Rosemary Beach: 2-Day Itinerary

Rosemary Beach is the ideal place for a perfect beach vacation. Quaint and picturesque, there’s a relaxed elegance to the Florida vacation rental homes here. Our 30A cottages put you right in the heart of this cozy area, footsteps away from the beach or a brief and breezy bike ride to nearby local restaurants and charming retail stores. If it’s your first time visiting Rosemary Beach, we’ve created a two-day itinerary to help you find where to go, things to do and what to eat while you’re there. Even if you’re familiar with Rosemary Beach, you may discover new spots to explore on our list.

Day 1

Morning

Wake up on the right side of the bed in our YOLO home. It won’t be hard because the 30A cottage boasts luxurious Purple® mattresses so you’re comfortable and sleep well all night long. Enjoy a cup of coffee on the porch before heading out for breakfast at one of our favorite local spots. Cowgirl Kitchen is a casual restaurant along Rosemary Beach’s Main Street. Sip their famous CK Bloody Mary and enjoy a breakfast burrito or waffles ranchero. If you like people watching, sit outside to watch the charming main strip come to life.

Afternoon

Spend the day on the water! Florida’s Gulf coast boasts crystal-clear waters and favorable weather the majority of the year—perfect for all your water-bound plans. Charter a boat and fish the Walton County’s beautiful coastal waters. 30Angler is a local fishing charter company with glowing reviews. Their twin-powered 20’ catamaran is stable, ideal for you and your guests of all ages. They launch from Grayton Beach, just minutes away from the best natural limestone reefs on the west coast of Florida. Captain Ted knows all the spots to ensure a successful fishing day on the water. If you’re traveling with family, this is a fun afternoon activity and a great way to spend a few hours. Pack drinks and lunch to enjoy on board or ask Captain Ted if there’s a nearby restaurant that will fry up your fresh catch.

Not a fishing fan? No problem. There are plenty of other water activities to enjoy. Rent a kayak or paddleboard for your daily dose of sunshine and exercise. If you haven’t tried stand up paddleboarding before, you might be surprised how much fun it is. While learning how to stand up can be a little tricky, it’s actually much easier than surfing, skateboarding and some other activities. It’s relaxing but it’s a great workout too!

Evening

We think the best way to spend your first night in Rosemary Beach is going out to dinner at one of the many incredible local restaurants. Enjoy fine dining at Cuvee 30A. Their elevated dishes are perfect for a memorable date night. Try escargot with garlic butter or their famous chef Creehan’s signature black pepper crusted yellowfin tuna. Wrap up the meal with a slice of key lime pie or indulge in gooey chocolate sin cake.

Enjoy the ocean breeze and Gulf views from Pescado Seafood Grill & Rooftop Bar. They have a selection of Spanish-inspired dishes like shareable Paella Valenciana with mussels, clams, shrimp, chicken thighs, Spanish sausage and calasparra rice or small plates like pan-roasted pork belly. After dinner, enjoy a late night stroll along the beach. It’s a peaceful way to wrap up your adventurous first day.

Day 2

Morning

What’s a vacation without sleeping in? Get a late start and head to Great Southern Café for brunch. They have Cajun dishes like Grits A Ya Ya, a sauté of smoked bacon, Portobello mushrooms and spinach over smoked Gouda cheese grits, spiced shrimp and sweet potato or Crab Cake and Fried Green Tomato Benedict. Top it off with a mimosa or bloody Mary.

One of the best parts of vacationing along 30A is the biking. Because everything is close together, it’s a convenient and fun way of getting around town. Spend the morning biking and hit the local shops. Main Street has a wide selection of stores and goods like surf clothing, toys, homemade soaps and home décor. Grab yourself the perfect souvenir or snack.

Afternoon

It’s not a 30A vacay without a visit to the beach! Spend the afternoon lounging and soaking up the sun but don’t forget the sunscreen. When the mid-day sun gets too warm, you can always cool off in the water or grab an ice cream cone at Marble Slab Creamery. If you’re on a family vacation, the kids will love building sand castles on the shore. For lunch, grab some pizza at Southside Slice. They have all of your favorite classic pies and some unique specialty creations too.

Evening

Since day one’s dinner suggestion was fine dining, we suggest a casual joint for day two. Just a short drive down 30A in Inlet Beach you’ll find Shades Bar & Grill. It’s a fun place to watch a game and try some brews, burgers and wings. Or get take out from a nearby restaurant and spend a night in your 30A cottage relaxing. Our top takeout suggestions: Cowgirl Kitchen has great Mexican-inspired dishes like drunken shrimp tacos, chicken tortilla soup and taco salad with grilled grouper. Step it up with five-star dining from home with La Crema Tapas & Chocolates. Their serrano wrapped figs, lobster stuffed mushroom caps, steak empanadas and lamb lollipops with rosemary are to die for. Open up a bottle of wine and enjoy the sunset from your 30A cottage vacation home.