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Exploring Pensacola Itinerary: In Search of the Best Beach

Updated: Jan 14

Our Summer 2022 Panhandle Family Vacation - The Road Trip expedition we needed!

Sitting on the Pensacola Beach Wall

If you are traveling to the Panhandle, this will help you to make an itinerary to fit your needs.

If you are not and you just want to share our journey, welcome!


Enjoy this 3-day Itinerary of what to do in the Panhandle. We spent 5 days in the area, the first arriving/ shopping/ getting settled, and the last packing it up. This was a seven hour drive from our home in Brevard County, so I didn't over plan the arrival and departing days. This is a “budget” adventure, but it was what we needed it to be. I planned for the expenses I felt were reasonable and while I will give tips to embellish, and some to make it even more affordable, I LOVED this entire trip!

Henderson Beach State Park

Living in a tourist hotspot like Florida keeps life interesting, this is the place everyone comes to visit. I admit, we get sucked into the hype from time to time. Since we’ve been in Florida now long enough, we’ve been trying to expand our world and see things we’ve left out of the rotation. Theme parks, beaches, springs. Botanical Gardens, and the main city spots have all been checked off. When we are driving north, we are typically headed out. This time we decided to explore the Florida Panhandle and see what was happening up in that area. Okay, I saw someone claimed the Panhandle had the “best beaches”, and I decided to take this into serious consideration.


We have been to some of the most amazing beaches. We are fortunate enough to live by the Atlantic Ocean in all her glory and we do frequent the beach often. I’ve been saying for years the further south you go, the better the beaches get. But the thought that the best beaches are located north, had me totally perplexed. I had no response as we have never explored that area and it was just about to drive me crazy when I decided to book a trip and see a place we’ve never been before. So, the question is... Did their beaches win?🌊🌊🌊🌊🌊


When you visit an area specifically for the beach experience, and the weather forecast calls for rain and clouds every day it could easily put a damper on your spirits. Not us! We went and bought umbrellas and decided to roll with it. Now fortunately, it seemed like wherever we were it wasn’t really raining, we just had rainy drives to get there. If you want some ideas for how to handle rain on your vacation, check out this link. - 8 Strategies to keep your vacation fun despite the weather.

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My original version of this trip was a beach front house where we could walk down to the Gulf and play on the shore. There are lots of those available with VRBO and Airbnb. But then I felt I’d be at one beach instead of seeing ALL the beaches.


There are some amazing luxury options if this is what you’re looking for, however I determined pretty quickly it was neither in my price range nor some thing that really resonated with all of the things I wanted to do. Any beach we stayed at was going to be a drive from every other place. I also looked at some condos that were available for less money but I still wasn’t quite finding what I was looking for.


I would not have expected to have found the perfect home to rent in Milton/Baghdad Florida. We found a Historic home that ended up the perfect homebase for our family. Why was it perfect? The porch. Sitting on the wraparound wooden boards overlooking the Blackwater Bay was the best way to start my day with my morning cup of tea in the rocking chair watching the sun come up. The house comes with a canoe and two kayaks, and this was my absolute vision. To just be able to have that water view and little bit of peace mixed with serenity was the answer to my searching. Link here to the Waterfront Historic Bruce/Ollinger Antebellum Home we stayed at in Milton Florida. Part of a vacation to me is really doing something different.

Pulling up to the chained driveway in the middle of no where was spooky at first. We are not used to this at all!! We live in a neighborhood with lots of people and neighbors. That was part of the beauty of this experience. Sheer blinds on the windows? That felt a bit too vulnerable. But by the next morning we appreciated the location. The trees, birds, and over an acre of land provided us with a space to clear our busy minds. A highschooler with straight A's, college student in Aerospace Engineering, new mom learning to manage the expectations of mother hood, and me; I don't have an easy way to describe myself except to say I needed a mental break is an understatement. The baby was just happy to be with her favorite people, God gave us a happy little girl thankfully.


