When we planned out our trip to Key West we tried to be strategic in our planning to allow for plenty of downtime to ENJOY the resort and all it had to offer!
I have always heard that Key West can be pretty wild so we booked our stay about an hour north of actual Key West (in Duck Key) and tried to plan out our days to just have ONE full day in legit Key West AND we planned that day for what we thought would probably be the least wild day (Friday over Saturday).
We had a FULL day on our arrival day and it was tough to get up early to hit the road again after so much traveling but it was well worth it to not have the traffic nightmares we’ve read about and to ensure as much of a family-friendly day as possible.
A big thing with Key West IS the DRIVE. It’s beautiful and I kept reminding the kids that soooo many people have that drive on their bucket lists as a dream experience so they needed to soak in alllll the beautiful views! It didn’t disappoint and I can totally see the appeal of renting a jeep and doing the drive with the windows down and music up. Could be really romantic and fun together when you’re not in a van with three kids 😉
We decided what to do at what times based on the timing of things opening. Since Fort Zachary Taylor opened the earliest, it was our first stop. I do think it was a GREAT thing to do in the morning time as well because it probably gets super hot and sticky later in the day.
However, a lot of the reviews we read about Fort Zachary Taylor also said it has an awesome beach! The cost to enter the fort was a low cost per vehicle so a super cheap family option that could be extended to take up a good portion of the day if you wanted to do more exploring or enjoy the beach options available.
We just really wanted to hit the highlights of the fort itself for our history buffs in the group. Plus I mean a fort named after Daddy is a must-visit right 😉
When it comes to tours I’m all about seeing the sights but really just a quick highlight over view and I’m GOOD. The girls are very much like their mama with this…we explored and took lots of pictures but we left the hardcore fact-reading to the boys. We let Kye be our “tour guide” and he read through the information at each stop on the self-guided tour.
We had the ENTIRE place to ourselves. We saw like one couple while we were in the actual fort and then as we were leaving we passed an elderly group of friends who were in bathing suits and the men didn’t have shirts or shoes on. Who knows what they were up to but it was funny to see them roaming around like that!
Needless to say, it was a VERY chill vibe! A great family-friendly activity and only took us an hour or so. For sure bring along some water and be sure to use the bathroom by the parking lot as there aren’t any bathrooms in the actual fort.
It’s also very worthwhile to climb up to the top for the beautiful views! The self-guided tour is very easy to follow along and doesn’t require any certain order. The facts are quick and Kye was the perfect age for this activity but I think even a little younger he would have enjoyed it.
Tess had to have the first, of what I knew would be many, piggy back rides of the day. She was already missing the stroller and we’d just barely had breakfast 😉
Seeing the wild roosters roaming around was really neat. The rumor is that when cock fighting was outlawed as a way to “rebel” against “the man” those who owned roosters in Cuba and used them for the fighting let them all go to roam the streets and now there are just tons of them all over!
They are pretty daring little guys too and didn’t seem fearful of us at all…but thankfully didn’t attack like their cousins the pelicans 😉
We drove into the town area and were again glad we planned to visit on a weekday as parking is SCARCE and I’ve heard it’s near impossible on the weekends! You do have to pay to park in most places and they charge hourly, so something to also keep in mind.
We didn’t have a set plan as to where we wanted to eat but Zach did have a list of places he’d heard were good options. We tried going into one place but it was VERY bar-like in the vibe. The table and floor were sticky and it just felt dark and dingey and not like a fun family vacation vibe.
So we walked a little further down and ended up at the Original Jimmy Buffett’s Margaritaville Cafe! We’ve eaten at the location in Panama City and knew the food was good and that the kids would be able to find something so we went for it!
This trip we tried to be super yolo when it came to food since we had originally planned to be eating all inclusive in Mexico. It did pain my heart to spend SO MUCH on FOOD though! So we still def tried to budget as much as possible and Tessie helped us out there as the child kept it simple everywhere she went. For lunch? She just wanted PLAIN LETTUCE haha.
The vibe in Margaritaville was PERFECT! Very tropical. Very VACAY MODE. Way better than the first spot we tried and we were eating nice and early (it was around 11:30ish) so we beat the crowds too and had a fantastic experience with the service too.
Zach and I both noticed how awesome the service was both at our breakfast the day prior as well as at our lunch! VERY impressed by that and it left an impression as so often in tourist spots the service suffers!
Growing up my next door neighbor bff and I would listen to Jimmy Buffet’s “Volcano” as we jumped from couch cushion to couch cushion. We also loved “Cheeseburger in Paradise” so the experience dining at the OG spot was very nostalgic for me.
Of course we browsed the gift shop and Britt and Tess cracked me up as they wanted to buy “the little cups for our American Girl dolls!” hahaha
Thankful the roosters didn’t attack…because the pelicans from Robbie’s did ENOUGH damage on their own! Sweet Tess was so brave about it all – even during the event she cried way less than Britt and Britt never even got bit!
