We’ve been to St. Augustine more times than we can count, and we still find new places. The food scene here punches well above its weight for a city this size — part history, part creative energy, part the fact that tourists with high expectations keep the standards honest. This isn’t a listicle of every restaurant on TripAdvisor. These are the places we actually go back to, the ones we tell friends about, and a few honest warnings about where to skip.

Restaurants Worth Your Time

St. Augustine rewards the curious. Some of the best meals are a short Uber ride off the main drag — and if you stay in the historic area only, you’ll miss half the story.

Asado Life

Type: Latin Grill | Our Favorite | Best View in Town | Reservations Recommended

If we had to pick one restaurant in St. Augustine, this is it — and it’s not close. The concept alone sets it apart: alongside standard table service, Asado Life offers an Asado Club experience where a small group gathers near an open fire grill and food comes to you — salads, fresh-baked breads, meats cooked right in front of you over a traditional Latin asado grill. Fish, beef, whatever they’re working with that evening. It’s communal, theatrical, and deeply satisfying.

The view is stunning — one of the best dining views in St. Augustine, full stop. The little market inside sells fresh chimichurri, house-made dressings, and other items to take home. And the bar program, led by one of the most well-known bartenders in the St. Augustine scene, is exceptional.

Trip Jar Pick: Do the Asado Club if you can. Call ahead, make the reservation, and give yourself time to linger. This is a dinner, not just a meal.

Odd Birds

Type: Pan-Latin Fusion | Hidden Gem | Speakeasy Inside | Reservations a Must

Odd Birds is a short Uber ride over the bridge from the historic district, and every bit worth the trip. The cuisine is pan-Latin influenced — think bold flavors, garlic-forward dishes, and combinations that sound strange on paper and land perfectly on the plate. The street corn gnocchi with pork belly is the kind of dish you think about for weeks afterward.

The speakeasy tucked inside is a genuine experience — not a gimmick. The drink program is exceptional, developed in part by people deep in St. Augustine’s bar community.

Heads Up: Reservations are not optional here, especially for the speakeasy. Plan ahead or you will be disappointed. And Uber in — you’ll want to enjoy the drinks properly.

Modern Rose

Type: Coffee & Small Bites | Eclectic & Artistic | Community Gem

Modern Rose is a coffee and small bites fusion spot with an aesthetic that stops you in your tracks — eclectic, artistic, unlike anything else in the city. The food is creative and thoughtfully made, artistic flavor combinations, and lattes worth writing home about. The lavender latte alone is reason enough to visit.

They host tea parties, bridal showers, and private events. And here’s something worth knowing: Modern Rose hires students from the Florida School for the Deaf and Blind. That’s a business worth supporting.

Good to Know: It gets packed. Go early, or expect to wait. Either way, go.

The Columbia Restaurant

Type: Cuban / Spanish | Historic Staple

The Columbia is an institution — a family-run Cuban and Spanish restaurant that has been serving the same recipes for generations, with locations in Florida. The building is beautiful and the history surrounding it is real. This is a great lunch spot and a genuine piece of Florida culture.

The 1905 Salad is their signature — tableside preparation, perfectly dressed, served with Cuban bread sourced from the same bakery the Columbia has used for decades. Their sangrias are some of the best you’ll find in the state, and the Original 1905 Martini with the house-made blue cheese stuffed olive is quietly one of the better drinks in St. Augustine.

Trip Jar Take: We wouldn’t call it fine dining, but we wouldn’t skip it either. Order the 1905 Salad, get the sangria or a martini, and appreciate what you’re sitting in the middle of.

River & Fort

Type: Upscale American | Special Occasion | Reservations Recommended

River & Fort is where you go when the night calls for something elevated. It’s a little pricey, the view is excellent, and the food is genuinely impressive. The fried green tomatoes here are among the best versions in the city.

Trip Jar Take: Not an every-visit restaurant, but a great choice for a special evening. Make reservations.

Casa Reina

Type: Elevated Mexican | Fort & Bay Views

Beautiful building with a stunning view of the fort, the bay, and the Bridge of Lions. The food is elevated Mexican — Tex-Mex influenced with upscale touches. The appetizers and cocktails are the stars here.

Trip Jar Take: Order appetizers and cocktails, enjoy the view, and you’ll leave happy.

Sandwich Shops That Earn Their Reputation

St. Augustine has a serious sandwich culture. Don’t overlook it.

Drake’s

Type: Sandwich Shop | Local Cult Favorite | Female Owned

Drake’s is a small, female-owned sandwich shop with a massive cult following among St. Augustine locals — and once you’ve eaten here, you understand why. No tablecloths, no pretense. Just exceptional sandwiches on phenomenal bread, made with real care. The muffuletta is a standout. The Italian Stallion and the King’s Roast (roast beef with Boursin) are perennial favorites. They also serve breakfast, but get a sandwich regardless of the hour.

