By: Lauren published: Sep. 11, 2021 2 Comments

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As you may or may not already know, St. Augustine is the oldest continually inhabited city in the United States, which makes it a historically important city. There are a ton of beautiful landmarks to see and explore, but rest assure, even if you aren’t into the history, you will absolutely swoon over the charm that is St. Augustine!

Before our trip, I was excited to soak in a new city, but let me tell you– it totally BLEW me away in the best possible way. So much so that I had to write a post JUST for it.

Whether you are thinking about taking a mother-daughter trip like we did, having a romantic weekend getaway with your significant other, or wanting a fun place to take the whole family, St. Augustine is a destination I would highly recommend!

So let’s get right to it shall we! Here’s my top picks for where to stay, what to eat, and what to do in this city full of so much historic, southern charm!

WHERE TO STAY IN ST. AUGUSTINE

When I was researching where to stay, the number one place that came up on every list was Casa Monica Resort & Spa. Not even joking! It was the TOP recommend place. It is a little pricier than some of the other places, but it is also completely 10 levels up from every other hotel in the city. It’s beautiful Spanish architecture is enough to get you to absolutely swoon. And it is just as beautifully decorated in the inside with Moroccan tapestries, ginormous chandeliers, and timeless blends of fine arts throughout. It is the perfect blend of historic charm and modern luxury! And the pool. The pool! Just such a lovely place, and in the HEART of the city! I am usually all about the cheaper option, but staying here was WELL worth the higher price tag for this trip.

HOTELS

But if you are looking to save a little, I understand that too. So here are some of the nicer hotels that are in the area as well.

BED AND BREAKFASTS + INNS:

Because of it’s southern charm, there are a number of old-fashioned inn’s and bed and breakfasts to stay at in St. Augustine. More quaint than taking the hotel route, these small inns provide more privacy and offer a more romantic and homey atmosphere. While we didn’t end up staying at one this trip, they are on my list for future visits! We walked past many while we were out exploring and even walked in the lobby of a few. Some are more antique like, and some are more modern. Definitely a wide range, so take a look at the pictures for yourself to see.

Here are my top picks– all located in walking distance and the heart of the city!

WHERE TO EAT IN ST. AUGUSTINE

BREAKFAST AND BRUNCH

Maple Street Biscuit Company – three words: the squawking goat (chicken breast, a fried goat cheese medallion, and house-made pepper jelly). That is all. 😍 this place is amazing, and they actually have a lot of options compared to many ‘biscuit’ places.
The Blue Hen Cafe – this place is absolutely adorable. So chic and retro! Located in the heart of the city with a menu full of homey, southern comforts, you can’t go wrong choosing here!
Farmhand Kchn – farm fresh with lots of options, this place has become a popular brunch spot in the city. Lots of color and flavor in their dishes– and a wide variety of vegan dishes as well.
Schmagel’s Bagels – if Brooklyn-style bagels are your jam, you MUST head over to Schmagel’s one more. SO. GOOD.
Nero’s Waterfront Cafe – delicious food, affordable prices, gorgeous waterfront view…. what’s not to love?

LUNCH AND DINNER

Keep reading for more details on each of these!

Harry’s Seafood, Bar & Grille

We stumbled upon Harry’s while walking and looking for a place to stop for lunch. We were instantly drawn in by their delicious smelling food and gorgeous light-strung patio! They specialize in cajun, creole, and southern cuisine, so if southern food with a touch of spice is your thing, you will love this place (and their gorgeous patio!). We tried the fried green tomatoes, salmon dip, and blackened shrimp salad– all were incredible!

Cap’s on the Water

This place was a little off the beaten path. Unlike all the other places, we had to drive here versus walk, but it was SO worth it (even if you want to Uber/Lyft there). Everything about this place gets 5 stars. The service, the food, the atmosphere, everything! Cap’s is located on the sound side of the water and the scenery is just incredible. They have loads of seating on the deck, right by the water and in the warmer months, they open the windows completely of the sheltered part too. It is just beautiful and so relaxing! They have delicious cocktails and the seafood is flavorful and fresh. Highly recommend saving room for the key lime pie cup. Best key lime flavored anything i’ve ever had.

The Floridian

This place is exactly what you would expect to see at a popular coastal city. It’s fun, it’s flavorful, it’s hip, and a foodie’s paradise. They specialize in down-home southern comfort foods, and lighter, healthier, vibrant dishes. With many vegetarian options too. The menu is seasonal and changes continuously with the seasons, but I can guarantee– you can’t go wrong here!

Columbia Restaurant

The exquisite Columbia Restaurant sits in the heart of St. Augustine in the historic district. It is incredibly breathtaking on the inside and outside with hundreds of hand-painted tiles and Spanish-style fountains. They specialize in Spanish/Cuban food and it is absolutely to die for. We loved everything about our dinner out here! I insist you try their sangria and famous 1905 salad!

From: St. Augustine Restaurants with a View

St. Augustine Fish Camp

If you love seafood (fresh or fried), add this place to your list! They absolutely kill the seafood game. Not only is it fresh and flavorful, but they offer a HUGE variety of main meal options and side items. There is something here for everyone to love. It’s also located on the water and the views are just beautiful!

