People often say that when dogs (or even people) get old, they’re no longer cut out for traveling. While getting older sometimes can bring limitations and disease, it’s not impossible to travel and I think that going on a little adventure every now and again is good for the soul and for the mind.
After having travelled with Rocky, my now 14-year old bull terrier, for several years, we have been taking it easy the last couple of years with only local and regional holidays. In December 2022 we moved back temporarily to stay with family in Florida and he’s been mostly enjoying local walks and small adventures as he has been struggling with some arthritis.
But last month, I decided to take him down to Key West, Florida. It’s a place I always wanted to visit and I wanted to take with me on a little adventure, just man and dog, for old time’s sake.
It would be the first holiday with Rocky in a long time and things are different now. He’s no longer able to walk for extended periods of time, especially in this furious summer heat. He’s also slowed down considerably, but he’s still up for sniffing around and gets the occasional trot in his step.
Now with this in mind, I purchased a little beach wagon and for the past couple of months we have taken him around in it on daytime walks and on little errands to the shops and beaches. He’s done well with it and anytime he wants to get out, I carry him out so he can walk for a bit.
So now back to Key West, I planned to go for a few days with a loose itinerary in my mind. Now, I love to read and Ernest Hemingway is one of my favourites. Many of his books are all-time classics.
I was inspired to travel to Spain and France due to ‘The Sun Also Rises’ and I was enamoured by ‘For Whom the Bell Tolls’. I’ve also read a biography (Conversations with Hemingway) and some of his short story collections including ‘Men without Women’.
With this in mind, I had put ‘The Hemingway Home and Museum’ at the top of my to-do list for Key West.
Beforehand I also managed to research some of the dog friendly places in Key West. There are some great guides online, but some of them do not cover a few of the places that we went to. This is why I decided to write down our experience due to how recent our trip was.
So off we went in our car, setting off from Central Florida to Key West on a road trip, just the two of us, like old times.
The drive time was roughly 8 hours, but we stopped and rested at a relative of ours in Miami for one night. I made sure to bring his wagon, his blanket, bed and plenty of snacks as well as some freeze-dried raw food and fruits.
About one hour into our trip to the south, I realised I had forgotten his portable dog bowl. So what did I do? Buy another?
No, I stopped by a supermarket and bought paper bowls for his food and water. I figured it would be easier rather than having to clean his bowl after every meal and I could then recycle the paper bowls.
So here are a few tips based on our few days in the keys. This is by no means meant to be an exhaustive list of all restaurants, shops and hotels, rather just a few that we experienced and are happy to recommend.
Hotels
Booking a hotel
 Right off the bat, I found it quite easy to book hotels online. Booking.com and Tripadvisor are excellent resources. I should note that I had booked just one week in advance of our departure date.
Most, if not all, hotels have a dog fee. Some of them can be quite expensive, so do some shopping around and if you can. Try to book well in advance so you can have more options.
If your dog is a service dog call or email the hotel ahead of time and let them know.
Also, it might be a good idea to let the hotels know that you are bringing your pet ahead of time, even if your pet is not a service animal.
When it comes to booking hotels, shop around online and then call the hotel to see if they would be willing to match or beat the online deal.
Key West can be expensive, especially if you have a dog. Also, always look at reviews and pay attention to any reviews from people who stayed with their dogs and read the Q and A as sometimes the hotel answers customer questions that pertain to its pet policies.
The hotel we booked
We stayed in a hotel called Courtney’s Place. It’s actually a charming and historic cottage right in the center of Old Key West. It’s perfect if you want to walk to the seafront or walk to the main roads and it’s also close to the Hemingway Museum.
If you have a senior pet, it’s important to make sure parking is close to the hotel and the parking in Courtney’s Place was perfect for us.
The room itself was cozy and spacious and it had an outdoor patio area where we could grab some fresh air.
As for our experience there, the staff was incredibly polite and welcoming and the cottage itself is not only dog friendly but animal friendly. You will find roosters, hens and cats roaming the property and they will even come up to you to say hi while you’re eating your breakfast.
There’s also a pool, which is small, but it’s pleasant in the summer and if you go in the middle of the week like we did, it’s not as busy so it feels like you have the entire pool area to yourself (well with the chickens too).
Other hotels
We only stayed at Courtney’s Place here and then travelled further up north to Duck Key.
If you happen to be driving and are heading back up north I recommend a little stopover hotel  in Duck Key called Conch Key Fishing Lodge. This place is dog friendly and has a lovely pool where your dog can join you on the deck area. They even hire kayaks and jet skis. Though I wouldn’t recommend going on a jet ski with your dog.
Restaurants and cafes
I did a quick search for dog-friendly places to eat around there and I had noted a few down but once I checked in to our hotel, a fellow guest greeted us and recommended a bar on the seafront that allows dogs.
So I ended up accepting the guest’s recommendation. Rocky seemed up for walking so we attempted to walk to the seafront, but it was way too hot so I went back to the hotel and brought out the wagon and we strolled to a bar called ‘Schooner Wharf Bar’.
