bugsy running on lone rock beach with the airstream and f-150 in the background

A week in Key West, FL–Florida in January trip

We were in Key West in January 2022, as part of our Florida in January trip.

the Airstream and a palm tree at night

Our week in Key West might be the longest we’ve ever camped in one place, other than when we lived in the Airstream for six months. We figured we should stay awhile since it’s so far away, and because it’s AWESOME. It’s picturesque, historic, entertaining, and full of good food and drink. We had so much fun in Key West! Bonus: the last few days of our visit overlapped with our moms’ vacation to Key West–yes, our moms vacation together! (The moms stayed in the CUTEST cottage. If you don’t have an RV and want to stay in town, consider renting this!)

It was a long drive (four hours or so) from our last stop, Juno Beach, but Key West is a long drive from anywhere. Route 1 through the keys has lots of places to stop and shop or eat, if you want to break up the drive.


Bugsy sleeping at our campsite

We stayed at Boyd’s Key West RV Campground, a huge and amenity-filled park with a busy pool and activity schedule, laundry, a boat launch, and a Cuban food truck. Our site was pretty perfect: we only had a small water view, but we had a grassy area that Bugsy loved, so it was worth not having the full water view. Warning: a campground worker told me a horror story about someone’s dog chasing an iguana from the campsite to the water’s edge and getting eaten by an alligator! Keep track of your dogs!

Bugsy at the campsite
Bugsy spent a lot of time in that spot

From the campground (Boyd’s is actually on Stock Island, across the bridge from Key West), it’s a 15 minute drive into town (our Ubers were particularly nice and quick to arrive here), but you can walk to a CVS, and it’s a short drive to a public golf course and marinas for water sports rentals. We could also walk (although it was a longish, no-sidewalk walk) to our favorite bar (Hogfish), and our favorite key lime pie restaurant (Matt’s).

pig walking through the campground
an RVing pig!

Also, and this is a first for us in our 6 years of Airstream travel: we got to see an RVing pig! One of our fellow campers was walking a big pig around the campground! I wish I could have talked to the pig’s parents, I had so many questions. [Side note from four stops later in the trip! Our campground host in Palm Harbor said the pig was there while we were! Somehow we missed it!]


Bugsy eating a french fry

Obviously we focused our eating on seafood and key lime pie!

Stock Island

special hogfish sandwich at Hogfish Grill
messy and delicious special hogfish sandwich at Hogfish Bar and Grill

Hogfish Bar and Grill – We loved Hogfish for the cool bar scene and reliably delicious food. We went multiple times: we walked there for a snack and split the special hogfish sandwich – yum! The hogfish tacos were fantastic, and the key lime pie was top-notch (more on that later). On our last night in town, we took the Moms for a sunset drink and to-go sandwiches (the frozen drinks are suuuper sugary, the Key West pink shrimp are delicious, and the fried hogfish won over the grilled hogfish sandwich). There’s some waterfront seating, and the inside is basically open-air with lots of ventilation. The walk from the campground was fairly sketchy, without sidewalks or lights, but doable.

Bugsy drinking a beer at Matt's on Stock Island
Bugsy waiting for her table at Matt’s with a beer from Salty Oyster

Matt’s Stock Island Kitchen & Bar was not too far from home on Stock Island, so we decided to walk there. That walk was also a little iffy, but fine. The marina area has Matt’s, which is a higher-end restaurant, and the Salty Oyster bar, where you can have a drink while you wait for the Matt’s to open for dinner. Matt’s is dog-friendly on the patio, and our food was so good: grouper with crawfish sauce, oysters from Vancouver… and the key lime pie! More on that later.

cuban food from Deluna's Cafe
doesn’t really look appetizing, but J loved the Cuban food from DeLuna’s

DeLuna’s Cafe is a Cuban food truck located IN the campground! Can’t get more convenient than that. J got lunch from them, and thought the food was great, but nothing on their meat-heavy menu excited me. I did enjoy helping J eat his tostones and flan!

fish tacos at Hurricane Hole
huge portion of fish tacos at Hurricane Hole

Hurricane Hole was a lunch of convenience: we picked up my mom at the airport and had to return soon to get J’s mom, so chose Hurricane Hole for airport proximity and waterfront location. I thought the mahi-mahi Reuben was scrumptious, but the fish tacos and fries less so.

cuban food from El Siboney
another messy Cuban mean, this time from El Siboney

El Siboney has been around forever, serving authentic Cuban food. We picked up El Siboney carryout on our last day in Key West, knowing we were heading into the wilderness for a couple days and would appreciate an easy, delicious meal, and we did! The meal was huge, inexpensive, and satisfying.

