St Augustine City Guide: Why You Should Visit America’s Oldest City

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Looking for a weekend getaway? Discover St. Augustine: a historic city packed with charm and history on the coast of Florida. 

I recently visited St. Augustine on a road trip from 30A to Disney World, and I absolutely fell in love with the city and can’t wait to plan a trip back! Whether you’re planning a girls trip or a romantic weekend getaway, the city offers something for everyone. 

Established in the 1600s by Spanish settlers, St. Augustine is a Florida gem you will fall in love with. The city is the oldest European settlement in America, and you will love strolling down the cobblestone streets admiring the colorful centuries-old buildings. With gorgeous beaches, fabulous restaurants, historic sites, live music venues, and amazing restaurants, I highly recommend adding St. Augustine to your Florida travel list. 

Keep reading for all of my travel tips on what to do, where to stay, and more! 

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How To Get There

Many airlines fly directly into the St. Augustine airport, so it’s a great destination for a weekend getaway. 

St. Augustine is located 30 minutes from Jacksonville, 1 hour from Daytona Beach, and 2 hours north of Orlando, so you can always fly into a nearby airport and rent a car or take a bus if you plan to add St Augustine to your journey!

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Where To Stay

• The Collector Luxury Inn & Gardens
• Casa Monica Resort & Spa
• Hotel Cordova
• Hilton St. Augustine Historic Bayfront Hotel 

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What To Do 

• Take a tour – whether it’s a history, culinary, or even ghost tour, schedule a tour to explore the history of the city. There are countless tour options – whether you choose a carriage ride, helicopter, boating, walking tour, trolley ride, or more – we highly recommend booking a tour to discover the history of St. Augustine. 
• Rent a tiki boat to experience your own floating island with cocktails in hand
• Enjoy a tasting – stop by the local breweries, distilleries, chocolate factories, restaurants, wineries, and more to enjoy a taste of the city 
• Enjoy a beach day – Relax on the beach, kayak, paddle board, plan a sunset cruise, take a surf lesson. The options are endless! 
• Roam the local shops and art galleries while you take in the stunning architecture
• Venue hop downtown for local concerts and live music

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Explore The Historic Sites

• Castillo de San Marcos – This is one of the oldest historic sites in the city and you can’t miss it. Climb to the top of the fort for a bird’s eye view of all of the gorgeous beaches. 
• Fort Mose Historic State Park – Fort Mose Historic State Park is located 2 miles north of Castillo de San Marcos, and this 40-acre historic site is the first free African settlement in North America.
• Ponce de Leon’s Fountain of Youth Archaeological Park – We’ve all heard about the Fountain of Youth, but did you know it was located in St. Augustine? Ponce de Leon discovered the natural spring and legend has it, the Fountain of Youth has healing powers to maintain your youthful appearance. While it’s hard to believe if the fountain actually works, it’s worth a shot! Plus you may see some peacocks along the way. 
• Colonial Quarter – Take a step back in time and explore the Colonial Quarter (also known as the Spanish Quarter) to experience over 300 years of St. Augustine’s history in this restored, colonial village. 
• Ponce de Leon Hotel – While the Ponce de Leon hotel is now home to Flagler College, the building was once a luxury hotel. Built in 1888 by millionaire Henry Morrison Flagler, this hotel was his first in a series of luxury hotels along the Florida coast. Stop by for a tour to explore the beautiful Spanish Renaissance architecture and history. 

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Where To Eat

• The Floridian 
• Sarbez – a lively nighttime pub/bar known for their grilled cheese
• Casa Reira – my personal favorite!
• Harry’s Seafood Bar and Grill
• Johnny’s Famous Fish House & Oyster Bar
• Mary’s Harbor View Cafe – great for breakfast
• Columbia
• River and Fort – another favorite

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We hope you love St Augustine as much as we did! Let us know if you have any favorites in the comments below!

Planning a trip to Florida? Explore all of our Florida travel guides here.