I’m hoping this title is read like an update on the pups and not about a date with pups. (Although, Ham has been flirting with a three pound Yorkie that lives in our building…)

It’s been six months with having two dogs on my own, and I feel like I’m finally in a good routine with them. It’s so hard, and I often feel outnumbered, but it’s not like they’re kids. It also helps that Hamilton is one and a half years now. The extra “half” makes ALL the difference. That dog has five times the energy Teddy does… phew!

KJP Dog Bandanas

I think the one thing that keeps everyone (the dogs and myself) sane is utilizing the fantastic dog daycare place in town. I love them, and the dogs love them even more. I get a little break, and the dogs get to socialize. It’s an added expense in the monthly budget, but worth it, especially since I work from home and spend nearly every waking minute with them anyway. They’re actually really spoiled there. I was dropping them off one day, and the guy that does the overnight shift asked if it was okay if they slept in the bunk room with him instead of the crate because they like to watch TV with him. (See, very spoiled.)

KJP Scalloped Dress

When I booked a Nantucket rental for a week in July, I did it in early December with the intention of bringing the dogs along. I’m not going to lie, I immediately (like literally seven months ago) started to plan in my head how I was going to get two rambunctious dogs to the island.

I had this whole scenario built up in my head like a nightmare. Teddy HATES driving in cars and Hamilton is unpredictable. The day would include a two and a half hour drive to New Bedford, a short wait at the ferry terminal, a two-hour ferry ride, and then a car to the house.

While I was on the ferry back from Round 1 to collect the dogs for Round 2, a woman a few seats over from me had a cat in a bag. The poor cat got really sick on the ferry, and my heart went out to the woman. It also set in a deeper fear that my dogs would not be okay on the boat.

It turns out I worried over nothing. The dogs were perfect on the ferry, and I think it was the best part for them. Ham snoozed the whole time on my lap the way there, and on the floor the way back… and Teddy enjoyed the attention from all the kids and grandmas on the boat who just wanted to give him all the head scratchies.

Hamilton Carly Prepster

Teddy Carly Prepster

Do I sound like a crazy dog lady yet? Spoiler alert: I am!!!

KJP Dress

The dogs and I had the best week together on Nantucket. I especially love knowing that I can travel with them more. They’re good sports, and as long as they get a little exercise, they’re good to go!

Nantucket Dog Vacation

Also, people were legit pulling their cars over to say how cute the matching gingham was. I 100% recognize that this is over the top and downright ridiculous but guys… I loved every second of it.

Nantucket Dogs

Photos by Carter Fish

KJP Shirtdress // Gingham Handkerchiefs  // Similar Belt // Jack Rogers (on sale!) // Sunglasses

Leave a Reply

Your email address will not be published. Required fields are marked *


Ashley Barker

These are photos are beyond adorable, ugh!! So happy for you Carls. And Carter’s photography is AH MAZING!! Esp here with all of the beautiful Nantucket scenery, sunlight, and those big blue hydrangeas!

Sarah Gouin

Love the matching gingham!!! Glad you have settled into a routine with the two dogs. We are now down to two from three but I can totally understand the time needed to care for them.


Love the update on the puppies! The matching gingham was so cute! I have a puppy (although she is turning 4 now so not really a puppy) and I live with my two sisters and she is so spoiled by all the attention she gets from three adults.


The dogs and YOU look absolutely adorable. I so enjoy your blog and glad you can take them with you to Nantucket.


Dogs are such troopers, and while it can take them a little time to adjust to new situations, I think that they are more adaptable than we know! And those bandanas are adorable 🙂 In our family we have matching t-shirts and bandanas for several occasions, haha!


Love this post! They both look SO adorable, I was lucky enough to have a pup of my own earlier this year for a couple months but unfortunately she was unwell and had to be put to sleep. Dogs are honestly the best thing you could ever have x


Hi Carly!
Great update! As a fellow dog mom, I’d love a post about where you find cute harnesses, collars, beds, and leashes for your pups. I’m forever on the hunt for cute accessories for my dog and would love to know where you find the cute stuff Teddy and Ham wear.


Teddy and Ham are so adorable, and clearly very loved! I don’t think the matching gingham is too over the top or ridiculous…I never leave the house without wearing my friendship collar bracelet to match my mini Aussie!


Such cute pictures! I’m definitely living vicariously since I am dog-less at the moment. And the fact that the dogs like to watch tv with the doggie daycare workers is just adorable – thanks for the pupdate!!

Jen Kessler

Haha! I do the matching thing with my little girl and I love it – I mean, any small kid or animal that matches their bigger person is adorable!


Carly! I still can’t get over how cute these pups are in gingham! I’m so glad you all had a blast in Nantucket and thank you for sharing your experience. It’ll come in handy for when I start planning for next summer!