We traveled a lot this summer. Some close friends got married in Asheville. Then we flew out to Seattle to visit my sister, who had just started an internship with Microsoft. We were also planning a beach trip with Holly’s sister and her family—where I was going to ask Holly to marry me.

Then we got COVID. Both of us had fevers and felt terrible—obviously, we were in no shape for a trip.

Even with our plans disrupted. I still felt like the beach was the right place to pop the question. Holly still wanted to do a beach trip, so on short notice we booked a tiny yellow cottage in downtown Port St. Joe.

A few days later we loaded up the dogs and were off to the beach!

A little yellow cottage. Two dogs look out the second story window.
Otto and Remi looking out the window of the tiny yellow cottage we rented.

We usually stay in Port St. Joe Beach, which is about 15 minutes north of downtown. All the houses are walking distance to the ocean. The only issue is there are no restaurants nearby and Uber and delivery services don’t operate down there. You’re on your own for meals.

The last time we stayed down here we discussed staying in downtown instead. That way we could walk to all the restaurants and coffee shops. This was our opportunity!

The little yellow cottage we rented was tiny, but had a good layout and a fenced yard for the dogs. And a window at the top of the stairs they both liked looking out of. 

Port St. Joe Beach

Holly took camping trips to Port St. Joe as a child. Last year she wanted to come here for her birthday and we fell in love with the place. The beaches are beautiful and secluded. It’s rare to see more than one or two other families out. The dogs can run free without us needing to worry about them bothering others. 

It was the perfect place to pop the question!

And she said yes!

You’re probably wondering where all the photos are. Well—it was just Holly, me and the dogs. Nobody else was there. And it didn’t feel right to try and take a selfie. We both were just enjoying the moment. 

Engagement ring.
This ring is a family heirloom. It belonged to my grandmother and is over 100 years old. This was taken after the beach, but thought I’d include it.

Holly’s never been one for spectacle, so this was the right way to do it. And it couldn’t have gone better.

We enjoyed the rest of the afternoon with the dogs on the beach.

Remi, who hates (or used to hate) the water, decides to take a dip in the ocean.

Our oldest dog, Remi, has never liked the water. So, to our surprise he spent a lot of time peacefully wading into the ocean. It was something we never thought we’d see.

He’s changed since we got Otto. Perhaps, he feels the need to be brave for his little brother? Whatever the case. I love this clip of him enjoying the water.

The dogs love the beach. When they weren’t chasing the balls or each other Otto spent a good part of the day digging, while Remi waded out into the ocean.

Remi and Otto chase each other on the beach.

Celebration dinner (and ice cream)

A colorful pink building decorated with smily faces and sprinkles. One side says "Life is sweet." The other says "Drink coffee. Eat Ice Cream. Be happy."
Holly attempting to get the dogs to pose. Mural on the side of a Sugar Shack in downtown.

To celebrate the occasion Holly picked out a Mexican restaurant a couple blocks away with a covered patio. We had margaritas, dinner and then went to the ice cream shop next door for dessert. 

Cape San Blas

The following day we decided to drive across to Cape San Blas. There’s a state park where we thought there might be some good hiking at the end of the peninsula. 

The beaches in Cape San Blas are spectacular, although more crowded. The beaches within the park don’t allow dogs, so this was about as far as we got. 

Hurricane Michael destroyed many of the park’s trails. They had never been rebuilt. A park ranger told us there was a small trail off the road towards the park entrance. He suggested checking that out if we wanted to do some hiking.

Holly walks the dogs along a sandy tree-lined trail.
The start of a trail at T.H. Stone Memorial St. Joseph Peninsula State Park. Remi looks for a place to poop.

The first leg of the trail was disappointing. It was largely small brush and pine trees. It didn’t look like we were going to get anywhere near the water. The dogs were hot and not happy about being in the sun for so long. We almost turned around.

Luckily, we decided to stick with it a little longer. It was the right move. The trail had this beautiful stretch that ran in the woods, right alongside the beach. It was gorgeous and I got a few outstanding pictures.

Otto makes some friends and the dog park.

I parked the car and we started making our way towards the beach. The sky was getting dark. There was a dog park not far from where we parked. We decided to let the dogs run around as much as we could before the rain started.

Fortunately, there were a couple friendly golden retrievers in the park who wanted to play. We only had about 15 minutes before the rain started, but the dogs got a lot of energy out.

We headed back to the house for the evening.

Coffee and a last walk downtown

The following morning, we cleaned up the house and packed the car. We stopped by our favorite coffee shop and had breakfast on their patio. We took a walk around downtown and then headed to the Gazebo out by the bay.

That’s it. A fantastic beach trip with the dogs and my girlfriend—now fiancée!

Posted by:Sam Solomon

I'm a designer, writer and tinkerer. I currently lead workflow and design systems at Salesloft.

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