For our final week in Florida we traveled as far south as it’s possible to go – Key West. We’d heard great things about the city, but when we arrived in the afternoon we initially weren’t too enamored with what we saw.
That feeling didn’t last long though. As we headed out that evening, we started to discover why it charms so many people. Shae and I ended up having a wonderful week there and didn’t want to leave, although our wallets are glad we did as it ended up being an expensive week!
Here’s what we got up to during our week in Key West.
Where We Stayed In Key West
Key West isn’t a cheap place to stay, with hotels and bed & breakfasts running at $300+. There aren’t many chain hotels down there and those that are there charge a high number of points.
Thankfully we had another option at our disposal – Vacasa vacation rental properties. They have a partnership with Wyndham Rewards whereby you can redeem 15,000 Wyndham points per night for every bedroom a property has. There was this pet-friendly property just off Duval St (the main road running through Key West where all the life is) which was a studio apartment.
That meant we only had to redeem 15,000 points per night, but it got even better than that. I have a Wyndham Rewards Earner Business credit card which gives a 10% discount on award stays. That means we only had to redeem 13,500 points per night which was tremendous value considering the cash price would’ve been $440.57 per night.
That’s an absurdly high cash price for the apartment given its size and the fact that the bed couldn’t have been more creaky, but being able to redeem points and it being in a great location meant it was a decent place to stay.
What We Did In Key West
Southernmost Point Of The Continental USA
Seeing as Key West is so far south, it lays claim to being the Southernmost Point of the Continental USA. There’s a concrete buoy at the most southern tip that’s a good photo opportunity, but keep an eye out for the occasional wave crashing over the sea wall!
Watched The Sunset From Mallory Square
With the far end of Key West facing west, it provides some beautiful, unobstructed views of the sunset. Shae’s mom told us the quintessential place to watch the sun go down was Mallory Square.
Sure enough, there was always a large crowd of people watching the sunset each evening, with many applauding as the sun disappeared over the horizon.
Coral Reef “Snorkeling”
Our most disappointing experience in Key West came when we tried to go snorkeling in the only coral reef in North America. We went on a ‘Reef & Ritas’ trip with Fury Water Adventures. They take you out on a catamaran where you can go snorkeling in the coral reef, then have unlimited margaritas or beer on the way back.
Sounds great, huh?
In theory, it would be. Unfortunately it didn’t work out at all well. I’d taken dramamine before we set off, but despite that I felt incredibly nauseous due to the choppy boat ride out to the reef.
I was still feeling rough by the time we reached the reef, with the rolling waves not helping matters. I told Shae to head in without me and that I’d meet her in the water once my stomach had settled down a little. 2-3 minutes after she’d gotten in the water I went to descend the stairs into the water. I had to wait several minutes though due to all the people already returning to the boat.
An incoming storm in the area was churning the water, leading to extremely high waves and strong currents. These people coming back on board the boat were already exhausted despite only being in the water for a few minutes, while one of the lifeguards on the boat had to swim out to help a couple of people get back to the boat as they were struggling so badly.
I eventually got towards the bottom of the steps and was surprised at how high the waves were. They were so powerful that I was concerned that trying to get in the water would only get me slammed back against the boat. Having also seen how exhausted everyone else was after only a couple of minutes in the water, I decided against getting in.
It was only a couple more minutes before Shae returned too. As with everyone else, she was exhausted. She’d had a hard time breathing while snorkeling because the waves were crashing so high that water was repeatedly going down her snorkel from the top.
In my opinion, it simply wasn’t safe for the company to have run the snorkel trip in that weather, so it was disappointing that we wasted ~$150 for the two of us (that price also includes the $15 per person cost to rent a wetsuit). From what Shae saw of the coral reef, it was apparently bleached and so wasn’t even very special.
Key West First Legal Rum Distillery
Key West has a couple of rum distilleries on the island. We did a free tour of the Key West First Legal Rum Distillery which was well worth doing.
This pet-friendly tour included free tastings of some of their rums, plus they had cocktails we could buy. Although Key West has an open container law, if you have a drink in a plastic cup while you’re walking around, it doesn’t seem to be a problem provided you’re not being rowdy or causing any issues.
Fun In Islamorada
Islamorada is a collection of five islands about a third of the way down the Florida Keys. On our way down to Key West we stopped at the History of Diving Museum, then returned during the week to go kayaking among mangrove tunnels and visit a couple of breweries. You can read more about the kayaking experience here and everything we did in Islamorada here.
General Wandering
Key West is a very walkable city, so we enjoyed exploring Key West by just wandering around. There are quite a few information signs along with historic homes which includes the Truman Little White House, the Hemingway Home & Museum and more.
You can also stop by the south end of the beginning of US Route 1.
Encountered Chickens
When walking around Key West, something you’re guaranteed to see are chickens. There are hundreds – if not thousands – of them roaming freely around the city. It’s initially a little bizarre seeing so many of them out and about, but it adds to the city’s charm and you’ll find all kinds of chicken-themed souvenirs in local stores.
Key Deer
Chickens weren’t the only wildlife we saw in the Florida Keys. We also saw an alligator, a raccoon and starfish while kayaking in Islamorada, then we stopped on Big Pine Key at the end of our visit to look for Key deer.
A family we’d met at one of the breweries in Islamorada had mentioned that there’s wild deer living on Big Pine Key, so we drove around a little in the hope of finding some. We got lucky when randomly driving down a side road as we come across a family of these cute creatures. What’s so special about Key deer is that they’re about a third of the size of white-tailed deer.
