Tips for traveling with a 5 month old Gasparilla Travel Guide from Abby Capalbo

We were so excited (and maybe a little nervous) to take our first trip with Henry. Traveling has always been a big thing for us. It’s always been something that brought us together even after the most hectic stretches of time. It’s been something to look forward to. Something to get us out of our comfort zone a bit and into a more comfortable zone for us - vacation mode. Andrew and I are our best selves on vacation, and I want Henry to see that side of us.

I want Henry to remember his parents on these messy trips. When things are a little less routine. When we are making inside jokes that will last for the rest of our lives. When we are belly laughing at the most random things. I want Henry to always remember us in these moments. And sharing those moments with him on this trip made it even more special than I could have imagined. It obviously helped that we went to a magical little island off the west coast of Florida - Boca Grande. We stayed at the Gasparilla Inn - a very old school in the best possible way sort of an inn. It’s a place steeped in tradition where jackets are required at dinner, you get around the island on a golf cart and everyone seems to know each other. It was the best place to start (what we hope) is a family tradition of being good vacationers (you have a lot to live up to, Henry). .

On our honeymoon, Andrew and I made an epic list of places we wanted to visit together. And then we made a side list. This little side list had all the places we wanted to visit or share with our future kids. And Gasparilla was on that list. We have friends who have gone for years, and we always loved the feeling of it being a family tradition. So one delirious night when Henry was just a few weeks old, we decided to see if we could make it a family tradition too.

Long story short, it was just what we needed. Sunshine after a long winter, great food, a wonderful atmosphere, gorgeous places to walk - just an all around perfect getaway for our wolfpack. We already booked for next year, and can’t wait to see this little tradition of ours grow.