A Local’s Guide to Restaurants Surrounding St. Augustine

Dream Finders Active Adult’s Reverie at TrailMark is located in the Oldest City in America, which is known for some of its Spanish colonial architecture, beautiful beaches and attractions such as The Castillo de San Marcos. But, St. Augustine restaurants are just as big of a draw to tourists and locals alike. Whether its fine dining, quick eats or desserts, this gem of a city has it all. We’re breaking down the top places to eat and how to do it “like the locals do!”

Harry’s Seafood Bar and Grille

Opened in 1995, this Cajun and Creole establishment became an instant classic in St. Augustine. Dine inside the historic two-story home, or opt for the Bayfront brick courtyard strung with enchanting twinkle lights – either atmosphere is an experience you won’t want to miss! Harry’s most popular dishes include Shrimp and Scallops Orleans, Chicken and Shrimp Creole, Crab-Crusted Red Fish Royale, Bourbon Street Salmon and Filet Mignon “Scampi Style.”


The Floridian

“Innovative Southern fare for omnivores, herbivores and locavores,” the Floridian’s website boasts. This top-rated spot features regionally inspired and locally sourced ingredients (From folks like Jax Bread Co., Mayport C&C Fisheries, Ben Wells Farms) to create a seasonally changing menu with featuring a twist of southern comfort as well as many vegetarian options.


Collage Restaurant

This award winning, romantic restaurant springs to the top of most lists centered around “best places to eat in St. Augustine” and it’s clear to see why – each dish is prepared from scratch, and uses fresh local ingredients like seafood and produce. If you’re looking for recommendations, a few favorites are the sauteed escargot wrapped in delicate puff pastry, lobster ravioli in pesto cream sauce or the sweet-and-savory grouper crusted in parmesan cheese, pecan and brown sugar.


Michael’s Tasting Room

St. Augustine is known for its history, and Michael’s is no stranger to that. The building that houses this “casually elegant” restaurant originally began as the Buchanti House, dating back to 1764. (Quick History Lesson: Joseph Buchanti was an Italian mariner who came to America with refugees. This house served as a popular center for community group meetings, parties and receptions.) Micheal’s menu features farm to table elements that change seasonally with a focus on seafood, steak and of course the award winning selection of wines.


Cap’s on the Water

You’ll be swept away by the stunning Intracoastal views at Cap’s on the Water. The menu features fresh local seafood with Southern and Mediterranean flavors. There are three bars serving award winning wines, as well as craft cocktails featuring local spirits and brews. You also have the option to sit at the Oyster Bar, which is the perfect laid back area to sip a few beers and slurp a few oysters while watching the sunset!


Prohibition Kitchen

Travel back in time when you enter this vintage gastropub. The menu features average bar fare with a twist. Prohibition Kitchen sources its ingredients from local farms such as Bee Hill Farms, Culver Farms and Snake River Farms. If you’re interested in brunch or breakfast, head to PK’s Roosevelt Room, their sister restaurant specializing in items like a Cookies and Cream Griddle Cake.


Catch 27

“Sea folk and Landlubbers will all find something they’ll enjoy.” Catch 27’s fish, shrimp, and clams are caught in Florida waters and delivered fresh every day. Each entrée is cooked from scratch with seasonal ingredients. You’ll be charmed by the atmosphere whether dining indoors or on the patio.


Must Try Desserts:

Cousteau’s Waffle Bar

This quaint café located on Hypolita Street is sure to indulge your sweet tooth. Their specialties feature dessert waffles with enticing toppings such as blueberry compote, bourbon whipped cream, local honey and candied bacon. If you’re not into waffles, they also have some pretty impressive milk shakes on the menu (Our favorite is the Calypso – Key Lime Pie IN a milkshake!)


Kilwin’s Chocolates

An old fashioned confectionary chain with a small town feel, this shop features something for everyone with a menu of ice cream, fudge, chocolates, carmel apples (just to name a few). It’s not out of the ordinary to see a line out the door of Kilwin’s, but the sweet treats are worth the wait!



This local scratch bakery and café features everything from breakfast, wine and desserts like cakes and cheesecakes. Enjoy the always beautiful St. Augustine weather with your favorite dessert on one of the patios. Or, you can choose between two floors of the indoor café!



Dream Finders Homes Active Adult Lifestyle isn’t just designing boutique homes and close-knit neighborhoods – it’s offering a full community package customized for 55+ residents in enviable locations, natural settings and a close-knit ambiance. Amenity-rich lifestyles are focused on health and wellness. Distinctive architecture and design deliver exceptional new home values.

Priced from the mid $200,000s, Reverie at TrailMark will offer a variety of single-family designs with decorator models slated to open in spring 2021. To learn more and to join the community’s interest list, call 866-223-1274 or contact us online.