4 days in pensacola, Florida

Written By Jessica Vanpoperinghe

Welcome to Pensacola! A coastal gem where the sand is soft, the sunsets are golden, and dolphins make daily cameos!!!

I traveled with my good friend and assistant Jess, and it was actually our first time taking a trip just the two of us. Safe to say… it was marvelous. From beachside laughs to spontaneous dance breaks and deep convos over fish tacos, this little girls' getaway is one I’ll always treasure.

This place blends laid-back beach town energy with a side of military history (hello, Blue Angels flyovers) and just enough quirky charm to keep things interesting. Whether you're here for sunrise walks, seafood feasts, or dolphin watching boat tours, this four-day itinerary is packed with moments you’ll remember, and probably post about later!

*This trip was generously sponsored by Visit Pensacola, who covered our flights and hotel stay! 

Let’s dive in. 🐬

DAY 1

DAY 2

DAY 3

DAY 4

———————————

Day 1: Flights, Ocean views, & Piña coladas

We flew into Pensacola International Airport (PNS) via Frontier Airlines which was blissfully painless. We grabbed our rental car, cruised over the bridge to the beach, and checked into the Fairfield by Marriott Inn & Suites Pensacola Beach. We had an incredible ocean view, and beds so comfy I briefly considered canceling evening plans in favor of a post-travel nap. 

Sunset: Before we even unpacked, we opened up our sliding door and watched the sunset from our hotel balcony. 

Dinner: It was 3-minute drive (or 9-minute walk) to Flounder’s Chowder House where the piña coladas were INCREDIBLY creamy! It’s an easygoing, waterfront spot with outdoor patios, live-music, and a family-friendly scene.

Day 2: Farmer’s market, fighter jets, & dinner in bed

Morning: We started our day wandering Palafox Market, the cutest open-air farmers market nestled between MLK Jr. Plaza and Plaza Ferdinand (open Saturdays from 9am–2pm). It’s packed with local produce, handmade art, jewelry, fresh flowers, baked goods, and the kind of vibey live music that makes you want to buy honey you definitely don’t need (but can’t seem to live without). We sipped on iced coffee, tried a few samples (ok, a lot), and picked up a couple of souvenirs.

Lunch: We walked over to Jaco's Bayfront Bar & Grille, right on the water, and had the most amazing grouper sandwiches!

Afternoon: After lunch, we made our way to the National Naval Aviation Museum, which was even more impressive than we expected. It’s huge, free to enter, and packed with historic aircraft suspended from the ceiling, interactive exhibits, and old-school flight simulators. Perfect for airplane nerds and people who just want to be indoors for a while (hi, that was us). Once we’d had our fill of jets and WWII history, we went back to the hotel and grabbed poolside drinks at Fish Heads.

Dinner: We were craving a cozy night in, so we ordered poke bowls for delivery (zero regrets) and had an early night in with our fluffy hotel robes, a little trash TV, and the sound of waves outside our window. Dream evening.

Day 3: Sunrise safari, LAzy river, & dolphins at dusk

Morning: We ran down to the beach for sunrise and sent off my drone above the water. We spotted black tip sharks, dolphins, manta rays, and jellyfish! The water was calm and glassy, the sky was pastel perfection, and we just stood there in awe, pointing and yelling “DID YOU SEE THAT?!” over and over.

Lunch:
After a few lazy laps in the Fairfield by Marriott Inn & Suites Pensacola Beach’s lazy river (which, by the way, is an elite pre-lunch activity), we walked a few minutes down the sand to Crabs on the Beach. Shocking twist: the crab was DELICIOUS. Tender and buttery! We also split the beer-battered fish, which was also amazing! An iconic beachside lunch.

Evening:We ended the day with a sunset dolphin cruise with Frisky Mermaid Dolphin Cruises, and it honestly felt like a scene from a movie. As the sun started to dip, we cruised through the bay and spotted multiple pods of dolphins, some of them swimming right alongside the boat. A few even leapt completely out of the water, and everyone onboard lost their minds. Just when we thought it couldn’t get better, the Blue Angels flew overhead on their way home from practice.