Where We Ate & Drank In Key West
The reason our week in Key West was so rough on our budget is because we spent so much eating out and drinking – essential parts of any Key West experience 
Smallest Bar In Key West
We kicked things off in style by having a drink at the Smallest Bar in Key West. Found tucked away on Duval Street, it’s only 72 sq ft.
It has a fairly limited drinks menu – not surprising given the bar’s size.
I got a beer, while Shae got a Key Lime Pie shot.
The Bull & Whistle Bar
Later that evening we stopped for a drink at the Bull which, as with many locations in Key West, is pet-friendly. They have an extended happy hour which includes margaritas, so Shae ordered a couple of those, while I went for another beer. And another.
The Bull’s building is in fact a collection of three bars in the same building. On the first floor is The Bull which is an open air bar. The second floor features the Whistle Bar which is more of a sports bar with pool tables, dartboards, etc.
The third floor is where to go if you’re feeling a little more adventurous. That’s where you’ll find the Garden of Eden which is a clothing optional bar on the building’s rooftop.
Southernmost Point Bar
Just up the street from the buoy marking the Southernmost Point of the Continental USA is the Southernmost Point Bar. We stopped there for a drink on their pet-friendly patio, enjoying a couple of drinks while listening to some live music.
Sitting there drink in hand, listening to music, sun shining down – it felt like a perfect day on our road trip!
Sunset Pier
After finishing work later that week, we walked up to Mallory Square and got a drink from Sunset Pier. Their outdoor seating overlooking the water was a lovely place to relax.
First Flight Island Restaurant & Brewery
I wanted to stop in for a drink at First Flight Island Restaurant & Brewery as the building it’s in was the birthplace of Pan American World Airways back in the 1920s.
They have a courtyard that’s pet-friendly, so we stopped for drinks and snacks out there.
It’s worth poking your head inside the bar as there’s a Sikorsky seaplane crashing through the ceiling, while the bar is made from the wing of an airplane.
Amigos Tortilla Bar
On the way back to our Vacasa property we stopped for dinner at Amigos Tortilla Bar. This place had caught our eye as they have a sign saying you can order square tacos.
Well, we both ordered tacos but they were round. It turns out that they only offer square corn tortillas, not flour tortillas, which we hadn’t realized. The tacos were very tasty though, although the side of black beans seemed like they’d only had a candle waved in their general direction to heat them up as they were cold.
Despite tasting good, Shae was inconsolable at the lack of square tacos.
Kermit’s Key Lime Pie Shop
As you might expect, Key West has a number of places selling key lime pies of one variety or another. Kermit’s Key Lime Pie Shop has dark chocolate key lime pie bars on a stick, so I couldn’t resist. It was good, but fairly expensive at about $6.50.
Wicked Lick Ice Cream
Shae decided to get a different dessert, so she stopped next door to Kermit’s at Wicked Lick Ice Cream and got a sundae which hit the spot.
The Conch Shack
Shae and I had seen several restaurants serving conch fritters, so we decided to stop by The Conch Shack to give conch a try.
We ended up having conch three ways by ordering their conch trio with fries. This came with conch ceviche, cracked conch and conch fritters. While it wouldn’t be my go-to meal if we visit Key West again in the future, it tasted nice enough and it was interesting trying conch. I preferred the conch ceviche and cracked conch to the conch fritters; the fritters were like fishy hush puppies.
Key Lime Pie Bakery
As mentioned earlier, there’s several places in Key West that sell key lime pie. On our final night we stopped at Key Lime Pie Bakery to get a slice of regular key lime pie which was delicious.
According to the guy working at Key Lime Pie Bakery that night, they’re the only outlet in Key West that actually makes key lime pies themselves; apparently other stores on the island have their pies manufactured elsewhere and then shipped in.
Mattheessen’s Candy Kitchen
Key West has at least a couple of Mattheessen’s Candy Kitchen stores. We’d walked past them several times and salivated over their giant half-pound cookies on display in the window. On our final night we couldn’t resist and got one of their chocolate chip cookies which was excellent.
Krust
We apparently didn’t spend enough money on food and drink in Key West because on our drive out of the Florida Keys we stopped for lunch at Krust in Tavernier. The family who’d mentioned looking for Key deer were the ones who recommended we also check out Krust.
It was a great recommendation as the thick crust square pizza was delicious. Shae went for regular cheese and tomato on her side, while I ordered pepperoni on my half.
Things We Didn’t Do In Key West
There were lots of places we didn’t have time to see and/or didn’t have enough in our budget considering how much we spent on everything else. Here’s some other stuff that seemed worth checking out:
- Dry Tortugas National Park
- Fort Zachary Taylor Historic State Park
- The Key West Butterfly and Nature Conservatory
- La Te Da bar – a friend of a friend DJs there
- Better Than Sex – A Dessert Restaurant
- El Siboney Restaurant – two people recommended this Cuban restaurant
- Key West Lighthouse
- Blue Heaven for breakfast
- Truman Little White House
- Mel Fisher Maritime Museum
- Garbo’s Grill @ Hanks!
- Schooner Wharf Bar
- Key West Historic Seaport
- Half Shell Raw Bar
- Hogfish Bar & Grill
The post A Fun (& Expensive) Week In Key West, FL: Here’s What We Did appeared first on No Home Just Roam.
