Discover Your Perfect Long Weekend Itinerary in Key West
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📍 Key West, Florida
The Florida Keys are the ultimate winter getaway destination. The ancient coral reefs that compose this 180-mile chain of islands at the base of Florida are as close as you can get to the Caribbean without having to leave the continental United States. Driving through the famous string of keys, you’ll pass small island towns, buzzing Tiki bars, and pristine beaches before you make it to Key West. Named aptly for being the western most key, Key West has a vibe all its own, and it's true that it may not be everybody’s speed. Historical and beautiful as it may be, a walk along the streets of Key West feels akin to a college town, and I don’t know about you, but I’m simply not cut out to partake in the drunken shenanigans that occur in the harsh daylight hours of Sloppy Joe’s Bar.
Here at Discovery Detour, we search for relaxed vibes, moments in nature, and lessons of science at every destination that we hit. If this type of vacation sounds right up your alley, then you’ll love this itinerary for a perfect long weekend in Key West. I’ve packed it full of beach destinations, wildlife encounters, and delicious eats to fuel you through your island getaway.
Let’s sip on some coconuts during the day and save the rum infused cocktails for the evening, leaving both your memories and your liver fully intact.
Nothing says “The Florida Keys” more than these overly complicated and colorful street signs. You will see these EVERYWHERE!
Friday:
Today, we’ll be lounging along the beach of the southernmost state park in the continental United States. Since it’s the first day of your vacation, we recommend sleeping in a bit, dressing in our bathing suit, and grabbing a morning brew at The Koffie House before meeting at our first destination.
Fort Zachary Taylor Park (Fort Tour)
Fort Zachary Taylor Park is one of the most popular day destinations in all of Key West. It costs $6 a vehicle to get in which will give you access to both the fort and the beach. As you wait for the sun to warm the morning air, enjoy a peaceful stroll atop the red brick path that weaves you around Fort Zachary Taylor. Named after the 12th president of the United States, this fort was finished in 1866, and was secured as a Union fortress throughout the civil war, deterring confederate forces from attacking this southern shore. Plaques placed around the fort make it easy to self-guide your way through the area, or, if you're lucky enough to go on the third weekend of each month, you may also get to witness a historical reenactment.
We recommend arriving at Fort Zachary Taylor Park before noon as the park is known to reach capacity at peak season.
Here, Drew walks along the Fort Square in search of some cannons.
Fort Zachary Taylor Park (Beach)
It’s time to soak up some rays on one of the most beautiful beaches at the key. Stunning, shallow, and turquoise waters meet powdery sand at Fort Zachary Taylor Beach which is why it is also one of the most popular beaches in the area. Plan to be here for several hours during the hottest part of the day and enjoy cooling off in the refreshing waters of the Gulf of Mexico. Pack a snorkel if you wish to spot fish which frequent the area, or binoculars if you’re more of a birder. Enjoy either a packed lunch or choose from one of the options from the on-site concession stand as you forget your worries in this tropical paradise.
Even on a cloudy day, the crystal clear waters of this beach are obvious.
Historical Home Tours
After you have rinsed off at one of the complimentary wash stations at the park, you should have some time to visit one of the historical houses in the key. For this stop, I give you a choice to explore the Truman Little White House, The Hemingway Home and Museum, or the Key West Lighthouse depending on your interests. For history buffs, the Truman Little White House was the winter White House for Harry S. Truman, the 33rd president of the United States. The Hemingway Home may appeal to literary lovers as it was home to the Nobel-prize winning author, Earnest Hemmingway, and is filled with mementos from his life. For everybody in between who may just prefer to get a better view of the island, the Key West Lighthouse is open for daily tours which allow you to climb the lighthouse and learn about one of the first female lighthouse keepers who took care of it after its initial development.
All of these houses require a small admission fee, and advanced tickets can be purchased on their websites which are linked above.
Key West First Legal Rum Distillery
As the sun begins to set, you should make your way to Mallory Square for its daily sunset celebration. But first, if time permits, take a detour to the Key West First Legal Rum Distillery where you can take a free tour of the distillery and sample their wide array of local rums. Kids and pets are welcome on the tour, and this stop is an excellent place to grab a drinkable souvenir, and to ease your way into the hustle and bustle that is the Mallory Square Sunset Celebration.