The hope of this trip was definitely a reset. Take a break from reality, remember to appreciate those who you cherish most, and invest in what you believe in. I wanted some history (I always want some history lol), some nature, and a new place to explore. This was all of that!

A little chicken noodle soup in the rain is ALWAYS a good idea. Yes I'm wearing a bathing suit even though it's raining, I got plans for sun! (The sun did come out) and man I love spending time with these guys. Happy Momma ❤


Our Itinerary/ Journal:

Day 1: I sat out on the porch before anyone was up enjoying my tea and listening to the thunder roll in from miles away. Made and ate a big breakfast, then packed up some lunch subs for the cooler. It was raining by then, so we ran to Big Lots and grabbed some roomy cool umbrellas to walk around with. However, by the time we got there we didn’t need them. The sky stayed pretty gray but on this warm humid day we got to enjoy ourselves. I knew the museums closed at 4 so I didn’t want to miss out, we were in route by 1:00.


Downtown Pensacola- so much to take in. History is there waiting to remember how the tale of 5 Flags happened. Exploring fun!! $10.00 per person for the museum circuit and show your pass to enter multiple sites.


Admission provides entrance to the Pensacola Museum of Art, the Pensacola Museum of History, the Pensacola Children's Museum, and Historic Pensacola Village. Buy tickets online and if you or someone in the family receive SNAP or EBT (food stamps) up to 4 people get in for free. If you use

Bank of America, their museum pass will also offer free entry.

When planning downtown, get there, find a place to park and expect to walk around the streets going in and out of several places. This is a very nice place to walk around and there’s a small nature playground behind the city square. A bigger park on the other side would be a nice place to walk or play. Your first museum will provide a map of all the historic sites in the area.


We visited:

1. The Pensacola Museum of History

2. Pensacola Museum of Art

3. Museum of Industry

And the Historic Village


We missed the tour which meets at 11:00 at the Lear/Rocheblave House, 1:00 at Old Christ Church, and 2:30 at the Well in Historic Pensacola Village. We decided to explore on our own, with a baby it’s sometimes easier to do that. She ended up sleeping, but she sang pretty loudly for about 30 minutes first 😁


The Museum of History explains the significance of the area, and the forts. Learning about Native American culture is always a favorite topic and this touched that subject while following the time line through present day. Each floor offers different exhibits. My kids especially enjoyed the black history floor and were quick to point out "we learned about that!" and "we never learned that".

The Trader Joe's collection - on the 2nd floor, holds lots of great memorabilia collected by a bar owner who moved from NY to Pensacola bringing his bank of items with him and continuing to grow his stock pile. As Pensacola is home of the Blue Angels, there is a lot of flight history found here. As Top Gun 2 is currently in movies this was a little more exciting. I could see pairing a day here with some movie nights working well!


The Blue Angels practice out of Pensacola, and if you are lucky you can be there to catch them fly! The week we were there was their week off - (Before the 4th of July). Officially known as the U.S. Navy Flight Demonstration Squadron, Pensacola Beach hosts a Blue Angels show every July while the Blue Angels host their last show of the season over Naval Air Station Pensacola every November. Check the schedules here: https://www.visitpensacola.com/things-to-do/blue-angels/air-show


This adventure ties into our next stop: Fort Pickins which is where they held Geronimo, the Apache Medicine Man when they captured him. A year later, his family joined him here. They moved them due to fear of yellow pox, but this gave us enough reason to drive down to Gulf Shores.

Driving over to Fort Pickins is very scenic! Entering the National Park we paid with our America the Beautiful pass I had purchased in the Everglades last summer. It's a few miles from the gate to the fort, and we all wanted to get out and see the water. Again the sky was threatening rain so we decided to do the fort first just in case. Driving on a narrow strip of land surrounded by sand dunes and water felt healing! We rolled down the windows and enjoyed the drive. Pictures don't do it justice - wow. Fresh air and beautiful water surrounded us. The speed limit through is 25 mph due to nesting birds and to protect the wild life. There are speed bumps along the way to help maintain.