Knowing the reputation surrounding Key West as a more “wild” location we purposely made set in stone PLANS and an agenda for the day. No just roaming around!
We booked a trolley tour for the mid-day as Zach and I love a good “get to know the city” tour when we visit somewhere new. It’s an awesome way to get some basic knowledge of the area and background and hit the highlights to see all the “must see” items.
This tour was really more of transportation than it was informative. It was enough info for me to be satisfied and I liked that it wasn’t overly detailed or boring but it also had a good bit of downtime that was more travel-time than it was learning stuff. Since we did have a vehicle we could have driven ourselves to the most southern point and could have skipped that portion of the trolley tour but we didn’t realize that until it was too late and really it all worked out fine anyway to just be along for the ride!
I do think it was a great way to avoid the party atmosphere while still taking in the sights but it wasn’t NEARLY as good as the trolley tour we did in Savannah and if you’re planning a trip to Key West without kids I’d skip it!
We passed some beautiful sites and also saw Hemingway’s home. It is listed on all the must-visit lists but yall a ton of cats? We’re good.
THE must-get photo in Key West is at the southernmost point. There is no fee or anything to visit the area but it is located a good haul from the main part of town and the main tourist hang out areas. So it’s an extra little trip just to say you’ve done it and get the photo but, duh, I was hardcore about doing it!
The trolley was a hop-on-hop-off so it stopped and we had 20 minutes to get the photo and get back on. There is a pretty lengthly line that forms for the picture and they do have social distancing markers set up but thankfully everyone was still very helpful in passing phones to the person behind them to take their picture! Gotta have the whole group in it right? 🙂
I love the fun fact that standing at that spot you’re closer to Cuba than you are to Walmart and that Key West is also known as Conch Republic.
We all needed a potty break and about missed the bus due to kids and their ability to somehow always have to poop during the most inconvenient times haha
We also passed by Mile Marker 0 on the bus but did not stop to get out as the actual Mile Marker 0 street sign was NOT there. The driver told us that it’s frequently stolen and is rarely ever actually there but that it looks exactly like this sign on this shop so I just took that photo and called it good 😉
The whole tour only took a couple hours to make the full ride. We opted to ride it non-stop, other than getting out at the most southern point, so we could get the full tour and explanations of all the areas etc.
We came back to the Mallory Square area (which seems to be the “hub” of Key West) and got some coffee from Cuban Coffee Queen (super yummy) and decided to walk around the village area and do some shopping and grab an early dinner.
There are tons of tourist shops and the kids loved going in the “Everything is $5” stores. We allowed each of them to get a souvenir and we had fun looking for something for Spear and a thank you gift for Big Papa and G-Mama too.
We found a burrito place (Bad Boy Burrito) on our walk and decided to go back there for dinner. We had a great little spot where no one was really around and we were able to sit outside and enjoy the beautiful weather (and the girls provided dancing entertainment) and visit with another family who also had young kids while we ate.
It was also, yet again, another FANTASTIC customer service experience at dinner. A BIG takeaway from Key West was the PEOPLE. Just really, really genuine kind people at pretty much every establishment we visited!
Eating dinner at 4:30 also helped avoid any rowdy crowd. We had ONE dude yell stuff at Zach while we were on our tour and we saw a few people being a bit loud as we rode around, and it made me glad we DID the tour as being on the trolley avoided us being in close proximity to all of that. I know it’s a place for people to have fun and let loose a bit but our goal and intent was to have family time together and not have our kids be in any sort of uncomfortable situation if it was avoidable!
We let the kids all choose a dessert…Kye and Britt opted for HUGE cookies covered in fudge, Tessie wanted ice cream and Zach and I shared a piece of frozen dipped key lime pie (a must have dessert item in Key West!).
I’d heard that Mallory Square at Sunset is a BIG DEAL. People take the sunsets in Key West super seriously and I hardcore wanted to make sure we experienced Mallory Square as well as the special Key West sunset!
We read that the Sunset Celebration at Mallory Square starts about 2 hours before sunset so we went right around when it was supposed to start in hopes to, again, beat the wild crowds 🙂
Basically the KEY to a family-friendly Key West vacation is GO EARLY to EVERYTHING. Go on a weekday to the Key West area, eat lunch early, eat dinner early, visit Mallory Square early! Anything you book, book for the earliest time possible. I truly think THAT was what made our day go so smoothly!
Zach went to move the car and the kids and I walked around and checked out the venders as they were getting things set up.
There are lots of little local venders selling crafts and other items as well as many performers. We for sure lucked out on the main performance that we watched. We heard one guy performing who was VERY vulgar so we avoided him and happened to see chair guy perform.
While yes, some of his language wasn’t ideal and yes, some of the subject matter was a bit off-color BUT overall the show it self was very kid-friendly and fun and his overall tone was upbeat and friendly and a happy vibe.
Many of the other performers we saw were more rude and crass and even super snarky to people watching the show. We watched the chair guy’s entire set and spoke to him after and thanked him for providing entertainment that we felt comfortable with our kids seeing!