Trip Jar Pick: Grab sandwiches from Drake’s and take them to the Castillo de San Marcos. Eat on the lawn outside the fort. It’s one of the great simple pleasures in St. Augustine.

Kaiser’s (Anastasia Island)

Type: Sandwich Shop | Beach Side

A few tables, walk-up ordering, and sandwiches that will genuinely surprise you. Kaiser’s uses the Datil pepper throughout their menu: in a Datil-infused Thousand Island on their Reubens, in pickles, and in a Datil mustard. Messy, fresh, and the people running it are genuinely friendly. A perfect pre-beach stop.

Pizza Worth a Detour

Brooklyn Pizza

Type: New York Style | Full Bar

On US-1, and some of the best pizza either of us has eaten in this city. The space is relaxed and industrial — open ceilings, interesting furniture, full bar. Works for date night or with kids equally well. The pizza speaks for itself.

Pizzali’s — The Chianti Room

Type: Classic Italian | Classic Atmosphere

Pizzali’s is classic. Old school Italian done right. Full bar, fresh pizza, and a menu of Italian dishes that are genuinely tasty. Order the amaretto sour. Seriously.

Nonna’s Trattoria

Type: Traditional Italian | Hidden Gem | Family Owned

Sitting right next to Forgotten Tonic on one of St. Augustine’s most interesting streets, Nonna’s Trattoria is a small, family-owned Italian restaurant that deserves more attention than it gets. A handful of tables, real tablecloths, candles, fresh pasta made in-house, sauces built from scratch. The puttanesca — olives, capers, anchovies, the whole traditional treatment — is outstanding. Patient, unhurried dining at its best.

Worth Saving Room For

Bar Harbor Cheesecake

Type: Dessert & Tea | Wildly Unique

There is no good way to explain Bar Harbor Cheesecake except to say: just go. It occupies a historic cottage decorated like a Victorian ladies’ parlor, and offers tasting flights of cheesecakes alongside tea pairings, small plate items, and wine. The strangest concept in St. Augustine — and it completely works.

Whetstone Chocolates

Type: Chocolate Factory & Café | Family Founded | Tours Available

Whetstone is a St. Augustine original — a family-founded chocolate factory you can actually tour. Watch the chocolate being made, browse the shop for treats to take home, and make sure you order the Frozen Hot Chocolate. It’s not a gimmick; it’s genuinely one of the best treats you’ll eat in the city. A great stop for families and anyone who takes chocolate seriously.

Crème de la Cocoa

Type: Chocolatier | End of San Marco Ave

A proper chocolatier at the end of San Marco Avenue. Worth a stop if you have a sweet tooth or need to bring something home.

On the BBQ Question

Smokin’ D’s (South on US-1)

Type: Barbecue | Local Favorite

If you’re serious about barbecue in St. Augustine, drive south on US-1 to Smokin’ D’s. Picnic tables, no frills, and the locals swear by it.

Skip the barbecue spot closer to the historic district — their whiskey program is honestly the better reason to stop there.

The St. Augustine Drink Scene

St. Augustine has a genuinely excellent bar culture. Here’s how to navigate it.

Prohibition Kitchen

Type: Prohibition Era Cocktails | Must Visit | Live Music

Right on St. George Street and one of the most interesting bar concepts in the city. The drink menu leans into Prohibition-era classics done properly: Sazeracs, Negronis, and other drinks that were being made a century ago and deserve to be made well. They do them well.

The design-your-own Old Fashioned is the signature move — choose your whiskey (all high-end), your sugar, and your bitters. The Demerara sugar with black walnut bitters is our standing order. Solid pub food, live music supporting local artists.

Heads Up: No reservations, always packed on weekends. Get there early or grab a barstool. It’s worth the wait.

Tini Martini — The Casablanca Inn

Type: Martini Bar | Historic Porch | Fort Views | Well Crafted, Be Careful

The Tini Martini bar at the Casablanca Inn is a St. Augustine rite of passage. The porch overlooks the fort and the bay — a legitimately beautiful view shared with about 150 of your closest new friends on any given weekend. The martinis are, without exaggeration, the strongest you will ever have. There appears to be minimal mixer involvement. One is plenty. Two is a commitment.

Skip: The breakfast at the Casablanca. Come for the martinis and the view.

Forgotten Tonic

Type: Craft Cocktail Bar | Underrated | Seasonal Menus

An upscale craft cocktail bar occupying one of the more interesting buildings on one of St. Augustine’s most interesting streets, Aviles St. The bar program here has produced genuinely talented bartenders over the years and the seasonal menus reflect that. At Christmas they go all out. Worth a visit any time of year.

