How to Spend a Babymoon in Pensacola, Florida

I have found that the trips I enjoy the most are ones where I allow myself to be spontaneous, and I know that’s why our babymoon in Pensacola, FL will always have a special place in my heart, because I never dreamed we would take a babymoon! At the last minute, we decided to take the trip and spend some much needed quality time together soaking up the sunshine. We wanted to intentionally allow ourselves to slow down and celebrate with the same excitement as we had in our hearts with our first baby, and Pensacola felt like just the place to do that.

With it’s pristine beaches and turquoise waters, Pensacola, FL is known to be a hot summer vacay spot, and for good reason! However, we had the opportunity to visit in what would likely be considered the “off season” and it was AMAZING. Because when I think of “babymoon” I think of some (much needed) down time and no rushing around to get from place to place. There was such little wait times for restaurants and our activities, which in the end, was one of our favorite aspects of our Pensacola, FL trip!

I LOVED planning the weekend itinerary for our Pensacola, FL babymoon, it felt like an endless amount of things to do and places to eat, all within such short proximity to each other. We stayed Friday afternoon through Sunday afternoon (middle of November), meaning we had two half days and one full day of exploring this fun beach town.

Within this blog post you will find my personal recommendations for where to eat, where to stay, and what to do during your babymoon to Pensacola, FL. PS – these recs aren’t just for a babymoon, if you’re planning a weekend trip with the main goal being relaxation, this is the perfect guide for you as well!

Be sure to head over to my Instagram and Tiktok to see a full recap of this itinerary complete with location tags and even more pictures and video on each location you’ll see in this post.

The restaurant scene in Pensacola, FL offers the perfect mixture of casual beachside dining, incredible sit-down options with a more formal flare, and everything in between. It’s easy to get caught up in the foodie scene here with all of the fresh seafood and the relaxed ambiance of the restaurants themselves.

After visiting and dining at some amazing local dives, my top four places to eat in Pensacola, FL are: 1) Whiskey Joe’s – a hip beachside dining option located right on the cutest little boardwalk. You can shop at beach stores like Ron Jon Surf Shop right outside the restaurant and enjoy watching all the little boardwalk wildlife after your meal. 2) Angelena’s Ristorante Italiano – If an Italian flare date night is your jam, then this is the restaurant for you! The chef has won Food Network’s Chopped 2x and recently Beat Bobby Flay. If there is one thing to try from this restaurant, it’s the Nola-Style BBQ Shrimp appetizer, hands-down the best shrimp I’ve ever had. 3) Red Fish Blue Fish – another delicious beachside dining option with even more outdoor seating. It’s on the same boardwalk as Whiskey Joe’s, just a little further down. 4) Drift – A must try restaurant in Pensacola, FL and it was our favorite place we ate at during our trip. If you are planning a date night, this is the spot!

Here’s a few more options for some of the best places to eat during your weekend trip to Pensacola, FL:

My pick / Beachside Casual – Whiskey Joe’s
My pick / Date Night – Angelena’s Ristorante Italiano
My pick / Beachside Casual – Red Fish Blue Fish
My pick / Date Night – Drift
Coastal Cuisine – Casino Beach Bar
Family – Water Pig BBQ
Variety – Flounder’s Chowder House
Breakfast – The Dog House
Variety / Food Hall – The Garden at Palafox + Main
Wine Tasting – The Wine Bar on Palafox
Lunch / Tapas – Carmen’s Lunch Bar

Below is an overview itinerary of suggested activities for a weekend trip to Pensacola, FL outlined by day (Friday – Sunday).

FRIDAY ACTIVITIES

Regardless of if you’re choosing Pensacola, Fl for a babymoon, a couples getaway, or a family weekend trip, there is no shortage of both relaxing and exciting things to do! Since this was our babymoon, we came with one goal in mind: relax and spend time together doing things we love. This for us meant equal time exploring and enjoying the beach while also taking advantage of the amazing foodie scene in Pensacola.

Our trip was a weekend trip where we arrived Friday (midday) and departed Sunday (midday), so our itinerary was planned around 2 half days and one full day.

