My goodness, I cannot believe it has already been almost a month since our family trip to Key West!
I was completely overwhelmed by the charm of Key West and just how lively of a little town it really was. Beautiful sites, good vibes, and live music galore. It’s just one big, fun beach town.
It was everyone in our groups first time visiting and I can honestly say that it was one of the best trips I have taken in a very long time. It was relaxing and low key, but still filled with adventure and fun! One thing I have to ‘pat our backs’ on though is how well we planned out the trip. Even though it was put together kind of last minute, everyday was “just enough” and spaced out perfectly! I really think it’s one of the things that made our trip so great! So instead of doing a typical guide, I thought I would take you all through exactly how we spent our five days in Key West!
If you are just looking for a quick and guide though, scroll all the way to the bottom and you’ll find it!
HOW TO SPEND FIVE DAYS IN KEY WEST
DAY ONE
(Arrival)
After a 7:00 am flight out of Houston the day after Christmas, we landed in Key West at 3:00 pm for our five-day family vacation! There are multiple options for getting to Key West (I discuss all the options below!) but we chose to fly directly into Key West (w/ 45 min layover in Miami) after finding a great deal on Google Flights through American!
Once we got in, we wasted no time and immediately ubered to our hotel, The Southern Most Resort, to check-in and change out of our travel clothes so that we could explore! This was everyone’s first time to Key West, so we were all really excited to get out there and see what it was all about.
(Duval Street)
One of the first things we wanted to check out was Duval Street, which just happened to start right at our hotel! One of the reasons we chose the Southern Most was because of its location! After doing a lot of research, we wanted to make sure we were in the heart of Key West and could walk anywhere as we pleased…including to Duval Street!
If you have never been to Key West, Duval Street is a famous 2-mile stretch that is lined with stores, bars, live music, hotels, and restaurants galore! It reminds me of a more charming and quaint but less raunchy Bourbon Street lol. So we walked the whole thing and explored until we reached the Sunset Pier at the end, just in time for our first Key West Sunset!!
The Sunset Pier Restaurant gets pretty busy, but we surprisingly found a table super easily!! So we had a few drinks, listened to the live music and watched the sunset before walking to dinner!
We went to Blue Heaven and I honestly cannot recommend it enough!!! It was the number one recommended spot by my readers and our best dinner of the trip by far! We sat outside, listened to more live music (one of my favorite things about Key West) and had the most amazing meal! I recommend the snapper, the mussels and you have to get the Key Lime Pie!
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DAY TWO
(Rent Golf Carts & Explore)
Day two, we slept in a little bit before meeting at Frenchie’s Cafe to grab coffee’s to-go before our walk to brunch! It was across the street from our hotel and quickly became our morning meeting spot to sit and discuss our plans for the day! We decided on Sarabeth’s for our first brunch and my gosh did we choose right! We loved it so much that we went twice!
Try to get there before 11:30 am to secure a spot outside!! That’s definitely where you’ll want to sit. The whole place is super charming though! Everyone that worked there was so nice and the food was so incredibly amazing/fresh. The mimosas were also really bomb and I personally recommend the smoked salmon…but also highly suggest getting the pancakes or the french toast for the table!
After brunch, we walked back to our hotel so that we could grab a golf cart at the rental place across the street and explore the rest of the island!
Everywhere you look around Key West, someone is driving a golf cart and after less than 24 hours of being there, we had major fomo and had to get one for ourselves! It was really cool because we had one that could fit all of us and we ended up making our way to the marina to shop and explore a little bit!
It was a really fun way to explore the island and could not recommend it enough!
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DAY THREE
(Boat Day)
Day three was our favorite day of them all!! Charting a boat to explore and fish was the one thing I wanted to do on this trip and it ended up being so fun!! We booked through Fun in the Sun Key West and would highly recommend them!
Our day started early and we were out of the marina before 9! We went to a few different sand bars, saw the Mangroves and did some fishing!! We saw stingrays, baby hammerheads and everything too!! The highlight was definitely fishing though!! Our captain (Captain Dan) went out of his way to make sure we caught a lot, so that was really cool and made the whole outing worth it.