It was about a 15-minute walk from the hotel but it felt longer due to the heat. There was no way we would’ve made it walking and this was the late afternoon heat too.
Rocky and I walked in and the waiters brought us a bowl of water. There was live music and nice selection of food and this is where we ate lunch/dinner. I definitely recommend it if you’re looking for a nice seafront outdoor place with a chilled atmosphere.
Afterward we walked around the port and Rocky was ever the popular tourist with many people commenting on him and his wagon. We stopped for long periods of time under the shade and sometimes the clouds moved to cover us, but when they moved again, the heat hit us and we rested under the closest shade.
After walking around Greene Street and Elizabeth Street, we ended up escaping the on and off again heat and getting dessert at this place called Mattheessen’s that serves Key Lime Pie, a specialty in the Florida Keys. I had asked the cashier if he was allowed in and she said yes and I managed to eat my dessert here and it’s a good thing because it was getting hot outside again.
So if you are looking for a dessert place that allows dogs there’s this place that you can add to your list.
Some galleries are dog friendly too
We spent enough time to here and waited for the afternoon to cool down and then walked down the road again to where many of the big shops were. We walked past Papa’s Pilar Rum Distillery and through Duval Street.
One small art gallery caught my eye and I thought I would bring Rocky inside, wagon and all. To be clear there were many of them that we passed, but colorful sculptures of dogs catch my eye and we were allowed inside and cooled down. The gallery was called Ocean Blue Galleries Key West.
The rest of the night I let Rocky rest at the hotel to get some ice cold air in the room while I explored the streets.
The following day we had breakfast in the hotel, accompanied by chickens and roosters. We then set off to visit the Hemingway Home and Museum, but before I get to the that, I will mention a few more places we stopped and got some food.
Moondog Cafe
This wonderful café was on the way back to the hotel and we stopped here for a drink and of course, a key lime pie. The patio was dog friendly so we strolled in wagon and all. The baristas inside came out and offered to bring a water bowl for Rocky. The area was nice and shaded and as a bonus, the mini key lime pie was delicious. They have plenty of selections for dessert.
Blue Heaven
Another dog friendly restaurant similar to Schooner’s with al fresco dining and a live band. If you like chickens and roosters wandering around, then this place is also for you. I would say they definitely give the place some character! Here I had a soup and another drink for lunch.
The restaurant is also historic and according to the restaurant’s website, throughout the years the property has hosted cock fighting, gambling and Friday night boxing matches refereed by Ernest Hemingway. A dance hall, a bordello and a playhouse have also occupied the second floor, so if you’re looking to experience more Hemingway history, this is a good place to go.
Louie’s Backyard
If you like dining or drinking (or both) with an ocean view, then Louie’s Backyard is a place not to be missed. In the afternoon we went to a dog beach at the end of Alberta St. and we were told by one of the locals to visit Louie’s for food. While I wasn’t hungry as I had just eaten at Blue Heaven’s, we did go for a drink at the fabulous patio which featured lovely views of the sea. The bartender was also a dog lover and offered Rocky a water bowl and let him even join her in the back of the bar to sniff around.
On another note, if you’re walking around Key West with your dog, it’s a good chance most restaurants or cafes with patios allow dogs.
Dog beaches
 If you’re planning on taking your dog to Key West, which. if you’re reading this, means that you are, then you’ll be thrilled to know that there are plenty of dog beaches to choose from.
According to Historic Hideaways, there are at least four dog beaches and a big dog park where you can take your dog so they can run about to their heart’s content.
We chose Key West Dog Beach which is located at the end of Alberta St. The water here has some sea weeds of course and it can smell, but if you can look and smell past that then you and your pup will have an enjoyable time.
It was quite hot so we hid under shade next to the patio of Louie’s Backyard then went for a dip several times and I let Rocky swim so he can work on his leg muscles.
The dog beach itself is small and it’s not enclosed either, but there are some benefits. Parking near Louie’s is free and you can simply walk from there to the beach. After your swim, you can cool off then go for a drink at Louie’s.
As for the other dog beaches, we didn’t get a chance to explore the others in Key West, but we did go for a kayak adventure in Duck Key at the Conch Key hotel that we stayed in.
Hemingway Home and Museum
When I looked up the rules for dogs at Hemingway Home and Museum, I was pleasantly surprised to find out that dogs are allowed, but with a caveat.
Dogs must be carried.
That means that dogs have to be small enough to be carried or you can have a larger dog and hope that your back doesn’t give out.
Why is this a rule? I am not certain, but I would imagine that it’s due to the cats. In fact, the ticket clerk mentioned it was the amount of cats and that they do not want to be disturbed.
The Ernest Hemingway Home and Museum is home to approximately 60 polydactyl (six-toed) cats, according to the museum website. Cats normally have five front toes and four back toes.
We did pause to take some breaks and some cats managed to get close to Rocky.
It was a lovely adventure overall, and if you have been to Key West, you might be familiar with how it almost feels like you’re in another country and everyone is so relaxed, including the animals.
If you made it this far, thank you for reading and we hope you hear about your Key West travels soon!