Fort Pickins – We pulled into the parking lot, used the rest rooms, and walked out onto the board walk there, to see the beautiful Gulf. It’s like they knew we needed to see the water first. Then we were ready to explore the fort! Rooms to rooms and doorways leading to doorways, the arched entries are so inviting. How fun just wandering and imagining how it must have been. If you have ever been to Saint Augustine, this is way cooler because rather than setting up exhibits in the rooms (which is helpful for understanding) this is just the remains. No writing to explain what happened in each room, no statues or documenting – just pure wandering and experiencing in your own mind. We spent a little over an hour here, taking pictures of the viewpoints, enjoying the architecture and using our imaginations vividly. We learned at the Museum of Industry that the government purchased millions of bricks from the brickmakers, I could see why once we wandered around here. I will say the site was well made and fun to explore.


Gulf Shores - On the curvy ride back we stopped at a beach access point to finally put our feet in the magnificent gulf and see how it felt. The sand here is pure soft white sand. Sometimes you can’t see the water from the parking lot, there’s so much sand! There was a little ledge created by the tide which was strong enough to sit on. The water was warm, clear and huge. It doesn’t feel like the Ocean, but you can’t see the sides or the end of it making the grandeur that much more powerful. The tide itself feels less intense, but it is consistent and powerful at the same time. We played there in the shallow waters under a rainbow for a little bit. The sky looked like rain, and we knew dinner in Pensacola was the next stop. It never did rain but after a quick dip we were back in the car on our way to the pier. ** Possibly because of the gray sky we didn’t get the full effect of the Emerald Coast on this day, but that comes tomorrow. Our first impression of the water was a good one. It's massive and beautiful. The water is much clearer than I expected, walking in I could still see my feet until I was more than waste deep.


Dinner @ Pensacola - There are lots of places along the Pensacola strip to eat.

We chose Crabs on the Beach this was an excellent choice. We sat up top, outside on the deck overlooking the water, beach, and some horseshoe crab races beneath us. Best seats in the house are along that back rail I believe. We didn’t know what to order since there were so many great options. I ordered a pina colada as the vibe was so beachy and even upsized it to the souvenir glass – it was that good. The baby learned to color (we all helped her) and service was good, but slow. I was okay with that I was enjoying every moment of being in the present moment with great company, my children. Take all the time in the world, it's all good in the moment.


All of the food was good, I spent more than I originally budgeted but decided it was worth every penny as we all enjoyed our food, had leftovers and the view was amazing.



Our next stop was the pier, we could see it there waiting for us and when we got to the entry way it was closed. Closed??!! But there were just people on there! I asked what time it closed. 7:40. It was 7:43. Remember when I said "take all the time in the world", could I have like 5 minutes back? lol...just kidding.


We settled for walking and pictures under the pier, and I got over the disappointment knowing I had two more piers on our itinerary still waiting for us.


We did enjoy the vibe of this beach, we put our feet in the water but the cloudy sky was gray and while the water was warm, we decided tomorrow would be our real beach day. But the Pensacola Beach had great soft sand, and nice waves rolling in. There were lots of groups of people here playing ball or swaying in their hammocks. The vibe here was uplifting and fun. People were all around enjoying the beach life.


Quality time with quality people = quality memories!

Day 2:

Started with a rainy thundery morning making it great to watch turtles on the property! The reason we picked a secluded house in the middle of nowhere was for mornings like this. If you’ve never been on a covered porch while it’s raining, please add it to your bucket list. This reminded me of my grandmother’s house growing up. I felt proud to offer this bit of peace not just to myself but to my kids, and sweet grandbaby who is 10 months old. Nasali practiced crawling all around and took a couple steps. We got up and moving at our own less hurried pace, I made a big breakfast and we packed lunches for the cooler. Once we got out the weather changed as we neared the beach!

