KEY WEST TRAVELOGUE-2026
KEY WEST TRAVELOGUE-2026
WELCOME BACK.
It's been a minute. Eight years in fact, since our last check-in with The Conch Republic. In between 2018 and 2026, a few things happened. There were some disruptions in 2020 you might have read about. We moved from the East Coast to the West Coast. But we finally made it back!
This entry is a brand new one. The previous entry may be of historical use, but I do not guarantee its accuracy. This entry is current as of April, 2026.
To review: Multiple visits to The Conch Republic. Cruise Ship stop in '05, Spring Break in '06, '07, '10, '13, and '15. Getaways in '17, '18 and now 2026. This travelogue is my attempt to help out folks who want to visit Paradise with a little advance intel. Not exactly an insider's guide, but more like Key West viewed through the eyes of a repeat offender. An opening word: SUNSCREEN! Seriously.
A little about my vacation style: I consider myself more a traveler than a tourist. I want to know where the locals eat, like to walk/bike around, and really get a "feel" for where I am. I like a good tourist attraction, but get great pleasure going on, as Pooh put it, "an explore." I prefer active over passive, local over chain. I'm not above a trip to Disney or stepping on board a cruise ship, but I'm really in my element discovering the out-of-the way, especially if food's involved.
So, Key West. My wife's birthplace. We first realized we loved the place when our cruise ship docked there April 7, 2005-Her birthday. First time she'd been back since infancy. As we explored, we started to wonder if we really had to get back on the boat. Thus began our love affair with The Conch Republic.
This entry is in progress.
When To Go
Fact: Key West is a serious tourist destination. Peak season is December through March, bleeding into April. March can be the busiest month with Spring Break, etc. As an example, the two main live theatres on the island basically run December to April. We travel to KW in their "Shoulder season," April/May. Our preferred time is first or second week in April. Temperatures are good, mosquitoes aren't out, still a few weeks away from hurricane season, and the crowds are manageable. Low season is June through November. If you don't mind heart & humidity, and the odd hurricane, you'll save a bunch. Fun fact: Key West has not taken a direct hurricane hit since 1919. (More on that later.)
This entry is in progress.
When To Go
Fact: Key West is a serious tourist destination. Peak season is December through March, bleeding into April. March can be the busiest month with Spring Break, etc. As an example, the two main live theatres on the island basically run December to April. We travel to KW in their "Shoulder season," April/May. Our preferred time is first or second week in April. Temperatures are good, mosquitoes aren't out, still a few weeks away from hurricane season, and the crowds are manageable. Low season is June through November. If you don't mind heart & humidity, and the odd hurricane, you'll save a bunch. Fun fact: Key West has not taken a direct hurricane hit since 1919. (More on that later.)
Getting There
People talk about making the drive from Miami. That's 3-1/2 hours, and frankly, you don't need a car on Key West. From Atlanta or from the Bay Area, I've always flown direct. American and Delta have a large presence. From Atlanta, Key West is a milk run for Delta. Coming from the West Coast, it was American, via Charlotte. EYW, the Key West Airport has upgraded. Gone are the days of walking across the tarmac. The recent renovations to EYW remind me of a slightly smaller version of MHT (Manchester-Boston). Once you're there, Uber/Lyft/Taxi to your lodging.
Where To Stay
For a look back at the places we've stayed over the years, check out the original post.
Where To Stay
For a look back at the places we've stayed over the years, check out the original post.
In 2026, we returned to a place that is not open to everyone: The Key West Naval Air Station. Are you a veteran or active member of our Armed Forces? Is someone in your family? A friend, perhaps? First up, thanks for your (or their) service. Secondly: You've just won the Key West Lottery. Thanks to the Navy Gateways (hotels)/Navy Getaways (Townhomes, etc), you've got access to hands down the best lodging deal on the island. Thanks to my step-mom (retired Army), we stayed in a three-bedroom townhome with a bath-and-a-half and full kitchen for $165/night. That's not per person. That's TOTAL. You have to book in advance, you must stay with the service person, and you have to pass through security each time you come "home," with the sponsoring military person, but my goodness, what an amazing deal. The Station is right next to a bus stop, and realistically only a 15-20 minute walk from the fun stuff. No maid service in the townhomes, but you can swap out your towels and linens any time you want. The decor is, as my Dad put it, "Early Econo-lodge." The grounds make for some pleasant walks, and there is a delightful food truck that makes very tasty breakfast and lunch. The only downside: A fair number of Key West Roosters on the base, so a white noise app and some earplugs for light sleepers, depending on whether or not a rooster views under your window as his turf. If you can at all take advantage of this service, do so. I must add: every Naval guard we encountered was the epitome of friendly and professional. Just make sure that you always have your ID. Oh, and if you'll be using Uber/Lyft, you'll need to exit the base before getting your ride. There is a useful pickup/dropoff area just outside the gate.
