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A First Timer's Guide to St. Augustine, Florida: Where to Visit, Eat, Shop, and Sleep

A First-Timer's Guide to St. Augustine, Florida: Where to Visit, Eat, Shop, and Sleep | CosmosMariners.com

Over its 450 years of existence, St. Augustine has had to reinvent itself many times to stay relevant and to continue thriving. The modern day city is no exception, and St. Augustine has found new life in reworked classic attractions, daring chefs, and upfitted shops and streets. It might have plenty of history, but St. Augustine, Florida, is anything but old and stuffy.

In my first time guide to St. Augustine, Florida, I'll give you my best recommendations on every part of your visit: from my favorite hotels to where to eat. All you have to do is book your St Augustine hotel and hit the road!

Where to Stay: My Favorite Hotels in St. Augustine


Since I'm a huge proponent of staying at locally owned accommodations, I'd be remiss if I didn't mention the city's 25 bed and breakfasts within the historic district.

The St. Francis Inn, where I stayed during my most recent visit, dates to the 1790s, and is located at the intersection of St. George and St. Francis Streets [read my review here].

The Hemingway House (just a block off of the bay) and the Inn on Charlotte (which dates from the early 1900s) are popular and well-situated.

A First-Timer's Guide to St. Augustine, Florida: Where to Visit, Eat, Shop, and Sleep | CosmosMariners.com
Lobby of the St. Francis Inn

Other popular places to stay include the recently built Hilton Bayfront Hotel, which overlooks the Mantanzas Bay, and the Casa Monica, a hotel from the Flagler era of St. Augustine, and upfitted in a beautiful neo-Moroccan style.

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The Best Restaurants in St. Augustine


So. Much. Good. Food. Come with an empty stomach because you're going to find plenty of places that will tempt your taste buds!

A First-Timer's Guide to St. Augustine, Florida: Where to Visit, Eat, Shop, and Sleep | CosmosMariners.com
Tapas at Taberna del Caballo


  • Johnny's Oyster Bar: fresh seafood, overlooks the bay
  • The Raintree: upscale food in a romantic setting. A St. Augustine staple!
  • O.C. White's: casual vibe, live music, amazing options from seafood to pasta, great drink menu
  • Taberna del Caballo: Spanish tapas and cocktails in the heart of the historic district
  • Hot Shot Bakery and Cafe: to-die-for breakfasts and paninis, home of the chocolate datil pepper challenge!
  • Hyppo: gourmet popsicles in over 450 unique flavors
  • Claude's Chocolate: handmade chocolates and sweets
  • Ancient Olive: not a restaurant, per se, but an olive oil and vinegar shop filled with unusual flavors and varieties
  • A1A Ale Works: craft beers served with Floribbean dishes, great location near the Bridge of Lions
  • Vino del Grotto: unique wines, and wine smoothies to go
  • Cafe Alcazar: Greek-American food in an unusual location (the deep end of the Hotel Alcazar's former pool!)
  • St. Augustine Distillery: tours of the facility and free samples of their gin and vodka

For a more in-depth opinion on many of these restaurants, check out my guide to eating your way through St. Augustine.

A First-Timer's Guide to St. Augustine, Florida: Where to Visit, Eat, Shop, and Sleep | CosmosMariners.com
Beef Wellington at The Raintree




What to Do in St. Augustine


This section would be much easier for me to write if I just entitled it "What not to see" (a list that would include practically nothing since St. Augustine is so awesome!). But that's not exactly compelling travel writing, so let's talk about some of the can't-miss sites in this beautiful city.

Castillo de San Marco has been a staple of the St. Augustine attractions for as long as I can remember. In fact, taking a guided tour of the Spanish fort is one of my earliest memories of visiting the city. Allot at least half a day to full explore the fort, and make sure to take one of the ranger-guided tours. Catch one of the re-enactments for a taste of life in the fort!

A First-Timer's Guide to St. Augustine, Florida: Where to Visit, Eat, Shop, and Sleep | CosmosMariners.com


Other classic, been-there-forever attractions include Ponce de Leon's Fountain of Youth (which really has no historical basis for Ponce's famed water, but it's still fun), the world's first Ripley's Believe it or Not, and the Old Jail (where Martine Luther King was held after his arrest in 1964).

Just across the street from Castillo de San Marcos is the St. Augustine Pirate and Treasure Museum, a pet project of Pat Croce, television personality, author, and former Philadelphia 76ers basketball team president. With pieces from his own personal collection and extensive research throughout, the museum is focused on education--and is far less hokey than you'd expect.