Dinner: We crossed the street from the dock and went straight to Bounce Beach Pensacola. Go for seafood + shareables with a craft cocktail, and book ahead on weekends if you want prime sunset seating! 

Day 4: easy hike, downtown coffee, & a tough goodbye

Morning: We caught sunrise again because we’re addicted, a quick pool and lazy river reset, then complimentary hotel breakfast (our daily fave) before heading to Tarkiln Bayou Preserve State Park for an easy, boardwalk-and-pine-forest nature walk. We cooled off after with a downtown coffee at Fosko.

Lunch:
We soaked up every last bit of sunshine with a relaxed meal at Red Fish Blue Fish, a casual waterfront spot just a short walk or drive from the hotel. With its colorful picnic tables, open-air layout, and awesome Gulf views, it was the perfect place to wind down. 

Afternoon:
 Eventually, reality knocked. We packed up our sandy bags, took one final deep breath of that salty ocean air, and said goodbye to the Gulf. Then it was off to Pensacola International Airport (PNS) for our evening flights home.

FINAL THOUGHTS

I thought I needed constant adventure. Turns out I just needed dolphins, fried seafood, and a hotel with a lazy river. Pensacola, you sneaky little slice of paradise, you got me good.

Until next time 🫶✨

What I Packed for pensacola

Here’s everything I brought that actually earned its space:

👕 Tops:

  • Breezy tanks/tees – easy for beach to dinner

  • 3 cropped tanks — cute + mix-and-match

  • 1 bathing suit cover up dress - to take you straight to lunch

  • 3 bikinis — one sporty, one cute, one backup

  • Leather jacket — for cooler evenings/AC blasts

👖 Bottoms:

  • Prana Stretch Zion Cargo Pants – Durable and full of pockets

  • 3 floral maxi skirts — use as cover ups or cute out-and-about options

  • Levi’s Cinch Baggy Jeans – Perfect for dinners

👟 Footwear:

  • Hoka Clifton L Athletics Sneakers – downtown wandering and dinners

  • Flip-flops — for the beach and pool

🎒 Misc:

  • Reef-safe sunscreen + SPF lip balm – reapply constantly

  • Cute beach hat 

  • sunglasses

  • Packable beach towel 

  • External battery 

  • Laptop, drone, tripod — content toolkit

  • Dramamine — just as a precaution for our boat tour!

How much did we spend in total?

This was a 4-day trip with from Denver to Pensacola in late August!

✈️ Flights: ~$220 total round trip per person (DEN→ PNS) *hosted

🚗 Car Rental: $166 total 

🛏️ Accommodations: ~$660 total (3 nights) *hosted

🍽️ Food & Drink: $265 per person (we ate out for every meal)

🎟️ Activities + Extras: $90 per person (boat tour, market souvenirs, parking, etc.)

💰 Total: ~$988 per person

Best time to visit Sedona

The best time to visit is April–May or September–October! Warm water, fewer crowds than peak summer, and dreamy sunsets. Summer is fun but hot and busy; expect pop-up storms and lively beach days.

Things you should know

 🚩 Beach flags matter. Respect surf and rip current warnings.


☀️ It’s sunny and humid. Hydrate, reapply sunscreen, and bring shade.


🅿️ Beach parking fills on weekends, arrive early or plan to walk a bit. OR stay at a beachfront hotel!


🍹 Casual rules. Throw a dress or button-down over your swimsuit and you’re dinner-ready.


🐚 Wildlife is abundant! Watch your step and shuffle in shallow water.


🎟️ Boat tours can sell out quickly. Book ahead if you can.

hope this helped plan your Pensacola trip!

Chasing views, dodging panic attacks, and thriving anyway - Jessy

Jessica Vanpoperinghe
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