Sunset Celebration at Mallory Square
You may have noticed around town that Key West boasts its title as being the “home of the sunset.” Nobody takes this more seriously than the vendors at Mallory Square. At the northeast corner of the key, Mallory Square serves as a congregation place for vendors, live musicians, rotating entertainers, and of course, tourists. This daily festival starts 2 hours prior to sunset, and is the perfect way to end your first day in Key West. Choose from any of the restaurants that line the square to satisfy your dinner cravings, and just be sure to be at the square to witness your first magical Key West sunset.
This is just one of the striking Key West Sunsets we saw while we were there.
Saturday:
I took it easy on you yesterday and let you relax by the beach for most of the day. Today, you’re going to see a little more around town so it’s time to lace up your walking shoes.
Lagerheads Beach Bar and Water Sports
Loggerheads opens at 10am every morning, making it a fantastic place to meet your friends for brunch. It’s stationed on its own private beach so you can enjoy your food with your feet in the sand and then lazily make your way into the water to cool off as the sun starts to heat up the streets. They are famous for their rum runner cocktails and their delectable fish tacos which come served alongside a soft chocolate chip cookie. Plan to stay here for a few hours to really enjoy the ambiance of this unique beach bar restaurant.
Chickens regularly join you as you relax atop beach loungers here, but if you don’t bother them, they won’t bother you.
Lagerheads reminded me of what I always knew to be true: there is nothing as relaxing as having a cocktail with your feet in the sand.
Walk south down Duval Street
If you’ve never heard of Duval Street, you can think of it like the Bourbon Street of Key West. Although it only takes roughly 30 minutes to walk, this historic street is nicknamed “the longest street in the world” because it connects the Gulf of Mexico to the Atlantic Ocean shores. Cuban influences can be seen in the architecture and in the cuisine of the many restaurants which line the street. Although I’m not much of a buyer, this street ended up being one of my favorite places to window shop because of the massive assortment of items they offer. Steering clear of the cheaply made souvenirs, we wandered into Cuban coffee shops, cigar humidors, and even took a rest in the Key West Hammock Company, almost tempting us to figure out how we could possibly fit an oversized hammock into our RV.
You’ll end your walk at the Southernmost Point of the Continental United States. Don’t forget to take your obligatory picture while you’re there!
There is usually a short wait to take a picture here, but the bonus to that is that there is always someone there to take your picture!
The Key West Butterfly and Nature Conservatory
At this point, you’ll be right next to one of my favorite stops of this entire weekend. The Key West Butterfly and Nature Conservatory is your unique chance to walk into a butterfly oasis and see these delicate beauties up close. As you walk through this enclosed, island habitat, you’ll witness hundreds of flowering plants, 50 butterfly species, and 20 exotic bird species including two striking flamingos. We visited the conservatory on a chilly day, so the warm climate of the indoor greenhouse was a pleasant escape. This experience is enjoyable and educational for the whole family. It’s $15 a person to enter, and your entry fee will give you unlimited trips to the conservatory throughout the rest of the day.
While you shouldn’t reach out and touch any of the butterflies, you can certainly enjoy it when they choose to grace you with their presence.
Dinner at The Lobster Shack
The humble little establishment of The Lobster Shack may not look like much from the outside, and you may have sticker shock when you see what the price is for a single lobster roll sandwich, but please believe me when I tell you that I would easily pay double the price for another Key West Lobster Roll.
Drew and I fell in love with lobster rolls when we visited Maine this past spring, and dare I say, that the Key West Lobster Roll was more delicious than any roll I got in that northern state. Served warm with melted butter and a splash of key lime juice, this sandwich is sweet, tangy and all but melts in your mouth. Their other options include traditional lobster rolls, and coconut shrimp to name a few, and they all can be washed down with their selection of cold beers and sodas.
My mouth is watering simply looking at this photo of the Key West Lobster Roll.
