For our anniversary, we decided on a week-long escape to southern Alabama, splitting our time between the historic port city of Mobile and the sandy beaches of Gulf Shores. We love a trip balanced with history, local brews, and great food—and this Southern Alabama adventure delivered perfectly. We ended the week feeling truly refreshed and relaxed, a perfect result for a major milestone trip!
Table of Contents
Days 1-2: Travel & Pensacola, Florida
Our flight to Pensacola was easy, getting the rental car was a piece of cake. Our first stop was to check into the hotel, and change our clothes as it was noticeably warmer. The front desk associate mentioned there was a festival downtown, so we put on our sneakers and walked the little over a mile, passing by some beautiful huge houses and views of the water. Following the music we found the festival and it was very well attended-people were everywhere enjoying food, drinks, vendors, and music. We got a can of beer and walked around leisurely checking the place out, deciding if we wanted to get lunch here or not. The lines were long and we weren’t feeling it. We eventually left to check out other areas of downtown stopping at a sports bar for a snack and to watch parts of the football game. The spinach fish dip was a delicious surprise. We continued to walk around and stopped at another bar for another snack where the pimento cheese balls were a yummy treat. We walked back to the hotel, took a short nap, and then watched another football game. No dinner.
You can read more details about our 24 hours in Pensacola here.
Days 2-4: Mobile
We instantly fell for Mobile. While it had a “sleepy” pace on Sunday and Monday, it possesses a great, walkable downtown core with fantastic neighborhoods and a genuine, friendly atmosphere. It’s clear the city is in the middle of a revitalization, with unique eateries popping up among the historic architectue.
Our base in Mobile was the magnificent Battle House Hotel, a true gem of historic luxury. Having Club access was a huge bonus, offering a pleasant spot for a small breakfast each morning and a quiet snack in the evening. We also took advantage of the partnership with a neighboring building for the gym and pool; which were really nice and reeks of relaxation.
Mobile’s history was on full display. The incredible USS Alabama Battleship Tour (read about our experience here), a morning spent at the History Museum of Mobile and Colonial Fort Condé, and the Historic Mobile City Tour. It was unexpected when we realized we were the only two people on the tour! Our guide was incredibly knowledgeable and pleasant. Despite a few moments where it was hard to hear him without the headset, his passion for the area was infectious. We not only learned a ton in our 90-to-120 minute journey but also got a fantastic lunch recommendation—an excellent payoff!
Beyond the downtown core, Mobile’s residential neighborhoods immediately captivated us. The streets are lined with charming, grand houses—classic Southern architecture featuring striking wrought ironwork and imposing, large windows. We got an up-close look at this heritage during our tour of the Bragg-Mitchell Mansion. Being the only two on the tour meant we received a personal and fascinating deep dive, hearing stories about the home’s owners, the area’s rich history, and even quirky historical tidbits, like how windows were once taxed, leading architects to incorporate large, beautiful doors that open up instead. These homes contribute significantly to the city’s overall “good feel.”
We celebrated our anniversary with our “fancy dinner” at Dauphin’s, which offered great food, generous portions, and truly stunning views of the Mobile skyline (even if we weren’t seated facing our preferred direction). The price tag was surprisingly reasonable for the quality and ambiance.
The next night, we sought out a local favorite: Las Floriditas, a speakeasy. Even without live entertainment that evening, it was a perfectly relaxed spot for a few great drinks, chips, and dip.
Our food hits included a lunch at Bob’s Downtown Diner. A few misses (The Original Oyster House, Dick’s Last Resort, and Pizza at the Pass were merely okay or disappointing) only made us appreciate the great spots even more!
Read about our eating and drinking in Mobile here.
Days 4-7: Gulf Shores
From Mobile we were going to try to the Oakleigh Mansion on our way to Dauphin Island, but narrowly missed the historic house tour (which, in retrospect, was fine given the long, hot day and our need to catch the ferry and visit Fort Morgan).
Our stop on Dauphin Island was a mixed bag. The folks at the visitor center couldn’t have been nicer. But we didn’t really plan our few hours on this Island and we were disappointed by how many restaurants were closed. However, the beach itself was beautiful, with calm, pleasant water. Lacking towels and chairs, our 90-minute dip & sun soaking was the perfect amount of time before catching the scenic ferry to the Gulf Shores peninsula. We saw quite a lot of dolphins from the mid-way point to our exit, making the ferry ride even more enjoyable.
After arriving at the Mobile side of the peninsula, we took time to explore Fort Morgan, a site that has guarded the entrance to Mobile Bay for centuries, from the War of 1812 through World War II. We walked through the visitor center museum to set the historical stage before heading out to the massive masonry structure. The history was fascinating, but the conditions were a bit challenging: the heat was intense, and we quickly learned about the notorious Gulf Coast biting flies! Despite the discomfort, we explored the grounds thoroughly, walking the defensive perimeter and ascending to the top for views over the bay. Descending the extremely steep and narrow staircases inside the fort was an adventure in itself, making the history feel very immediate and palpable.
