Road Trip from Chicago to Pensacola and Florida panhandle

Why Florida Panhandle or Pensacola?
Pristine white-sand beaches, quaint towns, emerald waters and much fewer crowds than the typical South Florida touristy spots.

The quartz, rich white sand of Emerald Coast beaches

How to Plan your road trip?

• It is a 14-hour drive, so plan your pit stop. We stayed over Nashville while heading to Florida but cranked through in a single day while coming back.

• Plan your activities – Here are some ideas:
Bayou Marcus Birding Trail, Fort Pickens, Scenic Highway 30A, Tarkiln Bayou Trail, Okaloosa Island Fishing Pier, Pensacola Naval Air Station – home of the Blue Angels, Crabs, Northern Terminus of Florida National Scenic Trail, Fort Morgan.

Water sports should definitely be on the menu as well, but it was too nippy for our December trip.

Bayou Marcus Birding Trail

The 3-mile out-and-back birding trail was a peach of a hike, worth the stellar views.

The entire trail is perched on the boardwalk

The temps were unusually lower for Pensacola, in the 30s!

All iced up and nowhere to go

After braving through the hike, the lengthy shadows were a cue for us to wind up and head back.


Q. What do you need after a hike through the chilly temps?
A. Pensacola’s best coffee joint – Coffee Guy Café.

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Santa Rosa Island

The next day, we ventured into Santa Rosa, a 50-mile island stretching from Pensacola to Destin.

We infiltrated the Scenic Highway 30A from the Pensacola side, stopping at a random beach access point as our first foray in to the gulf.


A short boardwalk led to a sugar-white sand beach.

And an hour of beachcombing and sun-kissed photography ensued.

We continued to venture east on the scenic 30A highway, next stop being the Okaloosa pier.

Okaloosa Island Pier

We paid a nominal fee to get to the famed Okaloosa Island Pier and timed our visit to hit the sunset. The 1200-ft long pier is renowned for sunrise and sunsets and even wild dolphins.

A gentle stroll led us to the edge of the pier.

There was plenty of wildlife diversity on offer.

This one was almost posing at the pier, unruffled by the people around.

And it was not the only one posing for the shutterbugs.

and there were ones perky enough for a quick bite from the hooman.

The pier is so far into the gulf that you can almost feel the free and wild sea ..

And there it was..

Glorious Florida Sunset #1

We remained till the last speck of the fizzling daylight..

Fort Pickens – Gulf Islands National Seashore

Rise and shine and hit the road, simple plans are the best!

We hit the Scenic Highway 30A again and aimed at the western banks of Santa Rosa Island.

An unexpected solitude greeted us when we hit the Fort Pickens area, visiting Pensacola during winter has its benefits.

The fort is managed by NPS and well-maintained. We watched the movie chronicling the history behind civil war era fort in the visitor center before heading to the fort.

The fort has a few battery structures, cannons and other “fortsy” things, definitely worth the visit.

Florida Trail – National Scenic Trail

When at the fort, don’t miss the trailhead leading to Northern terminus of Florida Trail, 1500+ mile long path running from here to Big Cypress National Preserve and one of 11 National Scenic Trails.


#lottery – we bumped into famed wildlife photographer Jim Wright aka @stonekettle with his mammoth gear and got a few wildlife photography tips and stories out of him.


We ventured about a mile in and headed back after hitting a bridge.


Almost missed this northern terminus plaque.

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Neatly tucked in under the first bridge from Fort Pickens side

Sunset at Fort Pickens Beach

While driving out of Fort Pickens, we decided to raid the beach at its eastern trip and it turned out great.

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We had the beach all to ourselves

The inland lake leading up to the beach looked unearthly.


Thanks to the retreat, wildlife was quite affable.


And while we got busy with the photo-ops and beach frolics, there it was..

Glorious Florida Sunset #2

Perdido Bay Trail at Tarkiln Bayou State Park

Home to several endangered plants, including carnivorous pitcher plants with their famed passive pitfall trap, Tarkiln Bayou State Park’s trails offer diversities for both flora and fauna, and plenty of solitude too.

The trail is a mix of boardwalk and natural turf. Some parts were still soggy.


The anticipation to see the pitcher plants was rising…

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But all we got was dried up pitcher plants and bunch of disappointed kids with their pessimistic commentary.


And just when we were about to give up..

Any takers for dipping the hand?

Tip – Go for the Perdido Bay Trail to get the live pitcher plants, if you are going in the cold season.

Fort Morgan

We made an impromptu decision to head west on the Florida panhandle, to explore the gulf shores on the Alabama side and elected Fort Morgan as our terminus.

#MildlyInteresting – 26 mile speed limit on our way to Fort Morgan

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The visitor center and the fort felt a little smaller as compared to Fort Pickens, but well maintained.


A burly cannon greets the visitors at the fort.


#OddStairsAlert – we saw one of the steepest stairs


Some parts of the fort were a little grubby.


Fort Morgan Beach

We rambled over to the beach around the fort, just in time for the sunset, again.

#MildlyInteresting – A seashell lined trail


Surprise #1 during beach combing – Jellyfish!


Surprise #2 – A pod of wild dolphins


And just like that ..

Glorious Florida Sunset #3

Another rousing view of the mandarin ball.

Glorious Florida Sunset #3

Naval Air Station – Home of the Blue Angels

We had the fortune to get to Naval Air Station, headquarters for the famed Blue Angels, the heroes of Chicago Air Show and one the best flight demonstration squadron in the nation.


You get to see the aircrafts of all shapes, sizes from a number of different nations..


And of course, there are actual Blue Angels zeppelins.

Crabs and Pensacola Beach

We decided to have our last meal at the coveted Crabs on the Beach restaurant, which overlooks the gulf. Flounders is another great choice, both owned by the same entity.

The serene gulf view from the Crabs

And there goes the last hurrah on Florida sunsets.


Wait, one more last look..

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That’s it. We really brought out the opacarophile in us by gazing sunsets 4-days in a row.

So long, Florida…

Please leave some feedback in the comments section on your thoughts on this post.

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