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Dogcation: Key West

Tags: key west west

If you read my previous post Dogcation: Taking the Train with My Dog , you will know we spent almost 18 hours on the Amtrak Auto Train from Virginia to Orlando, which I must say was a very positive experience. From Orlando the drive to Key West is about 7 hours. After not getting much real sleep and not having a real bed, we decided to stop in Miami- halfway between Orlando and Key West. We all needed to rest up for our spring break dogcation!

Getting to Exit 0

We found a great dog-friendly hotel, Daddy-O Miami which was posh and rather affordable too (fellow New Jersians may be familiar with their sister hotel in LBI). There is a complimentary happy hour each night, and we all enjoyed cocktails at the outdoor lounge.

While I knew there were dog-friendly restaurants in Miami, we were all just too beat from our trip and opted for take-out. Daddy-O is connected to The Palm Steakhouse. We enjoyed fine dining in our room before swan diving into the luscious king-size bed. This was a great stop to recharge before the next leg of our voyage.

The next day we dined on the dog-friendly patio at Perricone’s in the Brickell Village section of Miami. We had a fabulous Italian lunch in their lush, tropical setting before embarking to the Keys. Jaxson enjoyed a bite of mom’s antipasto. (Hey, we were all on dogcation!)

Since we knew we’d be a few hours on the road, we made a stop at the dog-friendly Cape Florida Light where Jaxson could run around and stretch his legs.

If you’re familiar with Miami and you love stone crab, you will have undoubtedly heard of Joe’s Stone Crab. Joe sources its stone crab from Key Fisheries, located in Marathon, FL on the way to Key West. We enjoyed dockside dining while gorging ourselves on stone crab without having to deal with the hustle and bustle or prices of the downtown Joe’s location (which also is not dog-friendly). Key Fisheries is definitely worth a stop!  

A fun fact – when you list your name at the takeout window, your “name” must be a song or singing group. It was pretty funny hearing over the loud speaker “Three Dog Night, your order is ready!”



So after about three days of traveling, we finally made it to our destination of Key West. Let the fun begin! While NJ was preparing for a snow storm, the first thing we wanted to do was get to the beach. There’s a lot of beach spanning Key West, but not a lot of it is dog-friendly. We found a section of Fort Zachary Taylor State Park where we set up camp. Jaxson enjoyed the shallow pools of water and basking in the 80 degree weather. 


Hiking isn’t really prevalent in Key West, but the Key West Tropical Forest and Botanical Garden will make you feel like you’re trekking through the wilderness. There are plants and flowers of all kinds and even a one-acre butterfly habitat. Jaxson enjoyed all the smells. 

Duval Street

Of course a trip to Key West would not be complete without walking down the famous Duval Street. We did a little shopping (open containers in hand!) in various retail stores. 

(Even the Coach outlet was dog-friendly!) There was a fantastic pop-up shop “cart” specifically for dogs, the Coconut Retriever Doggie Duds, which makes all their products locally. 

There’s a huge Southernmost point “buoy” landmark facing the water at the corner of South and Whitehead Streets and marks “90 miles to Cuba.” Needless to say it’s picturesque and there’s always a line to get a picture with it. If you insist on snapping a pic, I suggest going early or in the off season. We didn’t want to wait hours in line with Jaxson so we instead visited the coconut man who hangs out around that area and takes a freshly fallen coconut, drills a hole in it, gives you a straw, and voila! 


While we didn’t get a chance to go because there’s only so much you can do in 5 days, I think it’s worth mentioning that I called ahead and the Key West Aquarium is dog-friendly, so long as your dog is on a leash.

Activities Afloat

When in KWF, one must enjoy some time on the beautiful water…

We rented a two-person/(one dog!) kayak at Lazy Dog Kayaks. Jaxson thought he was captain! It’s a great route as you start in small, narrow areas of water that lead out to the ocean. Whether you’re an avid kayaker and want to be out on the open water or prefer a calmer paddle through the shallow waters, Lazy Dog Kayaks is for you. And your dog will love all the smells (and swimming if that’s his gig).

At the Key West Bight near Mallory Square there are tons of options for boat rides. We ended up going with Schooner American 2.0 as they were very open to having a dog onboard. They have early afternoon and sunset sails replete with hors d’oeuvres. It rained once we began the sail but it made the ride all that more adventurous. I’d highly recommend the Schooner American 2.0 to accommodate you and your pup. 


1.  Pepe's Cafe. There is dining of ALL KINDS for you and your pup in Key West. Without a doubt, our favorite restaurant.