Irish Kevin’s for drinks
I know I said we’re not much of a late night crew, but if you are in Key West, you should probably see what all the hype is about. For your night out, we recommend Irish Kevin’s, a local dive bar with strong drinks, good food, and lively music that makes the whole place feel like a non-stop party. If you have room in your stomachs before hitting the hay, we recommend that you try their chicktatoes, a strangely named but uniquely delicious treat. It’s basically a chicken nugget with a gravy center, coated in hash browns and then fried to perfection. Was there anything in that sentence that didn’t sound amazing? I didn’t think so.
Sunday:
Today, my friends, we’re going to take it slow, and if you had one too many drinks at Irish Kevin’s last night, then you’ll thank me for this. We’re also going to do a bit of easterly exploring as we take a drive to see more of what the keys have to offer. Just like Friday, dress in your bathing suit to enjoy the day, and plug Bahia Honda State Park into your GPS. For clarity, it’s about 37 miles east on The Overseas Highway.
Breakfast at Good Food Conspiracy
About halfway through your drive, you’ll pass a sign advertising fresh juice, and you’re going to want to check this out. The Good Food Conspiracy is a locally owned organic market, juice bar, and deli, stocked with freshly made smoothies, juices, and a rotating menu of lunch items. It’s a great place to nurse any looming hangovers with a healthy, fruit packed breakfast. If you’re inclined, you can also grab something to take with you to the beach, such as their famous Tuna Everything Sandwich, to enjoy later in the day over lunch.
Bahia Honda is my favorite state park in all of the keys for a few reasons. The small spit of land which it sits on means you can choose between an ocean and a gulf facing beach depending upon how much you like the ocean waves. Just like Fort Zachary Taylor Park, this park has excellent snorkeling opportunities. Snorkeling gear and kayaks can all be rented in their visitor center for a low cost, and you also have the opportunity to reserve a snorkel tour with a local guide from their dive shack. A good assortment of food is available at their snack bar, meaning you can literally stay here all day if that’s what you’re interested in. The nachos supreme which I ordered at this park surpassed all expectations about what a state park food hut could deliver and even had one of the grounds workers asking me where I ordered the delicious looking entrée!
If you do happen to stay until sunset, it is best witnessed at the peak of the Bahia Honda bridge which is just a short walk from the beach.
This is the view of Bahia Honda from the Bahia Honda Bridge.
Dinner at My New Joint or Mangrove Mama’s
Regardless of how excellent the concession stand is at Bahia Honda State Park, at the end of a long beach day, you are probably ready for a hearty dinner. As you make your way back to Key West, I have two recommendations for you to choose from. Mangrove Mama’s has a perfect laid back feel. They have outdoor seating, nightly music, and a Tiki bar atmosphere which would make you feel right at home if you can still feel the sand between your toes. Their Key Lime Martini is one of the best ways to wrap up your Key West adventure. If you’re looking a greater variety of food options, than My New Joint may be for you. It scores slightly higher in the foodie review scale, and has a laundry list of craft beers on draft. It also has nightly live music, but doesn’t offer the same beach vibes that you will get at Mangrove Mama’s. Readers choice for this one, because you simply can’t go wrong.
Bonus:
Although it wasn’t in this weekend's getaway guide, another amazing thing to do while in Key West is to take a trip to Dry Tortugas National Park. Dry Tortugas is one of the most remote National Parks in the country. It lies 70 miles off the west coast of Key West and is only accessible by boat or plane. It is an excellent destination for swimming, snorkeling, bird watching, and beach lounging. We had originally planned to spend a day in Dry Tortugas via the Yankee Freedom Ferry, but the tour was unfortunately canceled due to unforeseen choppy ocean conditions. While I can’t give you a first hand account of how the trip would have gone, I can tell you that I have never heard a negative review of the tour, and our desire to make up for this missed trip actually motivated us to start planning a trip to Key West next year! If you are also interested in seeing this beautiful National Park, you can book your Ferry tour here up to 6 months in advance. book early, because these tours do sell out fast!
If you went to Key West and you think there’s a destination that I missed, please leave us a comment. Also, don’t forget to subscribe to Discovery Detour to receive a notification every time we release a destination guide or travel tip centered blog.
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