The first ones up in the morning got to enjoy the view the most. I bought a big blanket on the back porch with all of her toys and we just played as the rain fell.

Stops for today:

1. Henderson Beach State Park. Blue skies and big white clouds were waiting for us today! The water is really green, it’s called the Emerald Coast for good reason. There are algae floating in the water. It’s technically chlorophyll emanating from plankton or algae, but it is oddly neon green. It’s weird. Took a while to adjust. The color of the water is breathtaking and beautiful no doubt, still the green stuff floating in the water feels like felt and gets in your hair, pockets and everywhere. I was hoping it was the good for you at least. Unlike the red tide algae blooms, it is harmless. We packed a good cooler and awesome beach bag of goodies, I planned this to be our great beach day! We stayed a couple hours, under the hot sun and there wasn’t much shade. We played some beach ball and the boys body surfed for a good while. We may have lasted longer with a good umbrella or shade pavilion. Loved the colors of the water, the shades of green, turquoise and blue made it very serene. We knew we had multiple stops planned and wanted to make the most of our day. Okay, packing it back up!

DJ represents Palm Bay better than anyone ♥


2. The Destin Boardwalk/ Harborwalk Village - not to be confused with the Fort Walton Pier (which was what we wanted to see). A bit of a tourist trap, $10 to park, and maybe fun for younger kids like 10. We walked, we got some very expensive ice cream and shakes that were not worth the $$. Cool things to do if you want to zip line, jet ski, dolphin cruise, or play carnival games. We left and headed out ready for more. If you want to rock climb or play the street games, I strongly recommend this stop! We were more in the market for a pier, and this was not it.

If you raise children you like spending time with, you will always enjoy the trips, start young, teaching them how to travel!


3. Walton Beach is the name of a town. If you want to go to the beach, it’s called Okaloosa Island. Google did us dirty on this navigation and took us right past the Walton Beach Pier I was hoping to stop at as well, taking me right to Fort Walton City Hall. This was not on my bucket list. Driving through Destin I realized this is a fun place for families, especially younger families with kids. We passed the water park and some great adventure stops – but really we were excited for the beach we heard was amazing. We had a mission! We made it over to Okaloosa Island and It is pretty. And green. We stopped and played a little, and take in the sights. Still searching for the “best beach”. We were hungry and headed over to Pensacola for dinner. I will say the sand is soft, and it doesn't get hot! It feels so good on your feet no matter what the weather is doing.

Uncle DJ and our beach baby!

Wing Stop – My son really wanted to try Wing Stop, which was past our exit towards North Pensacola. I had planned to eat at McGuire's, which was already behind us us or Lulu’s which was too far West at this point, so we opted for some wings, which were delicious!


Day 3: Another rainy day but the morning was temporarily clear so we adapted our plans to make the most of it.

Play time! Watching the rain roll in

Morning tea with Nasali on the porch ~~ Peace & Love ~~ Being present!


1.Kayaked in the Blackwater Bay before the rain rolled in. This was my daughter’s first time kayaking so it was a great way to learn in calm water. The Bay was tranquil and beautiful. I recommend enjoying the water while in this area, there are many places to kayak, we took advantage of the house having them available.


Listening to the thunder roll in from miles away, an hour before the rain even makes it to your door is pretty cool. We watched the rain approach across the Bay from the porch and time just stopped. Real family time, talking, laughing and relaxing just happened. I bought out some snacks and we just sat and watched the rain fall down. The rain covered the whole area, and we decided to go with the flow so we nestled and snuggled in to watch Stranger Things, who had a season finale on and enjoy all our left overs.

Just go! Explore more ~ Live more ~ Wander ~ Enjoy every minute


Next: Got ready and head to Navarre Pier. This is the closest beach to Milton!