While we were on the base, two other family members opted for Ambrosia on 622 Fleming Street. Ambrosia advertises themselves as a tranquil tropic resort in the heart of The Old Town Historic District. Amenities include a great outdoor space, pools, a concierge team, and breakfast. The family staying at Ambrosia thoroughly enjoyed their time there, noting the convenient location, less than 1/2 mile from the majority of Key west offerings, including easy access to groceries, coffee, and bars. They also commented that the room and common areas were clean and well maintained, and that the climate controls and comfortable bed made for quality sleep, especially welcome when dealing with a three-time-zone shift.
Getting Around
I'm going to start with a word to the wise: Download the CruiseMapper app, or get familiar with their website. "But Scott, I'm not on a cruise. Why do I care?"
Because when a behemoth vessel carrying the equivalent of 15% of the island's population hits the dock, life changes in a hurry. Suddenly, Duval Street is mobbed, you'll have no prayer of getting anywhere near the Southernmost marker, the touristy places like Sloppy Joe's are overflowing with people on a tight schedule, and Uber/Lyft rates skyrocket. Funny thing though: get a block off of Duval, and you'll never know the ship's in town.
Like I said earlier, you really don't need a car. But, for those with mobility issues, or little ones, you might want to look into electric vehicle rentals. There are golf cart-like vehicles that seat 6+. I've never rented one myself, but they do seem like a great way to get around. But be aware: you will need to pay to park. And meters are in effect until midnight.
Uber and Lyft have a huge presence on the island. You'll want to have both apps. I could never find a pattern. Sometimes, one was cheaper, sometimes the other. Rare is the ride that will cost you more than $10-12.
Key West recently replaced their on-island bus routes, including the free Duval Loop, with a fascinating Uber-style system using their buses. It's called Key West Rides. Essentially, it's an on-call shared ride system. It's not immediately intuitive, but it's well worth learning, since rides are $1-2, all the way down to $0.50 for ages 60+.
You start by downloading the app from either Apple or Google. You can pay on the bus with cash, but it's just as easy to use the app Token Transit. When you want a ride, you open the Rides app, and request a bus stop-to-bus-stop ride. (So, if you really need door-to-door, this is not for you.) You'll need to know basically where the stops are, but there are maps. You can add up to five additional riders on your request. When the system accepts your ride, it will tell you when to expect pickup. Just like the standard rideshare services, it ranges. I've seen anything from 5 to 25 minutes. While you're waiting, purchase your fares on Token Transit. As the bus arrives, activate the fares. They stay active for 30 minutes. Show your screen to the driver, and off you go. NOTE: The system will not always find a ride for you. Especially if a cruise ship has just docked. But, for cost savings alone, it's worth getting to know.
Duval Street
Duval is to Key West as Bourbon St. is to New Orleans. The main drag as far as tourists are concerned, but there are a few hidden gems to be found. This trip, didn't spend much time on Duval. Again, see the previous entry for a few more details.
Where to Eat
Uber and Lyft have a huge presence on the island. You'll want to have both apps. I could never find a pattern. Sometimes, one was cheaper, sometimes the other. Rare is the ride that will cost you more than $10-12.
Key West recently replaced their on-island bus routes, including the free Duval Loop, with a fascinating Uber-style system using their buses. It's called Key West Rides. Essentially, it's an on-call shared ride system. It's not immediately intuitive, but it's well worth learning, since rides are $1-2, all the way down to $0.50 for ages 60+.
You start by downloading the app from either Apple or Google. You can pay on the bus with cash, but it's just as easy to use the app Token Transit. When you want a ride, you open the Rides app, and request a bus stop-to-bus-stop ride. (So, if you really need door-to-door, this is not for you.) You'll need to know basically where the stops are, but there are maps. You can add up to five additional riders on your request. When the system accepts your ride, it will tell you when to expect pickup. Just like the standard rideshare services, it ranges. I've seen anything from 5 to 25 minutes. While you're waiting, purchase your fares on Token Transit. As the bus arrives, activate the fares. They stay active for 30 minutes. Show your screen to the driver, and off you go. NOTE: The system will not always find a ride for you. Especially if a cruise ship has just docked. But, for cost savings alone, it's worth getting to know.