And I know we’re the “odd ones” out so don’t get me wrong I in noooo way think that the entertainers SHOULD be geared towards kids. I know the scene is more of an older people thing and that the shows are for that audience and not meant for children. So we didn’t expect them to be but it was nice that his was more our kinda style and we appreciated that surprise!
I will also say there WERE a LOT of families everywhere we went so I do think there is a family audience that would enjoy and appreciate more of that sort of entertainment as well though too!
Britt was so funny because she was FREAKING OUT at his stunts and literally couldn’t look because she was scared he was going to fall 😉 However, after the performance she now cannot decide if she wants to perform in the Lion King show at Animal Kingdom, be a dolphin trainer at Theater of the Sea orrrr be a Mallory Square street performer when she grows up 😉
I loved also that the chair guy talked about how live entertainment is a dying thing and that it’s entertainment WITHOUT SCREENS. It’s so refreshing to see someone share their talent like that and I loved that point he made! I’m allll about giving my kids EXPERIENCES and this was def a great one!
Malloy Square got rowdy FAST. Lots of loud comments being made by entertainers and onlookers alike and we just got uncomfortable pretty quickly. We tried to watch another performer who was doing fire tricks but he was making very inappropriate, cuss-word filled, racist and sexist remarks so we didn’t last long there and decided just to find a less crowded spot to watch the sunset.
We walked down a bit and got to see a super cool yacht and take some pics of Mommy and Daddy for a change 😉
We then found a spot with only a couple other groups of people where we could still have a great view of the sunset so we just decided to hang out there and see it! Basically we avoid crowds as often as we can, even before covid-life 😉
While looking at the sights Tess suddenly started crying saying “I’m sorry I’m sorry”
She apparently had been leaning over to look at the water and her hat fell off and went for a swim! It was literally zero percent a big deal as it’s a hat that was Kye’s as a TODDLER haha. But Daddy had to save the day anyway and hoped over to a dock and fished it out for her 🙂
The sunset did NOT disappoint! It was GORGEOUS and it was so nice just having the big kids in that moment as they were all old enough to appreciate and ENJOY the moment WITH US. It’s hard seeing our babies grow up but there are a lot of perks to it as well and this trip def showed us many of those great times to come as Spear is getting older too!
I love the pic of me with the toy pirate axe sticking out of my book bag. Such a mom moment for sure. Always carrying allllll the things.
As soon as the sun set we headed back to the Mallory Square area to finish off our epic Key West day with the ultimate big-kid only trip experience: a ghost tour!!!
Zach and I really enjoy ghost tours but have never taken the kids on one yet! It has never worked out where all the kids are old enough to enjoy/handle a ghost tour when we visit St Augustine each summer and it’s a tradition we’re excited to start once they are all old enough. But since we ONLY had the big kids for this trip it was the PERFECT big kid activity!!!
We read through all the ghost tour options and in the end decided to go with the Ghosts and Gravestones trolley tour and were super impressed. It was VERY kid-appropriate (but would have been just as fun as an adults-only night too). We booked the earliest tour and it was nice that it was mostly riding the trolley around as it limited tired kids from having to do a lot of walking.
While everything had a “spooky” vibe it was also not overly scary and I think riding the trolley helped with that too. Our tour guide was awesome and was an excellent storyteller! We were all very engaged the entire time.
They also did a great job incorporating the wild tourists into the night. Whenever a tourist yelled at us (which did happen pretty frequently) we’d all yell back in unison “YES WE ARE THE DEAD” It was super fun and was a genius way to not allow the tourists to take away from the experience.
Part of the ghost tour also included entry into the Shipwreck Treasure Museum as a lot of ghost stories take place there. The kids each got a chance to be a bit hands on with the treasure which was fun and I think they enjoyed that portion of the tour the most! It would be a great place to visit during the day as well but we opted not to as I read that they had a lot of restrictions right now and that it would make the cost of entry less worth it. It was nice to get a taste of it though during the ghost tour!
The kids all loved the ghost tour and it was SUCH a fun way to end our super fun day! The day couldn’t have gone more smoothly and all flowed so well and went so well too!
We had a TON of people “warn” us that Key West wouldn’t be “our kinda town” but we truly loved it and Zach and I even talked about going back for our anniversary. I DO think that the party vibe could take away from our enjoyment of the town as even early in the day there were a lot of people on the streets clearly drunk and being loud. The reality is that it’s just not our kinda scene and we wouldn’t personally be comfortable being around too much of that sorta thing.
BUT with the right planning we really had NO issues whatsoever all day and the kids didn’t notice 99% of the little bit of things that Zach and I did (like the entertainers). It was easy to navigate them towards more family friendly activities and there were TONS of them to choose from!
We were missing Spear pretty hardcore and Facetimed him during our day….allllll he cared about was telling us that he rode a tractor with Big Papa so he def wasn’t missing us at all 😉
We all had a really great day but were also ready for some down time at Hawk’s Cay and to enjoy the water for the remainder of our trip!
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