You’re not quite outside; you’re not quite inside. You’re in a tropical relaxed getaway that you will only find in the Keys, replete with a cocktail of the day that starts being served when the restaurant opens. Self-described as “funky,” Pepe’s is open for breakfast, lunch, and dinner, and every meal was fantastic.  It’s safe to say we frequented this establishment quite a lot. The waitress brought over a dog bowl and there are doggie t-shirts for sale (unfortunately with Jaxson’s tumor even the XL didn’t fit but they were super cute).  It’s the epitome of Key West atmosphere while also being delicious and dog-friendly. (We are hoping to make the pet gallery!)

2. Sarabeth's. For those of you from the NYC area, you may have heard of this fine dining restaurant (there are 3 locations currently in Manhattan). The Key West owner used to manage one of the NYC locations so you’re getting the same quality of food at the Southernmost point. And the outdoor area is dog-friendly! 

3. Half Shell Raw Bar. Seafood lovers must visit (Half Shell gets its famous stone crab claws from Key Fisheries mentioned above). There is a dog-friendly patio and all the seafood we had was amazing. I found the sign about pets on the patio to be a nice touch. 

4. Mangia-Mangia served amazing authentic Italian fare and the outdoor courtyard was quaint and adorable.

 5. If you want high end steak and you want to bring your dog, Michael’s is undoubtedly the spot for you (and conveniently right across the street from Mangia Mangia). Celebs love it too - we missed Good Morning America host Amy Robach and her husband Andrew Shue by a few months!

6. Fat Tuesday is an obligatory stop for frozen drinks that you can bring anywhere while walking in Key West and for a quick sweet treat on Duval, try Mattheesseen’s, a local favorite. Smokin’ Tuna had excellent live music and great local fish dip.

7. Island Dog was a great stop just a hop skip and a jump off Duval for some bar food and hurricanes. It was nice because Jaxson was tired by this point and Duval was a bit too hectic, but at Island Dog we could still enjoy some late night beverages and snacks.

8. Firefly was a bit off the beaten path, but we loved it. It’s a modern restaurant specializing in Southern cuisine and artful cocktails. (And Jaxson loved the cracklins!)

Needless to say, there are so many dog-friendly places I had on my list that we didn’t even have time to try them all, if that gives you an idea of the magnitude of dining offerings.


What’s a trip to the Southernmost Point without a few speedbumps? Mind you, these aren’t encountered all year but they did occur during our trip so I feel it’s worth mentioning.

Upon entering the Keys there was a sign about a Screwworm epidemic that I did not know about. Bring your dog into some of the Keys at your own risk if he/she has an open wound, because your dog could contract this infection where larvae will feed on living flesh. Luckily Jaxson didn’t have an open wound and Key West was not one of the affected areas (needless to say we did not make any pit stop in areas noted). At the Animal Checkpoint going home everything was fine, but I do encourage you to research before any trip to the Keys to see if Screwworm is still prevalent.

One other note – March is prime time to visit Florida particularly if you’re from northern areas, but keep in mind St. Patrick’s Day also falls in this month. Thus, towards the end of our stay we noticed a marked increase in Spring Breakers, particularly at our hotel (while I was once one of them myself, I didn’t need to be awoken at 3 AM and 4 AM the night before an early drive all the way to Sanford to catch the Auto Train). My senior dog who has anxiety and is fearful of loud noises didn’t appreciate being constantly awoken by what sounded like bodies being thrown against our door.  We ended up getting that night free, but ultimately just a little something to keep in mind if you visit Key West during the week of St. Patrick’s Day and you want SOME quiet time after the wee hours ☺

If you and your pup can successfully get down to Exit 0, I promise you it will not disappoint. There are multitudes of things to eat, do, and see, and we can’t wait to go back and explore more.

Do You like to go on dogcations? Where is your favorite destination? 


*Note from Heather: Sadly a few weeks after returning from his dogcation, Jaxson went over the rainbow bridge. His Dogcation to Key West was by no means his last adventure and he lived every day to the fullest with his loving family. He will be sorely missed. 

Amy Molnar Schwebel is a New Jersey native who works in the publishing industry in marketing by day. When not working she enjoys travel, fine dining, live music, and her number one passion, spending time with her pooch Jaxson. Amy also revels in writing the Dogcation series for Bridle & Bone, hoping to inform other pet parents that the world is your oyster when it comes to journeying with your dog.  


This post first appeared on Bridle And Bone, please read the originial post: here

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Dogcation: Key West


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