St. Augustine has a knack for making history. More than 450 years since its founding, there’s a first, oldest, or only around nearly every corner. Walkable streets wind past Spanish colonial architecture and centuries-old landmarks, while the Atlantic coast offers a change of scenery just beyond downtown. Equal parts relaxing and enriching, America’s oldest city always has something new to discover.

Day one

Do | Old Town Trolley Tour
Get your bearings aboard this historic tour, including stops at the Castillo de San Marcos, Flagler College, the Fountain of Youth, and the Lightner Museum. Pro tip: The trolley also stops at the Colonial Quarter, where you’ll experience 500 years of St. Augustine lore, from blacksmithing to cannon firing.

An open-sided tourist tram passes a green park and historic stone fort, with palm trees, visitors, and a bright blue sky creating a calm, sunny scene.
Hop on and off this trolley tour as often as you'd like, all day long. | Historic Tours of America, Inc.

Eat | River & Fort
Take in bayfront views on the rooftop underneath massive palms. Pro tip: Pair the lobster flatbread with a crisp glass of pomegranate berry sangria.

Shop | St. George Street
This pedestrian-only thoroughfare is dotted with colonial-era buildings, kitschy boutiques, and hidden courtyards. Pro tip: Wander a little further to Florida’s Oldest House, where tours run every half hour.

Colorful historic buildings, including a dark wooden balcony and orange façade, sit beneath lush green trees on a quiet street, creating a charming, peaceful scene.
Don't miss the Oldest Wooden School House on St. George Street. | Michael Warren

See | Villa Zorayda Museum
Explore an eclectic collection of art and antiques inside this Moorish Revival-style mansion built in 1883.

Eat | Cap’s on the Water
Fresh seafood, award-winning wines, and vibrant sunsets await.

Do | Colonial Oak Music Park
Listen to live music underneath a 300-year-old oak tree.

Day two

Eat | The French Pantry
Begin your day with a French vanilla latte, then order a BLT, chicken salad sandwich, or bang bang shrimp po boy to-go.

Do | Vilano Beach
Unpack your lunch along this laid-back stretch of coastline. Pro tip: Proximity to the Matanzas Inlet creates waves ideal for surfing and skimboarding.

A quiet sandy beach stretches along low beachfront buildings, with one person walking near the water as gentle waves roll in under a clear blue sky.
Just north of St. Augustine, Vilano Beach is a treasure trove for shark-tooth hunters. | FloridasHistoricCoast.com

Do | St. Augustine Sailing
Test the waters during an Intro to Sailing lesson.

See | Magnolia Avenue
Take a detour down this picturesque stretch of road, where a canopy of ancient live oaks is draped in Spanish moss.

A quiet residential road winds beneath towering live oaks draped in Spanish moss, glowing in warm evening light, with a car in the distance.
Some call this the prettiest street in Florida. | Ken Badgley

Eat | Ice Plant
Settle in for a farm-to-table dinner inside a century-old factory. Pro tip: Start with the crab beignets, a house favorite.

Patrons sit at a large, historic bar inside the Ice Plant restaurant in St. Augustine, featuring high ceilings and exposed brick.
The Ice Plant pays homage to its roots by using three different types of ice in its cocktails. | Vy Nguyen Films

Drink | The Tini Martini Bar
Cap off the evening with a martini from a menu of more than 25 varieties.

Where to stay

Castillo de la Paz
Spend the night in a revived 1900s chapel within walking distance of St. George Street.

A green, cottage-style church with white trim, wooden doors, and wreaths sits amid tropical gardens beneath a pink-and-blue sunset, creating a warm, peaceful welcome.
Inside, there's a pool table and a bathtub wrapped in mosaic tiles. | Vrbo

Casa Monica
Built in 1888, this luxury stay combines Gilded Age style with modern amenities.

The historic Casa Monica Resort in St. Augustine glows with thousands of white holiday lights on its towers and palm trees.
Casa Monica Resort & Spa has the best of both worlds: architecture from 1888 and Marriott's modern touches. | CycleHere

Bayfront Marin House
Multiple historic homes were connected to create this award-winning bed and breakfast.

A yellow, cottage-style bed and breakfast features multiple houses with a lush courtyard in the middle.
Here, happy hour runs from 5 to 6 p.m. every day, featuring homemade sangrias and bites like Southern pimiento cheese and biscuits. | Bayfront Marin House

When to go

November-January | Nights of Lights
Over 3 million white lights turn the Ancient City into a winter wonderland.

February | St. Augustine Spanish Food & Wine Festival
Raise a glass to the city’s Spanish roots during a series of culinary and cultural events.

September | Sing Out Loud Festival
More than 100 free performances from local and regional musicians take over a dozen venues.

First weekend of every month | First Friday Art Walk
Time your visit with this monthly tradition, when galleries, museums, and shops stay open late.

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