For the 50+ Traveler

St. Augustine, Florida, is known as America’s Oldest City. The ancient city is filled with history. Ponce de Leon first discovered the area now known as St. Augustine in 1513. In 1565 Spanish Admiral Pedro Menedez de Aviles established St. Augustine.

This oceanside community beautifully reflects its Spanish heritage. With ancient brick streets that meander through the historic district like spider webs, this Old World city exudes a laid-back Southern magnetism that is hard to resist. Ancient buildings crafted from coquina shells line the streets, and remnants of the old city wall perch on the shimmering Matanzas River banks.

Located approximately an hour south of Jacksonville, St. Augustine is an ideal getaway for the mature traveler. Fly into Jacksonville, and meander down to St. Augustine along the seashore.

Note: Florida’s Historic Coast hosted my activities. All opinions remain my own.

Things To Do In St. Augustine

With a wide variety of activities, from lesser-known experiences to more popular adventures, St. Augustine is filled with fun.

The Old Town Trolley in St. Augustine, Florida.

Old Town Trolley

St. Augustine is a delightfully walkable city. But the best way to get an overview of this captivating city and its history is onboard The Old Town Trolley. The trolley slowly rolls down the old city streets as the driver regales you with St. Augustine’s history in a fun and engaging way, bringing the ancient city to life. Visitors can hop on and hop off throughout the tour.

Castillo De San Marcos in St. Augustine, Florida.

Castillo De San Marcos

The Castillo de San Marcos is one of the city’s most iconic landmarks. With its commanding view of the town and waterfront, the fortress is the oldest masonry fortress in the continental United States. The Spanish constructed the fort in 1672 to protect and defend Spain’s claim to Florida and her Atlantic trade route. Admission to the Castillo de San Marcos is $15. The National Park Service suggests checking the website for COVID-19 updates.

Shops and restauraints in St. Augustine's Colonial Quarter.

The Colonial Quarter

The Colonial Quarter gives visitors a peek into life in the old city. Four eras of history are featured within the park. This enables visitors to have an interactive journey through each period on the Living History tour.

The Pirate Museum in St. Augustine, Florida.

The Pirate Museum

Pirate Ship! These words would incite fear into the crews of the treasure ships that regularly sailed the Caribbean. The Pirate Museum brings these fearsome men and women to life. With exhibits that highlight such feared pirates as William Teach and Thomas Tew, the museum transports guests back to Port Royal, Jamaica, and the Golden Age of Piracy.

Be sure to keep an eye out for the Discovery Drawers throughout the museum. The drawers are marked with a skull and crossbones -- you never know what treasure you’ll find.

Kayakers on an Augustine Eco Tour in Florida.

Augustine Eco Tours

For a different perspective on America’s Oldest City, check out St. Augustine Eco Tours. On the water you’ll find treasures of a different nature. You’ll discover why dolphins call the Matanzas River home and why preserving this estuary is so critical.

Choose from kayaking, boating, or sailing tours. Each tour is different and unique. We loved our time on St. Augustine’s waterfront with a close-up view of the Bridge of Lions. Birds are also plentiful on the eco-tour, from Ibis and pelicans to roseate spoonbills.

The Lightner Museum in St. Augustine, Florida.

The Lightner Museum

The Hotel Alcazar has been transformed into the Lightner Museum. We fell in love with this fantastic museum many years ago and try to visit each time we are in St. Augustine. Henry Flagler, the railroad tycoon, built the hotel in 1889. This St. Augustine gem highlights America’s Gilded Age and is filled with breathtaking architecture and art.

One of our favorite exhibits is the stunning collection of stained glass. Stained glass was developed in Medieval Europe. During the end of the 19th century, American artists began incorporating new techniques that revolutionized the stained glass industry. With vibrant colors and rich textures, these new windows helped skyrocket the stained glass industry.

The exhibit now includes 12 new stained glass windows from the Lightner’s collection that have been restored.

Be sure to make time to have a bite to eat in the Cafe Alcazar. Located in the pool area, you’ll love the unique perspective that noshing on the floor of the pool offers. Looking upward, you’re surrounded by ornate balconies sporting hefty railings and steps leading down to the former pool. You can picture women walking along the balconies laughing as men dressed in swimming attire and sporting handlebar mustaches frolic in the pool.

The St. Augustine Lighthouse in Florida.
Jim Hill

The St. Augustine Lighthouse And Maritime Museum

The St. Augustine Lighthouse and Maritime Museum is one of our must-see attractions when visiting St. Augustine. The lighthouse offers spectacular 360-degree panoramic views and is worth climbing 219 steps to reach the top. There are eight landings, each with a bench to allow guests to rest before climbing some more.

Your $12.95 gives you admission to the lighthouse, Heritage Boatworks, the lighthouse keeper’s home, and several WWII-era buildings.

The Classic Car Museum of St. Augustine in Florida.
Jim Hill

The Classic Car Museum Of St. Augustine

The Classic Car Museum of St. Augustine is a relative newcomer to the area, but it is fantastic! The museum features over 30,000 square feet of event space and museum. It houses an impressive collection of vintage cars from the early 1900s to the present day.

