The Florida Keys look beautiful with that multi-colored turquoise water. It’s tropical without leaving the country. It’s a destination that it looks like everyone is exploring in my online world. This island paradise had been on my bucket list for years and is a reasonable drive from our Georgia home – done! However, that’s really all I knew about it before I started planning and bought the husband a ticket to Miami to meet us.

My family had a good trip May of 2022, but I’m also known for the honesty and pessimism realism. It could have been better. Key West is lovely, but none of the six of us care if we ever see it again. I can’t think of another place we’ve been where we would say that as most of the time we are looking to return to our desination ASAP.

Please don’t let this discourage you from going – I just want you to have realistic expectations. Sometimes travel isn’t as magical and pleasant as it appears from the pictures.

Affiliate disclosure: As an Amazon affiliate, I may earn commissions from qualifying purchases through Amazon.com. However, all of these books have been loved by us, and I whole-heartedly recommend them.

Playing in the Rocky Sand at Fort Zachary Taylor State Park in Key West
Playing in the Rocky Sand at Fort Zachary Taylor State Park in Key West

Why Are You Planning to Visit Key West?

Let’s get this out of the way first. Key West can be a familiy friendly island during the daytime in the water. However, this should not be seen as a kid destination, and you need to know this upfront.

With the kids, it’s a fun two-hour drive from Key Largo with beach stops as you search for the best Key Lime pie. Take big kids to the Ernest Hemingway house or President Truman’s LIttle White House. See some butterflies or visit the lighthouse. All of these are going to cost you extra.

Duval Street, the main drag in Key West, boasts that it alone has 43 bars; there are plenty additionally on side steets as well. While drinking alcohol on the streets is technically illegal due to their open container law, there will be people consuming alcohol in plastic cups all over town. We did not see any inappropriate behavior, so this wasn’t an issue. Follow the bar scene to listen to some live music from the street. My family wasn’t downtown past sunset, but I imagine it could be a very rowdy place at night.

If you aren’t drinking or waiting to drink, the other main downtown option is shopping. Many stores have touristy trinkets, but there are also some high-end art stores and designer clothing stores. We always enjoy going into Wyland Galleries to admire the art, and local paintings always make great souvenirs. While Key West does have historical places and some animal encounters, to us the town itself feels like a very high-priced cruise destination with bars, shops, and fancy food.

Play: Don’t Plan on Sandy Beaches

For the majority, the Florida Key beaches aren’t the soft fluffy sand of the gulf. Because of the nearby coral reefs, the normal erosion that causes nice sand hasn’t happened. The rocky texture and coarseness varies between location. Sand castle building and beach strolls are painful. Also, these are not the ideal places for boogie boarding. While my kids used theirs to float in the ocean, it’s hard to enjoy coasting onto the beach when you don’t have soft sand.

Plan to do an online search for sandy beaches before your trip to make your list. Even if your chosen beach claims to have sand, the surrounding areas may have you walking over stones. Consider sandals for walking around or even sand shoes for going into the ocean. There aren’t giant coral chunks in the ocean to cut your feet on, but there are rocks to step on. One of my kids even cut her foot while in the water from stepping on one. Not a game changer but still not fun.

Play: Check the Water Safety Report 

Your car finally gets up to the check-in booth at the beach only for you to read the sign that says “high bacteria levels”. The color of the water may look beautiful, and there are plenty of other people in the water. However, you’re not risking your kids getting sick because the sign says it’s not recommended to get in the water. Not to mention, the sign is only written in English and there are quite a few Spanish speakers – was it not worth translating for them to have the warning as well? Ug.

Thankfully, each beach is different, and the level of enterococci (read: bacteria from fecal matter) flucutates during each two-week testing period. During our recent visit, only one beach we went to had that warning. While this may not be a game-changer for you, learn why the level of enterococci (what’s being checked) might be something to pay attention to. Check ahead of time and avoid the frustration.

Walking Around Key West with Tropical Flowers Everywhere
Walking Around Key West with Tropical Flowers Everywhere

Play: Say “Summer Seaweed”

Every summer, the sargassum (seaweed) piles up from the end of May through November’s start of hurricane season. You will wade through piles of it in some places, and the air will smell like rotting fish. Look it up. It’s not me being dramatic. While the water further out in the ocean is still a beautiful color, plan to swim in seaweed up-close to the shore.

According to my online research, city and county beaches clean up the seaweed. State beaches do not. This means that local Smathers Beach and Higgs Beach will have less stink at the beginning of the day while Zachary Taylor will not have been cleaned.

The good? You get used to the smell and don’t notice it after awhile. Also, it doesn’t sting or hurt you unless there are animals hiding down in it. The sargassum in the sea provides essential hiding places for baby turtles and fish, so it does have a reason. However, you’ve been warned.

Play: Bring the Umbrella

Here’s the deal. Hope for perfect weather and water and wind, but you may have to make the best of a less-than-ideal reality. As the Keys are closer to tropical areas, there are distinct rainy and dry seasons; May to October often come with pop-up showers so bring the ponchos or umbrellas. Then there’s always hurricane season risks from June to November. This tropical paradise acts like the tropics.