The true highlight of this portion of the trip was when we rented e-bikes from a place walking distance from our hotel, and spent a blissful time exploring the amazing paths of the Hugh S. Branyon Backcountry Trails. E-bikes are an absolute game-changer for covering a lot of ground and having a blast while doing it! (We’re planning a full post on that adventure, too, stay tuned!)
And for a little quirky, on a chilly windy day we took a little drive for some roadside attractions (Read about that here) before sitting on the soft white sand at Orange Beach.
Days 8: Return to Pensacola for flight
We had an afternoon flight, so we decided to drove over to Big Lagoon State Park for a quick walk/view of the water, but one of the bridge trails was closed. It was also a bit windy, so we called it early. We were the first to arrive at Warrior Brewing Co where we enjoyed a beer and spoke at length with another visitor. We headed to the airport and had a quick lunch, before our flight was delayed.
Overall, this anniversary trip was a huge success. We came for the history and the beer, and left feeling deeply relaxed and charmed by the Southern Alabama hospitality.
Packing for the trip
Packing was fairly easy, summer was winding down at home so all our clothing was readily available. Since this was purely a vacation, it was even easier, the clothes in our bag were all casual, nothing for work.
- D Clothing: 1 pair jeans, 2 pairs shorts, 1 skirt, 3 tank tops, 3 short sleeve shirts, 1 long sleeve shirt, 1 casual dress, 2 bathing suits, 1 coverup, rain jacket, 1 hoodie/sweatshirt, 8 under ware, 2 bra, 6 socks
- J Clothing: 2 pair shorts, 1 pair pants, 1 hoodies, 5 short sleeve shirts, 1 long sleeve tee shirt, 8 under ware, 8 socks
- Accessories: hats, sunglasses, day bag, purse backpack, 1 thin small travel towel
- Shoes: waterproof sneakers, flip flops, sandals, watershoes
- Toiletries: sunscreen, medications, dental stuff, hair and eye products, shaving razors, makeup
- Other: iPad, Kindle, eye masks, chargers
What would we do different?
We really wanted to go to the Carnival museum, but it turned out to be closed for renovations when we were there. That was probably our biggest disappointment of the trip. Some of our restaurant choices were due to proximity not necessarily where we wanted to go — I hate spending so much time looking at menus online at all the places, but sometimes it is worth it to avoid high fee foods and menu with compatible dietary restrictions. Can’t fault the weather for not cooperating – one day it was so hot it just wore us out and we needed a break another day was windy and cold and we had to change plans from the beach. Flexibility is key.
I’d say that we went to the pool in Mobile, mid-day when it was hot. But the pool wasn’t heated, and was too cold to go into. The hot tub was nice — but it was about 98 degrees so only so long you want to stay in that. So I’d definitely have changed that day up to do more daytime activities and go up the the rooftop pool in the evening when it was cool to enjoy the hot tub. Knowing that when we were in Gulf Shores, I did just that. But this is such a small thing.
Mobile is a sleepy city on Sundays and Mondays. Had we realized that we may have done the itinerary in reverse.
Detailed Itinerary
| Activities (links below are all to that site) | |
| Day 1 – Pensacola | Flight Lunch at Heroes Sports Bar to watch football games ($41.58) Pensacola Seafood Festival ($20) Snack at Union Public House ($47.82) |
| Day 2 – Pensacola to Mobile | Breakfast at Ruby Slipper, Pensacola ($46.78) Pensacola Lighthouse & Maritime Museum ($20) National Naval Aviation Museum (free) Fairhope Brewing Walk downtown Mobile (free) Movie at Crescent Theater – Napoleon Dynamite ($38.72 w snacks) Dinner at Battle House Hotel Bar ($55.20) |
| Day 3 – Mobile | Parade Grounds (free) History Museum of Mobile + Colonial Fort Conde ($28) Historic Mobile City Tour ($32 + 20) Lunch at Bob’s Downtown Restaurant (~$38) Walk around town (free) Sit by hotel pool for an hour (free) Walk around town (free) Braided River Brewery ($23.20) Dinner at Dauphins |
| Day 4 – Mobile | USS Alabama ($32) Lunch on water at the Original Oyster House ($64) Bragg-Mitchell Mansion House tour ($23) Iron Hand Brewing ($19.50) Dinner at The Noble South Nightcap at Speakeasy: Las Floriditas |
| Day 5 – Mobile to Gulf Shores | Spend some time at beach on Dauphin Island (parking $5.35) Lunch at Pirate’s Bar & Grille on Dauphin Island ($45.9) Ferry to Gulf Shores Walk around Fort Morgan Check into hotel Dinner at Coastal Orange Beach |
| Day 6 – Gulf Shores | E-Bike Ride around Orange Beach & Gulf Shores ($124.63) Lunch at Dick’s Last Resort ($60.02) Big Beach Brewing Dinner in hotel room ($28.80 from grocery store) |
| Day 7 – Gulf Shores | Short road trip for roadside attractions (free) FloraBama ($26.50 + 53.91 + 15) An hour at the beach (buy 2 towels $22) Dinner at Pizza at the Pass |
| Day 8 – Gulf Shores to Pensacola | Big Lagoon State Park ($6) Warrior Beer Co Brewery |