Duval Street
Duval is to Key West as Bourbon St. is to New Orleans. The main drag as far as tourists are concerned, but there are a few hidden gems to be found. This trip, didn't spend much time on Duval. Again, see the previous entry for a few more details.
Where to Eat
Key West is a serious food town, with everything from grab-and-go to white linen. Again, more ideas in the previous entry, but here's where we wound up on this trip.
Breakfast
We treated ourselves to breakfast at Latitudes on Sunset Key. The restaurant for the Sunset Key Cottages is available to those not staying on the private island. While lunch and dinner can quickly add up, the breakfast options are more reasonably priced, and delicious, with attentive service. When my wife's eggs arrived over easy rather than the requested over medium, the mistake was quickly corrected. Bonus points for the restaurant using real maple syrup, specifically Grade A Dark, which stands up beautifully to the hearty fare offered. Your reservation time is actually your time to board the private shuttle ferry to the island. After your meal, boats return to Key West at the top and bottom of the hour.
Breakfast
We treated ourselves to breakfast at Latitudes on Sunset Key. The restaurant for the Sunset Key Cottages is available to those not staying on the private island. While lunch and dinner can quickly add up, the breakfast options are more reasonably priced, and delicious, with attentive service. When my wife's eggs arrived over easy rather than the requested over medium, the mistake was quickly corrected. Bonus points for the restaurant using real maple syrup, specifically Grade A Dark, which stands up beautifully to the hearty fare offered. Your reservation time is actually your time to board the private shuttle ferry to the island. After your meal, boats return to Key West at the top and bottom of the hour.
Coffee & More
I am not a coffee snob, but I do appreciate a good cup, and enjoy a well-made espresso drink. One of my all time favorite coffee places in any state is Key West's own Cuban Coffee Queen. They make excellent coffee, great food, and arguably have the greatest marketing slogan in the history of Java: "Drink More Cuban Coffee and Do Stupid Things Faster." Perfect for Key West. Oh, and if you've got a young Starbucks junkie in your party? The Cuban Frappe is what a Frappucino wants to be when it grows up.
Lunch & More
Key West is all in on craft beer. This year, we made it to one of the newer microbreweries: Southernmost Pint. The mark of a good brewpub is the ability to brew many different styles well. And
Blast Beer Co. does just that. I am not a hop-head, so I was duly impressed with their lineup of classic, easy drinking styles, especially their Cream Ale. But, there's lots to choose from for the IPA fan in your party. When it comes to beer, fresh is best, and Southernmost Pint delivers. Excellent food, including some great wings, and enough vegetarian and vegan choices to keep everyone happy.
Blast Beer Co. does just that. I am not a hop-head, so I was duly impressed with their lineup of classic, easy drinking styles, especially their Cream Ale. But, there's lots to choose from for the IPA fan in your party. When it comes to beer, fresh is best, and Southernmost Pint delivers. Excellent food, including some great wings, and enough vegetarian and vegan choices to keep everyone happy.
Dinner
This year, we discovered Kaya Island Eats on Duval. Are we glad we did. Chef Scott Taylor was the driving force behind Key West favorite Blue Heaven before opening Kaya in 2011, moving to Duval in 2021.
For $20/person, their Cook Your Catch menu was by far the best CYC experience we've ever had. Not only was the food spectacular, Chef Scott went the extra mile for us. Kaya is VERY friendly to those with special dietary needs. In our party of 6 we had:
1 person with a SEVERE almond & mustard allergy
1 person, gluten free, with mild almond allergy and the "cilantro tastes like soap" gene.
1 person, also gluten free with the "cilantro tastes like soap" gene.
We communicated with Chef Scott ahead of time, and the kitchen accommodated everyone brilliantly. Service is spectacular. Seriously one of my favorite KW dining experiences of all our trips.
Groceries, etc.
If you haven't been to Fausto's, you really haven't been to Key West. Established in 1926, this neighborhood grocery store with two locations is not only the oldest grocer on the island, it is the oldest business, period. They stock a great selection of local products, and their deli has some fantastic items for when you don't want to eat out, but don't have the facilities to prepare meals from scratch.
Things to Do
TSKW also offers classes, so check the schedule.
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