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The Ultimate One Day Coastal Mississippi Itinerary - What to do, see, and eat

When we started planning our trip to Mississippi, we really had no idea where to go or what to do. All we had ever seen of Mississippi were the stereotypes… fried foods, small towns, and country music. Don’t get me wrong… I love all of those things! In fact, it’s not far off from how I grew up! But we were hoping to find the Mississippi beyond the stereotypes... the hidden gems… the local secrets… the places that make you say... “This is Mississippi?!”. And that is exactly what we found in Coastal Mississippi! Or as they call it, the Secret Coast. Made up of 12 unique coastal towns, with a combined 62 miles of beautiful beaches which includes the nation's longest man made beach, Coastal Mississippi is the definition of a hidden gem! For this itinerary, we’ll be road tripping across the state from west to east, starting our day in the perfect little harbor town of Bay Saint Louis, and ending our day in one of the most idyllic southern beach towns you could dream of, Ocean Springs. Enough talking about it though!

Scroll to the bottom of the page for your FREE PRINTABLE itinerary!

Also, if you would like to see our experience in Coastal Mississippi, you can watch our “24 Hours in Coastal Mississippi” travel vlog

Let’s dive in!

8:30am: Breakfast at Mockingbird Cafe (110 South 2nd Street, Bay St. Louis)

We kicked the day off with a light breakfast at the adorable Mockingbird Cafe. The coffee is excellent, the chai tea is to die for, and the breakfast muffin is… well… just trust us, you’ll want to get it! It’s a biscuit meets muffin with an entire egg cooked into the middle! So good! If you’re looking for something a little heartier, Mockingbird has you covered with an impressive full breakfast menu, including Pulled Pork & Grits and Chicken & Waffles! Needless to say, we don’t think you’ll be disappointed!

9:30am: Explore Downtown Bay St. Louis

  • Angel Trees in Bay St. Louis

  • Ruth’s Roots Community Garden

Once you’ve gotten your caffeine fix, you’ll want to head over to Ruth’s Roots, a community garden that serves as an enrichment program to the Hancock County troubled youth. Visually, it’s more of an art display than garden, but when you look beyond the colorful planter boxes, painted “yellow brick road”, and fascinating folk art, you realize that Ruth’s Roots is truly a marvel. In the garden where you’ll find seasonal fruits, vegetables and herbs, as well as a chicken coop, a rabbit pen, and honeybees! Much of the produce, honey, and eggs are donated to another local non-profit. Beyond the produce, you’ll find a little library and a blessing box. Grab a book, sit in the garden and take a load off! The blessing box operates under the motto: “Take what you need, leave what you can”. If you couldn’t tell already, Ruth’s Roots was a highlight of our time in Bay St. Louis!

Now, you’ll go check out the Angel Trees before heading east. I could try to explain what they are and the amazing story behind them, but I would be sure to mess it up, so I’ll just give you exactly what the placard states…

“In the early 1900’s Ovenia de Montluzin looked out her kitchen window and saw workers starting to take down this oak, a sapling at the time, to clear a way for de Montluzin Avenue to be constructed. She asked them—successfully—to stop, because the young tree was an oak and would be beautiful one day.

At that time, this tree stood 225 feet west, down de Montluzin Avenue.

On the morning of August 29, 2005, Hurricane Katrina bore down on the de Montluzin family home, a turn-of-the-century villa which had become the Bay Town Inn. Of the seven people in the Inn that morning, four made it through the water and were rescued in the afternoon.

Kevan Guillory, Doug Niolet, and Nikki Nicholson Moon, along with her Scottish Terrier Maddy, managed to get to this tree once the tidal surge washed away the historic home. they held on for several hours as the waves washed over them, the eye passed, and they were able to jump down and find shelter for the night.

Years later, the tree was carved and moved to this location.”

10:30am: Drive east on Highway 90 (along the nation's longest man-made beach) to Gulfport (30 min) You will pass through the lovely harbor towns of:

  • Pass Christian (Henderson Park)

  • Long Beach (Friendship Oak)

This section will be more of a road trip section, but the Friendship Oak on the Gulf Park campus of the University of Southern Mississippi, is worth the stop if you have the time. It’s a 500+ year old southern live oak that stands nearly 60 feet tall with a trunk that’s almost 20 feet around!