I’ll confess that my heart was stopped by a pink 1950s Thunderbird, but there are so many fabulous vintage cars that you won’t know where to look first. Sidney Hobbs, the museum’s creator, shared with me that he drives each vehicle on the showroom floor regularly, which in and of itself is stunning.

Shrimp and grits from St. Augustine Fish Camp.
Jim Hill

Best Restaurants In St. Augustine

St. Augustine’s culinary scene has exploded over the last year, and there are more options than ever for foodies.

The Tasting Tours

The Tasting Tours are a great way to truly get a feel for St. Augustine’s culinary scene’s depth and breadth. There are a variety of tasting tours and libation tours to choose from. All tours include stops at five fabulous venues and a guided tour of the city. The tours last 3 hours. I love the Wine and Dine tour myself. The Wine and Dine is a chauffeured tour and perfect for a romantic evening.

St. Augustine Fish Camp

St. Augustine Fish Camp is a newcomer to historic St. Augustine, but it is fabulous! Located at 142 Riberia Street, St. Augustine Fish Camp has a neighborhood vibe. I love that their incredible food is presented in a fun and creative way.

I am a snob when it comes to fresh seafood, and I was blown away by the crab cakes. They were filled with succulent fresh crab meat with little to no filler. The caper dill aioli was delicate and not overpowering.

You’ll be hard-pressed not to order dessert; their signature dessert, a white chocolate bread pudding, is absolutely divine. The key lime pie ran a close second, with a perfect balance of tart with a hint of sweetness. The crust was crunchy and flavorful, with an unexpected nuttiness that was fantastic.

A cheese board from The Floridian in St. Augustine.
Jim Hill

The Floridian

The Floridian is another new face on St. Augustine’s food scene. I honestly did not know what to expect when we walked up to The Floridian. A rustic-chic interior and an outdoor dining space with outdoor lights offer a casual, laid-back atmosphere. The servers were knowledgeable, the servings were huge, and no one leaves unhappy.

The food is locally sourced, regionally inspired, and refreshingly innovative in presentation while keeping things simple and letting the food be the shining star. I loved the creative twist on old Southern favorites on the menu.

The cheese board was artfully presented and was the real surprise for me. The cheese selection was delicious, and paired with grapes and apples, candied pecans, and local Florida honey was outstanding. Be warned that the servings are enormous, and a salad bowl is enough for two.

Other restaurants of note in St. Augustine include the Raintree restaurant, the Columbia, and O.C. White’s Restaurant.

The Collector, a hotel in St. Augustine, Florida.
Jim Hill

Best Hotels In St. Augustine

The Collector

The Collector Luxury Inn and Gardens has been named by USA Today as one of the 10 Best New Hotels in America. After experiencing The Collector, I would agree. With its location on the historic district’s fringe, you are surrounded by peaceful surroundings that allow you to relax. The Collector is an adults-only property, making it ideal for a romantic getaway for two.

You’ll find The Collector to be a hidden oasis. Their amenities include Valet Service and Parking, daily European Continental Breakfast, and Wi-Fi. A heated pool tucked away in the corner of the property is a welcome find. The Collector also includes turndown service (a really nice feature), bicycles to explore St. Augustine, lawn games, daily afternoon and late-night happy hours, and more.

The Well at the Collector is an experience you will not soon forget. Cocktails are not only handcrafted; they are handcrafted specifically for you. The bartender will chat with you to find out your preference of spirit, type, and profile of drinks and then custom craft a cocktail for you.

Casa de Suenos Bed and Breakfast in St. Augustine.
Jim Hill

Casa De Suenos Bed And Breakfast

Casa de Suenos is located right in the heart of historic St. Augustine, and its history and charm just seep from its walls. Casa de Suenos is an intimate inn with only seven guest rooms, just perfect for a romantic St. Augustine getaway.

Amenities include a sumptuous breakfast each morning, comfortable and cozy robes, clock radios with iPhone/iPad Bluetooth connection, hairdryers and power strips, Wi-Fi, wine glasses and corkscrew, Turkish towels (a nice touch!), fresh flowers, and evening dessert.

The St. Francis Inn bed and breakfast in Florida.
Jim Hill

The St. Francis Inn Bed And Breakfast

Located right in the heart of the historic downtown, The St. Francis Inn Bed and Breakfast offers 19 guest rooms uniquely decorated and well-appointed. The St. Francis Inn is perfect for couples looking for a cozy yet luxurious bed and breakfast stay.

We love the courtyard area of the inn. Hidden behind wrought iron fencing and boasting lots of lovely flora and fauna, it is the perfect spot to begin your day with a cup of coffee and a delightful breakfast.

The inn also has an inviting pool area, so after a day of sightseeing, take a cool dip in the pool.

Though St. Augustine truly is a year-round destination, I prefer to visit in the fall when it is cooler outside and less crowded. Spring is also a lovely time to visit, though days on the water for eco-tours can be a bit nippy. But my favorite time of year to visit St. Augustine is during the city’s Nights of Lights. Seeing the entire historic downtown come alive, lit by millions of tiny twinkling lights, is a truly magical experience.

If Florida is calling your name, here are a few of our other recommendations in the beautiful state of Florida!