2. Navarre Pier- Free parking, $1 per person to walk out on the pier. We finally made it on a pier, and this was the most amazing quarter mile walk out and back! WOWOWOWOWOWOWOW!!!

We saw dolphins playing, fisherman pulling up a catch, and watched all the activities below as surfers, paddle boarding, and swimming was all the fun! After dolphin watching until my heart was content, we went down in the water and jumped in. We quickly discovered this is the actual best beach. Clear water, warm beautiful waves and calm, soft sand. There is still a green tint, but much less chlorophyll floating, and waste deep I could still see my feet. Our sweet baby was learning to swim and families all around us played in the warm amazing gulf. Finally!!

The end of the Pier looking back to shore

More dolphin watching 💙🐬as a big dolphin chased a fish to shore for dinner, and everyone screamed yelling “shark shark!” I happily moved closer videoing the entire event.

The shaded showers here are great. Pavilions offer shade and picnic benches. There is a restaurant right before the crosswalk over to the beach which serves drinks and grilled items. Heaven on earth. We found it.


We cleaned up here and headed to eat.

Delicious dinner! Love the atmosphere

Dinner at the Seville Quarter, ate at Khon's

The kindest staff was friendly and attentive. We enjoyed the street curb dining and enjoyed people watching. Our food was tasty but there was something a bit odd - my daughter and I got huge bowls with more food than we could finish. My sons ate all their food and were still hungry for more. The portions were inconsistent. But we were totally satisfied after walking down the street for dessert and finding the best gelato.



This was a Saturday night and parking was scarce, so I opted for a paid parking lot which was easy and inexpensive as far as larking can go. Under $7/ 2 hours. You can text a number provided in the lot to get the link or use the QR graphic in the lot. Premier Parking was one of the easier paid parking experiences I’ve had. And they texted me when I had 15 minutes left with the option to add more time if I needed to. I didn’t 😊


We headed back to the house to organize and wash our wet clothes towels and blankets, knowing check out was 10 am the following morning. Our trip was coming to a close.


For your consideration:

Scenic Highway 30A

Taking the beach view... this 24 mile strip of road that follows the coast line is BEAUTIFUL at every inch! If you drive along this route be prepared for rolling sand dunes, beach grass and Gulf coast pictures, many piers, and beautiful architecture. You will really see the colors pop with the emerald water against the white crystal sand. There are many places to eat or drink or souvenir shop along the way. I enjoyed many walks by myself and took a ton of pictures in December, it was amazing! While we visited in the summer, this stretch which was originally on my to do list was SO BACKED UP it was not realistic to experience. I returned later on a work trip in December and was able to drive along making many stops to see all of the beauty in a completely different way. It is almost hard to appreciate it all when it is full summer season.


Saint Andrew's State Park

See the Gulf of Mexico on one side and St. Andrews Bay on the other. The rock jetty creates a cove perfect for snorkeling, especially for the younger kids. Swimming, snorkeling, surfing, fishing, and picnicking are happening here in abundance. I watched dolphins playing in the water and ate my picnic in some of their benches overlooking the water. This park is a great place to end your 30A scenic route in Panama City. There are a few hiking trails if you are just looking to get out and stretch your legs, and even camping if that is more your speed. As I was leaving the clouds were rolling in bringing some rain. How fitting I thought since my summer trip here was also surrounded by the rain clouds!


A few other favorites

I planned more than we had time to accomplish on this adventure! However I returned for work to the area and was able to enjoy my left over list with my new coworkers! Staying in Fort Walton was a joy, my room was the Tru by Hilton, and some of our work party stayed at the Residence Inn. The Residence in was much more spacious. I'd only recommend Tru by Hilton if you are a single person staying temporarily not spending much time in the room. It was a small room, although clean and great free breakfast options. What I didn't like was the closet rack is open and hangs above the small fridge. So if you need counter space your clothes are hanging over it.


