Before we ever even started looking for Kimber, we knew we wanted a few things in a pup.

I had been dreaming of having a GSP for 5 years, so…she had to be a GSP.

She had to be a she. After years of boy pups, who we loved fiercely, but were always in a pissing match with each other…I wasn’t about that ‘mark everything as mine’ life.

We wanted a pup that was young enough to still have adventures with, and still really feel like we RAISED — but just old enough to know where the bathroom is, and — WE JOKED — that “9pm was bedtime, and 7am was wake up time.” 😂

And we KNEW we wanted a pup we could take everywhere with us – yes, even on vacations.

I don’t know that we realized quite how literal Kimber would be in the take everywhere concept, since we still really can’t leave her solo at our house, buuuut…we love her fiercely, and she’s so well behaved, that most times she’s welcome anywhere we go anyway.

There were moments in the Great Puppy Search of 2016 that I really thought we’d have to wind up settling — maybe, we’d just have to get a boy. Maybe we’d need to get a true, hardcore puppy — or, a pup that was just a little older.  Maybe even a different breed? No, no, no, back to looking at GSPs…

And, then.  There was Kimbee.

We honestly could not have dreamed up a better pup.

When we started looking at places to go for Pupcation 2016 – my mind (and heart) went immediately to The Keys. I researched, I found things for us to do — even a boat trip to look at dolphins! — and a place to stay. But, in the long run, we just weren’t sure if an 8 hour drive, one way, was a good move for the first Pupcation.

So, we started looking a little closer — and landed upon St. Augustine, FL.

Let me back track here for a secondThe Rules of Pupcation are pretty simple — you take your dog on vacation, and you DO THINGS WITH YOUR DOG.  This isn’t a “leave your dog in a hotel room” scenario. Not.Even.Close.

So, we needed a super fun, dog friendly city — and we totally wanted a beachy, chill vibe too.

St. Augustine was PERFECT.


We drove up on a Thursday afternoon, after work – which is about an hour and a half ride from where we are in Orlando. Kimbee slept the entire way.

After arriving and checking into the Vilano Beach Garden Inn, a storm rolled through, but it was the perfect opportunity to rest up a little before exploring that night. The Vilano Beach Garden Inn was a great choice — super affordable, and walking distance to the beach (which is also dog friendly) — they also had a little fenced in potty area for the pups.  We still kept Kimber on leash here though as she could easily hop this fence, and the road seemed busy enough next to us not to want her getting any ideas of an adventure on her own.

We loved that our room provided enough space for Kimber to play with a few beach toys we had brought her, and she even had a little place for her bed — almost immediately, she felt right at home.

That night, after the storm, we ventured out for dinner and stumbled upon Harry’s Seafood Bar & Grille. We sat outside, with live music owning the night, and ordered a couple of drinks with their Signature Crab Cakes, Crispy Calamari, and Voodoo Shrimp appetizers to make it a tapas style night. We, of course, ended the meal with their Oreo Beignets.


They brought out a bowl of water for Kimbee, and she just sat quietly at our feet — which grabbed the attention of a couple next to us, who complimented how well she was behaving with everything going on.  It’s kind of crazy to think, but at this time — we had only been in our Pawfection classes with Kimbee for just THREE months at the time!

We wrapped up the evening by taking a stroll down St. George Street – as a little preview of the next day to come, before heading back to the hotel and crashing hard.


We woke up bright eye and bushy tailed. We walked over to Vilano Beach (again, dog friendly) and took a stroll.  It was pretty windy, and the waves were pretty fierce, but Kimbee did great! She’s getting better with the water, but last summer she really had NO concept of it and it always made her jumpy — even just as she walked alongside it.

Next up was breakfast — we took a drive over to Historic St. Augustine and hit up Schmagel’s Bagels on Hypolita. Kimbee and Sean waited outside while I ran in to get us the noms.

From there, it was off to Castillo de San Marcos! The Castillo itself is not dog friendly, however, you’re able to walk around the Castillo with your pup — and that’s a pretty nice little walk around the waterside. Unbeknownst to us, the US National Parks were celebrating their Centennial and entry was free, so while Sean and Kimbee waited outside — I did a quick little tour of the Castillo and grabbed a few photos from inside before we made our wait over to St. George Street to walk around again.

A LOT of the stores on St. George Street are super dog friendly — not just allowing her in, but greeting her with warmth and lots of pets and treats! Kimbee must’ve felt like a little celebrity….especially when another visitor stopped us and asked to take a picture of her right there on the street.

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While wandering around, we stopped at Scarlett O’Hara’s for a few drinks and to sit in the shade. Kimbee made herself more than comfortable under the table and was happy for the rest. By this time, the heat was rising — because, Florida. In August.  So we drove back over the bridge to Vilano Beach for naps and AC time before a big adventure that night!

At 8:30pm sharp, it was time for our GHOST TOUR with A Ghostly Encounter! Yep! St. Augustine has a PUP Friendly GHOST TOUR! We signed up immediately upon hearing about it, and were excited to see where the night would lead.

We “splurged” and rented an EMF reader (just because I wanted to feel like a true Ghostbuster) and once our group was all together, the tour set out for a night of exploring.