After over four hours out in the water, we headed back to the marina where Captain Dan filleted all of our fish so that we could enjoy everything that we caught for lunch! It was seriously SO cool and the fish tacos that were made were some of the best fish tacos all of us had ever had!! There is a little beach and pool by the marina so we just hung out there, enjoyed our fish tacos and drank daiquiris for the rest of the afternoon. What I would do to go back and relive it over again!
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DAY FOUR
(Bikes, The Beach Day & a Sunset Sailboat Ride)
Day Four, I got up to go for a run and explore a little bit myself. One of my favorite things to do when traveling to a new place is to go for at least one morning run because you get to really see the area in a whole different way! While out, I came across the Key West Farmers Market and it was so cute that I had to stop. I walked around for a bit and loved seeing all of the local vendors. From jewelry to clothes, paintings, fresh fruit, beauty products, and more! It was all there!
Afterward, I ran back to the hotel to change so that we could rent bikes and head to the beach for the day!
One of the interesting things about Key West (that we did not know before) is that it isn’t super known for it’s long, white sandy beaches. It’s a very rocky island and nice beaches are few and far between. Luckily, after talking to a few locals the day before, it was recommended to us to go to Fort Zachary State Park to get our beach fix and it ended up being exactly what we were looking for.
To get there, we decided to rent bikes from our hotel, which I highly recommend doing during your trip! It ended up only being a five-minute ride but we loved it and ended up biking around the island for the rest of the day before heading back to the hotel to get ready for our sunset sail.
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We – aka “the kids” set up a sunset sail for all of us to go on as a thank you to Colton’s parents for putting the whole trip together. We booked our sail through Sunset Sail Key West and loved that we had the whole boat to ourselves as opposed to sharing one with 50+ other people. It was BYOB so we brought wine and beer. They made a cheese board for us, we sailed out into the ocean to watch the sunset and it was all around the perfect way to end our trip!
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DAY FIVE
(Brunch, a Dip in the Pool and Departure)
On our last day, we woke up and packed our bags first thing so that we could have the rest of the day to enjoy and not have to worry about packing and checking out later. Our flight wasn’t until 7:00 pm that night, so we were really able to have a full day! Luckily, our hotel kindly held our bags, let us access them as we needed and even had showers available for us to use before heading to the airport.
(the moon dog cafe)
Throughout our trip, we had passed by this restaurant, The Moon Dog Cafe, multiple times and every time we saw it, I made a mental note of how cute it was! Not to mention, every time we passed by, it didn’t matter if it was 10 am or 8 pm… it was packed (!!) so I took that as a good sign and really wanted to go before we left.
Luckily for me (since I was the one that suggested it and drug everyone there) it was AMAZING. The lemon quinoa pancakes?!? Heavenly. The fresh watermelon juice?? Divine. Both Colton and his sister got the fish tacos and couldn’t stop raving about those either. I also loved their cute little covered patio that overlooked the sidewalk… which served up some premium people watching 🙂
After brunch, we all kind of split up to do our own exploring, so Colton and I made our way to Earnest Hemingway’s Home since it was just down the street and on the way back to our hotel.
One of our good friends was in Key West a few weeks prior and highly recommended us checking it out – so it was at the top of our list to do before we left! It ended up being super interesting, the property was gorgeous and the famous “six-toed cats” did not disappoint!! Also, let me just say, there was not just one six-toed cat…but like 30 (lol)!! Hemingway was gifted his first one from a sea captain in the 1930s who believed that these cats were a sign of good luck and it just took off from there!
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Afterward, we made our way back to the resort to relax by the pool for the rest of the day until we had to leave for our flights! It was the hottest day we had experienced thus far and all agreed that an afternoon in the pool was the best way to end the trip.
So would we go back??