11:15am: Explore Downtown Gulfport

  • Fishbone Alley

  • Jones Park

After a short road trip from Bay St. Louis, you’ll find yourself in downtown Gulfport. One of the highlights of Gulfport has to be Fishbone Alley, an ever evolving public art display that consumes the entirety of the 300 ft. alley that was once nothing more than a utility alley used for trash and maintenance. There are multiple restaurants and bars directly attached to the alley and many others nearby, including Chandeleur Island Brewing Company which is an excellent local brewery! Their H90 Pineapple Wheat was a favorite of ours.

12:00pm: Lunch at The Chimneys (1640 East Beach Boulevard, Gulfport)

You’ve probably worked up an appetite after all of this exploring, so it’s time for some lunch! Serving classic coastal cuisine and fresh seafood dishes to locals and tourists alike since 2000, The Chimneys is a white-tablecloth restaurant operating out of a beautiful replica of an historic home featuring salvaged bricks from the original house, brick hearths with a central chimney gracing the dining areas, and heart pine floors from an 1820's-era home in Vaiden, MS. If the weather permits, getting a table on the front porch is a must! The views of the Mississippi Sound through the Spanish moss covered Southern Live Oaks.

2:00pm: Drive east on Highway 90 to Biloxi (30 min)

  • West Biloxi Beach Boardwalk

  • Biloxi Lighthouse and Visitor Center

  • Downtown Biloxi – newly renovated Howard Avenue + public art

  • Biloxi Small Craft Harbor

One hour definitely isn’t enough to explore all of these sites in Biloxi, but if you have to pick and choose, we definitely suggest the West Biloxi Beach Boardwalk, the Lighthouse, and Visitor Center. The West Biloxi Beach Boardwalk is a half-mile stretch of boardwalk along the beautiful, white-sand beach making it a perfect place for a sunset stroll.

3:00pm: Check-in to The Roost (604 Porter Avenue, Ocean Springs)

We know you’re probably ready to take a load off at this point, and maybe even catch some shut-eye, and The Roost is the perfect place to recharge before the next adventure! This boutique hotel has all the charm and character you could ever dream of in a hotel. With 11 one of a kind suites, you’re sure to find the perfect room for you. Every room comes with complimentary WiFi, a flat screen TV, lush bedding, locally roasted coffee, and organic bath amenities from Gilchrist & Sommes. We can’t say enough how highly we recommend staying at The Roost!

4:30pm: Beach chairs, fire pit, and charcuterie setup on Ocean Springs Front Beach with Food, Booze, & Hiccups

After a quick freshen up and power nap, you’re ready for an unforgettable night on Ocean Springs Front Beach with an amazing collaboration between Food, Booze, & Hiccups and Belly Up Beach Rentals. It’s a match made in heaven, really! Belly Up Beach Rentals provides the beach loungers and Food, Booze, and Hiccups does the rest… a delicious charcuterie board (with local, artisan items), DIY s’mores (with homemade marshmallows), the most adorable tablescape, and a fire pit! All while watching the sun set over the gulf. We felt like we were living in a dream!

8:00pm: Drinks at The Wilbur (604 Porter Avenue, Ocean Springs)

You can’t stay at The Roost without visiting their renowned on property bar, The Wilbur. It’s been said to be the most beautifully designed bars in Mississippi by Architectural Digest, and for good reason. It’s quaint, but there’s a welcoming warmth as you walk in the door. Straight ahead as you walk in, you’ll see a bookcase that is the secret entrance to the lounge/seating area. Or you can do what we did and grab a seat at the bar and learn a thing or two about cocktails from their extremely knowledgeable bartenders. Either way, you can’t go wrong!

11:00pm: Bedtime

After having a nightcap or two at The Wilbur, you can mosey back to your room (that’s probably within 100 ft of The Wilbur) and cash in for the night. It won’t take long to fall asleep on the memory foam mattress and plush bedding… it’s that good!

We hope that this itinerary makes planning for your trip to Coastal Mississippi a little easier, or that it has encouraged you to make a visit to the Secret Coast! Let us know your favorite things to do in Coastal Mississippi, and check out our "24 Hours in Mississippi" travel vlog to see more of our experience!

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