I am no stranger to finding things to do in Key West, Florida. When Mr. Family Trip and I were expecting our oldest, we babymooned in Florida, starting in Miami and driving the Keys to Key West (thinking we’d enjoy sun and water, but, really, it felt more like me watching lots of people party in South Beach while feeling huge!).
When we took our kids to the Florida Keys for a vacation recently, we stopped in Islamorada before getting down to Key West. So when my mom, sister, and I were in Key West for the day, it all felt familiar to me.
This was a stop on my first-ever cruise experience, which meant we only had a day here – one day for me to revisit Key West (this time as a not-pregnant person).
About Key West - Getting There
Key West is the last in a string of coral islands off Florida. Given its location, Key West is officially the southernmost point in the contiguous U.S.
Legend has it that Key West was originally used as a boneyard/graveyard for native peoples, which meant when the Spanish came by for the first time, the place was littered with bones.
The Spanish governor of Cuba gave Key West to Florida (I guess he wasn’t into the massive amount of skeletons lying around?), and then Florida entered the United States in 1821. There was a bit of an ownership spat between two men who saw Key West as strategically located for shipping routes. Eventually, it became a strategic military base.
Today, Key West is known for its party vibes, great weather, and beautiful water. Through the past few decades, though, the year-round population has been in decline and a couple of major storms have hurt the town.
Tourists and visitors, like me, however, love it. While it isn’t a spot that has gorgeous beaches (that just isn’t what the Keys offer, being coral cays), its open container laws and good-natured energy make it a blast to enjoy. Key West blends a good margarita and old with new. It is where a coastal city from the 1900’s meets modern-day tourists with disposable income looking to escape their cares.
Key West has become iconic. And it is worth the trip.
The ways to get to Key West are:
- By cruise ship (not kidding – it’s a popular cruise ship stop for those boats heading out of Florida and off to the Caribbean)
- Fly into Miami, rent a car, and drive down the Florida Keys (for more fun, rent a convertible). It is a four-hour drive, but a fun one.
- Fly direct – there is a small airport in Key West that receives flights from around the U.S.
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Enjoy Duval Street
Duval Street is where all the action is. It is a charming combination of upscale artists’ boutiques, fancy clothing shops, and dive bars that will let you express your wilder side.
Drinks can be had to-go, so this becomes quite a party scene at night (and sometimes during the day!), but it is fun to stroll.
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See the Southernmost Point (or don't)
Key West is officially the southernmost point in the contiguous United States. There is a marker indicating this that visitors are free to take a picture of.
Of course, in today’s world of increased tourism and Instagram popularity, the wait and line to take a picture with the marker can take quite a long time. (When I first visited over 15 years ago, we just walked right up!)
Whether you want to wait in line today is up to you!
Snorkel
This was one of my favorite adventures I’ve done in the Florida Keys so far. (For the record, we’ve snorkeled Grand Cayman, Belize, the Great Barrier Reef, and Biscayne Bay, so snorkeling is a thing I generally enjoy.) We did a snorkel tour, like this one, that took us to a reef outside of Key West.
The water was beautiful, so sailing along above the water was as enjoyable as snorkeling in the water. When we arrived at the reef, the snorkeling was fantastic! I saw so many colors, so many fish, and I just didn’t want to leave that magical world.
The agent we booked our cruise through recommended Sebago Watersports, which was a good choice, too. We barely made it to the catamaran on time, but managed to spend a fantastic day exploring the waters of Key West (complete with mimosas!) once we got there.
Kayak
During our first trip to Key West, Mr. Family Trip and I did a kayak trip through the mangroves, like this one.
(While on my most recent trip to Key West, we didn’t have time to do this, but it would have been an add-on experience quickly if we had more time!)
Rent Bikes
Hands down the best and easiest way to explore Key West. Key West is flat, and not terribly big. Bikes make it really easy to get around town (especially if you are hitting up Sloppy Joe’s and shouldn’t be driving a car).
You don’t need to rent a bike in advance. And, honestly, most of the bike rental companies are about the same. So just pick the one closest to you when you arrive and/or use Google Maps to pick the company that appeals the most. No need to overthink it.
I will say that while there are some bike lanes and bikers are all over, you will be biking on main roads sometimes. Be cautious and use common sense.
Otherwise, this is a great way to get off the mainland and see tucked-away communities and areas.
Eat Key Lime Pie
You don’t have to be in Key West to do this (we had fantastic Key Lime pie on our family vacation to Islamorada).
But, of course, if you are in the Florida Keys, a huge chunk of heavenly key lime pie is a must.
This visit, we ended up at one of the Kermit locations, just by way of convenience and because the Internet said it was good key lime pie. This was delicious! Key lime pie tastes like summer.
Eat Delicious Food
There are so many places in Key West to eat fresh seafood and taste bright flavors.
I’ve been to the very popular Blue Heaven before. Be prepared to wait for a table there, but I remember enjoying the atmosphere the most.
This particular visit, we asked our bike rental clerk his favorite place to eat, and where the locals go, and without hesitation, he recommended Square Grouper. In fact, he told us if we didn’t like it, come find him and he’d pay the bill. That wasn’t necessary since we loved it!
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Click HereGet a Drink at Sloppy Joe's
Key West is known for its party vibe, and open container laws! There are tons of places to grab an adult beverage. But none is more iconic than Sloppy Joe’s.
I love a good beach bar after a day of salt and sun, and Sloppy Joe’s (while it can get crowded) offers the best of what these are. Live music is performed on stage, people laugh and mingle, the drinks are a little too sweet but frozen, the windows are open, and the transition between inside and outside is blurred.
The location is great, and there is a reason why this place has been around since Prohibition ended in 1933. It is an institution – complete with Ernest Hemingway lookalike competitions.
Mallory Square Party & Sunset
Unfortunately, on our most recent trip, we had to be back on the cruise ship before sunset. But in the past, we’ve joined the crowds at Mallory Square for sunset.
Here, street performers offer shows in everything from fire eating, cat training, acrobatics, juggling, and more. The highlight? Waiting for the sun to set over the big ocean horizon in the hopes that you’ll be one of the ones lucky enough to see the “green flash.”
About Dry Tortugas National Park
As you know, we LOVE national parks. And I tried very hard this past visit to Key West to get to Dry Tortugas National Park. Key West is, after all, one of the best jumping-off points to make it to this remote park. However, I quickly learned that the excursion would take the better part of the full day and, additionally, tickets for the ferry needed to be booked months in advance. If this is high on your to-do list, be sure to give yourself an extra day in Key West and plan way in advance.
With More Time
Each time I have been to Key West, the time goes too quickly! There is a lot to do in this little town on the ocean.
If you are looking for more activities, though, here are some options:
- Ernest Hemingway House and Museum (I so wish I had time for this since I feel an affinity for him after eating at his favorite Madrid restaurant)
- Key West Lighthouse
- Truman Little White House
- Beach time at Smathers Beach
- Visit a retired Coast Guard ship and museum
Overall, take the time to enjoy all of Key West by going slowly. Enjoy the old maritime life and then grab a cold drink at a bar listed on the national register of historic places, where a new musician plays modern tunes. It’s Key West. It’s both old and new. And it occupies its own space in time.
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