On Friday after our lunch at Whiskey Joe’s, we walked along the little pier that the restaurant sits on. Teeming with little fish and sea birds, we walked the pier and sipped our Whiskey Joe’s to-go lemonades as we watched the little waves and crabs scuttle along the bottom of the ocean. The restaurant is also just steps away from beach shops like Ron Jon Surf Shop, so we made sure to stop in and take a look while we waited for our hotel. There is also the much larger Pensacola boardwalk right across the street with free parking in front, another great way to spend time enjoying the ocean views before ever even checking into the hotel!

Once we were able to check-in to The Hilton Pensacola Beach, the rest of the evening was spent exploring downtown Pensacola and Palafox Street. We took a short 10 minute drive from our hotel and then strolled along famous Palafox Street for Gallery Night and fell in love with the twinkling lights on the palm trees and boutique buildings that line the streets. During Gallery Night (happens once a month), there are tons of vendors along the streets selling everything from home decor to fresh baked goods. And, since it was closer to Christmas time during our visit (Nov 17-19), the holiday activities were just getting started! We were able to take a really fun Grinch themed holiday trolley around town, which older kids would love. And for the littler ones, Santa and Mrs. Clause were in appearance underneath the snow machine!

SATURDAY ACTIVITIES

Saturday was our only full day in Pensacola, but we didn’t feel rushed at all! We decided to start our day by heading back down to Palafox street for breakfast at The Dog House and a stroll around the downtown Pensacola farmer’s market. There are several murals and painted cubes around the market that make the perfect picture backdrops!

After our farmer’s market morning, the beach was calling our name! Our hotel was located right on the beach so we didn’t have to stroll far. The pristine, calm waters were a bit chilly, but perfect for a mid morning stroll to look for shells. It felt like we had the beach all to ourselves during this time, which I’m sure is vastly different than during those peak summer months!

After our beach walk, we headed to lunch right across the street to Red Fish Blue Fish to fuel up for our most anticipated activity of the trip: exploring Gulf Islands National Park! I knew this was a must do for us as two people who love exploring outdoors and history. The drive into the park felt unreal, almost untouched with the rolling sand dunes and grasses with views of the ocean on both sides.

Aside from driving along the long main road into the park and taking in its beautiful scenery, we wanted to take a few hours to explore Fort Pickens: a civil war era fort located within the National Park that is free entry to the public to explore. We opted for the free tour which just happed to be starting as well arrived, and I’m so glad we did! The guided tour didn’t take long, but my husband loved knowing the details behind why things were build the way they were. After the tour, we walked through the fort again and took all the time we wanted exploring all the different rooms. In my opinion, this is one of the coolest things you can do in Pensacola with or without kids! It’s free, it’s absolutely incredible to see, and it makes for some amazing pictures.

SUNDAY ACTIVITIES

Our last half day was spent exploring another free activity in Pensacola, FL: The National Naval Aviation Museum. Much like Fort Pickens, I couldn’t believe that the museum was free! The attention to detail is unmatched here and can be appreciated by anyone at any age. With over 150 restored aircrafts as far as the eye can see, we spent a few hours walking around getting up close and personal with over 4,000 Navy, Marine Corps and Coast Guard artifacts from our nation’s history.

On our way out of the museum grounds, we stopped at both the Pensacola lighthouse and another fort: Fort Barrancas. The lighthouse was so pretty sitting back among the natural flora and fauna. Although I was feeling too “pregnant” at the time to climb the lighthouse, just seeing it in person was amazing. Fort Barracas was much smaller in size and scale than Fort Pickens, but still incredible to see. This would be a great place to stop and explore with kids before heading to the airport!

Pensacola, FL is known for their beaches, but another thing they should be known for is their beautiful lodging options! It doesn’t matter if you’re hoping for an Airbnb, hotel, or resort, Pensacola has them all! We stayed at The Hilton Pensacola Beach and I would stay here 100 times over we loved it that much! With on site pools and a hot tub, easy beach access and ocean front views, the option for breakfast, a Starbucks in the lobby, rentable cabanas, and gorgeous rooms, we will definitely be coming back here as a family.

All images taken at The Hilton Pensacola Beach

If you’re thinking of planning a Babymoon, or any trip to Pensacola, FL then be sure to head over to my Instagram and check out the highlight “Pensacola, FL” for a full itinerary re-cap with even more images and videos!

Please note: All content and media within this blog post is owned by Indiana Hannah and cannot be used without permission from said owner. Legal repercussions apply and will be taken for any content and/or media used without permission from said owner. This blog post is part of a paid promotion (AD) with Pensacola, FL.