Key West

We mainly stayed off Duval Street for our Key West dining and drinking. Maybe we are fuddy duddies, but Duval at night, with the crowds and noise, is not our scene. It’s like a baby Bourbon Street.

fish tacos and lobster roll at Garbo's
Garbo’s fish tacos and lobster roll

Garbo’s Grill is an Airstream food truck in the backyard of Hank’s, a crowded, dog-friendly bar with live music. We ordered fish tacos and a lobster roll from Garbo’s, and a painkiller from Hank’s. The lobster roll was super (and we know lobster rolls), the painkillers were delish, the live music was fun, but the fish tacos were meh (and we know fish tacos). Overall, it’s a great spot.

cocktail at Blue Heaven
dinner view at Blue Heaven

Blue Heaven serves Caribbean food on a gorgeous patio, with live music and a focus on local and seasonal ingredients. The history of the restaurant and the property is neat, and our experience was good: we loved the scene and the service was great, but the food and band were great-minus. You have got to see their Key lime pie (which you can also order across the street at Andy’s Cabana; see below). It’s a work of art, although it wasn’t our #1 Key lime pie… more on that later.

Santiago’s Bodega for dinner was incredible. We went with the Moms for a fun tapas meal and had a feast of ceviche, Brussels sprouts, carpaccio, short ribs, chicken, patatas, pear avocado salad, and sangria. It was super good, even if they don’t have Key lime pie. I didn’t take a photo because we were having too much fun.

Fish tacos and lobster roll at Eaton Street
fish tacos and lobster roll from Eaton Street

Eaton Street Seafood Market is a couple blocks from the house the Moms rented. We had a lovely lunch there: excellent lobster roll from Maine (the mom from Boston scoffed but it was legit, on perfectly buttered and toasted bread), the choose-your-fish fish tacos were fab (the staff recommended porgy, which we weren’t familiar with, but it was a winner), the crab cake on a croissant got raves, and I’ll discuss the Key lime pie below.

lunch at Louie's Backyard
ocean view from Louie’s Backyard

Louie’s Backyard is a highly-rated beach-front spot, and my aunt’s bestie recommended that we go for lunch rather for dinner, for the ocean views. It was a good recommendation! The fish tacos were yummy, and J loved his French dip, but the fries were sad. We were too full for Key lime pie, and when we returned later after wandering around town for an hour, the kitchen was closed. 🙁

A&B Lobster House was our attempt to impress the Moms, and it was a fantastic evening, other than our waiter being grouchy. We shared lobster tail, grouper, shrimp cocktail, burrata salad, and, of course, Key lime pie.

cocktail at Pirate's Cove
view of the marina at Pirates Cove

Pirates Cove surprised us as we hadn’t heard of it, and it’s a cool spot with water views and good food. We enjoyed tasty painkillers, fish tacos, and mahi-mahi salads while on our Conch Train tour.


painkiller at Andy's Cabana
one of many painkillers consumed, this one at Andy’s Cabana

Obviously we focused our drinking on tiki drinks–especially painkillers! We had trouble finding beer we liked and wished we’d stocked up more on Civil Society in Jupiter!

Stock Island

Bugsy and the Stock Island Christmas tree
the Stock Island Christmas tree

When we walked to Hogfish, we noted Absinthe House, just a couple blocks from the campground. It’s only open Thursday through Sunday and we completely forgot to go back over there. We’re not super into absinthe, but their yard looks like a fun place to have a cocktail, and the proximity to Boyd’s can’t be beat. Next time!

I mentioned Hogfish earlier, but will note them again here, because we liked the scene there. It’s a big, open-air restaurant, with a row of tables next to the boats in the little marina, and is just a fun place to hang out.

Key West

Bugsy at Andy's Cabana
Andy’s Cabana dog-friendly patio

Andy’s Cabana was our main hangout while we were in Key West. We ended up there pretty much every day for painkillers or beers and live music and a super chill vibe. It’s basically the waiting room for Blue Heaven across the street, a shady yard with a window serving drinks and snacks and Key lime pie.

cocktails at The Roost
streetside at The Roost

The Roost is a tiny cocktail bar close to our moms’ house, on a quiet street just off Duval. We enjoyed a fancy drink at a sidewalk table our first night in town, and on a subsequent night learned they’ll do cocktails to go! The Roost is a true craft cocktail bar and served the best drinks we had in Key West, with a chill, not-touristy scene.

