✈️ July 28–August 5: Fort Lauderdale, Fort Myers & The Keys Adventure
📌 Table of Contents
- July 28–29: Red-Eye Travel, Everglades, and Naples
- July 30: Injection Day
- July 31: Nature Walks, Planetarium, and Breweries
- August 1: Across the Everglades to Key West
- August 2: Southernmost Sights, History, and a Legendary Meal
- August 3: Gators, Outlets, and a Tropical Winery
- August 4: Skydiving, Sticker Shock, and Mall Marathon
- August 5: Homeward Bound
July 28–29: Red-Eye Travel, Everglades, and Naples
We had a red eye that left around 11:55. The flight was with JetBlue, so the service was a bit better than Spirit. We had the seats behind the exit row and had some extra leg room.
We arrived in Fort Lauderdale around 8am. We got our bag quickly, hopped on the shuttle to the car rental center, and we were in line at Fox for about 10 minutes before getting to the counter. Fox was by far the worst with scare tactics on insurance extras, but we already purchased through Hopper. They also con you on the toll pass for $15 per day, but some of the tolls here can’t be paid in person or online without the pass. You can purchase the pass, but they can’t be transferred to another vehicle, or at least that’s my understanding. We hope to buy one this trip to take with us for the next one because it’s still probably cheaper to buy one than rent one.
We ended up with a basic car with an actual key, ie 90s style where you literally have to insert the key to unlock each door.
We loaded up and headed to Lester’s Diner. This is a classic looking diner that even has counter service. I ordered the corned beef hash with eggs, an English muffin, and country potatoes. The boyfriend got a waffle sandwich that was essentially filled with a cheese, egg, and meat omelet. Both were delicious. The service was great. The only real complaint is that the coffee was just meh. If you are in the area, I highly recommend stopping.
We hopped on the 75 heading for Naples. We stopped at the Skunk Ape Research Headquarters where they are trying to prove the existence of the Skunk Ape, which also resembles Sasquatch. It has a pretty unique gift shop and some pretty cool shirts. Outside they have some large statues. They also have a $5 per person animal exhibit with snakes and alligators. I’d say save your money on this. However, the admission supposedly helps feed the animals, so you could also justify the modest $5 fee for that purpose.
The one downside here is the mosquitos. I looked down at one point and had about five on me. The only recourse was to stand in front of a powerful fan. We of course decided not to bring bug spray this trip, so we hustled out of there.
We headed to Everglades City and stopped at the Everglades Museum. It was located in a historic building and was the best kind of museum: free. So yes, it’s worth a stop. It’s small but has some interesting information about the area and its first inhabitants. They also had a rotating display on the front that was put on by the local kids. It had references to the Skunk Ape.
The final stop was the Smallwood Store on Chokoloskee, a small island you can drive to via a bridge. This area is called one of Florida’s last frontiers. The store was established in 1906 as a trading post and post office. It became a historic place in 1974 and eventually closed its doors in 1982. Most of the goods were left inside, and it was reopened in the 1990s as a museum. The fee is $5 to wander the museum and they have a gift shop. I’m not into time capsules of random items, so I probably did not appreciate it enough, but the exterior is pretty cool.
We spent a little time looking at the items and then headed back on the road to Tin City Waterfront Shops in Naples. There is ample parking that is free. Some of the parking is covered. The shops are indoors and air conditioned. They have several restaurants in the area and a lot of seafood and fish, which is right up my alley. The shops included a Mon“key” bread coffee shop, clothing stores, an ice cream shop, souvenir shops, a candle shop, etc, just about everything you’d expect for a touristy shopping area.
We decided to eat at Riverwalk at Tin City. I had the seared seafood Niçoise salad and it hit the spot of being healthy and delicious. My boyfriend got some sushi and our service was good. The seating was outside on the water and made for a good view, but it was hot despite the many fans.
I then grabbed some ice cream at M&M Cafe at Tin City, which hit the spot with the heat. They offer samples and friendly service. They did have a vegan option too.
We headed back to the car and drove to the hotel. A day with very little sleep in the 90 degree plus humid heat is tiring, and I’m here to get my neck and back injections tomorrow. So once we checked in, we relaxed and went to bed around 7:30pm. Being in bed felt amazing after more than 36 hours of sitting and standing.
July 30: Injection Day
Today was my day for injections, so we had breakfast at the hotel, which is included. The AC appeared to be out in the lobby, so it was pretty hot. The breakfast included French toast, hashbrowns, scrambled eggs, pork sausage, and oatmeal. It was good, but the lobby was 84 degrees.
