How to Surprise Your Mom with a Trip to Pensacola Beach

When it comes to family vacations, going to the beach has, typically, been our thing. And, if I do say so myself, it’s a thing we do quite well.

No matter if it’s the Great Lakes or  the Gulf Coast, we’ve got the full-day outing down pat: sunscreen, comfortable chairs, a few snacks, and an umbrella for those members who can’t hang in the sun for hours on end like the rest of us. Afterward, we head straight to dinner for a feast of fresh seafood. It might be a simple routine, but it’s one that we’ve all come to love.

For Mother’s Day and my mom’s birthday, my sister and I — now old enough to treat our parents like they’ve treated us over the years — wanted to plan a beach trip to remember for our mom.

It would be a girls’ trip for the books in a part of Pensacola we knew mom would love. Here’s everything you need to know for your trip to Pensacola.


Aim for the shoulder season

Florida’s beaches, especially in Panama City and Pensacola, aside from being very hot, get amazingly packed in the summertime. We purposely planned the trip for the shoulder season — and actually pretty nicely timed it for Mother’s Day weekend — just ahead of Memorial Day.

Here’s the thing about the shoulder season in the South: It’s still feels like summertime. In fact, I would argue the best time to head to places like PCB and Fort Walton and Pensacola is during April and May and September and October.

By going in the cusp of the shoulder season, we were able to enjoy a relatively kid-centered hotel as adults, avoid long wait times for restaurants and other outings, and usually start or end the day feeling like we had a corner of the beach (and sometimes the pool) to ourselves. It was quality time done right.

Know Your Beach

Growing up, we were able to drive to Panama City and Destin for the day with ease. While we had visited Pensacola as a family before, I felt — for a long time — that its beaches were so-so compared to the perfectly turquoise waters all along the Gulf Coast I knew. Then, I went on a work trip with Travel Mindset to Pensacola and I realized I was completely, 110% wrong.

The trick to finding the perfect beach on Pensacola is to head across the bridge away from Gulf Breeze toward the Pensacola Bay area, where the water really is clear as can be and the crowds are fewer and far between.


Plan a Special Outing

As mentioned earlier, my family sticks to a heavy trend called “we’re not leaving the beach for several hours.” This time, my sister and I decided we would have one special moment for every day of the our three-day trip. Luckily, Pensacola is more than just a beach town: it’s a beach town with character and a ton of great activities and restaurants to enjoy on and off the beach.

  • Book a midday dolphin cruise with Jolly Sailing. Despite all the beach trips, none of us had gone on a dolphin cruise together. We saw so many dolphins on our cruise with Jolly Sailing, which took us to the very tip of Fort Pickens. Jolly Sailing was clearly a favorite with locals and long-time beachgoers to Pensacola, and they were friendly and easy-going. Drinks were included on our cruise, and the crew was happy to explain how they knew where to find the dolphins and offer more details about the area itself.
  • Make Reservations at The Grand Marlin. This was easily the best meal I’ve ever had — at any beach — period. Reservations aren’t required but heavily encouraged for this spot just on the bridge coming into the Bay. The restaurant’s windows remain open, so if you score a table near a window like we did, you could enjoy a great ocean breeze while watching the boats cruise by just before sunset. We ordered from the seafood specialties and none of us were disappointed. Pictured above is my order, the grouper piccata, but my mom’s tuna and sister’s salmon were each just as wonderful (and drool-worthy).
  • Make time for sunset (and sunrise) on the beach: It sounds so simple, but this turned out to be our favorite couple of hours we had together from the entire trip. I think part of it might be because we did what we were good at: we grabbed a few towels, poured a glass of wine, and just sat on the beach and watched the rays ride in the surf as the sun went down.


Pick a hotel that’s a destination too

After a lot of trips, I’ve really come to appreciate a hotel that is more than just a place to lie down after a long day out and about. A hotel should have a nice coffee shop, a bar — something more than just a pool. I was first introduced to the Holiday Inn Resort at Pensacola during that work trip with Travel Mindset I mentioned earlier. That event was held in October, and Laura and I absolutely fell in love with its amenities, views and lazy river. When my sister and I started planning this trip, there was no other hotel in my mind. And, for our mom (who loves a lazy river more than anyone else I know), it was a no-brainer, too.

This isn’t a sponsored post. I really do enjoy this hotel. There are fire pits and porch swings along the outer edges of the pool area that are perfect for the late evening. Hot tubs in case you catch a chill from the pool. A lazy river with an endless amount of tubes. And, perhaps the best part, it’s all just steps away from the beach (and the bar). The hotel is clean and nearly every room comes with an iconic view.

Admittedly, we did book this hotel a few weeks before the summertime rush — and I had stayed here in the fall, long after the crowds are gone. I could see how this hotel is overrun with young kids and parents at the peak of summer, but if you play your cards right and if you want a hotel with a bit of everything — that’s within walking distance to several restaurants and even to the pick-up point for the Jolly Sailing excursion — this is the hotel for you.

So, when are you planning a trip to Pensacola? Did I leave something out? Stayed tuned for a follow-up post on Pensacola in just a few. In the meantime, drop me a note below and tell me what you think!

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