Culinary Outfitters

This restaurant has become a St. Augustine landmark! With more than 250+ seats, open-air dining, fire pits and conveniently located on the water- this place has it all. With the way the food is prepared and presented, you think you would be high dollar prices, but prices are actually very affordable for a nice dinner!

DRINKS AND COCKTAILS

The Ice Plant – you MUST go here. I absolutely insist! Coolest industrial atmosphere with some of the best mixologists in the country! Everybody there was just raving over how delicious their cocktail was! We would have gone back here multiple times if we didn’t want to try something new.
The Tini Martini Bar – intimate cocktail bar at the Casablanca Inn offering a verandah with bay views.
No Name Pub – cute little beach bar in a great location.
Trade Winds Lounge – if you’re looking for the classic bar scene with less fancyness, this place is it. Drinks are solid, music good– it’s a good time.
The Cellar Upstairs Wine and Jazz Bar – upstairs from the San Sebastian Winery, is a St Augustine Night Life hotspot that features wine by the glass or bottle, a famous sangria, and one of the best beer selections in St. Augustine.
Dog Rose Brewing Co – if craft beers is your thing, Dog Rose is your place! Lots of variety here.

DESSERT AND SNACKS

Mayday Ice Cream – if you love ice cream, you MUST stop here. I HIGHLY RECOMMEND the Cloud 9 flavor– a deliciously light sweet and salty almond ice cream with flakes of sea salt and a homemade marshmallow fluff– I have never had such delicious ice cream in my life. And they have homemade waffle cones and sprinkles (both also amazing!)
Key Lime Shop – calling key lime lovers! This store has literally everything you could ever want in key lime flavor. While you are there, you must grab a frozen chocolate dipped key lime pie!
The Hyppo– a unique popsicle shop with a ton of fresh fruit flavors. A lot of gluten-free and vegan options and a good option if you’re wanting something sweet but lighter.
Kernel Poppers – the ULTIMATE popcorn shop! Full of every flavor imaginable. A great place to take the kids! Or if you are just a popcorn lover yourself 😂
Kilawins – Kilawins is just the best. We couldn’t walk pass Kilawins and NOT pick up some fudge.
Whetsone Chocolates – local to Florida, this chocolate shop is full of charm just like the city it’s in! Unlike many chocolate shops, they offer tours and samples. And the chocolate is just downright indulgent.
Creme de la Cocoa – a fancy (Food Network competitor!) bakery specializing in hand-crafted cakes, cookies, and all kinds of desserts of the sort! Come here at your own risk.
Cousteau’s Waffle and Milkshake Bar – Located in the heart of Historic Downtown Saint Augustine, Cousteau’s offers Belgian Liege Waffles and Hand-Spun Milkshakes. Dreams are made here.
Peace Pie – pie filling and ice cream stuffed in two giant shortbread cookies. This place is unique and a a popular hit-up spot in the city!

WHAT TO DO

Despite it being a fairly small and quaint city, there are tons of things to do. We already have a list of more things we need to do and check out when we go back!

Walk the streets of St. George Street – this road is closed off to cars, so pedestrians can walk the streets, stop at shops and restaurants and take in the beautiful old town scenery.
Go to the beach! I mean when in Florida right? All of them are beautiful, you can’t go wrong with which one you pick.
Fun on the water – from fishing to kayaking and boarding, swimming with dolphins and everything in between- there are so many fun water options!
St. Augustine Distillery – free tour and tasting! And you get to sample four signature cocktails. When you’re done, head to the Ice Place bar next door for a drink!
Flagler college – walk around and explore the beautiful artictecturhe of Flagler college. Maybe i’m partial because I love beautiful architecture, but WOW. It is just such a beautiful sight to take in!
Castillo de San Marco – a lot of history here. Built by the Spanish in St. Augustine to defend Florida and the Atlantic trade route, Castillo de San Marcos National Monument preserves the oldest masonry fortification in the continental United States and interprets more than 450 years of cultural intersections.
Ripley’s Believe it or Not – the oldest Ripley’s still standing, this is a must go if you have kids! Even if you don’t and you love goofy things!
Fountain of Youth – the Fountain of Youth, a mythical spring, allegedly restores the youth of anyone who drinks or bathes in its waters. And it’s here in St. Augustine!
Chocolate tasting tour – take a chocolate tasting tour at Whetstone Chocolates! Taste freshly made chocolates and confections while you walk through the actual factory!
Old Town Trolley Tour – everything is pretty close, so we opted to walk everywhere, but if you want to sit back and let someone tell you all about all the iconic landmarks, the trolley is a great option.
World of Golf Hall of Fame – we didn’t go here, but people who love golf praise this place.

This is only a tiny list, a FRACTION, of all the things there are to do in St. Augustine! Not only that, but you will also be JUST AN HOUR AND A HALF from Disney World, so if that has been on your list, it is SO worth the short drive!!!! We took a day and did Disney and had the most amazing time!