After that we hung out in the room and left to arrive at 9am. I had the curve correction appointment and some progress has been made, which is good news. Afterwards, I had a 9:45am appointment for the injections, which didn’t happen until closer to 11:30. This was the worst, which was probably a combination of anxiety and lower blood sugar.
After the injections, I was initially shaky and weak. Afterward I went back to the hotel and we had McAlister’s, where I had half a chipotle chicken spud and a cup of chicken tortilla soup. It hit the spot.
After the injections, I have a large amount of swelling, which makes my throat have a full feeling and swallowing is hard for a few hours. The rest of the day was spent on an ice pack and laying around trying to be as comfortable as possible.
July 31: Nature Walks, Planetarium, and Breweries
We woke up and had breakfast just before 8am. The lobby had a lot more fans, so the air was moving and felt more comfortable. Today we had turkey Canadian bacon, scrambled eggs, waffles, and country potatoes.
We went up to the room, got ready for the day, and headed to Four Mile Cove Ecological Preserve. This was a boardwalk through some mangroves. It is about 1.5 miles roundtrip and ends at the Iwo Jima monument.
Afterward we headed to the Calusa Planetarium and Nature Center. Inside they have a lot of critters, including multiple turtle species, an alligator, and fish. Then outside they have an aviary which included bald eagles, vultures, and hawks. Lastly, they have a butterfly habitat with a few butterflies. It’s mostly geared toward kids, but I also enjoyed it.
The planetarium had a show at 12:15 and it had an animated presentation that started at noon about astronauts. Then they discussed constellations in the night sky and had a presentation on extreme weather in space that was based off models and CGI and not actual footage. The entire place and the show was $13 for adults, and we had the option to have an animal presentation and another planetarium show.
We left around 1pm and headed to Wicked Pub, where I had grilled buffalo chicken mac and cheese and the boyfriend got mac and cheese pizza. Mine was delicious. I’m picky about mac and cheese and they did it well. The bartender was also nice and attentive, and the space was clean but small.
From there we headed to the hotel to shower and change. We headed to the Edison Mall and stopped at Macy’s to shop a little. The mall itself was small and about 25 percent of it was vacant. However, I had a nice salesperson and found the experience to be good.
Then we headed to Swamp Cat Brewery. This place is at an old church and they have their brewing equipment visible. They have a nice sized indoor area and a large outdoor area with lots of shade. The beer was good. They also had a great elderberry cider. Inside is a Latin fusion restaurant where we tried the ceviche, which is served with plantain chips. The bartender was nice and interactive and overall it is probably our favorite brewery in Florida so far.
We came back to the hotel to prepare for the long road trip tomorrow.
August 1: Across the Everglades to Key West
We woke up early and packed. We had breakfast at the hotel at 6:30am and then got on the road. We hit some traffic from a car accident in Fort Myers and then had clear sailing to Big Cypress National Preserve, Oasis Visitor Center.
This is supposed to have a lot of alligators, but the only real wildlife we saw were mosquitos, and it was from the instant we opened the car door. The bug spray only partially helped. It has a ranger station, bathrooms, and some information, as well as a short boardwalk. If there was more, that’s as far as we got out. Being eaten alive wasn’t jiving today, so we headed to the car and carried on.
The next stop was Robert Is Here Fruit Stand. It’s kind of in the middle of a residential area. It has ample parking and sells fruits, veggies, and snacks. They also make shakes on site and had a Mexican food truck out back. The property is large with rescued birds and animals, some exotic and some of the barnyard variety. Chickens are running free range, and they have quite a few bathrooms, including the private trailer porta potty variety. I especially enjoyed the animals. I picked up some strawberries, a popsicle, and fresh squeezed orange juice.
Heading further west and officially into the Keys territory, we stopped at the Blond Giraffe Key Lime Pie Factory. The pie slice is pricey, as we opted for the meringue variety, but it was delicious. They also have a peaceful outdoor garden with a seating area and love locks. We enjoyed the pie in a shady spot and moved on our way to find some lunch.
We attempted Morada Bay Beach Cafe, and despite having an easy time parking and being seated, we sat outside for 10 minutes and were never even greeted by a server, so we opted out.
We left and headed to Islamorada Fish Company, which was much busier with attentive service. They had ocean views and a man playing music. The food was just okay, though. We tried the wahoo wrap and mahi tacos. The mahi mahi was overcooked and something else on the tacos had a competing taste that didn’t mesh well. The wrap was good. This is a mega restaurant and they have service designed to rotate a large number of people in and out, and it shows. I don’t even mean that in a bad way.