The answer is YES, YES, YES! Throughout our whole trip, we all kept saying how much we were enjoying ourselves and how much we loved it there. Key West just offers so much for everyone, it’s so beautiful and lively and I honestly can’t wait to go back! It was truly one of the best trips we had been on in a really long time.
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KEY WEST TRAVEL GUIDE
A Few Things…
Don’t get too worked up about where you stay
Key West isn’t exactly a lounging on the beach, resort kind of vacation destination. There is a lot (and I mean a lot) to do/see and you’ll barely spend any time at the hotel. As long as you’re in a good location, you’re good to go!
There are very few bright, white sandy beaches
As I mentioned above, this was something we were not expecting until we got there and found out for ourselves. The water is still beautiful and the island is everything.. but if you want to strictly lounge on the beach, Key West might not be for you.
There is no ‘open container law’
Okay, technically there is… but it’s definitely not enforced lol.
You’re going to walk EVERYWHERE
Seriously though, do not worry about renting a car but do make sure you pack good walkinng shoes. Everything is within walking distance and super easy to get too. Anything that is a tad farther you can just uber too!
It’s SUPER casual
I was told this before going but I don’t think I realized just how casual of a place Key West really was! Everyone is constantly in their swimsuits, shorts and flip flops. Even for dinner at the “fancier” restaurants!
How to Get There
Take a Direct Flight into Key West
This is what we did and it was super easy, but I do have to say… it was also very pricey! We luckily found a great deal on American Airlines (which we never fly but found through Google Flights) and had a quick 45-minute layover in Miami both ways but all around got really lucky and ended up paying half of what everyone else paid on United.
Airlines that operate in Key West: American, United, Delta, and Jet Blue.
Fly into Miami and Drive
A much more affordable option! It’s easy to find inexpensive flights into Miami ( & Ft. Lauderdale!) and if you do so, you can rent a car and make the drive to Key West. It’s only about 3 hours from Miami, which isn’t bad at all and I’ve heard from many people that the drive is beautiful!
Fly into Ft. Myers and Take the Ferry
Another great, more affordable option and I love how unique it is! If you can find decently priced tickets into Ft. Myers. taking the ferry from there to Key West is super easy and takes about 3.5 hours! The ferry takes off at 8 am and gets into Key West around noon.
Where to Stay
The Southern Most Beach Resort
For this trip, we stayed at The Southern Most Beach Resort and were all around really happy with it. This was our first time to Key West and were all a little bit confused about where we should stay but it all ended up working out just fine.
A few of our “musts” when looking for a hotel included:
- Being in a great location that was walking distance to everything.
- Pretty Views // Close to the beach
- Updated clean rooms
- Nice pools and pool bars
- Beach Access
So when we found The Southern Most, we were all around thrilled that it checked off everything on our wish list. With that being said though, overall we were not impressed or wowed by it at all. The photos online definitely made it look better than it was in real life… The rooms were large and spacious, but nothing special and we were super bummed that our group was completely separated. They legit put our rooms on complete opposite ends of the property (literally blocks apart from one another) so that just kind of sucked… but at the end of the day we made the best of it. The beach area was another let down because what we saw online was very different in person and the three pools on property were very ‘meh’.
I feel bad not saying only positive things because we all around did enjoy our stay there… it was just expensive and a little bit of a let down is all. Like I mentioned above though – the location was everything!!
Next time though….. we definitely want to rent an Airbnb!!
Where to Eat & Drink
Coffee
Frenchie’s Cafe – I kid you not, we literally went here every single day! It’s very small, but has a sweet little garden area in the back and a few seats on the porch in the front!
Keys Coffee Company– Super cute They have coffee ice cubes for their iced coffee, enough said! Their breakfast sandwiches are also great!
Breakfast/Brunch/Lunch
Sarabeth’s– Best Brunch in Key West! We loved it so much that we went twice! If you can, get a table outside!! Amazing spot for mimosas but if you want a non-alcoholic option, get the flower juice! It was so so refreshing. As for dishes, my favorite dish was the smoked salmon but highly recommend the pancakes or the french toast for the table!
