The Pearl Hotel
🌸 Planning the Ultimate Bachelorette Trip to Rosemary Beach, Florida
When it comes to planning a bachelorette getaway that’s equal parts relaxing, luxurious, and unforgettable, Rosemary Beach checks all the boxes. Nestled along Florida’s scenic Highway 30A, this charming coastal town offers the perfect backdrop for a stylish send-off into married life. Think walkable streets lined with boutique shops, rooftop cocktails at sunset, soft white-sand beaches, and a few adventure-filled surprises in between.
Here’s your complete guide to planning a dream bachelorette weekend in Rosemary Beach:
🏡 Where To Stay
Boutique Hotels or Beach Houses
The Pearl Hotel – A sophisticated adults-only boutique hotel right in the heart of Rosemary Beach, perfect for small, upscale bachelorette groups. Features a rooftop lounge, spa, and poolside cabanas.
30A Vacation Rentals – For larger groups, renting a beach house with multiple bedrooms, a pool, and walkability to town is ideal. Look for homes near the beach or Main Street for easy access to all the action.
🗓️ Sample Weekend Itinerary
Day 1: Arrival + Beachside Welcome
Check-in and Unpack: Settle into your beautiful home base.
Afternoon Beach Time: Kick off the celebration with some sunshine. Rosemary Beach’s private shoreline is exclusive to guests and residents—bring a cooler and soak up the serenity.
Evening Picnic or Dinner: Book a luxury beach picnic through Fresco Picnic Co. for a dreamy setup right on the sand, or dine at Edward’s Fine Food & Wine for a romantic courtyard meal with live music.
Day 2: Explore + Indulge
🌞 Morning: Brunch + Bikes
Start with a group brunch at The Summer Kitchen Café—great coffee, mimosas, and southern-inspired fare.
Rent bikes and cruise along 30A’s Timpoochee Trail, hopping between neighboring towns like Alys Beach and Seacrest for photo ops and boutique shopping.
🛍️ Afternoon: Shop + Spa
Treat yourselves to some retail therapy at local favorites:
Pish Posh Patchouli’s (luxury skincare)
Disco (fun gifts and beachwear)
The Hidden Lantern Bookstore
Schedule a spa session at The Pearl’s Spa Pearl—facials, massages, and mimosa service included.
🍽️ Evening: Rooftop Dinner & Dancing
Dinner at Pescado – A must. Their rooftop dining space is perfect for golden hour cocktails and fresh Gulf seafood.
After-dinner fun: Head to The Courtyard at Pescado or The Havana Beach Bar for live music and late-night laughs.
Day 3: Crab Island Catamaran Adventure 🛥️🌊
Your Signature Bachelorette Moment
Set sail with Crab Island Luxury Adventures:
Board a private catamaran departing from the Sandestin Golf and Beach Resort.
Lounge in comfort with ample indoor and outdoor seating, Bluetooth speakers, and an onboard restroom.
Cruise to Crab Island, a sandbar party scene with crystal-clear waist-deep water, floating food vendors, and epic photo ops.
You can even beach hop or chase dolphins—it’s a totally bespoke experience tailored to your group.
Bring matching swimsuits, champagne, and floaties for an unforgettable Insta-worthy adventure!
Day 4: Farewell Brunch + Wind Down
Start slow with coffee from Amavida Coffee Roasters, then head to Cowgirl Kitchen for a hearty brunch before packing up.
Enjoy one last walk on the beach or group yoga session before checking out.
🍴 Restaurant Recs at a Glance
| Meal | Where to Go |
|---|---|
| Brunch | Summer Kitchen Café, Cowgirl Kitchen |
| Lunch | Wild Olives, Big Bad Breakfast |
| Dinner | Edward’s, Pescado, The Citizen (in Alys Beach) |
| Drinks | Pescado Rooftop, Havana Beach Bar, The Courtyard |
🎉 Extra Bachelorette Fun Ideas
Themed Beach Day – Matchy swimsuits or coordinated outfits and a fun Spotify playlist.
Professional Photographer Session – Capture group portraits at golden hour in front of Rosemary’s iconic white architecture or the beach boardwalks.
Surprise the Bride – With custom swag bags, monogrammed robes, or a memory book full of photos and wishes.
💡 Pro Tips for Planning
Book Early: Rosemary Beach is a hot destination, especially during spring and summer. Secure lodging and excursions 3–6 months in advance.
Transportation: Most everything is walkable, but golf carts and bikes are great for getting around.
Split Costs Fairly: Use apps like Splitwise or Venmo to keep things simple.
✨ The Bottom Line
A bachelorette trip to Rosemary Beach is more than a getaway—it’s a curated celebration in one of Florida’s most beautiful and intimate coastal towns. Whether you’re sipping cocktails at sunset, shopping the boutiques of Barrett Square, or dancing on a catamaran at Crab Island, this is the kind of weekend your bride tribe will never forget.
Ready to start planning? Tag your girls and start the countdown! 💍☀️🕶️