We carried on, passing the remaining keys, several bridges, and gorgeous views, and arrived at the Hilton Garden Inn Key West, The Keys Collection. We checked in easily, located our parking space, and unpacked a bit.
We then headed back to the lobby to get tickets for the free shuttle to the downtown area. It stopped at Waterfront Brewery. We decided to eat here and I got the catch of the day, wahoo, which was served with rice and broccoli, and it was great. The boyfriend got ribs and a flight of beer. They only have preset flights and he wasn’t overly impressed with the beer or the ribs. The brewery was huge, though, with an arcade inside and a marina outside.
We wandered up and down Duval Street and then stopped at the Salty Frog for a cocktail to kill a bit of time until sunset. Two cocktails were $37 with tip, so definitely inflated prices. I can’t speak to the food, but the service was okay. The environment was chill and they had music playing, but not at an obnoxious level. However, they did have a psychic chicken machine that tells you a fortune, so you know I did that.
I like the free range chickens and got a kick out of watching them throughout town. I think it adds a nice amount of quirk and I’m a fan.
After our drinks, we walked over to Mallory Square to catch the sunset over the water. We stood around the barricades for about 20 minutes before the action happened, but it was a nice experience. The square is a hot spot at that time with street vendors selling snacks, art, and even a few street performers. It was lively.
We caught an Uber and headed back to the hotel. It was a long day and we will have another one tomorrow.
August 2: Southernmost Sights, History, and a Legendary Meal
We woke up and headed out via Uber around 7:45am. We were dropped off at the Southernmost Point of the Continental USA. It is marked by a statue and its neighbor is property owned by the government. It’s simple but still pretty cool.
From there we had a decent walk to Fort Zachary Taylor Historic State Park. Fort Zachary Taylor, built from 1845 to 1866 to guard Key West’s harbor, stayed under Union control in the Civil War and later served in coastal defense through World War II. The top tiers were removed in 1898 for modern batteries. Declared a National Historic Landmark in 1973, it became a Florida state park in 1985, preserving the fort and one of the largest collections of Civil War cannons.
It was $2.50 per pedestrian and gives you access to the beach and fort. You can climb to the top of the fort as well. The beach offers a refreshing breeze and rentals. Admission is from sunrise to sunset and you can come and go. The parking seemed ample too, in case you want to drive.
We walked up to Blue Heaven for breakfast. They had some live music and were pretty busy. Tables had a 20 minute wait, but we were able to sit at the bar. I had eggs, potatoes, bacon, and sausage. It was all really good and the service was great despite the busy environment. The music was easy listening and at a good volume.
Then we walked over to the Key West Lighthouse, which is $19 for admission and you can climb to the top. We passed on this but did peek at the lighthouse, then headed across the street to the Hemingway House, which was about $19 for admission and includes a 30 minute guided tour.
Almost all the estate is up for grabs and you learn a little history about the house and the man, including his wives, in particular the second one who technically owned the house. On the property are 57 cats, so they are just as much a part of the tour as the house itself. Many have six toes and a few have seven toes. You get a decent view of the top of the lighthouse from one of the balconies, which was also how Hemingway found his way home many times when he indulged too much at the bar. It also has a gift shop on site.
We then headed up to the Key West Cemetery. Tip: you can only enter off Margaret Street. The Key West Cemetery was established in 1847 after the October 1846 hurricane washed away the earlier burying ground. Some older markers, for example 1829 and 1843, were relocated there. On 19 acres atop Solares Hill it holds an estimated 80,000 to 100,000 graves, many above ground due to the high water table, and includes historic memorials such as the USS Maine Mast.
It isn’t shaded, and by this time it was hot and humid and we were basically dripping with sweat, so we wandered a little bit and then headed for AC, which led us to Southernmost Pint Brewpub, Blast Beer Company Brewery. The bartender was awesome, attentive, and social. I had a Good Boy vodka drink and the boyfriend tried a flight. He was impressed with the beer. We both relished in the AC and we really didn’t want to leave.
However, we had one more brewery to complete the trifecta on Key West, so we headed to First Flight Island Restaurant and Brewery. The boyfriend tried a beer, but the real showstopper here was the food. We had a bunch of appetizers and everything was incredible. It was hands down the best meal of the trip. We had the ahi tuna poke, sweet corn curls, deviled eggs, and shrimp scampi flatbread. It was a $100 meal for sure, but it was worth every penny. The service was also good, and they have both AC inside and an outdoor patio.