Louie’s has a beach bar down the hill from the upscale dining porch. Our hope was to return after post-lunch wandering for a piece of Key lime pie to take home with us, but alas, the kitchen was closed between lunch and dinner. We drowned our sorrows with a drink and it was a nice spot to relax and watch the dogs play on the little dog beach next door.

beer at Waterfront Brewery
sunset at Waterfront Brewery

Waterfront Brewery is the only brewery we made it to in Key West. We didn’t like the look of the other brewery, First Flight–it looked like a sit-down restaurant instead of a taproom–so we skipped it. Waterfront scored big points with me for the sunset view and the Key lime sour, but they didn’t have a hazy IPA for J.

cocktails at General Horseplay
glitter drink at General Horseplay

General Horseplay is a lively speakeasy-feeling cocktail bar with a small outdoor space and very creative drinks. Mine had glitter! We sat on the porch and listened to the live music over at Hanks. Our only complaint is that the service was suuuuuper slow.

beer at Sunset Pier
almost oceanfront at Sunset Pier

Sunset Pier is a popular spot near Mallory Square to watch the sun set (duh). We had an unremarkable cocktail and beer to break up a marathon sightseeing day, but enjoyed the breezy pier.

Willie T’s is a bustling bar on Duval, and it’s probably a very fun place to hang out if you like those sorts of places. As I said before, we no longer do, but we thought hey, why not grab a painkiller to go, for our sightseeing enjoyment? It wasn’t good, in our expert opinions.


Our normal Airstream trips are hiking-focused, but for a Florida trip it seemed more appropriate to bring our road bikes. So expect to read more about cycling than usual over this next batch of posts!


biking the Overseas Trail

We loved the Overseas Heritage trail. It’s a multi-use, paved path running for 90 miles down the keys along an old railway bed, and the section we rode was mostly separated from the highway and felt very safe. And do I need to mention that there are no hills? We did, however, get the first of many flat tires of the trip riding this trail.

coffee and pizza bagel at Baby's Coffee
Baby’s Coffee treats

Our recommendation: starting from Stock Island, ride about 11 miles north to Baby’s Coffee for a snack break. The coffee is fab and the pizza bagel is to die for. We did this ride twice while in Key West, and we also stopped at Baby’s with the Airstream on our way back to the mainland.


kayaking through a mangrove tunnel

When you’re surrounded by so much water, you have to get out and explore it, right? We wanted to rent kayaks, didn’t want to do a tour, didn’t want to drive far, and wanted to explore scenic areas rather than busy boat areas. We chose Lazy Dog, a woman-owned company on Stock Island, for a 2-hour rental. It was inexpensive and awesome: we paddled through winding mangrove tunnels and saw zillions of kooky Cassiopeia jellyfish, lots of pelicans and ospreys, but alas, no turtles or stingrays or manatees. It was a super fun outing. Hurricane Hole restaurant, mentioned above, is adjacent to Lazy Dog.

Touristy stuff

holiday lights on palm trees
they love the holidays in Key West

Walking around town is the best way to get a feel for Key West. The historic section is compact and full of sights. Our advice is to pick your priorities and focus on those, because there’s a lot to see: the Southernmost House and Southernmost Point marker, the butterfly conservatory, Mallory Square, the state park, Hemingway House, the Little White House…

the Southernmost House
the Southernmost House

Our thoughts are as follows:

  • The Southernmost House is pretty. Go admire it, but don’t expect to get a picture by the Southernmost Point marker, because the line will be stupid long.
  • I didn’t get the appeal of Mallory Square. It’s a crowded square with vendors selling crap.
  • The state park is too far if you’re on foot. We were walking, and bailed halfway there. Please tell me if it’s cool.
  • Aunt Lynn LOVED her experience at the butterfly conservatory. We were still being careful with indoor activities due to Omicron, so we saved that for next visit.
  • Our moms did the Hemingway House and Little White House and appreciated the history and the grounds of each place, particularly Hemingway’s polydactyl cats
  • I got a kick out of the Route 1 Mile 0 Start and End signs (probably only interesting if you’re an East Coaster), and we had them all to ourselves
start of US Route 1
Bugsy at Mile 0 of Route 1

The main touristy activity we did was the Conch Tour Train and it was great! It’s a 90-minute guided tour around the historic part of town, with a few stops if you want to jump off and catch a later train–which we did and grabbed lunch at Pirates Cove. We learned about the origin of the ubiquitous chickens, the fantastical Kapok trees, the story of the independence of the Conch Republic, and funny epitaphs in the cemetery. It was delightful.

