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Experience the Gilded Age of Glory


St. Augustine is rich in history, and in the late 1800s, "rich" was the operative word. This little town became the premier resort destination for the well-to-do – and it all began in 1883 with an auspicious visit by Henry Morrison Flagler, John D. Rockefeller’s partner in founding Standard Oil Stroll back in time as you explore St. Augustine in all its Gilded Age glory with this free Gilded Age Itinerary. We’ve included suggestions for drinking, dining and discovering your way through an opulent era of lavish architecture and conspicuous luxury.

MORNING | Breakfast and Flagler Legacy Tour

The Blue Hen Café

Quaint and quirky comfort food with options like blue crab quiche, corned beef hash and eggs, chicken biscuits, and more.

(904) 217-3777

Flagler Legacy Tour

Built by Henry M. Flagler in 1888 and one of the most exclusive resorts of its day, Historic Tours of the former Hotel Ponce de Leon highlight the Spanish Renaissance architectural heritage of what is now Flagler College.

(904) 823-3378

AFTERNOON | Lunch and Explore Downtown and Flagler's Churches

The Floridian

Local, seasonal and sustainable ingredients in a comfortable and casual atmosphere. Taste southern comfort food, and vibrant, creative dishes with many vegetarian options.

(904) 829-0655

The Hyppo Gourmet Ice Pops

The Hyppo makes delightful all-natural ice pops from everything under the sun, and over 450 flavors later, we're still going!

(904) 217-7853

Cathedral Basilica of St. Augustine

As you explore downtown, visit the beautifully adorned Cathedral-Basilica of St. Augustine. America's first parish and the oldest Catholic Church in the city. Explore this exquisite building and view the Spanish-inspired architecture.

(904) 824-2806

Memorial Presbyterian Church

Henry Flagler had a hand at constructing many of the oldest churches in St. Augustine. Visit the Memorial Presbyterian Church, where Flagler and his family were laid to rest.

(904) 829-6451

Plaza de La Constitucion

Visitors can enjoy local events at the plaza like a seasonal concert series or the Nights of Lights during the holidays. The plaza is surrounded by large cannons which make for a fun vacation photo op.

(904) 829-6451

EVENING |Dinner and Exploring

The Ice Plant Bar

Set in a 1927 industrial building, this eatery offers locally sourced dishes & seasonal cocktails. Shortly following the Gilded Age, the original building supplied the city with manufactured ice as a modern convenience for the wealthy.

(904) 829-6553

Tour the St. Augustine Distillery

Visit the museum and experience a free guided tour. Located within a beautifully restored ice plant from the turn-of-the-century, St. Augustine Distillery’s mission is simple: Educate and inspire guests about local, handcrafted, award-winning rum, whiskey bourbon, gin, and vodka.

(904) 825-4962

MORNING | Breakfast and Musuem Tour

La Herencia Café

Dine in this small Cuban-American restaurant in the heart of historic downtown St. Augustine, serving Cuban food from family recipes and breakfast all day.

(904) 829-9487

Tour the Lightner Museum

A monument to the lavishness of the Gilded Age, the museum features three floors of artifacts from the 19th and 20th centuries, including exquisite Victorian clothing and art, stained Tiffany glass, and paintings and oddities from around the world.

(904) 824-2874

AFTERNOON | Lunch and Art Galleries

Café Alcazar in the Lightner

Formerly Henry Flagler’s Alcazar Hotel, which closed in 1932. The indoor pool, now the location of Café Alcazar, was the largest in the world in its time. At certain times, the pool was drained, and elaborate gardens were installed on the pool’s floor.

(904) 825-9948

Explore Aviles Street and King Street Art Galleries


Explore Aviles Street, now one of the area’s most diverse arts districts, filled with galleries and restaurants. It was paved with bricks so that the shoes of ladies from New York would not be soiled walking through muddy streets.

EVENING | Dinner and Live Music

Costa Brava in the Casa Monica Hotel

Take a culinary journey along the Mediterranean at Costa Brava. A sumptuous meze-style menu features fresh and flavorful coastal cuisine, perfect to share with family and friends.


Henry Flagler purchased the hotel in 1887, including all fixtures, furnishings, silver, hardware, linen, bedding, parlor, hall, dining room, and kitchen furnishings and all other chattels.

(904) 827-1888

Preserved Restaurant

Enjoy upscale, locally-sourced Southern cuisine in the historic Victorian neighborhood of Lincolnville. Architecturally, the restaurant has retained the original structure of the building, which was built between 1865 and 1885.

(904) 679-4940

The Colonial Quater

Enjoy live music each weekend under the Colonial Oak at The Colonial Quarter. The stage area is nestled in a collection of replica buildings of St. Augustine’s 17th Century Spanish and 18th Century British rule, and a restored 1740 colonial home, the De Mes-Sanchez House.

(888) 991-0933

Castillo de San Marcos National Monument


Visitors to St. Augustine, such as Flagler’s distinguished guests, sometimes golfed on the lawn of the Castillo. Tour the grounds of the 17th century Spanish fort, imagining its elegant use in the Gilded Age as a tourism destination for America’s Elite.

(904) 829-6506

Interactive Map - Gilded Age Itinerary


The map below will help you plan your route through historic St. Augustine as you enjoy the sights, sounds, and flavors.

Video - Experience The Gilded Age in St. Augustine

To download a PDF version of this itinerary, click here.