We walked over to Clinton Square Market, which has some unique stores and restaurants and is located in a historic building. We then stopped by the Smallest Bar, which lives up to the name, before heading to Hemingway Distillery.
Here you have the option of a $35 tour, flights in the tasting room, or flights and or cocktails in the social club. We opted for the social club and sat at the bar. We had a drink and spent some time enjoying the atmosphere. A woman was also using us as guinea pigs, trying out some new sips of cocktails she was making for a tasting menu.
Sunworn, sweaty, and tired, we grabbed an Uber and returned to the hotel. We were pretty worn out, so we ordered dessert from Better Than Sex to our hotel room. I had to see what such a highly rated dessert place had to offer, 4.8 stars out of 5 with over 4,500 reviews.
We got the Pervert, which is a peanut butter silk pie, and the Pimp, which is a caramel salted popcorn cheesecake. Both were rich and delicious. I can definitely understand their rating. It’s hands down a delicious dessert. The only downside about the place is the limited hours, 6 to 11pm, hence the Uber Eats to the room.
We called this dinner, as we were still pretty full from our tapas meal earlier. We relaxed for the rest of the night and fell asleep early.
August 3: Gators, Outlets, and a Tropical Winery
We woke up and packed to get on the road. We attempted to go to Clarence S. Higgs Memorial Beach, but when we arrived at the parking lot, it didn’t look particularly nice, so we decided to just head inland.
We drove north to The Morning Joint, which is a coffee shop and breakfast place with a 420 theme. I had a bacon, egg, and cheese bagel sandwich and an iced chai latte, and it was great. The place isn’t cheap and you will easily spend $40 on drinks and breakfast for two. They have a small sitting area and efficient service.
We carried on north and stopped at Everglades Alligator Farm. I pre purchased tickets for $36, and in person they are $39. We arrived and were given an airboat time of 12:20pm. They like to keep you busy because we arrived just before noon and they had an alligator feeding at noon.
They have a breeding pond with over 200 alligators, about five females to every one male. The feeding show took about 10 minutes and included some education about alligators and their breeding practices.
We headed to the boat loading area and loaded up. We enjoyed a 20 minute airboat ride, mostly at high speeds, with some 360 and 180 degree turns. They warn that you will get wet and the front seats are the wettest. This is not a ride to see alligators. There are companies geared toward that elsewhere. This is more for the thrill. They also provide ear protection.
Afterward, we grabbed some fried gator nuggets and walked around the park. They have baby gators, snakes and reptiles, emus, birds, and other animals that you can check out. They also have some encounters that you can pay extra for, but these also require paying admission.
Then they had another show at 1pm, which included some gator wrestling, which basically was gentle and alligator friendly. They then offered people the chance to hold a baby gator at the end. It was a great experience and worth the $36.
We headed back to Homestead and hit the Florida Keys Outlet Marketplace. This is a pretty small outlet mall with some of the usual stores: Nike, Puma, Under Armour, and Columbia. However, it has some unique stores I’ve never heard of before. It was a quick stop since we are flying and were at 46 pounds when we left, sharing a suitcase.
The mall itself was just okay. You can tell it’s a bit old and rundown. The food court was Mexican and Cuban cuisine and they lack any other snack type places, think Auntie Anne’s, Cinnabon, Mrs Fields, etc.
We headed to the hotel, Super 8 Gateway to the Keys, and checked in. This is nothing fancy at less than $60 per night, but it is cleanish and the staff was nice. The room was a bit nicer than the standard Super 8, though, and appears to be renovated. It includes breakfast as well, so I can’t complain.
We then jumped in the car and drove the nine miles to Skydive Miami to check out the drop zone, as a storm was moving in. Hopefully, the boyfriend can sneak on the first load in the morning.
Just down the road from there is Schnebly Redland’s Winery and Brewery. They have a good restaurant and a set menu for $45, and I got the ahi tuna tartare, blackened mahi mahi with black bean rice, and fried churros with vanilla ice cream. I loved it all.
Then I went over to the wine tasting room and sampled five fruit wines. They don’t use any grapes, only other fruits, so it’s a unique winery. The five samples were $25, though, so it’s a bit crazy price wise. They have a brewery and tour on site too. The place is also beautiful and worth a stop if you are in the area.
We headed back to the room and called it a night.