Kapok tree
we were mesmerized by the Kapok trees!

Key Lime Pie

Key lime pie at Blue Heaven
Blue Heaven’s Key lime pie wins for the most photogenic

I took this task very seriously: I wanted to find the best Key lime pie in Key West, and I wanted to eat a piece a day. This research is for you, dear blog readers. By the end of the week I was really struggling to hit that daily requirement, but I persevered!

Here’s our ranking:

  1. Matt’s Stock Island Kitchen and Bar: perfect tart-sweet custard, great crust, delicious whipped topping
  2. Eaton Street Seafood Market: tart custard, tart, nice whipped topping. It’s made by Kermit’s, a local bakery
  3. Hogfish Bar and Grill: a good all-around pie with tart custard and lots of whipped topping
  4. A&B Lobster House: nice and fresh, but a bit softer. Merengue top rather than whipped cream, but merengue gave it an interesting smokiness
  5. Southernmost Key Lime Shop: a little too sweet? Made by a local bakery; the counterperson didn’t want to give me much info. J said “at this point they all taste the same to me”
  6. Blue Heaven: it’s a work of art, but ratio of custard to topping is way off, and the giant marshmellowy cloud has a weird surface skin
  7. El Siboney: It was fine, but didn’t have any whipped topping. In their defense, an authentic Cuban restaurant only has Key lime pie on the menu for the tourists
Bugsy chasing birds
Bugsy keeping us safe

To do

We definitely want to return!

Next stop, the Everglades!


11 responses to “A week in Key West, FL–Florida in January trip”

  1. […] leaving Atlanta, we were in a rush to get to Key West, over twelve hours away. We decided to suck it up and have one loooong day of driving and one more […]

  2. Uncle Jim Avatar
    Uncle Jim

    Something you may or may not already know, pigs are actually smarter and easier to train than dogs or cats and also cleaner than both. contrary to popular belief they do not like to wallow in the mud. that’s just something a lot of old red necks like my ancestors’ thought was an easy way to handle the animals.
    Sounds like you guys have enjoyed missing all our lovely weather up here, but its February now so you can come back home. By the way, what the hell is a HOGFISH?? A cross between a pig and a catfish???

    1. bugsy Avatar

      Ha, now I’m picturing a swimming hotdog! It was delicious, whatever it was. Here’s what the internet says about Hogfish: it gets its name from it’s piggy snout that it uses to root around in the sand, they start out as female and become male as they mature, and they can change their skin color to camouflage themselves. Neat!

  3. elizabeth Avatar

    Thanks for not showing any pictures of me filling my fat face. Fond memories of my second trip to Key West. I actually enjoyed it even more as we stayed in town. Learned a lot more while touring Hemingway’s home and Truman’s White House. I had a different perspective having been a tour guide for 11 years. I was last in KW in 2010. And, as I am not a big dessert fan, I didn’t feel the urge to consume Key Lime Pie. However I will make one for you ( Lauren). I loved our “happy” house, the little pink dollhouse. Thanks to you three (Bugsy included) for a wonderful trip. You forgotten to warn people about letting their little canine babies chase critters into the water….danger!

    1. bugsy Avatar

      Ack you’re right, I added the alligator danger warning! Thank you!

  4. […] second best food was fish dip from Eaton Street Seafood Market in Key West. Now that I think about it, we (humans) didn’t actually eat any food from Ft Myers Beach. We […]

  5. […] drive from Key West to Everglades National Park was about three hours, but we broke it up with an early stop at […]

  6. […] in general (if you’re counting, this is our second flat of the trip so far, after the one in Key West), so we didn’t ride very much of the bike path system, but judging from the map it’s a […]

  7. […] to the Pinellas Trail (more on that later) and has an ice cream joint next door. If you read our Key West post, you may remember that the RVing pig was at Caladesi when we were, which was a fun […]

  8. […] a dog-friendly taproom. They had a key lime sour, so I was happy–I guess I recovered from my Key West key lime overdose. J didn’t like his hazy […]

  9. […] the basement of a historic shipping storehouse, and the cocktails (and key lime pie tart! you know I love anything key lime!) were scrumptious. Their food is supposed to be outstanding, and based on that tart, we believe […]

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