During our trip, the wind was really strong, so ocean play was very rough. We got drenched the afternoon of our sail trip, and it definitely added to our memories. Last in my pity party, I had built up the sunsets as this huge sky of pink with the most amazing sunsets. Nope, we gathered with everyone else at Mallory Square for the Sunset Party for clouds and a gray sky.

Pack some ponchos and don’t bring anything irreplaceable. You’ll be fine.

Sail, Snorkel, and Kayak with Danger Tours
Sail, Snorkel, and Kayak with Danger Charters

Pay: Schedule A Day at Sea

Ignorant moment here. Many of the beaches say they offer snorkeling, but I’m very glad this was not the only snorkeling I had scheduled. In my head, beach snorkeling meant that the kids would be able to put on their awesome new one-piece snorkel masks and find some tropical fish right off the beach. This is only partially correct. Some of the beaches do have rocky areas not too far out or a pier where you can snorkel along the pier. However, this only makes for good snorkeling if the water clarity is decent and the waves aren’t ridiclous enough to bash you against said rocks.

To see the coral reef in Key West and to be among the beautifully turquoise water, you will need to pay to get off the island. Whether this is a half-day snorkel trip with a tour guide or a family jet ski rental, this is the gold of your Key West trip. If you want to truly have the full Key West experience, allow for time and the finances to include this in your itinerary.

The highlight of our trip was a half-day eco-tour with Danger Charters. Our tour sailed out about an hour to the reef and sea kayaked through a mangrove island with a guide. The highlight was snorkeling in the open sea where we saw lots of tropical fish, some stingrays, giant barracudas, and sponges on the ocean floor.

Make sure you leave an excursion like this in your budget. Grab your waterproof phone bag to take some families pictures in the ocean. Don’t forget your reef-safe sunscreen to keep the reef healthy for future explorers. To me, trips like these are the whole point of Key West. Go see the coral reefs, and check out Danger Charters. They were a great company.

Pay: Budget (a lot) for Lodging

I looked for cheap hotels. They don’t exist for a family of six. I even reduced our stay from three nights to two and still paid $900 for a mid-week, not-downtown, mainstream hotel during one of the cheapest parts of the year. There are adorable bed and breakfasts all over Key West if your family is smaller and can stay in only one room.

As this is going to be the biggest part of your budget, I would definitely consider starting here to figure out the best time to travel. Staying downtown has the perks of being able to walk downtown easily, but check to see the cost of parking your car at your hotel or bed and breakfast.

If we were to do it again, I think we would consider staying maybe on a smaller key and only drive in for the day. The less crowded islands are cheaper, and sometimes the beaches are better. Your stay would definitely be quieter and less crowded.

The Red-Orange of the Royal Poinciana Trees Whichs Blooms May to July

Pay: Park the Car

Many people in Key West get around on golf cart, bicycle, or moped. The reason? Ease of finding a spot and cost of parking in the small downtown area. While some street parallel parking is hourly, good luck squeezing in finding one of these spots. There are many paid parking lots each with their own hours, own fee, and own difficulty getting out of spots. While there are some paid by the hour lots, many are not, and you will pay for four hours even though you’re only there for two. Make sure you bring cash for this.

Upon check-in to our hotel, the family in front of us was told that their large van would never find a spot, and it was suggested that they rent a golf cart. I would say that perhaps this was an expensive money-making plan and not necessary. At least during the time of our visit, they could easily have found a spot in a lot; it would have been a lot cheaper than the high-priced rental. However, if you’re going during the high season, it’s possible you would have had a difficult time parking.

With only an eight mile area, this compact downtown is very walkable and easily maneuvered. Given the cost of parking, consider going downtown only once during your trip, and staying for awhile. Wear good shoes to walk around, carry some water to refill, and bring a sunhat and sunscreen. However, I predict that you will be back more than one day, so make sure you include at least fifteen dollars a day in your budget for parking.

Pay: Enjoy the Food 

Fresh seafood, bar snacks, fabulous breakfasts, locally-owned cafés… There’s something amazing for every meal. I think I could stay in Key West just to eat well. Granted, that means I would have to pay to park everytime.

Food in Key West is going to cost you, but most of it is money well-spent. For a McDonald’s Coke, we paid a dollar more than our “normal”. Our family of six ended up spending about $100 each meal and that’s with meal-splitting and drinking only water. Cheaper food can be found outside of downtown with the perk of free parking, but it’s still going to cost you more than you pay at home. Don’t plan to save money and time with a fast food restaurant downtown; it doesn’t exist other than one Wendy’s.

Our trip had three fabulous meals. Make sure you check out Moondog Cafe and Bakery right next to the Hemingway House for food all day. Goldman’s Bagels was a great stop for a big breakfast and homemade bagels before our snorkel trip, and Blue Heaven was declared the trip favorite food with amazing pancakes.

Walking the Streets of Key West Among the Tropical Plants

As my husband had to remind me several times during our trip, the only one disappointed and frustrated by the lack of apparent perfection — was myself. Everyone else had a good time going with the flow. Hopefully, these Key West insights can help you be more realistic on your trip expectations, so you will be less grumpy than myself. It’s definitely a good place to see even though it has some drawbacks.

Anything you wish you’d known before your trip to the Keys? Know before you go so you can focus on the beauty of the island and your time together.

2 thoughts on “Key West: Know Before You Go

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