There are beach towns... and then there’s Rosemary Beach. With its cobblestone streets, gas lanterns, and a blend of Caribbean charm and European architecture, it’s one of those rare places that makes you breathe a little deeper the moment you arrive.

And tucked right into the heart of it is The Pearl, one of my absolute favorite places to relax, unwind, and feel completely taken care of. Whether I’m planning a romantic weekend, a slow-paced girls’ trip, or a peaceful solo recharge, The Pearl never disappoints. From the complimentary beach chairs and rooftop cocktails to the cozy mornings with coffee on the balcony and the endless options for dining and shopping just steps away—this is the kind of place that feels like a true escape.

If you're dreaming of a couples getaway or planning something special for an anniversary, this blog shares exactly how to spend a perfect 3-day weekend in Rosemary Beach, staying at The Pearl.

Why I Love Staying at The Pearl

There’s just something about The Pearl. Maybe it’s the way the black-and-white awnings flutter in the breeze, or the attention to detail in every corner of the hotel. It’s luxurious but never pretentious, stylish yet comfortable.

Here’s what makes The Pearl the ultimate couples’ retreat:

Complimentary beach chairs & umbrellas (this alone makes mornings so easy)
Bikes available for guest use—perfect for breezy morning rides
A gorgeous pool & rooftop lounge
Full-service spa, ideal for a couples massage
Balconies with a view, cozy robes, and turndown service that makes you feel truly pampered
Havana Beach Bar & Grill on site, plus room service if you want to stay in

It’s centrally located, which means you can park the car and forget about it. Everything you need—from dinner reservations to bookstore browsing—is just a short walk or bike ride away.

A Perfect 3-Day Rosemary Beach Itinerary

Day 1: Live Music, Rooftop Views & a Dreamy Dinner

Afternoon:
Check in to The Pearl, get settled in your room, and soak in that Rosemary charm. Unpack just enough to feel at home, then head out for a walk through town. The pace here is slow in the best way—perfect for easing into vacation mode.

Early Evening Drinks:
Start the night at The Courtyard at Pescado, tucked into the lower level of the Pescado building. This space has a slightly hidden feel to it, with twinkle lights, Spanish-inspired decor, and often live music playing in the background. It’s one of my favorite spots for a relaxed pre-dinner cocktail—the kind of place where you lose track of time in the best way.

Dinner:
After drinks, head upstairs to Pescado Seafood Grill & Rooftop Bar for dinner. The rooftop views of the Gulf are absolutely stunning, especially around sunset, and the service is always impeccable. Whether you order fresh seafood or one of their beautiful shareable plates, everything is thoughtfully prepared and beautifully presented.

The cocktail menu here is incredible too—I always recommend trying one of their seasonal specialties. Reservations are a must, especially on weekends or during high season, so be sure to book early.

It’s the kind of dining experience that feels both elevated and intimate—the perfect way to kick off a romantic weekend.

Day 2: Bikes, Beach Time & an Unforgettable Dinner

Morning:
Grab your morning coffee at Amavida and take advantage of the complimentary bikes from The Pearl. Ride through Rosemary’s winding streets, past the gorgeous homes and green spaces like Barrett Square, or venture a little farther to explore nearby beach towns.

Midday:
Head to the beach for a few hours of pure relaxation. The Pearl’s complimentary beach chair setup makes it so easy—you just show up with your book and sunglasses and enjoy.

Afternoon Drinks:
Stop by Gallion’s for a stylish cocktail and people-watching. This place has such a fun energy in the late afternoon, and the drink menu is full of thoughtful twists on classics.

Dinner:
Tonight is Restaurant Paradis, a cozy, upscale favorite for a romantic dinner. The ambiance is polished but intimate, and their fried beef & blue cheese tortellini appetizer is one of my favorite dishes anywhere on 30A. Don’t skip it!

Day 3: Brunch, Boutiques & One Last Sweet Bite

Morning:
Start the day with brunch at Havana Beach Bar & Grill, located right inside The Pearl. The outdoor terrace seating is breezy and beautiful, and the Southern-inspired menu is full of comfort classics. It’s one of those places where the coffee flows and time slows down.

Midday Shopping:
Spend your final afternoon wandering the boutiques in town—some of my favorite shops include:

The Tracery – Stylish coastal home design and decor
Rosemary Beach Trading Company – Great for local gifts and apparel
Disco – Fun, fashionable, and full of personality
The Hidden Lantern Bookstore – One of my absolute favorite bookstores to browse
Patchouli’s – Fragrance and skincare in the best beachy way
Luminary Lifestyle – Trendy, effortless clothing and accessories
Faherty – Laid-back, high-quality essentials

Pre-Dinner Option:
If you’re not in a rush to sit down for dinner, consider making the most of golden hour by heading straight to the beach. The sunsets in Rosemary Beach never disappoint—the sky turns soft pink, deep coral, and glowing orange as the sun dips into the Gulf. It’s a peaceful, romantic way to end the day, toes in the sand and the sound of waves in the background. Trust me, dinner can wait when the sunset looks like that.

Dessert Stop:
After sunset, make your way to La Crema Tapas & Chocolate—a Rosemary Beach gem that blends cozy charm with rich, flavorful dishes. This is one of my favorite spots for a relaxed evening where dinner feels indulgent and unhurried. Share a few tapas (you can’t go wrong with the crab cakes or patatas bravas), then lean into the sweet side of the menu.

La Crema is famous for its chocolate tapas, and if you’ve never tried their hot chocolate molten lava cake, you're in for something special. Rich, warm, and perfectly portioned, it’s one of my all-time favorite desserts on 30A—and the best way to end a dreamy weekend in Rosemary Beach.

Departure Day: Easy & Delicious

Before hitting the road, swing by Cowgirl Kitchen for a casual breakfast. Their breakfast tacos, biscuits, or even a mimosa make for a great farewell meal before you leave the beach behind… at least for now.

Final Thoughts

Every time I stay at The Pearl, I’m reminded of how special a weekend can be when it’s beautifully simple. Great food, long walks, beach mornings, afternoon bike rides, and time to just be together. Whether it’s your anniversary, a special celebration, or just a much-needed escape, Rosemary Beach has a way of making you feel like you’re exactly where you’re supposed to be.

At Styled Travel, we’d love to help you plan your own romantic getaway—with all the best dinner reservations, room recommendations, and hidden gems included. Let’s make it unforgettable.

The Perfect Romantic Weekend at The Pearl in Rosemary Beach: 3-Day Itinerary & Travel Guide