OCS graduation and Pensacola Road Trip recap



Anyone else ever feel like they need a vacation to catch up from their vacation? That’s where I’ve been this past week. It didn’t help that I hadn’t at all planned to be on vacation for the entire week, but that’s what tends to happen when you’re significant other is in the military. You can plan all day long, but you should probably have about 3 or 4 backup plans just in case.

My favorite vacations are the ones that are very loosely planned and spontaneous. When I know or even think I’m going on a vacation somewhere, I extensively (almost to an obsessive level) research the area. Having about 4 or 5 different itineraries in my head really helps when we’re feeling too tired to do something or we decide to sleep in, then there’s a really great backup plan ready to go. One of my biggest peeves on vacation is wasting time figuring out what to do.

So I didn’t mind that we found out less than 24 hours before we started driving that we would be headed to Florida ASAP. I had already mapped out 3 different routes, and knew all of the major cities we would drive through when we needed to stop.

First was graduation in Newport, RI. I was so nervous about this part especially. I wanted everything to be perfect, from my pedicure to each little hair on my head to even the gift bag I had purchased for his graduation gift. I couldn’t tell you how many hours I spent scouring the racks at Macy’s, Lord & Taylor, and Bloomingdales to find the just right dresses for each night. I even set notifications on my phone for various retailers so I would know about new dresses and I obsessive checked every sale on RueLaLa. Sometimes, I plan a little too much.

Not seeing your significant other for 3 months is hard, y’all. Really hard. But it’s worth every single night where I wondered, “what in the world did I sign up for here?”

Naturally, I wanted everything to be perfect for that first night back together. Thankfully in Newport, there’s no shortage of cute little hotels and restaurants. We decided to splurge a little and go with the newly renovated Marriott since it was so conveniently close to everything and was just so cool.



Let me tell you, it was definitely the right choice. They were so accommodating and friendly – the front desk agent even upgraded our room to a higher floor and balcony. This really got the weekend off to a great start.


That night they hosted a cocktail party, something I had been stressing about for months and it was the first time we really got to see each other, also parents and lots of pictures were going to be involved. I must have tried on more dresses the most difficult clients on Say Yes to the Dress, before deciding on a royal blue one I found on sale at Lord & Taylor. My favorite thing about this dress was how it flowed when I walked and I loved the somewhat hi-lo hem.


Dress: Laundry by Shelli Segal | Shoes (not pictured): B Brian Atwood

After the cocktail hour we went to the most wonderful little restaurant, The White House Tavern. Supposedly, the oldest tavern in America and has been in business since 1673. Everything from the service to the atmosphere to the meal itself was absolute perfection. It’s an absolute must if you’re looking for a romantic, but not too stuffy, dinner date night.

Graduation day was absolutely hectic. He had to be up and back on base by 5:30 AM, and about 2 hours before graduation received his orders confirming that he would need to be in Pensacola in 4 days. Even though this meant less time together and having to be apart for a couple of months, in my head all I could process was, “VACATION TIME, ROAD TRIP TO FLORIDA, BEACHES, WARM WEATHER, LET’S DRIVE NOW”.


Dress: Lilly Pulitzer | Earrings (old, similar style linked): Kendra Scott, similar | Necklace (sold out in white): Kendra Scott 

The worst part of the drive was from Rhode Island to northern New Jersey. Rush hour traffic in Connecticut is no joke.


One of my favorite parts of a road trip is finding the best food wherever we stop. My dream job is to do something similar to Diners, Drives and Dives. For the first night, I found a little hole in the wall in North Carolina for some BBQ. It was just what this homesick southerner needed.

After two and a half days of driving we finally made it to the beach, after being in the car for so long nothing feels better than the salty ocean air and warm sun. We stayed the first night in Destin, mainly so we could go to Margaritaville for dinner and I had never been to Destin despite growing up only 10 hours away.

Destin did not disappoint. From the sugary white sands and warm, emerald-toned water it was everything you need in a beach.


Margaritaville and the boardwalk at night was one of my favorite parts of the trip. Getting to go on a real date again where we weren’t both totally wiped out was so nice.

We spent the last couple of days I had in Florida in Pensacola. I have no doubt we’re going to love it there. The beach is absolutely spectacular and I loved being able to walk along the beach to dinner with a mixed drink called Sunshine in a Cup in my hand.

Anyone live/have lived in/frequently visit Pensacola or any of the nearby areas have any suggestions for next time?





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