August 4: Skydiving, Sticker Shock, and Mall Marathon
We woke up and had “breakfast.” It included a waffle maker, pancake maker, yogurt, juice, and scrambled eggs. It was mediocre but free.
We headed to Skydive Miami, where the boyfriend was able to skydive. This drop zone is definitely geared toward tandems, but the first load had some fun jumpers. The interior had a small packing area, a small sitting area for tandem passengers to watch videos, and a restroom. They have a shaded area outside with picnic tables.
The runway is right next to the building and the landing area is a bit out there. They do provide a shuttle service that picks you up and drives you back. The airport is pretty busy with other planes and helicopters in the air. The staff was friendly, though.
We left and headed to the room to pack and head out. We stopped at the Coral Castle, but they wanted $25 plus tax to wander outside in a sculpture garden and museum. They have it all enclosed, so we couldn’t even see inside, and the ticket counter is outside. Homestead in general seems like a cash grab, as almost everything costs exorbitant amounts of money for what it is.
We obviously opted to skip it. Ten dollars? Maybe even fifteen? Sure. Twenty five? No.
We headed toward Fort Lauderdale and ate at 411 South Bar and Grill. The food was pricey and the quality was low. The view was great and they did offer two hours of parking validation. I had fish, rice, and salad. The fish was basically seasoned with capers, the rice was dry, and the salad was small. I actually make this exact meal at home for much less money. I’d recommend skipping here.
We took advantage of the free parking and jumped across the street to the beach. It was gorgeous. It has beautiful blue aquamarine water. However, August and the humidity made for a short visit.
We opted for some indoor, free activities: The Galleria at Fort Lauderdale. This mall is a bit interesting, as some areas require you to go up and down several escalators and have a lot of empty space. Then you enter another part that is a bit more busy with more stores. I bought a few killer sale items at Macy’s, not so much for a free activity, and the salesperson was very friendly and chatty. She actually told us about another mall where we could get a cheaper meal.
We headed toward our hotel, Hampton Inn Ft Lauderdale Plantation. This hotel is undergoing renovation and we had a newly renovated room. Most items looked to be new or close to it, the hair dryer still had the packaging on it. So to say the room was clean is an understatement. The bed was comfy and the bathroom was large. The AC was also so cold that I had to turn it down a little, which has not been the theme of this trip.
We decided to hit up the other mall the sales lady recommended, as we just couldn’t do another outing that caused us to be dripping in sweat: Sawgrass Mills. This place was insane, a ton of stores including bougie ones, outlet ones, and classic department stores, with a mix of TJ Maxx and Burlington Coat Factory.
It was also packed with people, like the busiest mall I’ve seen in the US in ages, and even included people pushing around suitcases, either meaning business or stopping by while traveling.
We decided to eat at Nathan’s to save some money and avoid disappointment. Fort Lauderdale and Key West have been the priciest areas for food, and a lot of the time it was not worth it.
We headed back to the hotel to pack due to an early wake up.
August 5: Homeward Bound
We woke up and got on the way to the airport at 5:30am. We returned the car and made it through security uneventfully. We ate some breakfast at Dunkin’ Donuts and our flight left on time.
We made it back to Vegas around 10:30am and attempted to adjust back to the time change.
🗺️ Key West Trip Map
✨ Trip Summary — Key West & South Florida
This stretch of Florida delivered long driving days, intense heat, unexpected wildlife, medical pit stops, tourist chaos, excellent breweries, and some truly standout meals. Between airboats, sunsets, quirky museums, wandering chickens, and recovery time after injections, the trip balanced effort with adventure.
Highlights included:
- Sunset celebrations at Mallory Square 🌅
- Fort tours, lighthouse views, and Hemingway history 🏛️
- Brewery hopping with strong AC breaks 🍺
- Airboat spins and baby gator encounters 🐊
- That unforgettable tapas feast at First Flight 🍽️
- Key lime pie in a shaded garden 🍋
💡 Tips for Key West & South Florida
🌴 Weather & Packing
- Expect extreme heat and humidity, even early in the morning.
- Bug spray is not optional in the Everglades.
- Indoor breaks with AC will save your sanity.
🚗 Driving & Getting Around
- Plan extra time for traffic entering and leaving the Keys.
- Parking in Key West fills fast. Shuttles can be easier.
- Toll systems are confusing, so research ahead.
🍴 Food Strategy
- Prices are high. Reviews do not always equal quality.
- Reservations or patience may be necessary in peak areas.
- If you find great AC, enjoy it.