The tour itself is an hour and a half long, and begins at the Love Tree Cottage. You then stroll the darkened streets of America’s Oldest City where you visit TWO cemeteries, a haunted house, Ripley’s, and you can go into a building built on an Indian Village and Burial Ground (this is the only part of the tour that isn’t dog friendly as they’re not allowed into the building.)

Kimber did amazing during the entire tour, where we walked quite a ways between each stopping point (it’s not a long distance, but it is a WALKING tour, so keep that in mind) — everyone was interested to see how SHE responded to the locations and possible spirits who came to visit, but she was pretty quiet throughout.

Our tour guide was great, and even if you’re not totally comfortable with the paranormal — I’d recommend these tours as there is a TON of HISTORY shared here as well! We did our best to get photographs of spirits…but I don’t think we came out with it beyond much more than a camera shake.  It was still a lot of fun, and really enjoyable and something we look forward to doing again on our next trip!

AFTER the tour had ended, we decided to stop by the first cemetery which was right next door to the Love Tree Cottage — just for one more chance to see if we could catch any spirits on camera. We didn’t. But what we DID experience was pretty wild — as we walked up to the towering gates of the cemetery and peered in, Kimber reared up – her hair stood straight – and she let out the meanest, angriest bark we’ve ever heard her make as she stared out into the darkest part of the cemetery.  She’s NOT a dog that ever really barks – let alone angry barks – unless there’s a reason.

We couldn’t see anything.

But HER response pretty much said it all…SOMETHING was out there that she DID.NOT.LIKE.

After calming her down, we started walking back to St. George Street — but not without her looking over her shoulder and huffing a bit towards the cemetery.


The day started with breakfast at the Maple Street Biscuit Company where we had delicious breakfast sammies, and I kicked it off with a refillable coffee. Kimbee took the opportunity to watch the cars pass by and nap a little bit (hey, it’s tough being on Pupcation!) as we sat outside on the patio.

We decided to drive around a bit in the cool AC of our Ford Escape, and found ourselves over by the St. Augustine Lighthouse.  The grounds here are also dog friendly (entry is $12.95 for adults), but we decided to keep moseying along after taking a few photos with Kimbee and the Lighthouse — which might be some of my favorite photos of her, ever.

Next up, we stopped by the St. Augustine Distillery! The tours here aren’t dog friendly (although they are free!) so we had to put the tour on hold for our next trip (which we finally did in June 2017 and LOVED) — but Kimber was welcome in their store. Which was great news for me, because I grabbed a St. Augustine Distillery Vodka and Florida Mule set to go!

Lunch time, already? Time flies when you’re on pupcation! So we went over to Beaches at Vilano — a beachside restaurant, where from the patio, Kimbee had a front row seat to another pup that was paddle boarding with his owner. After lunch and drinks, it was time to rest up and cool down (we were also concerned about the temperature of the ground on Kimber’s feet during the hottest part of the day) — so back to the hotel we went!

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Our next adventure was a PUPCRAWL with St. Augustine Historic Walking Tours! Yep! St. Augustine even has a Pub Crawl that is PUP friendly! (There’s also other dog friendly tour options here) We wound up being the only folks on the tour too — so, yay for VIP-ness!

On the Pupcrawl, you learn about pets throughout history in America and there’s a few fun stops just for the pups! One pint/full glass of premium, craft or local beer, sangria, wine or soda is offered at each stop. Most places also brought out water and treats for Kimber along with our drinks.

I believe we stopped at four or five different locations, from Stogies and Scarlett O’Hara’s to Faux Paws and Mojo BBQ. Our tour guide was stocked full with incredible stories (you learn very quickly that almost everyone in St. Augustine is an amazing Story Teller!) and gave us the option of which stories we wanted to hear at each location.

After we wrapped up the tour, we were off to the Barley Republic Public House for some Irish fare. I got the Reuben sammie and Sean grabbed a burger.  It was pretty late, so from there — it was back to the hotel to catch some Z’s.

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We got up suuuuper early and set out before the sun, and watched the orange glow of a new day lift over the Atlantic Ocean from the Castillo’s walls.  Kimbee joined us up on the ledge, and quietly sat next to us — watching as small waves crashed below us and birds flew above us.

Once the day had started, we went back to pack up and grab a little breakfast and coffee for the road. We made it back home just before lunch and a good afternoon storm – where naps were all in order after a very successful First Pupcation!

Have you taken a Pupcation or are you thinking about it? We’d love to hear where you went (or where you’re thinking of going!) Feel free to ask any questions you might have too!


Where are we headed for Pupcation 2017?! We’re mixing it up this year and taking day trips around Florida with Kimbee in the next few months on “Extended Pupcation” — if you’ve got a great place for us to try or an adventure you think we’d love with Kimbee, let us know! Our first day trip will be this weekend! 😍

Be sure to Follow @KimbeeTheGSP to see where we wind up!


Have you seen Kimbee on Buzzfeed?! Check her out as she made appearances for Shark Week and Rocking Her Pupcation Sunglasses!

Tags : #KimbeeTheGSPAdventuresDog FriendlyKimbeeKimbee The GSPKimberPupcationTravelTraveling with DogsVacation
Casie {kay-cee; KC}

The author Casie {kay-cee; KC}

Photographer | Social Media Strategist | Frequently Found in Theme Parks | St. Baldricks Advocate | GSP Mommy to @KimbeeTheGSP |

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