guests to the island could still be restricted while the community recovers.

Festivals in Key West

Next to weather and temperatures, when choosing the dates for your visit, be sure to consider the calendar of festivals for Key West.  These events could be activities that you want to plan to attend or you may wish to avoid the crowds that may be present for one of the larger celebrations.  Be sure to check www.keywest.com/calendar for upcoming events.

Where to stay

For its size, Key West is a robust tourist town as well as home to roughly 30,000 proud, permanent residents. Despite Key West’s size, there are a lot of options for accommodations that fit varying budgets and preferences such as hotels, resorts, bed and breakfasts, Inns, and rentals of all kinds. Depending on the time of year you plan to visit and since Key West is a prime vacation spot, planning where to stay should be done well in advance to ensure that your ideal location is available. We have planned our trips to Key West three to six months in advance to get the rental we wanted most and if you are planning to travel to Key West in the busiest months, it would be my advice to begin making plans even further out.

We enjoy staying in the historic district and on a previous trip with friends, my husband and I stayed in an apartment that we rented through Historic Hideaways. For us, location and amenities are big considerations and we enjoy staying in a condominium just steps from Mallory Square and Duval Street that includes a pool and a front-row seat for the famous Key West sunsets.

Offering rentals of historic homes, villas, and condos, Historic Hideaways boasts comfortable accommodations at the same or less cost as a hotel room. This is especially a great option if you are planning to travel with family or friends since many of their options sleep large groups. We enjoy having a comfortable home away from home in a perfect location that is clean, quiet, and peaceful. We highly recommend Historic Hideaways and you can find the accommodations they offer at www.historichideaways.com.

Our Historic Hideaway in Truman Annex.

Make the most of your rental

Key West and the whole of the Florida Keys can be an expensive spots to vacation. In addition to this area being a big tourist draw, other reasons for high prices include high demand and the steep cost of supplies that must be brought down from the Florida mainland. We prefer to rent versus staying in a hotel. We enjoy having a comfortable, home-like place to stay for our longer stays. Hotels can also be loud, not conveniently located where we want to be, and we end up spending so much on food. We try to beat some of the expenses of food by cooking some of our meals in our rental kitchen. Eating out in Key West can be very expensive and the wait to be served in the best restaurants can be an hour or more. Being able to use our rental kitchen to cook some easy meals helps us to save a little on expenses while making the most of our rental. Of course, we always visit our favorite restaurants when we visit. Key West has great food that you won’t want to miss!

Visit Duval Street

Duval Street is probably the most famous street on Key West.  It is loaded with bars, restaurants, live music that spills into the street and mashes with the next musician as you stroll along, art galleries, and shops of every shape and size.  Duval Street is worth exploring but if you are traveling with children, it may be a much more kid-friendly atmosphere during the day and much less crowded. After dark, Duvall Street can be crowded, loud, and over the top.   

Great places to watch Key West Sunsets

Undeniably, Key West has some of the most spectacular sunsets and as you plan your trip, you will read about the nightly sunset celebration at Mallory Square.  This is an experience that you should have at least one night of your stay.  If you enjoy the carnival atmosphere and watching a romantic sunset with hundreds of your closest friends, you will enjoy your time at Mallory Square.  However, if you prefer a peaceful sunset experience with much smaller crowds, consider alternative locations such as the Truman Annex Marina boardwalk and the Truman Waterfront  Park. 

Get out on the water

Don’t forget that Key West is an island and you’re surrounded by some of the most beautiful water in the United States.  Do your research for trips offering snorkeling, kayaking, fishing trips, jet ski rentals, parasailing, and sailing excursions to fit any preference.  We enjoy getting on the water in Key West and chose to go on a dolphin-watching/sunset cruise with Sebago Watersports.  They took us where a pod of dolphins swam and played together all around our catamaran.  It was a magical sunset experience.  Get on the water in whatever way you are comfortable.  You won’t regret it!

Remember that you’re surrounded by water on Key West

Key West beaches

If you envision yourself going to the beach during your trip, be aware that Key West is not well known for having a lot of beaches but the beaches that are available are beautiful and you should check them out. They are Smathers Beach, Higgs Beach, and Fort Zachary Taylor State Park.

Our favorite places to grab a bite to eat

Glazed Donuts, 420 Eaton Street: We visit Glazed Donuts every time we visit Key West. They open at 7am and the line to grab these heavenly, fresh-made treats starts before the door is unlocked. My favorite is the Maple bacon donut. Before you go, be sure to check their website or social media channels for any changes in their hours but generally, they are closed on Monday.

Garbo’s Grill @ Hanks, 409 Caroline Street. If you love a good food truck, Garbo’s is actually an Airstream camper that serves tacos, burritos, burgers, hot dogs, poke bowls, and lobster rolls. If you like shrimp, I recommend the Yum Yum Shrimp Tacos. The title says it all!

Blue Heaven, 729 Thomas Street. Serving breakfast, lunch, and dinner, Blue Heaven is a popular spot. We waited for an hour to have breakfast and it was delicious. I loved the banana pancakes, both of which were almost larger than my plate.

Glazed Donuts (Maple Bacon!), Garbo’s Grill Yum Yum Shrimp, and Banana Pancakes at Blue Heaven

Plan a visit to the Dry Tortugas National Park

One of the least visited U.S. National Parks is just 2 hours west of Key West, the Dry Tortugas National Park is accessible only by boat or plane so plan your visit early. Reservations are limited and fill very quickly.

Ideas for your list of things to do while visiting Key West

There is so much to do and see in Key West.  Here is a list of fun activities we would recommend.  Remember, you don’t have to do them all.  You want to have a reason to go back!

Take a sunset cruise.

Pose for a picture at the iconic Southern Most point marker but go very early in the morning before the line starts to form.

Visit the Key West Butterfly Conservatory.

Explore Fort Zachary Taylor State Park.

Have an adult beverage at Sloppy Joe’s

Visit the home of Ernest Hemingway, the Hemingway House, and the Key West lighthouse, just across the street.

Visit the Turtle Hospital on Marathon Key.  This is a neat spot to visit either on your way down from the Florida mainland or drive up to explore for part of the day.  It is an hour north of Key West and we felt that it was worth the drive to visit, exploring the Keys along the way.  Tours of the hospital are 90 minutes each.

Grab some ice cream and enjoy the sunset. 

Get up early and read a book, enjoy your coffee, and listen to the neighborhood roosters.  Key West is so peaceful in the morning. 

People watch.  Key West is a great place to people watch.

Take a food tour.

Rent a golf cart and take a spin around town.

Grab a piece of Key Lime pie!

Take a selfie at the 0-Mile Marker.

Visit a museum.  Key West has several that are worth a visit. 

Try Cuban food.  Key West is 90 miles from Cuba and Cuban food is easy to find.

There is so much more to do and see in Key West but the #1 thing I would recommend is to make sure to adjust your attitude to match the laid-back Key West vibe. Make your time in Key West what you want. Whether you like the wild and rowdy or the peaceful you can find it in Key West.

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