America's Oldest City: Exploring St. Augustine

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Advisor - Jessica Joy
Curated By

Jessica Joy

  • Beaches

  • City Travel

  • Florida

  • St. Augustine

  • Relaxation

Advisor - America's Oldest City: Exploring St. Augustine
Curator’s statement

Welcome to America's oldest city: St. Augustine, Florida, founded in 1565! From a photographer's point of view, St. Augustine was a dream to explore. It is one of those places where you can walk around with your camera and always find something interesting to capture. The restaurants and little shops around town are an amazing bonus on top of the historical architecture and scenery.

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Where to stay in St. Augustine

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Things to do in St. Augustine

Lightner Museum

  • Castillo de San Marcos National Monument: Located just a short drive from downtown, this fort was built by the Spanish in 1742. Castillo de San Marcos is the oldest masonry structure of its kind in the continental United States. It was built and constructed to guard the coastline against invasion. I enjoyed taking some time to wander around this massive fort that overlooks the sea.

  • St. Augustine Lighthouse & Maritime Museum: Climb to the top of the 165-foot tower and take in the breathtaking views of historic downtown St. Augustine, the beaches, and the ocean to get a new perspective of the city. You will also get the chance to discover some of St. Augustine's maritime history at the site of Florida's very first lighthouse.

  • Lightner Museum: Located in the heart of downtown St. Augustine near the historic city center, you will find the Lightner Museum. Housed within the former Alcazar Hotel, which was built by Henry Flagler in 1888, the museum features an impressive collection of 19th-century art. You’ll find many art pieces and collections to explore. The exhibits rotate, so even if you've been before, it may be worth your time to check it out again.

  • Anastasia State Park: If you're a nature and beach lover like me, you won't want to miss this chance to get away from city life to check out four miles of white quartz sand beaches or watch the sunrise. Embrace the nature surrounding you in this hidden gem! The park's protected wildlife area and trail system are a perfect way to really connect with nature. Untouched sand dunes and shorelines surround the park, perfect for relaxing or a day of adventure. Don’t forget the camera—you will have a lot of photo opportunities!

  • St. Augustine Scenic Cruise: Taking a scenic cruise is a great way to get a unique view of the city and a unique way to enjoy St. Augustine’s historic landmarks and natural beauty along the coast. Not only will you get to relax and enjoy the ocean and historical city views, but you will also get a chance to learn a lot along the way.

Places to eat & drink in St. Augustine

  • The Floridian: A unique take on traditional Southern cuisine in a nice atmosphere. As someone with celiac disease, I loved seeing how they cater to various dietary restrictions, such as gluten-free, vegetarian, and vegan!

  • The Reef: If you’re looking for a St. Augustine restaurant that offers fresh seafood with beautiful ocean views, The Reef is for you. This restaurant boasts a classy ambiance, complete with white tablecloths and wood-paneled ceilings. The Reef is the perfect setting for a romantic date night!

  • Osprey Tacos: Tacos are one of our favorite types of food, because usually I can find a good corn tortilla or gluten-free hard shell. Osprey Tacos had a really friendly staff, an outdoor seating area, and amazing food!

  • Alms+Fare: This gluten-free bakery and coffee shop offers a delightful variety of nutritious and delicious treats made fresh daily. They prioritize organic, non-GMO, dairy-free, gluten-free, and naturally sweetened ingredients without sacrificing flavor.

  • Beachside Diner: This newer addition to St. Augustine Beach offers a classic diner experience that is open daily for breakfast and lunch. Their breakfast menu features traditional diner favorites, including omelets, avocado toast, pancakes, and waffles. They also offer lunch options such as burgers, sandwiches, seafood, and sliders.

Need to know

St. Augustine, Florida, is a great place to visit for history, beaches, and fun. The city is filled with charming shops, delicious food, and endless family-friendly activities to enjoy!

Advisor - Jessica Joy

Travel Advisor

Jessica Joy

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For more inspiration and insider recommendations, visit our Florida page.