A First-Timer's Guide to St. Augustine, Florida: Where to Visit, Eat, Shop, and Sleep | CosmosMariners.com
Artifacts in the Pirate Museum


The shops and restaurants along the pedestrian-only St. George Street are at the heart of the historic district. Check out the Colonial Quarter to walk through 400 years of St. Augustine history--you won't be disappointed with the amazingly talented (and thoroughly amusing) tour guides who will have you enthralled to learn about the diverse history of the city.

A First-Timer's Guide to St. Augustine, Florida: Where to Visit, Eat, Shop, and Sleep | CosmosMariners.com
The thoroughly entertaining Colonial Quarter guide, Mr. Grimm, at the artillery demonstration


Head over to the quiet Aviles Street to browse through art galleries and cute boutique shops, or sip your coffee at one of the sidewalk cafes. The Ximenez-Fatio House Museum is down this road, and is a great place to learn more about the entrepreneurial women who helped create 19th century St. Augustine.

A First-Timer's Guide to St. Augustine, Florida: Where to Visit, Eat, Shop, and Sleep | CosmosMariners.com
Aviles Street: supposedly America's oldest street!


It might be an institution of higher learning now, but a guided tour of Flagler College allows you to walk through the building that helped define St. Augustine's golden period under Henry Flagler. You'll see the opulent ladies' room, the stunning Tiffany windows in the dining hall, and the incredible details that Flagler put everywhere in his hotel. These tours are run by students and all proceeds go back to help the ongoing preservation efforts of the property.

A First-Timer's Guide to St. Augustine, Florida: Where to Visit, Eat, Shop, and Sleep | CosmosMariners.com
The former Ponce de Leon hotel, now the women's dormitory at Flagler College


The nearby Lightner Museum was also a Henry Flagler hotel and now houses an eclectic collection of antique housewares, costumes, and home furnishings.

While a walking tour is a great way to see the city, you might want to check out the two tram companies: Old Town Trolley Tours (the green and orange trams) and the Red Train Tours (the red ones, obviously). Both zig zag all over the historic district and include running commentary to help you with your local history.

Another great way to see the city is through a boat tour: with an emphasis on environmental protection and education, the staff at St. Augustine EcoTours goes out of their way to make each boat tour more than a trip around Mantanzas Bay. All proceeds from EcoTour go back into the preservation of St. Augustine's waterways and a joint research venture with Flagler College.


What to Know before You Visit St. Augustine




  • Parking is extremely hard to come by in the historic district. The city recently put up a parking garage near the Visitors' Center to help alleviate some of the parking woes. Look for the well-marked signs pointing you to the Visitors' Center and the garage as you enter St. Augustine. 
  • September 2015 marks the city's 450th anniversary of continual habitation, a milestone that makes it an older city than both Jamestown, Virginia, and Plymouth, Massachusetts (which were founded earlier, but have not had people living there continuously). While the biggest events--including potential visits by both Pope Benedict and the Spanish royal family--are in September, St. Augustine is celebrating throughout the year with concerts, a special exhibit in the Visitors' Center, and tours. 
  • Be prepared to walk. While historic St. Augustine isn't a huge area to cover, you'll still want to strap on your best walking shoes to get the most out of the city. Because of the parking issue and the many pedestrian-only areas, your best bet for navigating the city and its attractions quickly and easily is to hoof it. 
  • The least crowded times to visit the city are in early fall (after school takes back in) and early spring (late January and February). If you plan your trip during these times, you'll have more of the attractions to yourself and you don't have to traipse around in the sweltering heat of the most popular months: July and August. 
A First-Timer's Guide to St. Augustine, Florida: Where to Visit, Eat, Shop, and Sleep | CosmosMariners.com

Have you visited St. Augustine? What are you favorite places to see? Where is your one can't-miss restaurant? What would you be most excited to do from this first timer's guide to St. Augustine, Florida?

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This post contains affiliate links. If you choose to purchase through one of the above links, I will receive a small commission at no additional charge to you. 

If you liked this guide, you'll love my other first-timer's guides! Check out the guides to other cities by clicking on each image:
First-Timer Travel Guides First-Timer's Guide to St. Augustine, Florida First-Timer's Guide to Savannah, Georgia First-Timer's Guide to St. Pete Beach, Florida First-Timer's Guide to Charleston, South Carolina
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