Fort Walton Pier AKA the Island Pier, originally known as the Okaloosa Island Fishing Pier (no wonder we couldn't find it) which we originally missed on the first trip I was happy to finally circle back to. After a long day in a training room I walked the 1262 feet or quarter mile at sunset, watching fisherman, pelicans, and surfers below enjoying every moment of the fresh air. There is an octagon at the end of the pier with slatted metal grates for easy views and that 360 is amazing. In December the colors of the sky contrasting with the sunset was stunning. The surfers below must have been cold but they were fun to watch. And a golden lab who walked with his owner seemed happy to be there while the pelicans growled at him from the light posts as he passed.

The air and scene were exactly what I needed to mentally reset.


We enjoyed Lulus of Destin which even in December was a hot spot! Live music, great Christmas decor and a great menu made our visit memorable. However, it was unusually cold in Florida and they had the big bay windows closed. I still recommend this as a stop, however the view and outdoor seating is one of the highlights!

Locals highly recommended The Shack in Fort Walton Beach. We ate here and were greatly pleased with all of our food. This was almost right across the street from our Hotel being very convenient. Another fun upbeat environment, with music playing and a view overlooking the marina and dock. We took some pictures outside on the dock before going in and being seated. They have a turtle feeder there and a few hungry turtles that wait for people to come down and splurge on them.


Next trip we will eat at McGuires Irish Pub which was on our list both times, and even the waiter from Lulu's recommended their ice cream!


This trip was all about the beach quality. But how to judge the beach….

Sombrero Beach flashback!

What makes a good beach?

Water clarity, sand quality, smooth bottom with easy walking for the feet, clean, warm water, scenery… these are the considerations we use when creating our list of favorites and this is our current order of best beaches we’ve been to in Florida.

#1. Jupiter

#2. Zach Taylor

#3. Coconut Point

#4. Sebastian Inlet

#5. Sombrero Beach


The Beaches we visited while in the Panhandle were:

Navarre

Gulf shores

Pensacola

Henderson state park

Okaloosa Island beaches


And we’ve determined our new favorite beach in the Florida is: Navarre Beach!

Navarre used to have the catch phrase of “America’s best kept secret” and is known as "Florida's Most Relaxing Place". For the record, it is also the closest beach access to Milton, where our Airbnb was located. Located on the Santa Rosa Barrier Island that extends from Pensacola Beach through Gulf Islands National Seashore, Navarre Beach is conveniently nestled between Pensacola Beach and Destin with it's own character and vibe. Why is the sand so pure? Sugar white soft sand here is the outcome of finely ground quartz that was washed down from the Appalachian Mountains. While most of the sand in the Panhandle was exceptional, here there is a little something special creating a beautiful place. Sand dunes line most of the coast line, and boardwalks over from parking lot to beach are plentiful. The pier is great too, not too touristy, there is a gift shop with tons of souvenirs and ice cream where you buy your tickets out to the pier.

There are 3 man-made reefs just offshore close to the pier. The reefs are located to the east of the pier and they make it easy for you to find them with posted signs. Click here for a map of the reef locations. A resident octopus can often be seen here. Scuba diving, snorkeling and kayaking are very popular because of this. The shallow waters stretch from across the shore making it easy to swim to the reefs. These reefs attract fish, coral, octopus, and sea turtles! It is the best way to see the sea turtles in their natural habitat during sea turtle season.


Our 3 Day Itinerary:

Day 1 - 1. The Pensacola Museum of History

2. Pensacola Museum of Art

3. Museum of Industry/ and the Historic Village

4. Drove to Fort Pickins (Used America the Beautiful pass - click here for info)

5. Gulf Shores

6. Pensacola Strip - Ate at Crabs on the Beach

7. Pensacola Pier


Day 2 - 1. Henderson Beach State Park

2. Destin Bay Front Board Walk

3. Fort Walton / Okaloosa Island Beach

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