Blue Heaven – We initially went here for dinner but everyone in the world recommended it for brunch too! Great outdoor vibe with live music, but be sure to get there early since they don’t take reservations!
Moon Dog Cafe – After walking passed it multiple times during our stay, we finally stopped and I’m so glad we did! Both the inside and front porch patio were so cute and it didn’t matter if it was 10 am or 8pm… it was always packed. I suggest getting there before 11 on the weekends to avoid a wait! I highly suggest the lemon quinoa pancakes, the fresh watermelon juice! If you’re wanting more of a “lunch” dish though, go with the fish tacos!
Dinner
Blue Heaven: We LOVED THIS PLACE. I’m telling you… if there is one place on this list that you try… make it this. Blue Heaven was our first dinner spot and favorite meal of the trip. It’s a Key West staple that you have to experience that offers a fun dining experience with both indoor/outdoor dining. Everything on the menu is to die for but they are specifically known for their Key Lime Pie!
Little Pearl– Romantic atmosphere, an intimate space with lots of great seafood!
Latitudes: One of our favorite experiences and dinners of the trip! **Definitely make a reservation in advance though!** Just a quick boat ride away and you’ll be dining on the private islands of the Sunset Cottages. The scenery and views were truly breathtaking and it was all around just really nice to get off the island and experience something different. The property was seriously gorgeous. Ordering wise, I highly suggest skipping ordering your own entre and recommend just trying all of the shared plates and maybe splitting a few salads! We had a few and were blown away by how good they were but were very unimpressed with our actual meal. Everyone was in agreeance that we wish we would have just ordered another appetizer or two and then skipped the main meal.
Drinks
Sloppy Joe’s– The original and first Sloppy Joe’s location with all the dive bar feels
Sunset Pier– The perfect spot for sunset drinks! I loved the live music and all the views!
Willie T’s– A fun spot for after dinner or late night drinks when there’s a band playing.
Green Parrot – I never made it here… but my father-in-law did and had the time of his life lol!
Key Lime Pie
- Kermit’s
- Blue Heaven
- Better Than Sex Desserts – make a reservation!
What To Do
-Duval Street: Ah, the famous Duval Street! The infamous two-mile stretch of shops, hotels, restaurants, bars, live music and burlesque shows! It’s very charming, busy and a darn good time! It’s the place to be at any time of the day.
-Rent a Golf Cart or some Bikes and Explore the Island: We did both of these and really enjoyed them both! I personally liked the biking more… but the golf carts really were cool and allowed us to see even more of the island.
-Charter a Boat/Fishing Excursion: The best part of our trip! We used Fun in the Sun Key West and truly had the best time boating, visiting the sand bars, and fishing for the day!
-Lounge by the Beach at Fort Zachary State Park: I highly recommend biking there as opposed to driving because the car line gets pretty long, while the bike line had none! Key West isn’t exactly known for its beaches, but the beaches in the park really are beautiful!
-Sunset Sail: There are multiple companies you can book this through but we booked with Sunset Sail Key West! We loved that we had the boat to ourselves, it was BYOB and they made a cheese board for us to enjoy as well!
-Check out the Key West Light House: It was actually very cool because it’s in the middle of the island!
-Southern Most Point Pier: Literally the southernmost point of the US – only 90 miles from Cuba!
-Explore the Marina: We did this one afternoon and really enjoyed it! There is a lot going on down there and so much to see! Lots of shops and restaurants all around that line the marina as well!
-Go to Sunset Pier: The perfect place to grab drinks, listen to live music and watch the sunset.
-Go to the Ernest Hemingway Home & Museum: I was very surprised how much we enjoyed this! It was only $15 to enter, the grounds were beautiful, and you’ll love seeing all the six-toed cats lol.
-Nighttime Neighborhood Ghost Tour: According to Haunted American Tours, Key West is the 4th most haunted location in the whole country. Checkout Ghosts & Gravestone Tours
Until next time Key West!
xo,
Lauren
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