Trade Winds

Type: Dive Bar | St. Augustine Legend

If Bourbon Street in New Orleans had a St. Augustine cousin, it would be Trade Winds. One of the city’s most famous dives — walls covered in photos and history, still allows smoking inside. More importantly, this is a bar where famous musicians have been known to walk in unannounced and pick up a guitar. Tom Petty was among them. Go at least once.

A Few More Worth Knowing

• Roosevelt Room: Right next door to Prohibition Kitchen on St. George Street. Solid breakfast with elevated Southern standards — shrimp and grits, good eggs, fair prices, beautiful atmosphere.

• Harry’s: New Orleans-style cuisine, small chain, decent if that’s what you’re in the mood for.

• Food Truck Scene: St. Augustine had food trucks before most of Florida figured out the concept. Check local listings for where they’re gathered on any given weekend.

• The Datil Pepper: St. Augustine’s official hot pepper — unique to the area and showing up in everything from mustard to martinis to hot chocolate mix. Try it somewhere. It’s worth knowing.

The Honest Local Tips

• Make reservations. St. Augustine is packed, especially on weekends. If a restaurant takes reservations, make one. If they don’t, get there early or put your name in and explore while you wait.

• Uber if you’re drinking. Parking in the historic district is already a headache. If you’re planning to enjoy the drink scene, Uber in. The city is walkable and the rides are short.

• Leave the historic district for dinner. Some of the best restaurants — Odd Birds, Asado Life, Brooklyn Pizza — require a short drive or Uber. Don’t limit yourself to St. George Street alone.

• The fort picnic is underrated. Grab sandwiches from Drake’s or Kaiser’s, walk to the Castillo de San Marcos, and eat on the lawn outside. Free, beautiful, and one of the most St. Augustine things you can do.

• You won’t run out of places. We’ve been going for years and still find somewhere new every visit. That’s the best thing we can say about any food town.

Planning a trip to St. Augustine? Search hotels and flights at gettripjar.com.

We’ve done St. Augustine more than once. In fact, more than we can count. That alone tells you something. When you live in Florida and you keep returning to the same city on your days off, it’s earned it.

St. Augustine isn’t a theme park. It doesn’t try to be. It’s 450 years of actual history sitting right there on the street — cobblestones, cannons, and all — and somehow it never feels like a museum. It feels like a living town that just happens to be really, really old.

The Trip At a Glance

• Where: St. Augustine, FL

• Best for: Couples, families, history lovers, weekend warriors

• Drive from Melbourne, FL: About 2 hours north on I-95

• How long: 2 nights is the sweet spot

• Vibe: Slow, walkable, surprisingly romantic

Getting There

For us, from the Space Coast it’s an easy drive — straight up I-95, exit 318. Pretty easy to get to from about anywhere though. Skip the GPS shortcuts. Just stay on 95. Parking downtown can be tricky on weekends. We recommend parking at the St. Augustine Visitor Information Center on Castillo Drive — it’s cheap, central, and puts you steps from everything.

The Old Town Is the Whole Point

St. George Street is the main pedestrian strip and yes, it’s a little touristy — but it earns it. Walk it slowly. Duck into the side streets. The real St. Augustine is in the alleyways, the courtyards, and the old buildings that have been standing since before the United States existed.

The Castillo de San Marcos is a must. It’s a 17th century Spanish fort sitting right on the water and it’s remarkably intact. Budget an hour. Read the plaques. It’s the kind of place that makes you feel small in a good way.

What We’d Recommend

The ghost tours are better than they sound. We almost skipped ours. Don’t. Even if you’re skeptical, the history woven into those tours is legitimately fascinating and the guides know their stuff. Book in advance on weekends — they fill up.

Flagler College is worth a slow walk around even if you’re not a history buff. The building is stunning and the story behind Henry Flagler and his role in Florida’s development is one most Floridians don’t know nearly well enough. Don’t miss The Lightner Museum across the street. Amazing place to visit and the A/C works well!

For food, skip the obvious tourist spots on St. George and find something a block or two off the main drag. Better food, better prices, better experience.

What We’d Skip

The wax museum. Just trust us. Maybe that’s your thing. Heck, give it a shot.

What It Actually Cost

A solid St. Augustine weekend for two runs roughly:

• Hotel (mid-range, walkable location): $150–$220/night

• Food (2 dinners, 2 lunches, coffees): ~$150–$180 total

• Castillo admission: $15/person

• Ghost tour: ~$25–$30/person

• Parking: ~$20–$30 for the weekend

• Total: Approximately $500–$650 for two nights

Not bad for a genuine reset.

The Bottom Line

St. Augustine is one of those rare places that rewards slowing down. No agenda, no packed itinerary. Just walk, eat, look around, and let the city do its thing. Jodie and I have done it multiple times and we’ll do it again.

If you’re a family or a couple who hasn’t been — go. If you’ve been once, go back. It’s different every time.

Planning a St. Augustine trip? Search flights, hotels, and deals at gettripjar.com.