3 Destinations in Florida for A Southern Summer Road Trip

If you haven't already hit the road this summer, it's time to take a moment and start checking items off your summer bucket list. I’ve loved seeing so many of my girlfriends creating beautiful memories with their friends and families (and on solo adventures too!) already this summer!

Miami on Film by Ben Alleman

This summer has been slow for me — and I’ve loved the change of pace. In ‘17 I spent the summer road tripping around the US and in ‘18 I was on a plane somewhere new every week. I'm considering weekend getaways to a few of my favorite Florida destinations to be an easy ways to keep that wanderlust spirit alive.

Each of the destinations featured in this post are included in the pages of my book - I'm including a few outtakes from Wanderful too! Plus read on for some good reminders of how to have a successful summer road trip — truly making sure you're prepared before you hit the highway is so important!

What's on my preparation list?

Music, snacks and cute outfits of course, however - as important?

jumper cables

a tire patch kit


hand sanitizer


essential oil aromas to keep the car smelling fresh.

I also always take our SUV in for service before long haul road trips: have your tires checked, fluids topped and certainly get your oil changed if your nearing the mileage mark for that. 

Oui We On the Beach

Once you've gotten the essentials checked off your list it's time to hit the road! So here we go, 3 destinations for a southern summer road trip:

Rosemary Beach

Vibe: Old World European village meets small town hospitality. The silhouettes in the town center are inspired by the West Indies, New Orleans and Charleston style architecture. Deep eaves, high ceilings, gardens, and fountain-filled courtyards pepper the community. Most 30A (that's the name of the stretch of highway running along these coastal beaches) first timers comment that they never knew America had such beaches -  they’d maybe traveled to Hawaii or to the Southern Caribbean thinking that’s the only place they’d find white sandscapes and emerald waters like these.

What to Wear: A monochromatic or floral romper, maybe pack one of each, a new bikini and a flowy caftan for the evening out.

Hang outs: Rent a bike, grab a beach ball and go play on the sprawling green lawn. Strolling around the town center, you’ll find there’s a little of everything, candy and coffee shops, restaurants and boutiques. At sunset the sky in Rosemary is a tapestry of colors making it an artist's delight.

Rosemary Beach Town Hall


Vibe: Nostalgic and energizing, with shiny chrome and faded pastels filling your eye. Miami is cleverly referred to as the “American Riviera.”

What to Wear: I like to imagine a 1940’s Rita Hayworth double dating with Orson Welles, their crew fully dressed to the nines. It's a place to summon your inner bombshell. Throw on a sheer printed mini shirt dress over your crocheted monokini, add shiny sandals and statement jewelry and you’re set! 

Hang outs: The beach of course, however there's the Art-Deco District, with properties ranging from some of the finest hotels in the world to luxury hostels, with summer camp vibes; there's the Wynwood Art District comprised of art complexes, eclectic restaurants and cafes and one of the largest open-air mural installations in the world and Little Havana, where fruit stands, coffee windows (or ventanitas), art galleries and cuban-afro beat music keep things lively.

Miami on Film By Ben Alleman

Seaside Beach

Vibe: Like Rosemary Beach, Seaside sits along Highway 30A; the vibe is Truman Show (it was filmed in and around the area) meets Airstream party and picket-fence perfectness.

What to Wear: Seaside caters to the girl that always has a towel stashed in her jeep, sunscreen in her glovebox and a bikini in her bag.

Hang outs: There’s really three places to hang out in Seaside: the beach, for all the same reasons we talked about above; the town center, which is the central hub of all of 30A, and then the Ruskin Place Artist colony, which originated as a workshop district with artisans living above their workspaces surrounding sculpture-filled Fairy Park. 

The Beauty of 30A

When it comes to summer road trips, I've got quite a few checklists so be sure to take a look at those if you need a packing list, if you're going glamping, need a beauty must have list or might be spending time in the deserts out west.  

summer road trip shopping edit:

I can't wait to see where you guys are adventuring to this summer! Be sure to leave a comment below to share your #summerbucketlist dreams!

Thanks for following along my wanderful friends!

Wanderfully yours,


photos 1 & 4 Ben via 35mm, photos 2, 3, 5 Hunter Holder for Wanderful. 

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Andi Eaton

Andi Eaton is a creative director, author, entrepreneur, and cultural influencer in a variety of media. She produces Oui We (ouiwegirl.com) the modern bohemian's guide to everything from travel and style to beauty and holistic wellness. Andi and her projects have been featured on Domino, Glitter Guide, A Beautiful Mess, Southern Living, SELF, Hello Giggles, Refinery 29, WWD, Elle Canada and more; in 2017 she wrapped a year of road tripping throughout the U.S. photographing and documenting travel, style and culture stories available in her new book: "Wanderful: The Modern Bohemian's Guide to Traveling in Style".